N Properties for Sale in Winter Park, FL
305 Matching Listings
Order By: 
$485,000
Winter Park
$449,000
Winter Park
$695,000
Winter Park
$445,000
Winter Park
$11,795,000
Winter Park
$1,690,000
Winter Park
$209,000
Winter Park
1000 S Semoran Boulevard Unit, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 1
$260,000
Winter Park
$2,100,000
Winter Park
$300,000
Winter Park
215 Sandlewood Trail Unit 7, Winter Park, FL 32789
Condominium -
Waterfront No
Days Listed: 3
$644,900
Winter Park
7921 Pleasant Pine Circle, Winter Park, FL 32792
Single Family -
Waterfront No
Days Listed: 3
$469,900
Winter Park
$209,000
Winter Park
110 Lewfield Circle Unit 110, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 4
$2,790,000
Winter Park
$250,000
Winter Park
200 Saint Andrews Boulevard Un, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 5
$2,495,000
Winter Park
$775,000
Winter Park
$209,999
Winter Park
1000 S Semoran Boulevard Unit, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 7
$230,000
Winter Park
7448 Woodburn Court Unit 30, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 7
$4,250,000
Winter Park
$1,800,000
Winter Park
$635,000
Winter Park
$1,550,000
Winter Park
101 S New York Avenue Unit 304, Winter Park, FL 32789
Condominium -
Waterfront No
Days Listed: 9
$550,000
Winter Park
$625,000
Winter Park
$639,900
Winter Park
1051 Aragon Avenue Unit 1051, Winter Park, FL 32789
Townhouse -
Waterfront No
Days Listed: 9
$725,000
Winter Park
$749,900
Winter Park
Data feed last updated 04-27-2024 at 6:00 AM
Most Recent Sales - (2892) - COLONIES as of 2024-04-27
| Sale Date | Address | Sale Price | $/SF | List Price | Sq. Ft. | Type | Bd/Ba | Days Listed |
| 04-26-2024 | 3069 AARON BURR AVENUE UNIT 1 | $80,000 | $148 | $99,000 | 537 | Condominium | /1 | 55 |
| 04-25-2024 | 1331 WOODDALE AVENUE | $1,875,000 | $506 | $1,995,000 | 3,703 | Single Family Residence | 5/4 | 114 |
| 04-25-2024 | 1835 CLEMATIS LANE | $395,000 | $297 | $400,000 | 1,328 | Single Family Residence | 4/2 | 37 |
| 04-24-2024 | 668 GRENADINE COURT | $264,000 | $195 | $270,000 | 1,350 | Condominium | 3/2 | 188 |
| 04-23-2024 | 431 FLETCHER PLACE | $1,700,000 | $420 | $1,795,000 | 4,045 | Single Family Residence | 4/4 | 30 |
| 04-23-2024 | 7482 CANFORD COURT UNIT #7482 | $250,000 | $179 | $259,000 | 1,393 | Condominium | 2/2 | 61 |
| 04-23-2024 | 2527 EASTBROOK BOULEVARD | $430,000 | $263 | $439,000 | 1,630 | Single Family Residence | 4/2 | 48 |
| 04-23-2024 | 3146 LOWNDES DRIVE | $466,000 | $296 | $465,000 | 1,570 | Single Family Residence | 3/3 | 35 |
| 04-23-2024 | 1943 STRATHAVEN ROAD | $984,000 | $377 | $975,000 | 2,609 | Single Family Residence | 4/3 | 42 |
| 04-22-2024 | 200 SAINT ANDREWS BOULEVARD UNIT 711 | $180,000 | $226 | $185,000 | 793 | Condominium | 1/1 | 53 |
| 04-22-2024 | 3204 SHADY PINE AVENUE | $355,000 | $219 | $355,000 | 1,615 | Single Family Residence | 4/2 | 24 |
| 04-22-2024 | 266 N RANGER BOULEVARD | $465,000 | $293 | $485,000 | 1,582 | Single Family Residence | 3/2 | 41 |
| 04-19-2024 | 1766 MONDRIAN CIRCLE | $1,150,000 | $477 | $1,150,000 | 2,407 | Townhouse | 3/4 | 58 |
| 04-19-2024 | 3364 RIVER VIEW WAY UNIT 51 | $200,000 | $193 | $210,000 | 1,031 | Condominium | 2/3 | 60 |
| 04-19-2024 | 2100 LAKE DRIVE | $2,090,000 | $587 | $2,145,000 | 3,555 | Single Family Residence | 4/4 | 211 |
| 04-19-2024 | 2387 FLAMINGO WAY | $280,000 | $274 | $280,000 | 1,020 | Townhouse | 2/2 | 50 |
| 04-19-2024 | 274 N RANGER BOULEVARD | $470,000 | $330 | $470,000 | 1,420 | Single Family Residence | 3/2 | 1 |
| 04-19-2024 | 753 GILBERT ROAD | $680,000 | $292 | $675,000 | 2,328 | Single Family Residence | 4/3 | 46 |
| 04-18-2024 | 1661 HILLCREST AVE | $1,800,000 | $569 | $1,899,777 | 3,161 | Single Family Residence | 4/4 | 52 |
| 04-18-2024 | 2500 LEE ROAD UNIT 104 | $214,000 | $223 | $225,000 | 956 | Condominium | 2/2 | 42 |
| 04-17-2024 | 195 SCOTTSDALE SQUARE UNIT 195 | $92,000 | $153 | $100,000 | 600 | Condominium | 1/1 | 29 |
| 04-17-2024 | 7408 WOODBURN COURT UNIT 22 | $225,000 | $227 | $225,000 | 990 | Condominium | 2/2 | 88 |
| 04-17-2024 | 1433 SARAZENS PLACE | $2,350,000 | $594 | $2,350,000 | 3,954 | Single Family Residence | 5/6 | 55 |
| 04-17-2024 | 2520 ROXBURY ROAD | $320,000 | $377 | $320,000 | 847 | Single Family Residence | 2/1 | 1 |
| 04-17-2024 | 404 BARCLAY DRIVE | $420,000 | $251 | $437,000 | 1,672 | Single Family Residence | 4/2 | 169 |
| 04-16-2024 | $410,000 | $121 | $469,999 | 3,383 | Single Family Residence | 6/4 | 78 | |
| 04-16-2024 | 728 CORNWALL ROAD | $750,000 | $320 | $775,000 | 2,342 | Single Family Residence | 3/3 | 118 |
| 04-15-2024 | 101 S NEW YORK AVENUE UNIT 309 | $1,625,000 | $547 | $1,695,000 | 2,966 | Condominium | 3/4 | 55 |
| 04-15-2024 | 1651 ONECO AVENUE | $2,345,000 | $597 | $2,345,000 | 3,924 | Single Family Residence | 5/5 | 2 |
| 04-15-2024 | 664 W MORSE BOULEVARD | $4,200,000 | $721 | $4,299,000 | 5,819 | Single Family Residence | 4/6 | 475 |
| 04-15-2024 | 2722 EASTERN PARKWAY | $560,000 | $307 | $550,000 | 1,821 | Single Family Residence | 3/2 | 29 |
| 04-12-2024 | 2019 NATALEN ROAD | $1,375,000 | $444 | $1,375,000 | 3,093 | Single Family Residence | 4/4 | 344 |
| 04-12-2024 | 7109 NATHAN COURT | $360,000 | $157 | $365,000 | 2,282 | Single Family Residence | 4/4 | 22 |
| 04-12-2024 | 1716 PALMER AVENUE | $855,000 | $263 | $947,000 | 3,243 | Single Family Residence | 3/3 | 238 |
| 04-11-2024 | 1701 SUMMERLAND AVENUE | $1,250,000 | $397 | $1,359,000 | 3,148 | Single Family Residence | 4/3 | 182 |
| 04-10-2024 | 700 MELROSE AVENUE UNIT E 26 | $239,000 | $327 | $239,000 | 730 | Condominium | 1/1 | 55 |
| 04-10-2024 | 1148 HOWELL BRANCH ROAD | $615,000 | $351 | $615,000 | 1,749 | Single Family Residence | 4/2 | 49 |
| 04-09-2024 | 1771 CHESTNUT AVENUE | $835,000 | $407 | $860,000 | 2,051 | Single Family Residence | 3/3 | 41 |
| 04-08-2024 | 2786 BRIGHT BIRD LANE | $444,190 | $232 | $444,190 | 1,907 | Townhouse | 3/3 | 42 |
| 04-05-2024 | 285 SCOTTSDALE SQUARE UNIT 285 | $125,000 | $116 | $129,900 | 1,070 | Condominium | 2/2 | 114 |
| 04-05-2024 | 157 LEWFIELD CIRCLE UNIT 157 | $167,000 | $246 | $167,000 | 678 | Condominium | 1/1 | 37 |
| 04-05-2024 | 669 W COMSTOCK AVENUE | $200,000 | $200,000 | / | 404 | |||
| 04-05-2024 | $360,000 | $256 | $360,000 | 1,404 | Single Family Residence | 2/2 | 21 | |
| 04-05-2024 | 690 OSCEOLA AVENUE UNIT 410 | $380,000 | $331 | $399,000 | 1,148 | Condominium | 2/2 | 117 |
| 04-05-2024 | 1193 SPRINGVIEW RUN | $405,000 | $238 | $399,900 | 1,696 | Single Family Residence | 4/3 | 72 |
| 04-05-2024 | 1010 N LAKEMONT AVENUE | $390,000 | $317 | $399,998 | 1,227 | Single Family Residence | 3/1 | 110 |
| 04-05-2024 | 1741 W CHERYL DRIVE | $485,000 | $312 | $485,000 | 1,550 | Single Family Residence | 3/2 | 38 |
| 04-05-2024 | 1907 LOCH BERRY ROAD | $500,000 | $388 | $515,000 | 1,288 | Single Family Residence | 3/2 | 46 |
| 04-05-2024 | 1411 BUCKINGHAM ROAD | $575,000 | $322 | $623,000 | 1,783 | Single Family Residence | 3/2 | 63 |
| 04-05-2024 | 1131 OXFORD ROAD | $700,000 | $435 | $750,000 | 1,608 | Single Family Residence | 2/2 | 53 |
| 04-04-2024 | 190 BALFOUR DRIVE UNIT 1 | $345,000 | $281 | $348,000 | 1,225 | Condominium | 2/2 | 84 |
| 04-03-2024 | 2787 BRIGHT BIRD LANE | $467,400 | $262 | $467,400 | 1,782 | Townhouse | 3/3 | 20 |
| 04-03-2024 | 104 S INTERLACHEN AVENUE UNIT 414 | $650,000 | $513 | $675,000 | 1,267 | Condominium | 2/2 | 56 |
| 04-02-2024 | 5157 LAZY OAKS DRIVE | $285,000 | $282 | $285,000 | 1,008 | Condominium | 2/2 | 30 |
| 04-02-2024 | 4411 GLENVIEW LANE | $450,000 | $203 | $459,999 | 2,215 | Single Family Residence | 3/2 | 131 |
| 04-01-2024 | 1138 BELLA LAGO COVE | $1,475,000 | $293 | $1,400,000 | 5,032 | Single Family Residence | 4/4 | 39 |
| 04-01-2024 | 2138 LAKE DRIVE | $2,725,000 | $534 | $3,050,000 | 5,100 | Single Family Residence | 4/4 | 424 |
| 03-29-2024 | 1554 HARRIS CIRCLE | $1,075,000 | $383 | $1,075,000 | 2,801 | Single Family Residence | 3/3 | 373 |
| 03-29-2024 | 1750 CAROLLEE LANE | $1,430,000 | $440 | $1,430,000 | 3,249 | Single Family Residence | 4/4 | 22 |
| 03-29-2024 | 1450 LEITH AVENUE | $395,000 | $434 | $405,000 | 910 | Single Family Residence | 2/1 | 75 |
| 03-29-2024 | 1768 MONDRIAN CIRCLE | $970,000 | $442 | $950,000 | 2,193 | Townhouse | 3/4 | 61 |
| 03-28-2024 | 1780 MONDRIAN CIRCLE | $1,260,000 | $545 | $1,200,000 | 2,310 | Townhouse | 3/4 | 50 |
| 03-28-2024 | 420 KILLARNEY BAY COURT UNIT 2 | $338,000 | $291 | $349,500 | 1,160 | Condominium | 2/2 | 38 |
| 03-28-2024 | 534 GENIUS DRIVE | $3,350,000 | $612 | $3,600,000 | 5,473 | Single Family Residence | 6/6 | 70 |
| 03-28-2024 | 2639 CARVELL COURT | $411,000 | $314 | $409,900 | 1,308 | Single Family Residence | 3/2 | 37 |
| 03-28-2024 | 1589 SPRINGTIME LOOP | $415,000 | $235 | $425,999 | 1,764 | Single Family Residence | 3/2 | 199 |
| 03-28-2024 | 2775 BRIGHT BIRD LANE | $458,590 | $240 | $458,590 | 1,907 | Townhouse | 3/3 | 2 |
| 03-28-2024 | 674 DOUGLAS AVENUE | $452,500 | $359 | $465,000 | 1,260 | Single Family Residence | 2/2 | 42 |
| 03-28-2024 | 1840 ANZLE AVENUE | $450,000 | $341 | $489,999 | 1,319 | Single Family Residence | 2/2 | 105 |
| 03-28-2024 | 8485 ANSON WAY | $535,000 | $259 | $539,000 | 2,062 | Single Family Residence | 4/2 | 28 |
| 03-27-2024 | 814 HAMILTON PLACE COURT | $1,060,000 | $364 | $1,125,000 | 2,907 | Single Family Residence | 4/4 | 15 |
| 03-27-2024 | 2531 LAFAYETTE AVENUE | $1,382,000 | $504 | $1,399,000 | 2,742 | Single Family Residence | 4/4 | 243 |
| 03-26-2024 | 603 SAINT JOHNS COURT UNIT S | $185,000 | $243 | $175,000 | 759 | Condominium | 1/1 | 34 |
| 03-26-2024 | 2847 LION HEART ROAD | $646,000 | $390 | $625,000 | 1,656 | Single Family Residence | 4/2 | 27 |
| 03-26-2024 | 420 WORTHINGTON DRIVE | $675,000 | $368 | $699,700 | 1,830 | Single Family Residence | 3/2 | 19 |
| 03-25-2024 | 100 S VIRGINIA AVENUE UNIT 402 | $1,242,802 | $478 | $1,250,000 | 2,599 | Condominium | 3/3 | 55 |
| 03-25-2024 | 1250 S DENNING DRIVE UNIT 111 | $256,000 | $281 | $262,000 | 908 | Condominium | 2/2 | 41 |
| 03-25-2024 | 200 SAINT ANDREWS BOULEVARD UNIT 1807 | $280,000 | $229 | $289,000 | 1,219 | Condominium | 2/2 | 39 |
| 03-25-2024 | 2778 BRIGHT BIRD LANE | $427,000 | $223 | $435,890 | 1,907 | Townhouse | 3/3 | 76 |
| 03-22-2024 | 7329 CEDAR CREEK COURT UNIT 73 | $222,500 | $224 | $222,500 | 990 | Condominium | 2/2 | 57 |
| 03-21-2024 | 931 BUNGALOW AVENUE | $1,210,000 | $489 | $1,199,900 | 2,472 | Single Family Residence | 4/4 | 36 |
| 03-21-2024 | 2790 BRIGHT BIRD LANE | $465,790 | $261 | $465,790 | 1,782 | Townhouse | 3/3 | 53 |
| 03-21-2024 | 1951 LINDEN ROAD | $485,000 | $254 | $485,000 | 1,903 | Single Family Residence | 3/2 | 37 |
| 03-20-2024 | 1106 PALMER AVENUE | $3,300,000 | $527 | $3,300,000 | 6,256 | Single Family Residence | 4/6 | 63 |
| 03-19-2024 | 2417 LAFAYETTE AVENUE | $1,025,000 | $476 | $1,095,000 | 2,149 | Single Family Residence | 4/3 | 204 |
| 03-19-2024 | 151 N VIRGINIA AVENUE | $1,600,000 | $575 | $1,695,000 | 2,778 | Single Family Residence | 2/3 | 134 |
| 03-19-2024 | 2083 LEANNE COURT | $330,000 | $218 | $340,000 | 1,512 | Single Family Residence | 3/2 | 23 |
| 03-19-2024 | 1818 WILLOW LANE | $409,000 | $318 | $419,000 | 1,286 | Single Family Residence | 3/2 | 65 |
| 03-19-2024 | 7519 VILLAGE GREEN DRIVE | $470,000 | $281 | $472,900 | 1,670 | Single Family Residence | 3/2 | 75 |
| 03-19-2024 | 723 BONGART ROAD | $510,000 | $311 | $475,000 | 1,637 | Single Family Residence | 3/2 | 41 |
| 03-18-2024 | 307 SCOTTSDALE SQUARE UNIT 307 | $105,000 | $133 | $120,000 | 785 | Condominium | 1/1 | 48 |
| 03-18-2024 | 2905 CHANTILLY AVENUE | $440,000 | $364 | $439,000 | 1,208 | Single Family Residence | 3/2 | 47 |
| 03-18-2024 | 1568 SUGARWOOD CIRCLE | $480,000 | $234 | $497,500 | 2,044 | Single Family Residence | 4/2 | 46 |
| 03-18-2024 | 1256 MICHIGAN AVENUE | $575,000 | $274 | $589,900 | 2,091 | Duplex | 4/4 | 61 |
| 03-18-2024 | 1770 MONDRIAN CIRCLE | $825,000 | $376 | $825,000 | 2,193 | Townhouse | 3/4 | 50 |
| 03-15-2024 | 1949 STRATHAVEN ROAD | $660,000 | $381 | $665,000 | 1,730 | Single Family Residence | 4/2 | 114 |
| 03-14-2024 | 1560 HOLTS GROVE CIRCLE | $3,200,000 | $693 | $3,200,000 | 4,616 | Single Family Residence | 5/6 | 32 |
| 03-14-2024 | 2413 WINTER PARK ROAD | $3,270,500 | $666 | $3,270,500 | 4,905 | Single Family Residence | 5/7 | 22 |
| 03-14-2024 | 3356 BALSAM DRIVE | $440,000 | $316 | $440,000 | 1,390 | Single Family Residence | 3/2 | 45 |
| 03-13-2024 | 1841 & 1831 W FAIRBANKS AVENUE | $1,550,000 | $369 | $1,550,000 | 4,198 | Retail | / | 231 |
| 03-13-2024 | 168 SCOTTSDALE SQUARE UNIT 168 | $153,000 | $122 | $172,000 | 1,250 | Condominium | 3/2 | 69 |
| 03-12-2024 | 1305 HEAVENLY COVE | $1,070,000 | $403 | $1,095,000 | 2,654 | Single Family Residence | 4/3 | 139 |
| 03-12-2024 | 2676 BARBADOS DRIVE | $320,000 | $183 | $329,800 | 1,743 | Townhouse | 3/2 | 116 |
| 03-12-2024 | 2770 LAKE HOWELL LANE | $780,000 | $204 | $835,000 | 3,819 | Single Family Residence | 4/4 | 103 |
| 03-11-2024 | 161 SCOTTSDALE SQUARE UNIT 161 | $110,000 | $145 | $121,500 | 756 | Condominium | 1/1 | 95 |
| 03-11-2024 | 189 SCOTTSDALE SQUARE UNIT 189 | $105,000 | $138 | $125,000 | 756 | Condominium | 1/1 | 42 |
| 03-11-2024 | 1916 ERUDITE WAY | $466,790 | $261 | $484,290 | 1,782 | Townhouse | 3/3 | 209 |
| 03-11-2024 | 7641 VILLAGE GREEN DRIVE | $490,000 | $250 | $490,000 | 1,958 | Single Family Residence | 3/3 | 35 |
| 03-11-2024 | 1272 S PENNSYLVANIA AVENUE UNIT 11 | $935,000 | $477 | $949,000 | 1,957 | Townhouse | 3/3 | 92 |
| 03-08-2024 | 914 MOSS LANE | $1,725,000 | $502 | $1,650,000 | 3,431 | Single Family Residence | 4/4 | 22 |
| 03-07-2024 | 3352 RIVER VIEW WAY | $240,000 | $208 | $239,900 | 1,151 | Townhouse | 3/3 | 105 |
| 03-06-2024 | 237 SCOTTSDALE SQ UNIT 237 | $115,000 | $112 | $130,000 | 1,020 | Condominium | 2/2 | 107 |
| 03-06-2024 | 216 BLOSSOM LANE | $500,000 | $258 | $519,000 | 1,933 | Single Family Residence | 4/2 | 149 |
| 03-05-2024 | 1470 GLENCOE ROAD | $2,150,000 | $678 | $2,250,000 | 3,169 | Single Family Residence | 5/5 | 39 |
| 03-04-2024 | 1913 S LAKEMONT AVENUE | $1,075,000 | $515 | $1,179,000 | 2,085 | Townhouse | 3/4 | 162 |
| 03-04-2024 | 2068 HOUNDSLAKE DRIVE | $345,000 | $268 | $349,900 | 1,284 | Single Family Residence | 3/2 | 95 |
| 03-04-2024 | 7320 FIELDCREST AVENUE | $360,000 | $187 | $400,000 | 1,919 | Single Family Residence | 3/2 | 98 |
| 03-04-2024 | 2852 SHERIFF WAY | $660,000 | $324 | $679,900 | 2,036 | Single Family Residence | 4/3 | 61 |
| 03-01-2024 | 135 SCOTTSDALE SQUARE UNIT 135 | $110,000 | $145 | $124,990 | 756 | Condominium | 1/1 | 17 |
| 03-01-2024 | 2301 CHANTILLY AVENUE | $1,250,000 | $373 | $1,350,000 | 3,350 | Single Family Residence | 4/5 | 79 |
| 03-01-2024 | 1306 MERRYDALE WAY | $420,000 | $209 | $435,000 | 2,002 | Townhouse | 3/3 | 136 |
| 03-01-2024 | 1455 BROAD WING LANE | $440,000 | $250 | $445,000 | 1,755 | Townhouse | 3/3 | 152 |
| 03-01-2024 | 1381 GLADIOLAS DRIVE | $444,000 | $233 | $449,900 | 1,898 | Single Family Residence | 4/2 | 16 |
| 02-29-2024 | 242 SCOTTSDALE SQUARE UNIT 242 | $100,000 | $132 | $100,000 | 756 | Condominium | 1/1 | 27 |
| 02-29-2024 | 1737 INDIANA AVENUE | $1,249,000 | $418 | $1,249,900 | 2,984 | Single Family Residence | 4/4 | 175 |
| 02-29-2024 | 1602 ALABAMA DRIVE UNIT 203 | $1,295,000 | $630 | $1,295,000 | 2,053 | Condominium | 2/2 | 36 |
| 02-29-2024 | 518 W SWOOPE AVENUE | $1,464,000 | $535 | $1,495,000 | 2,734 | Townhouse | 3/3 | 162 |
| 02-29-2024 | 2394 DOMINICA RUN | $220,000 | $149 | $240,000 | 1,467 | Townhouse | 3/2 | 33 |
| 02-29-2024 | 2335 INAGUA WAY | $286,500 | $223 | $284,900 | 1,284 | Townhouse | 3/2 | 35 |
| 02-29-2024 | 1312 S PENNSYLVANIA AVENUE UNIT 1 | $312,000 | $361 | $320,000 | 864 | Condominium | 1/1 | 15 |
| 02-29-2024 | 1908 ERUDITE WAY | $441,490 | $231 | $446,490 | 1,907 | Townhouse | 3/3 | 198 |
| 02-29-2024 | 1635 BERKSHIRE | $559,000 | $408 | $525,000 | 1,367 | Single Family Residence | 3/3 | 32 |
| 02-29-2024 | 1774 MONDRIAN CIRCLE | $955,000 | $473 | $895,000 | 2,016 | Townhouse | 3/4 | 20 |
| 02-28-2024 | 669 GRENADINE COURT UNIT 669 | $237,000 | $228 | $239,000 | 1,037 | Condominium | 2/2 | 104 |
| 02-28-2024 | 2727 AMSDEN ROAD | $383,000 | $265 | $400,000 | 1,440 | Single Family Residence | 3/2 | 4 |
| 02-28-2024 | 2211 KING RICHARDS COURT | $467,500 | $253 | $475,000 | 1,845 | Single Family Residence | 4/2 | 148 |
| 02-27-2024 | 1531 PLACE PICARDY | $1,775,000 | $447 | $1,775,000 | 3,964 | Single Family Residence | 4/4 | 21 |
| 02-27-2024 | 7227 SWALLOW RUN UNIT 7227 | $185,000 | $235 | $185,000 | 784 | Condominium | 2/2 | 48 |
| 02-27-2024 | 200 S INTERLACHEN AVENUE UNIT 450 | $2,200,000 | $707 | $2,399,000 | 3,110 | Condominium | 3/4 | 118 |
| 02-26-2024 | 1814 BARKER DRIVE | $1,775,000 | $432 | $1,850,000 | 4,100 | Single Family Residence | 5/4 | 144 |
| 02-26-2024 | 1921 DARTMOUTH AVENUE | $235,000 | $238 | $274,000 | 987 | Single Family Residence | 3/2 | 105 |
| 02-26-2024 | 2748 BRIGHT BIRD LANE | $426,000 | $223 | $434,990 | 1,907 | Townhouse | 3/3 | 245 |
| 02-26-2024 | 1900 ERUDITE WAY | $449,170 | $235 | $452,990 | 1,907 | Townhouse | 3/3 | 195 |
| 02-26-2024 | 7309 DANIEL WEBSTER DRIVE UNIT B | $84,000 | $142 | $89,500 | 590 | Condominium | /1 | 78 |
| 02-26-2024 | 2430 ROXBURY ROAD | $969,000 | $311 | $990,500 | 3,110 | Single Family Residence | 4/4 | 313 |
| 02-23-2024 | 3322 NETHERWOOD DRIVE | $270,000 | $228 | $270,000 | 1,182 | 1/2 Duplex | 2/2 | 68 |
| 02-23-2024 | 341 BECKETT COURT | $485,000 | $313 | $475,000 | 1,548 | Single Family Residence | 3/2 | 51 |
| 02-23-2024 | 100 S INTERLACHEN AVENUE UNIT 108 | $520,000 | $577 | $525,000 | 901 | Condominium | 2/2 | 23 |
| 02-23-2024 | 103 LONGHORN ROAD | $700,000 | $200 | $749,000 | 3,493 | Single Family Residence | 5/3 | 47 |
| 02-22-2024 | 3348 BALSAM DRIVE | $399,000 | $266 | $399,000 | 1,500 | Single Family Residence | 4/2 | 74 |
| 02-22-2024 | 1661 PALM AVENUE | $795,000 | $617 | $799,900 | 1,288 | Single Family Residence | 4/3 | 56 |
| 02-22-2024 | 1661 PALM AVENUE | $795,000 | $799,900 | / | 25 | |||
| 02-21-2024 | 621 HUNTINGTON AVENUE | $1,400,000 | $583 | $1,400,000 | 2,399 | Single Family Residence | 3/4 | 16 |
| 02-21-2024 | 5316 HALYARD COURT | $427,584 | $309 | $420,000 | 1,380 | Single Family Residence | 3/2 | 107 |
| 02-21-2024 | 8097 PLEASANT PINE CIRCLE | $555,000 | $277 | $548,000 | 2,003 | Single Family Residence | 4/2 | 48 |
| 02-21-2024 | 648 BRECHIN DRIVE | $525,000 | $297 | $580,000 | 1,765 | Single Family Residence | 4/2 | 135 |
| 02-21-2024 | 1660 N WALNUT AVENUE | $550,000 | $486 | $595,500 | 1,130 | Single Family Residence | 2/2 | 77 |
| 02-20-2024 | 40 PALMER AVENUE | $1,450,000 | $348 | $1,595,000 | 4,166 | Single Family Residence | 5/5 | 160 |
| 02-20-2024 | 2228 HOWARD DRIVE | $525,900 | $289 | $524,900 | 1,816 | Single Family Residence | 4/2 | 27 |
| 02-16-2024 | 1772 MONDRIAN CIRCLE | $1,250,000 | $569 | $1,150,000 | 2,193 | Townhouse | 3/4 | 101 |
| 02-16-2024 | 2737 BRIGHT BIRD LANE | $477,790 | $268 | $497,790 | 1,782 | Townhouse | 3/3 | 148 |
| 02-16-2024 | 8000 PLEASANT PINE CIRCLE | $655,000 | $258 | $650,000 | 2,535 | Single Family Residence | 5/3 | 31 |
| 02-15-2024 | 1400 BONNIE BURN CIRCLE | $1,225,000 | $265 | $1,195,000 | 4,622 | Single Family Residence | 3/4 | 28 |
| 02-15-2024 | 1405 CHAPMAN CIRCLE UNIT OR | $1,285,000 | $435 | $1,375,000 | 2,950 | Single Family Residence | 3/4 | 78 |
| 02-15-2024 | 700 MELROSE AVENUE UNIT K3 | $265,000 | $246 | $279,999 | 1,074 | Condominium | 2/2 | 98 |
| 02-15-2024 | 5042 TANGERINE WAY | $445,000 | $276 | $460,000 | 1,607 | Single Family Residence | 3/2 | 113 |
| 02-15-2024 | 2216 FAIRGLENN WAY | $559,000 | $272 | $578,900 | 2,052 | Single Family Residence | 4/2 | 40 |
| 02-14-2024 | 466 GENIUS DRIVE | $3,450,000 | $485 | $3,450,000 | 7,113 | Single Family Residence | 5/7 | 43 |
| 02-13-2024 | 1019 MINNESOTA AVENUE | $301,000 | $279 | $250,000 | 1,076 | Single Family Residence | 2/1 | 40 |
| 02-12-2024 | 1400 CANTERBURY ROAD | $899,000 | $342 | $899,000 | 2,627 | Single Family Residence | 4/3 | 23 |
| 02-10-2024 | 2484 FIRSTLIGHT WAY | $430,000 | $245 | $429,000 | 1,755 | Townhouse | 3/3 | 188 |
| 02-09-2024 | 220 LEWFIELD CIRCLE | $249,900 | $192 | $249,900 | 1,300 | Condominium | 2/3 | 146 |
| 02-09-2024 | 1529 BANTAM WAY | $465,000 | $201 | $470,000 | 2,308 | Townhouse | 3/3 | 67 |
| 02-08-2024 | 620 PINETREE ROAD | $2,200,000 | $556 | $2,200,000 | 3,956 | Single Family Residence | 4/4 | 3 |
| 02-08-2024 | 2906 BANCHORY ROAD | $660,000 | $304 | $674,900 | 2,171 | Single Family Residence | 4/2 | 35 |
| 02-08-2024 | 1443 HIBISCUS AVENUE | $800,000 | $401 | $799,999 | 1,994 | Single Family Residence | 3/3 | 168 |
| 02-08-2024 | 617 S PHELPS AVENUE | $945,000 | $446 | $989,900 | 2,118 | Single Family Residence | 3/2 | 87 |
| 02-07-2024 | 413 BALMORAL RD | $1,375,000 | $357 | $1,470,000 | 3,845 | Single Family Residence | 3/3 | 125 |
| 02-07-2024 | 200 SAINT ANDREWS BOULEVARD UNIT 609 | $199,000 | $273 | $199,000 | 727 | Condominium | 1/1 | 65 |
| 02-06-2024 | 5037 LAKE HOWELL ROAD | $385,500 | $302 | $415,000 | 1,276 | Single Family Residence | 4/2 | 35 |
| 02-06-2024 | 2711 BRIGHT BIRD LANE | $434,619 | $243 | $434,619 | 1,782 | Townhouse | 3/3 | 10 |
| 02-06-2024 | 1780 MIZELL AVENUE | $585,000 | $445 | $615,000 | 1,314 | Single Family Residence | 2/1 | 33 |
| 02-05-2024 | 7429 DANIEL WEBSTER DRIVE UNIT D | $112,500 | $139 | $112,500 | 809 | Condominium | 1/1 | 57 |
| 02-05-2024 | 7421 DANIEL WEBSTER DRIVE UNIT A | $116,000 | $143 | $120,000 | 809 | Condominium | 1/1 | 168 |
| 02-05-2024 | 624 LANGHOLM DRIVE | $595,000 | $250 | $595,000 | 2,378 | Single Family Residence | 3/2 | 23 |
| 02-02-2024 | 1415 GROVE TERRACE | $1,680,000 | $448 | $1,680,000 | 3,746 | Single Family Residence | 4/3 | 7 |
| 02-02-2024 | 1250 S DENNING DRIVE UNIT 126 | $219,025 | $245 | $239,900 | 893 | Condominium | 2/2 | 92 |
| 02-02-2024 | 2003 CANNY COVE | $423,900 | $237 | $429,900 | 1,782 | Townhouse | 3/3 | 59 |
| 02-02-2024 | 4860 N ORANGE AVENUE | $470,000 | $257 | $474,000 | 1,828 | Single Family Residence | 3/2 | 79 |
| 02-01-2024 | 829 HALIFAX AVENUE | $767,000 | $414 | $767,000 | 1,850 | Single Family Residence | 4/2 | 1 |
| 01-31-2024 | 1695 LEE ROAD UNIT D109 | $140,000 | $219 | $140,000 | 638 | Condominium | 1/1 | 79 |
| 01-31-2024 | 670 W CANTON AVENUE | $410,000 | $305 | $399,900 | 1,342 | Single Family Residence | 3/2 | 58 |
| 01-31-2024 | 720 W NEW ENGLAND AVENUE | $351,300 | $322 | $399,900 | 1,089 | Single Family Residence | 2/1 | 78 |
| 01-31-2024 | 2719 BRIGHT BIRD LANE | $408,990 | $408,990 | Townhouse | 3/3 | 1 | ||
| 01-31-2024 | 819 APPALACHEE AVENUE | $412,500 | $237 | $425,000 | 1,738 | Single Family Residence | 4/2 | 43 |
| 01-31-2024 | 2727 BRIGHT BIRD LANE | $459,190 | $240 | $459,190 | 1,907 | Townhouse | 3/3 | 8 |
| 01-31-2024 | 1902 ARBOR PARK DRIVE | $820,000 | $374 | $875,000 | 2,192 | Single Family Residence | 3/2 | 92 |
| 01-30-2024 | 1742 CHESTNUT AVENUE | $680,000 | $393 | $689,000 | 1,729 | Single Family Residence | 4/2 | 82 |
| 01-29-2024 | 203 SCOTTSDALE SQUARE UNIT 203 | $92,000 | $121 | $119,000 | 756 | Condominium | 1/1 | 34 |
| 01-29-2024 | 3651 N GOLDENROD ROAD UNIT 103 | $185,000 | $220 | $195,000 | 840 | Condominium | 2/2 | 205 |
| 01-29-2024 | 633 S PHELPS AVE | $3,045,000 | $615 | $3,095,000 | 4,950 | Single Family Residence | 5/5 | 84 |
| 01-26-2024 | 607 ELLEN DRIVE | $338,500 | $350,000 | / | 47 | |||
| 01-26-2024 | 674 W MORSE BOULEVARD | $3,325,000 | $757 | $3,800,000 | 4,390 | Townhouse | 4/5 | 121 |
| 01-24-2024 | 5255 SEMINOLE AVENUE | $240,000 | $270 | $234,900 | 887 | Single Family Residence | 2/1 | 40 |
| 01-23-2024 | 1020 N PENNSYLVANIA AVENUE | $1,695,000 | $649 | $1,895,000 | 2,609 | Single Family Residence | 4/3 | 103 |
| 01-23-2024 | 2619 WINTER PARK ROAD | $600,000 | $191 | $600,000 | 3,130 | Single Family Residence | 4/4 | 118 |
| 01-19-2024 | 2610 EXUMA WAY | $240,000 | $219 | $249,000 | 1,094 | Townhouse | 2/2 | 61 |
| 01-19-2024 | 722 WARRENTON ROAD | $291,000 | $213 | $290,000 | 1,362 | 1/2 Duplex | 2/2 | 36 |
| 01-19-2024 | 2503 FIRSTLIGHT WAY | $430,000 | $218 | $440,000 | 1,964 | Townhouse | 3/3 | 76 |
| 01-19-2024 | 3710 HAWTHORNE LANE | $495,000 | $300 | $499,999 | 1,647 | Single Family Residence | 3/2 | 47 |
| 01-19-2024 | 1720 PALM AVENUE | $950,000 | $572 | $949,000 | 1,658 | Single Family Residence | 4/2 | 25 |
| 01-18-2024 | 2040 JEWELL AVENUE | $470,000 | $391 | $470,000 | 1,200 | Triplex | 3/3 | 86 |
| 01-17-2024 | 1441 CARDINAL COURT | $3,650,000 | $897 | $3,850,000 | 4,066 | Single Family Residence | 4/6 | 17 |
| 01-16-2024 | 314 SCOTTSDALE SQUARE UNIT 314 | $118,000 | $108 | $130,000 | 1,085 | Condominium | 2/2 | 40 |
| 01-16-2024 | 1331 HIBISCUS AVENUE | $1,587,381 | $383 | $1,598,880 | 4,137 | Single Family Residence | 5/5 | 194 |
| 01-16-2024 | 106 S INTERLACHEN AVENUE UNIT 219A | $1,725,000 | $883 | $1,895,000 | 1,952 | Condominium | 3/2 | 66 |
| 01-16-2024 | 2452 HARBOUR WAY | $282,000 | $180 | $289,900 | 1,560 | Townhouse | 3/2 | 109 |
| 01-16-2024 | 2709 NORRIS AVENUE | $665,000 | $389 | $665,000 | 1,706 | Single Family Residence | 3/3 | 69 |
| 01-16-2024 | 513 DUNBLANE DRIVE | $950,000 | $314 | $967,000 | 3,022 | Single Family Residence | 3/3 | 182 |
| 01-15-2024 | 2721 SALISBURY BOULEVARD | $329,900 | $305 | $329,900 | 1,080 | Single Family Residence | 2/1 | 98 |
| 01-12-2024 | 1927 S LAKEMONT AVENUE | $950,000 | $451 | $1,000,000 | 2,104 | Townhouse | 3/4 | 110 |
| 01-12-2024 | 1270 ARLINGTON PLACE | $1,400,000 | $472 | $1,450,000 | 2,964 | Single Family Residence | 3/4 | 100 |
| 01-12-2024 | 1640 ONECO AVENUE | $2,400,000 | $600 | $2,350,000 | 4,000 | Single Family Residence | 5/6 | 57 |
| 01-12-2024 | 205 E ROCKWOOD WAY | $3,600,000 | $822 | $3,600,000 | 4,376 | Single Family Residence | 6/7 | 29 |
| 01-12-2024 | 1316 CANTERBURY ROAD | $700,000 | $372 | $700,000 | 1,881 | Single Family Residence | 3/2 | 31 |
| 01-12-2024 | 1717 GOLFSIDE DRIVE | $765,000 | $378 | $785,000 | 2,020 | Single Family Residence | 4/2 | 44 |
| 01-11-2024 | 1581 MAGNOLIA AVENUE | $1,362,000 | $507 | $1,350,000 | 2,685 | Single Family Residence | 4/4 | 36 |
| 01-10-2024 | 1772 PINE AVENUE | $2,270,000 | $579 | $2,395,000 | 3,914 | Single Family Residence | 4/5 | 29 |
| 01-10-2024 | 5236 LAKE HOWELL ROAD | $280,000 | $209 | $285,000 | 1,338 | Single Family Residence | 3/2 | 55 |
| 01-10-2024 | 300 S INTERLACHEN AVENUE UNIT 503 | $3,450,000 | $1,028 | $3,450,000 | 3,355 | Condominium | 3/4 | 1 |
| 01-09-2024 | 2563 FIFESHIRE DRIVE | $720,000 | $308 | $749,900 | 2,332 | Single Family Residence | 4/3 | 98 |
| 01-08-2024 | 601 OLOLU DRIVE | $350,000 | $274 | $350,000 | 1,274 | Single Family Residence | 3/1 | 52 |
| 01-05-2024 | 344 SCOTTSDALE SQUARE UNIT 344 | $136,000 | $133 | $136,000 | 1,020 | Condominium | 2/2 | 71 |
| 01-05-2024 | 7340 DANIEL WEBSTER DRIVE UNIT A | $145,500 | $114 | $155,000 | 1,267 | Condominium | 2/2 | 115 |
| 01-05-2024 | 2409 ANTILLES DRIVE | $325,000 | $189 | $324,900 | 1,719 | Townhouse | 3/2 | 103 |
| 01-05-2024 | 7051 GREEN NEEDLE DRIVE | $385,000 | $250 | $379,999 | 1,536 | Single Family Residence | 3/2 | 71 |
| 01-05-2024 | 3469 ARNEL DRIVE | $419,000 | $259 | $419,000 | 1,613 | Single Family Residence | 3/2 | 67 |
| 01-05-2024 | 2114 SHADYHILL TERRACE | $457,500 | $281 | $450,000 | 1,626 | Single Family Residence | 3/2 | 23 |
| 01-05-2024 | 2469 FIRSTLIGHT WAY | $462,500 | $200 | $469,000 | 2,308 | Townhouse | 3/3 | 100 |
| 01-05-2024 | 2705 WRIGHT AVENUE | $515,000 | $304 | $515,000 | 1,694 | Single Family Residence | 3/2 | 86 |
| 01-05-2024 | 1705 MICHIGAN AVENUE | $773,000 | $332 | $770,000 | 2,325 | Single Family Residence | 4/3 | 115 |
| 01-04-2024 | 3378 CEDAR SPRINGS PLACE UNIT 154 | $205,500 | $199 | $205,500 | 1,031 | Townhouse | 2/3 | 1 |
| 01-04-2024 | 5539 ALBERT DRIVE | $378,100 | $285 | $369,900 | 1,325 | Single Family Residence | 3/2 | 15 |
| 01-04-2024 | 3452 ARNEL DRIVE | $406,000 | $251 | $405,000 | 1,613 | Single Family Residence | 3/2 | 63 |
| 01-03-2024 | 1447 VIBURNUM LANE | $369,990 | $314 | $369,990 | 1,176 | Single Family Residence | 3/2 | 167 |
| 01-03-2024 | 2760 BRIGHT BIRD LANE | $429,190 | $225 | $429,190 | 1,907 | Townhouse | 3/3 | 191 |
| 01-03-2024 | 1443 HARMON AVENUE | $475,000 | $297 | $475,000 | 1,596 | Townhouse | 3/4 | 77 |
| 01-02-2024 | 1968 KING ARTHURS COURT | $335,000 | $198 | $335,000 | 1,689 | Single Family Residence | 3/2 | 3 |
| 01-02-2024 | 1871 BARKER DRIVE | $620,000 | $277 | $399,900 | 2,231 | Single Family Residence | 3/3 | 173 |
| 01-02-2024 | 3437 BOWMAN DRIVE | $430,000 | $321 | $445,000 | 1,336 | Single Family Residence | 3/2 | 104 |
| 12-29-2023 | 690 OSCEOLA AVENUE UNIT 504 | $1,175,000 | $565 | $1,200,000 | 2,079 | Condominium | 3/3 | 89 |
| 12-29-2023 | 1049 TUSCANY PLACE | $1,325,000 | $536 | $1,395,000 | 2,471 | Single Family Residence | 4/2 | 40 |
| 12-29-2023 | 1805 HARLAND PARK DRIVE | $1,475,000 | $483 | $1,550,000 | 3,052 | Single Family Residence | 4/4 | 36 |
| 12-29-2023 | 130 BURKS CIRCLE | $2,140,920 | $573 | $1,899,000 | 3,733 | Single Family Residence | 4/5 | 626 |
| 12-29-2023 | 1612 EASTBROOK BOULEVARD | $320,000 | $258 | $299,900 | 1,240 | Single Family Residence | 3/2 | 212 |
| 12-29-2023 | 811 W WEBSTER AVENUE | $335,000 | $262 | $379,000 | 1,274 | Single Family Residence | 3/1 | 64 |
| 12-29-2023 | 3221 ATHENA DRIVE | $449,900 | $288 | $449,900 | 1,557 | Single Family Residence | 3/2 | 23 |
| 12-29-2023 | 914 GROVER AVENUE | $445,000 | $368 | $450,000 | 1,209 | Single Family Residence | 2/1 | 30 |
| 12-29-2023 | 2400 ROXBURY ROAD | $997,500 | $320 | $997,500 | 3,110 | Single Family Residence | 4/4 | 80 |
| 12-28-2023 | 4469 GABRIELLA LANE | $430,000 | $212 | $435,000 | 2,021 | Single Family Residence | 3/3 | 43 |
| 12-28-2023 | 7875 PLEASANT PINE CIRCLE | $560,000 | $246 | $560,000 | 2,268 | Single Family Residence | 4/3 | 33 |
| 12-28-2023 | 1710 WINTER PARK ROAD | $669,000 | $429 | $699,000 | 1,556 | Single Family Residence | 3/2 | 99 |
| 12-28-2023 | 1352 HEAVENLY COVE | $710,000 | $243 | $699,900 | 2,921 | Single Family Residence | 4/3 | 71 |
| 12-27-2023 | 601 ELLEN DRIVE | $1,400,000 | $492 | $1,450,000 | 2,841 | Single Family Residence | 4/5 | 649 |
| 12-27-2023 | 2612 ROXBURY ROAD | $425,000 | $171 | $495,000 | 2,472 | Single Family Residence | 3/3 | 54 |
| 12-26-2023 | 2744 BRIGHT BIRD LANE | $445,990 | $250 | $455,990 | 1,782 | Townhouse | 3/3 | 183 |
| 12-22-2023 | 1800 TEMPLE DR | $1,725,000 | $523 | $1,750,000 | 3,298 | Single Family Residence | 4/4 | 22 |
| 12-22-2023 | 5324 POINSETTA AVE | $395,000 | $175 | $449,990 | 2,250 | Single Family Residence | 5/3 | 93 |
| 12-22-2023 | 5430 ARDMORE DR | $450,000 | $288 | $459,000 | 1,560 | Single Family Residence | 3/2 | 52 |
| 12-22-2023 | 615 GLENRIDGE WAY | $475,000 | $285 | $499,000 | 1,664 | Single Family Residence | 2/2 | 79 |
| 12-21-2023 | 7348 DANIEL WEBSTER DR #F-1d | $190,000 | $174 | $194,900 | 1,090 | Condominium | 2/3 | 78 |
| 12-21-2023 | 3076 NICHOLSON DR | $433,000 | $301 | $433,000 | 1,438 | Single Family Residence | 3/2 | 35 |
| 12-21-2023 | 1724 W CHERYL DR | $445,000 | $268 | $445,000 | 1,656 | Single Family Residence | 3/2 | 34 |
| 12-21-2023 | 2764 BRIGHT BIRD LANE | $457,790 | $256 | $464,790 | 1,782 | Townhouse | 3/3 | 178 |
| 12-21-2023 | 106 S INTERLACHEN AVENUE UNIT 416 | $660,000 | $577 | $695,000 | 1,143 | Condominium | 2/2 | 77 |
| 12-20-2023 | 1525 WILBAR CIRCLE | $1,200,000 | $422 | $1,275,000 | 2,842 | Single Family Residence | 4/5 | 77 |
| 12-20-2023 | 2624 PASSAMONTE DR | $343,000 | $191 | $349,500 | 1,790 | Townhouse | 3/3 | 30 |
| 12-20-2023 | 2756 BRIGHT BIRD LN | $427,990 | $224 | $424,990 | 1,907 | Townhouse | 3/3 | 177 |
| 12-20-2023 | 2726 BRIGHT BIRD LANE | $426,190 | $426,190 | Townhouse | 3/3 | 7 | ||
| 12-20-2023 | 2752 BRIGHT BIRD LN | $434,090 | $227 | $436,090 | 1,907 | Townhouse | 3/3 | 177 |
| 12-20-2023 | 2877 CLEVER LN | $430,980 | $241 | $439,980 | 1,782 | Townhouse | 3/3 | 290 |
| 12-20-2023 | 300 S INTERLACHEN AVE #601 | $5,995,000 | $1,104 | $5,995,000 | 5,430 | Condominium | 4/5 | 26 |
| 12-20-2023 | 1740 WINTER PARK RD | $640,000 | $441 | $649,900 | 1,451 | Single Family Residence | 2/2 | 42 |
| 12-19-2023 | 1602 ALABAMA DRIVE UNIT 107 | $1,000,000 | $1,007 | $1,049,000 | 993 | Condominium | 2/2 | 37 |
| 12-19-2023 | 2714 BRIGHT BIRD LN | $440,690 | $231 | $437,690 | 1,907 | Townhouse | 3/3 | 176 |
| 12-19-2023 | 808 DENSMORE DR | $450,000 | $308 | $460,000 | 1,460 | Single Family Residence | 3/2 | 111 |
| 12-19-2023 | 1645 BERKSHIRE AVE | $510,500 | $331 | $499,000 | 1,539 | Single Family Residence | 2/2 | 20 |
| 12-19-2023 | 1570 ONECO AVE | $925,000 | $543 | $949,500 | 1,703 | Single Family Residence | 3/2 | 44 |
| 12-18-2023 | 1420 MAGNOLIA AVE | $1,550,000 | $488 | $1,445,000 | 3,174 | Single Family Residence | 4/4 | 32 |
| 12-18-2023 | 3077 NICHOLSON DR | $400,000 | $219 | $429,900 | 1,821 | Single Family Residence | 4/3 | 89 |
| 12-18-2023 | 2630 AMSDEN RD | $446,000 | $247 | $449,900 | 1,800 | Single Family Residence | 3/2 | 116 |
| 12-18-2023 | 2612 LAFAYETTE AVE | $430,000 | $175 | $499,900 | 2,447 | Single Family Residence | 3/3 | 53 |
| 12-18-2023 | 7984 PLEASANT PINE CIRCLE | $750,000 | $214 | $750,000 | 3,496 | Single Family Residence | 5/4 | 46 |
| 12-15-2023 | 1887 LAKE SPIER DR | $1,090,000 | $588 | $1,099,000 | 1,852 | Single Family Residence | 4/2 | 51 |
| 12-15-2023 | 121 E FAWSETT RD | $1,100,000 | $718 | $1,100,000 | 1,530 | Single Family Residence | 2/2 | 3 |
| 12-15-2023 | 250 E KINGS WAY | $1,440,000 | $479 | $1,450,000 | 3,003 | Single Family Residence | 4/4 | 39 |
| 12-15-2023 | 617 MONTEGO BAY CT #617 | $223,000 | $215 | $230,000 | 1,037 | Condominium | 2/2 | 52 |
| 12-15-2023 | 4970 TANGERINE AVE #4970 | $235,100 | $222 | $235,000 | 1,059 | Condominium | 2/2 | 37 |
| 12-15-2023 | 140 E MORSE BLVD #I | $2,200,000 | $960 | $2,399,000 | 2,291 | Condominium | 3/2 | 88 |
| 12-15-2023 | 200 SAINT ANDREWS BLVD #1807 | $215,000 | $176 | $240,000 | 1,219 | Condominium | 2/2 | 39 |
| 12-15-2023 | 1597 LAWNDALE CIR | $375,000 | $269 | $380,000 | 1,390 | Single Family Residence | 3/2 | 37 |
| 12-14-2023 | 2387 FLAMINGO WAY | $200,000 | $196 | $235,000 | 1,020 | Townhouse | 2/2 | 104 |
| 12-14-2023 | 5233 LAKE HOWELL RD | $557,000 | $313 | $562,000 | 1,778 | Single Family Residence | 4/3 | 106 |
| 12-13-2023 | 178 LEWFIELD CIRCLE # 178, WINTER PARK FL 32792 | $169,000 | $249 | $185,000 | 678 | Condominium | 1/1 | 78 |
| 12-13-2023 | 7433 BLUE JACKET PL E, WINTER PARK FL 32792 | $364,900 | $214 | $364,900 | 1,704 | Single Family Residence | 3/2 | 53 |
| 12-12-2023 | 901 GOLFVIEW TERRACE, WINTER PARK FL 32789 | $6,300,000 | $1,165 | $6,475,000 | 5,406 | Single Family Residence | 5/6 | 168 |
| 12-11-2023 | 132 BURKS CIRCLE CIRCLE, WINTER PARK FL 32789 | $1,281,550 | $424 | $1,349,000 | 3,022 | Single Family Residence | 4/5 | 39 |
| 12-11-2023 | 324 SCOTTSDALE SQUARE # 324, WINTER PARK FL 32792 | $130,000 | $127 | $135,000 | 1,020 | Condominium | 2/2 | 42 |
| 12-11-2023 | 5408 PEACO PLACE, WINTER PARK FL 32792 | $230,000 | $159 | $249,900 | 1,439 | Single Family Residence | 3/2 | 62 |
| 12-11-2023 | 1833 LOCH BERRY ROAD, WINTER PARK FL 32789 | $660,000 | $387 | $699,900 | 1,705 | Single Family Residence | 3/2 | 40 |
| 12-08-2023 | 1931 CANNY COVE, WINTER PARK FL 32792 | $447,990 | $251 | $447,990 | 1,782 | Townhouse | 3/3 | 6 |
| 12-07-2023 | 1700 DIANA DRIVE, WINTER PARK FL 32789 | $1,075,000 | $366 | $1,199,000 | 2,935 | Single Family Residence | 5/4 | 102 |
| 12-06-2023 | 1721 BRAZILIAN LANE, WINTER PARK FL 32792 | $395,000 | $246 | $385,000 | 1,604 | Single Family Residence | 3/2 | 78 |
| 12-04-2023 | 3310 DEREK COURT | $475,000 | $213 | $475,000 | 2,230 | Single Family Residence | 4/2 | 49 |
| 12-04-2023 | 381 PERTH LANE, WINTER PARK FL 32792 | $515,000 | $342 | $529,900 | 1,502 | Single Family Residence | 3/2 | 67 |
| 11-30-2023 | 1911 S LAKEMONT AVENUE | $899,000 | $431 | $1,050,000 | 2,085 | Townhouse | 3/4 | 67 |
| 11-30-2023 | 3307 AMBER WOOD WAY # 106, WINTER PARK FL 32792 | $225,000 | $218 | $233,000 | 1,031 | Condominium | 2/3 | 60 |
| 11-30-2023 | 1611 SUMMERLAND AVENUE, WINTER PARK FL 32789 | $3,539,000 | $825 | $3,595,000 | 4,287 | Single Family Residence | 5/7 | 98 |
| 11-30-2023 | 2739 RIDDLE DRIVE, WINTER PARK FL 32789 | $615,000 | $319 | $620,000 | 1,925 | Single Family Residence | 4/3 | 65 |
| 11-30-2023 | 1530 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $680,000 | $389 | $684,900 | 1,747 | Single Family Residence | 3/2 | 67 |
| 11-29-2023 | 7781 COUNTRY PLACE # 1, WINTER PARK FL 32792 | $249,000 | $202 | $249,000 | 1,227 | Condominium | 2/2 | 28 |
| 11-29-2023 | 1977 CANNY COVE, WINTER PARK FL 32792 | $453,890 | $254 | $453,890 | 1,782 | Townhouse | 3/3 | 156 |
| 11-28-2023 | 1714 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $875,000 | $413 | $875,000 | 2,114 | Single Family Residence | 3/3 | 63 |
| 11-27-2023 | 620 MONTEGO BAY COURT # 620, WINTER PARK FL 32792 | $255,000 | $227 | $269,000 | 1,120 | Condominium | 2/2 | 53 |
| 11-27-2023 | 5418 TANGERINE AVENUE, WINTER PARK FL 32792 | $302,000 | $219 | $360,000 | 1,375 | Single Family Residence | 3/2 | 54 |
| 11-27-2023 | 1576 KAHKWA COURT, WINTER PARK FL 32792 | $820,000 | $345 | $785,000 | 2,376 | Single Family Residence | 3/2 | 25 |
| 11-27-2023 | 1909 S LAKEMONT AVENUE | $879,000 | $417 | $950,000 | 2,104 | Townhouse | 3/4 | 64 |
| 11-21-2023 | 100 S VIRGINIA AVENUE UNIT 201 | $1,000,000 | $362 | $1,100,000 | 2,756 | Condominium | 3/3 | 79 |
| 11-21-2023 | 1517 LAWNDALE CIRCLE | $365,000 | $287 | $369,900 | 1,271 | Single Family Residence | 3/2 | 41 |
| 11-20-2023 | 2315 JANICE AVENUE, WINTER PARK FL 32789 | $1,010,000 | $310 | $1,099,000 | 3,249 | Single Family Residence | 5/3 | 206 |
| 11-17-2023 | 1834 MAYWOOD ROAD, WINTER PARK FL 32792 | $410,000 | $334 | $419,000 | 1,225 | Single Family Residence | 3/2 | 40 |
| 11-17-2023 | 1978 CANNY COVE, WINTER PARK FL 32792 | $445,182 | $249 | $445,182 | 1,782 | Townhouse | 3/3 | 1 |
| 11-17-2023 | 1324 INDIANA AVENUE, WINTER PARK FL 32789 | $699,000 | $413 | $699,000 | 1,692 | Single Family Residence | 4/3 | 112 |
| 11-16-2023 | 101 S NEW YORK AVENUE # 301, WINTER PARK FL 32789 | $1,350,000 | $425 | $1,350,000 | 3,176 | Condominium | 3/4 | 35 |
| 11-16-2023 | 2333 ANTILLES DRIVE, WINTER PARK FL 32792 | $299,933 | $233 | $299,900 | 1,284 | Townhouse | 3/2 | 21 |
| 11-16-2023 | 2411 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $546,000 | $269 | $575,000 | 2,028 | Single Family Residence | 4/2 | 158 |
| 11-15-2023 | 851 MILES AVENUE # 25, WINTER PARK FL 32789 | $225,000 | $278 | $235,000 | 808 | Condominium | 2/1 | 108 |
| 11-15-2023 | 1512 WESTDALE AVENUE, WINTER PARK FL 32792 | $345,000 | $206 | $369,900 | 1,671 | Single Family Residence | 3/2 | 63 |
| 11-15-2023 | 1414 BESSMOR ROAD, WINTER PARK FL 32789 | $430,000 | $412 | $430,000 | 1,043 | Single Family Residence | 3/1 | 27 |
| 11-14-2023 | 1390 MILLER AVENUE, WINTER PARK FL 32789 | $420,000 | $239 | $420,000 | 1,753 | Single Family Residence | 3/2 | 3 |
| 11-14-2023 | 1411 MILLER AVENUE, WINTER PARK FL 32789 | $779,900 | $430 | $779,900 | 1,813 | Townhouse | 3/4 | 85 |
| 11-13-2023 | 1320 BESSMOR ROAD, WINTER PARK FL 32789 | $1,260,000 | $488 | $1,349,000 | 2,577 | Single Family Residence | 5/3 | 46 |
| 11-13-2023 | 526 GENIUS DRIVE | $2,700,000 | $447 | $2,875,000 | 6,027 | Single Family Residence | 4/5 | 31 |
| 11-13-2023 | 512 BALFOUR DRIVE, WINTER PARK FL 32792 | $418,000 | $256 | $418,000 | 1,630 | Single Family Residence | 4/2 | 2 |
| 11-13-2023 | 341 CORNWALL ROAD, WINTER PARK FL 32792 | $625,000 | $260 | $647,500 | 2,400 | Single Family Residence | 4/3 | 42 |
| 11-10-2023 | 1120 PALMER AVE, WINTER PARK FL 32789 | $1,650,000 | $493 | $1,695,000 | 3,341 | Single Family Residence | 3/4 | 40 |
| 11-10-2023 | 2734 AMSDEN ROAD, WINTER PARK FL 32792 | $391,000 | $286 | $389,900 | 1,364 | Single Family Residence | 3/2 | 37 |
| 11-10-2023 | 5535 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $423,000 | $377 | $432,900 | 1,120 | Single Family Residence | 3/2 | 51 |
| 11-10-2023 | 418 GILBERT ROAD, WINTER PARK FL 32792 | $690,000 | $410 | $699,000 | 1,680 | Single Family Residence | 3/3 | 61 |
| 11-10-2023 | 1409 MILLER AVENUE, WINTER PARK FL 32789 | $779,900 | $430 | $779,900 | 1,813 | Townhouse | 3/4 | 245 |
| 11-09-2023 | 2715 WRIGHT AVENUE, WINTER PARK FL 32789 | $1,275,000 | $408 | $1,345,000 | 3,120 | Single Family Residence | 4/4 | 36 |
| 11-09-2023 | 617 PENN PLACE, WINTER PARK FL 32789 | $2,450,000 | $501 | $2,695,000 | 4,888 | Single Family Residence | 4/5 | 189 |
| 11-09-2023 | 1983 CANNY COVE, WINTER PARK FL 32792 | $448,790 | $251 | $458,790 | 1,782 | Townhouse | 3/3 | 95 |
| 11-08-2023 | 3041 GEORGE MASON AVENUE # 15, WINTER PARK FL 3279 | $109,000 | $134 | $115,000 | 809 | Condominium | 1/1 | 29 |
| 11-08-2023 | 2329 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $1,475,000 | $492 | $1,550,000 | 2,992 | Single Family Residence | 5/5 | 29 |
| 11-08-2023 | 1407 MILLER AVENUE, WINTER PARK FL 32789 | $789,900 | $426 | $789,900 | 1,851 | Townhouse | 3/3 | 170 |
| 11-07-2023 | 641 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $775,000 | $447 | $775,000 | 1,732 | Single Family Residence | 3/3 | 12 |
| 11-07-2023 | 3606 N GOLDENROD ROAD, WINTER PARK FL 32792 | $425,000 | $266 | $850,000 | 1,592 | Single Family Residence | 3/2 | 102 |
| 11-06-2023 | 5206 N INDIANA AVENUE, WINTER PARK FL 32792 | $350,000 | $233 | $365,000 | 1,500 | Single Family Residence | 3/2 | 95 |
| 11-06-2023 | 707 ELLENDALE DRIVE, WINTER PARK FL 32792 | $375,000 | $247 | $375,000 | 1,516 | Single Family Residence | 3/2 | 151 |
| 11-06-2023 | 2940 ROUEN AVENUE, WINTER PARK FL 32789 | $450,000 | $254 | $450,000 | 1,769 | Single Family Residence | 4/2 | 1 |
| 11-03-2023 | 7401 WYNNEWOOD SQUARE # 170, WINTER PARK FL 32792 | $235,000 | $204 | $260,000 | 1,151 | Condominium | 3/3 | 30 |
| 11-03-2023 | 7114 TIMBER DRIVE, WINTER PARK FL 32792 | $336,000 | $304 | $325,000 | 1,104 | Single Family Residence | 2/2 | 17 |
| 11-03-2023 | 1995 CANNY COVE, WINTER PARK FL 32792 | $404,990 | $212 | $404,990 | 1,907 | Townhouse | 3/3 | 5 |
| 11-03-2023 | 1405 MILLER AVENUE, WINTER PARK FL 32789 | $779,900 | $421 | $779,900 | 1,851 | Townhouse | 3/3 | 200 |
| 11-02-2023 | 130 ARLA COURT, WINTER PARK FL 32792 | $439,000 | $252 | $429,999 | 1,740 | Single Family Residence | 4/2 | 111 |
| 11-01-2023 | 106 S INTERLACHEN AVENUE UNIT 518B | $1,162,500 | $633 | $1,225,000 | 1,834 | Condominium | 3/2 | 97 |
| 11-01-2023 | 3651 N GOLDENROD ROAD # E101, WINTER PARK FL 32792 | $200,000 | $238 | $204,999 | 840 | Condominium | 2/2 | 79 |
| 11-01-2023 | 2519 LEEWARD WAY, WINTER PARK FL 32792 | $230,000 | $269 | $230,000 | 854 | Condominium | 2/1 | 62 |
| 11-01-2023 | 251 E CANTON AVENUE # 251, WINTER PARK FL 32789 | $360,000 | $491 | $335,000 | 733 | Condominium | 1/1 | 27 |
| 11-01-2023 | 1999 CANNY COVE, WINTER PARK FL 32792 | $435,990 | $228 | $403,990 | 1,907 | Townhouse | 3/3 | 233 |
| 11-01-2023 | 1640 MEADOWGOLD COURT, WINTER PARK FL 32792 | $430,000 | $314 | $408,700 | 1,368 | Single Family Residence | 3/2 | 79 |
| 11-01-2023 | 626 S RANGER BOULEVARD, WINTER PARK FL 32792 | $563,000 | $306 | $549,000 | 1,834 | Single Family Residence | 4/3 | 29 |
| 10-31-2023 | 7288 DANIEL WEBSTER DRIVE # 5, WINTER PARK FL 3279 | $152,000 | $123 | $159,900 | 1,230 | Condominium | 2/3 | 99 |
| 10-31-2023 | 4770 TANGERINE AVENUE # 4770, WINTER PARK FL 32792 | $182,500 | $242 | $190,000 | 753 | Condominium | 1/1 | 47 |
| 10-30-2023 | 673 GRENADINE COURT S # 673, WINTER PARK FL 32792 | $259,900 | $250 | $259,900 | 1,037 | Condominium | 2/2 | 34 |
| 10-30-2023 | 7128 KNOTTYPINE AVENUE, WINTER PARK FL 32792 | $412,500 | $256 | $409,900 | 1,609 | Single Family Residence | 3/2 | 26 |
| 10-30-2023 | 2448 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $445,000 | $214 | $454,500 | 2,076 | Townhouse | 3/3 | 109 |
| 10-30-2023 | 1425 CHESTNUT AVE., WINTER PARK FL 32789 | $560,000 | $513 | $599,000 | 1,090 | Single Family Residence | 2/1 | 74 |
| 10-30-2023 | 2732 LION HEART ROAD, WINTER PARK FL 32792 | $624,000 | $315 | $632,000 | 1,975 | Single Family Residence | 3/2 | 47 |
| 10-27-2023 | 2323 ANTILLES DRIVE, WINTER PARK FL 32792 | $260,000 | $202 | $260,000 | 1,284 | Villa | 3/2 | 5 |
| 10-27-2023 | 1476 GROVE TERRACE, WINTER PARK FL 32789 | $2,995,000 | $517 | $3,250,000 | 5,792 | Single Family Residence | 5/7 | 143 |
| 10-27-2023 | 102 S INTERLACHEN AVENUE UNIT 510 | $550,000 | $610 | $575,000 | 901 | Condominium | 2/1 | 39 |
| 10-26-2023 | 614 GRENADINE COURT # 614, WINTER PARK FL 32792 | $155,500 | $204 | $159,900 | 759 | Condominium | 1/1 | 30 |
| 10-26-2023 | 2156 TALMAN COURT, WINTER PARK FL 32792 | $2,050,000 | $264 | $2,100,000 | 7,762 | Single Family Residence | 5/8 | 67 |
| 10-26-2023 | 7320 FOREST HILL COURT # 236, WINTER PARK FL 32792 | $218,000 | $220 | $229,000 | 990 | Condominium | 2/2 | 155 |
| 10-26-2023 | 5110 LAZY OAKS DRIVE, WINTER PARK FL 32792 | $245,000 | $243 | $240,000 | 1,008 | Condominium | 2/2 | 46 |
| 10-26-2023 | 2033 CANNY COVE, WINTER PARK FL 32792 | $413,790 | $216 | $411,790 | 1,907 | Townhouse | 3/3 | 297 |
| 10-25-2023 | 1531 SUNSET DRIVE, WINTER PARK FL 32789 | $1,200,000 | $458 | $1,195,000 | 2,619 | Single Family Residence | 4/3 | 36 |
| 10-25-2023 | 1523 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $525,000 | $431 | $495,000 | 1,218 | Single Family Residence | 3/2 | 37 |
| 10-25-2023 | $600,000 | $254 | $620,000 | 2,361 | Single Family Residence | 4/2 | 63 | |
| 10-24-2023 | 3075 AARON BURR AVENUE # 8, WINTER PARK FL 32792 | $113,000 | $210 | $120,000 | 537 | Condominium | 1/1 | 63 |
| 10-24-2023 | 350 BELOIT AVENUE, WINTER PARK FL 32789 | $2,750,000 | $858 | $2,750,000 | 3,205 | Single Family Residence | 3/4 | 15 |
| 10-24-2023 | 3230 ATHENA DRIVE, WINTER PARK FL 32792 | $453,000 | $273 | $449,900 | 1,654 | Single Family Residence | 3/2 | 36 |
| 10-24-2023 | 2680 FITZHUGH ROAD, WINTER PARK FL 32792 | $630,000 | $305 | $630,000 | 2,064 | Single Family Residence | 4/3 | 37 |
| 10-24-2023 | 1825 LOCH BERRY ROAD, WINTER PARK FL 32789 | $800,000 | $346 | $820,000 | 2,308 | Single Family Residence | 3/2 | 138 |
| 10-23-2023 | 1740 SUMMERLAND AVENUE, WINTER PARK FL 32789 | $2,125,000 | $505 | $2,250,000 | 4,201 | Single Family Residence | 5/6 | 101 |
| 10-23-2023 | 2861 CLEVER LANE, WINTER PARK FL 32792 | $421,990 | $221 | $421,990 | 1,907 | Townhouse | 3/3 | 36 |
| 10-23-2023 | 2037 CANNY COVE, WINTER PARK FL 32792 | $436,590 | $245 | $436,590 | 1,782 | Townhouse | 3/3 | 294 |
| 10-20-2023 | 7340 DANIEL WEBSTER DRIVE # 7, WINTER PARK FL 3279 | $169,900 | $125 | $179,900 | 1,356 | Condominium | 3/2 | 72 |
| 10-20-2023 | 3197 CROWN JEWEL COURT, WINTER PARK FL 32792 | $340,000 | $241 | $360,000 | 1,408 | Townhouse | 3/3 | 36 |
| 10-20-2023 | 7109 NATHAN COURT, WINTER PARK FL 32792 | $320,000 | $140 | $415,000 | 2,282 | Single Family Residence | 4/3 | 53 |
| 10-20-2023 | 5520 ALBERT DRIVE, WINTER PARK FL 32792 | $418,000 | $248 | $435,000 | 1,680 | Single Family Residence | 3/2 | 79 |
| 10-20-2023 | 2464 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $479,500 | $207 | $479,500 | 2,308 | Townhouse | 3/3 | 29 |
| 10-20-2023 | 5112 TANGERINE AVENUE, WINTER PARK FL 32792 | $487,500 | $279 | $515,000 | 1,745 | Single Family Residence | 4/2 | 80 |
| 10-20-2023 | 3301 OLDE WHARF RUN | $510,000 | $199 | $554,900 | 2,562 | Single Family Residence | 4/4 | 67 |
| 10-20-2023 | 1725 CAROLLEE LANE, WINTER PARK FL 32789 | $885,000 | $379 | $885,000 | 2,335 | Single Family Residence | 3/2 | 65 |
| 10-19-2023 | 1461 PALM AVENUE, WINTER PARK FL 32789 | $2,000,000 | $582 | $2,100,000 | 3,436 | Single Family Residence | 4/5 | 160 |
| 10-19-2023 | 527 CORNWALL ROAD, WINTER PARK FL 32792 | $515,000 | $317 | $569,900 | 1,620 | Single Family Residence | 4/2 | 67 |
| 10-18-2023 | 151 SCOTTSDALE SQUARE # 151, WINTER PARK FL 32792 | $675,000 | $859 | $115,000 | 785 | Condominium | 1/1 | 40 |
| 10-18-2023 | 1608 MEADOWGOLD COURT, WINTER PARK FL 32792 | $465,000 | $267 | $450,000 | 1,740 | Single Family Residence | 3/3 | 34 |
| 10-17-2023 | 224 SCOTTSDALE SQUARE # 224, WINTER PARK FL 32792 | $130,000 | $127 | $139,900 | 1,020 | Condominium | 2/2 | 34 |
| 10-17-2023 | 110 SCOTTSDALE SQUARE # 110, WINTER PARK FL 32792 | $150,000 | $138 | $149,999 | 1,085 | Condominium | 2/2 | 40 |
| 10-17-2023 | 730 CALLAHAN STREET, WINTER PARK FL 32789 | $330,000 | $201 | $323,000 | 1,634 | Single Family Residence | 2/2 | 97 |
| 10-17-2023 | 2445 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $460,000 | $228 | $475,000 | 2,010 | Townhouse | 3/3 | 78 |
| 10-17-2023 | 2779 WILL O TH GREEN, WINTER PARK FL 32792 | $510,000 | $314 | $490,000 | 1,620 | Single Family Residence | 3/2 | 35 |
| 10-17-2023 | 1274 RICHMOND ROAD, WINTER PARK FL 32789 | $750,000 | $258 | $750,000 | 2,906 | Single Family Residence | 5/3 | 2 |
| 10-16-2023 | 2025 CANNY COVE, WINTER PARK FL 32792 | $409,060 | $214 | $406,590 | 1,907 | Townhouse | 3/3 | 270 |
| 10-16-2023 | $550,000 | $550,000 | / | 5 | ||||
| 10-13-2023 | 292 SCOTTSDALE SQUARE # 292, WINTER PARK FL 32792 | $135,000 | $124 | $150,000 | 1,085 | Condominium | 2/2 | 95 |
| 10-13-2023 | 663 CALLAHAN STREET, WINTER PARK FL 32789 | $430,000 | $347 | $465,000 | 1,238 | Single Family Residence | 2/1 | 54 |
| 10-13-2023 | 3035 GEORGE MASON AVENUE # B, WINTER PARK FL 32792 | $75,000 | $136 | $85,000 | 549 | Townhouse | 1/1 | 30 |
| 10-12-2023 | 1842 PURITAN AVENUE, WINTER PARK FL 32792 | $281,000 | $153 | $299,900 | 1,836 | Single Family Residence | 4/2 | 42 |
| 10-12-2023 | 2021 CANNY COVE, WINTER PARK FL 32792 | $429,790 | $225 | $429,790 | 1,907 | Townhouse | 3/3 | 266 |
| 10-12-2023 | 2009 CANNY COVE, WINTER PARK FL 32792 | $443,390 | $248 | $443,390 | 1,782 | Townhouse | 3/3 | 266 |
| 10-12-2023 | 1547 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $595,000 | $331 | $595,000 | 1,796 | Single Family Residence | 3/2 | 29 |
| 10-11-2023 | 559 GENIUS DRIVE | $2,000,000 | $515 | $1,900,000 | 3,879 | Single Family Residence | 3/4 | 45 |
| 10-10-2023 | 1879 LAKE SPIER DRIVE, WINTER PARK FL 32789 | $1,164,000 | $495 | $1,195,000 | 2,350 | Single Family Residence | 3/2 | 42 |
| 10-10-2023 | 1455 W FAIRBANKS AVENUE, WINTER PARK FL 32789 | $950,000 | $568 | $1,250,000 | 1,672 | Business | / | 188 |
| 10-10-2023 | 511 FAIRFAX AVENUE, WINTER PARK FL 32789 | $1,400,000 | $404 | $1,485,000 | 3,463 | Single Family Residence | 4/3 | 110 |
| 10-10-2023 | 870 GEORGIA AVENUE, WINTER PARK FL 32789 | $1,950,000 | $719 | $2,094,000 | 2,709 | Single Family Residence | 3/3 | 478 |
| 10-10-2023 | 2029 CANNY COVE, WINTER PARK FL 32792 | $409,590 | $214 | $406,590 | 1,907 | Townhouse | 3/3 | 260 |
| 10-10-2023 | $409,590 | $214 | $409,590 | 1,907 | Townhouse | 3/3 | 11 | |
| 10-10-2023 | 633 BRECHIN DRIVE, WINTER PARK FL 32792 | $456,000 | $237 | $456,000 | 1,916 | Single Family Residence | 4/2 | 8 |
| 10-10-2023 | 104 RANCH ROAD, WINTER PARK FL 32792 | $709,000 | $245 | $750,000 | 2,885 | Single Family Residence | 4/4 | 41 |
| 10-09-2023 | 7612 WAUNATTA COURT, WINTER PARK FL 32792 | $400,000 | $213 | $445,000 | 1,871 | Single Family Residence | 4/2 | 89 |
| 10-06-2023 | 2435 CHANTILLY AVENUE, WINTER PARK FL 32789 | $1,600,000 | $523 | $1,649,000 | 3,055 | Single Family Residence | 4/5 | 78 |
| 10-06-2023 | 186 LEWFIELD CIRCLE UNIT 186 | $177,000 | $261 | $180,000 | 678 | Condominium | 1/1 | 40 |
| 10-05-2023 | 973 WILMA AVENUE, WINTER PARK FL 32789 | $435,000 | $371 | $449,000 | 1,171 | Single Family Residence | 3/2 | 86 |
| 10-04-2023 | 1290 N PARK AVE | $3,001,950 | $1,144 | $3,295,000 | 2,623 | Single Family Residence | 3/4 | 266 |
| 10-04-2023 | 3409 FERNDELL DRIVE, WINTER PARK FL 32792 | $392,000 | $277 | $391,700 | 1,412 | Single Family Residence | 3/2 | 147 |
| 10-04-2023 | 7104 WRENWOOD WAY, WINTER PARK FL 32792 | $447,000 | $251 | $445,000 | 1,778 | Single Family Residence | 4/2 | 24 |
| 10-04-2023 | 173 SCOTTSDALE SQUARE # 173, WINTER PARK FL 32792 | $95,333 | $121 | $89,900 | 785 | Condominium | 1/1 | 21 |
| 10-04-2023 | 648 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $965,000 | $454 | $995,000 | 2,125 | Single Family Residence | 4/3 | 66 |
| 10-01-2023 | 2189 SUSSEX ROAD, WINTER PARK FL 32792 | $355,000 | $199 | $365,000 | 1,776 | Single Family Residence | 3/3 | 60 |
| 09-30-2023 | 1500 HARRIS CIRCLE, WINTER PARK FL 32789 | $905,000 | $464 | $899,000 | 1,950 | Single Family Residence | 2/3 | 230 |
| 09-29-2023 | 7472 WOODBURN COURT # 37, WINTER PARK FL 32792 | $210,000 | $212 | $215,000 | 990 | Condominium | 2/2 | 40 |
| 09-29-2023 | 712 BONGART ROAD, WINTER PARK FL 32792 | $380,500 | $195 | $399,900 | 1,950 | Single Family Residence | 5/2 | 37 |
| 09-29-2023 | 1941 NATALEN ROAD, WINTER PARK FL 32792 | $595,000 | $384 | $624,900 | 1,547 | Single Family Residence | 3/2 | 31 |
| 09-28-2023 | 200 E ROCKWOOD WAY, WINTER PARK FL 32789 | $3,400,000 | $813 | $3,499,900 | 4,178 | Single Family Residence | 5/5 | 43 |
| 09-28-2023 | 460 VIRGINIA DRIVE, WINTER PARK FL 32789 | $4,500,000 | $935 | $4,500,000 | 4,809 | Single Family Residence | 5/7 | 8 |
| 09-28-2023 | 7103 TIMBER DRIVE, WINTER PARK FL 32792 | $438,500 | $245 | $455,000 | 1,784 | Single Family Residence | 4/2 | 56 |
| 09-28-2023 | 555 S RANGER BOULEVARD, WINTER PARK FL 32792 | $650,000 | $269 | $669,900 | 2,414 | Single Family Residence | 4/2 | 109 |
| 09-27-2023 | 218 SCOTTSDALE SQUARE # 218, WINTER PARK FL 32792 | $128,000 | $125 | $135,000 | 1,020 | Condominium | 2/2 | 147 |
| 09-27-2023 | 1209 CARVELL DRIVE, WINTER PARK FL 32792 | $384,900 | $168 | $407,000 | 2,279 | Single Family Residence | 4/2 | 65 |
| 09-27-2023 | 5360 LANYARD COURT, WINTER PARK FL 32792 | $400,000 | $261 | $410,000 | 1,527 | Single Family Residence | 3/2 | 42 |
| 09-27-2023 | 1842 SHADYHILL TERRACE, WINTER PARK FL 32792 | $420,000 | $266 | $433,333 | 1,577 | Single Family Residence | 3/3 | 69 |
| 09-27-2023 | 674 OSCEOLA AVENUE UNIT 674 | $679,000 | $522 | $679,000 | 1,300 | Townhouse | 2/3 | 36 |
| 09-27-2023 | 412 FLETCHER PLACE, WINTER PARK FL 32789 | $768,000 | $244 | $899,000 | 3,146 | Single Family Residence | 3/4 | 63 |
| 09-26-2023 | 170 S PHELPS AVENUE, WINTER PARK FL 32789 | $2,350,000 | $548 | $2,699,000 | 4,288 | Single Family Residence | 4/5 | 256 |
| 09-26-2023 | 5201 ORANGE AVENUE, WINTER PARK FL 32792 | $378,000 | $290 | $380,000 | 1,301 | Single Family Residence | 4/2 | 26 |
| 09-25-2023 | 5080 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $385,000 | $269 | $380,000 | 1,430 | Single Family Residence | 3/2 | 245 |
| 09-25-2023 | 7537 VILLAGE GREEN DRIVE, WINTER PARK FL 32792 | $435,000 | $270 | $444,900 | 1,607 | Single Family Residence | 3/2 | 45 |
| 09-25-2023 | 1960 STAUNTON AVENUE, WINTER PARK FL 32789 | $480,000 | $362 | $499,000 | 1,323 | Duplex | / | 32 |
| 09-25-2023 | 423 LONDON ROAD, WINTER PARK FL 32792 | $778,000 | $253 | $799,900 | 3,072 | Single Family Residence | 4/3 | 40 |
| 09-22-2023 | 2012 ARBOR PARK DR, WINTER PARK FL 32789 | $1,995,000 | $545 | $1,995,000 | 3,660 | Single Family Residence | 4/4 | 57 |
| 09-22-2023 | 7494 BETTY STREET, WINTER PARK FL 32792 | $450,000 | $304 | $459,000 | 1,477 | Single Family Residence | 3/2 | 97 |
| 09-22-2023 | 1855 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $465,000 | $168 | $469,900 | 2,760 | Single Family Residence | 5/3 | 65 |
| 09-21-2023 | 2708 BONGART ROAD, WINTER PARK FL 32792 | $425,000 | $286 | $425,000 | 1,486 | Single Family Residence | 4/2 | 72 |
| 09-20-2023 | 5571 S LAKE BURKETT | $424,900 | $291 | $424,900 | 1,460 | Single Family Residence | 3/2 | 56 |
| 09-19-2023 | 7425 DANIEL WEBSTER DRIVE # 12, WINTER PARK FL 327 | $125,000 | $154 | $125,000 | 809 | Condominium | 1/1 | 103 |
| 09-19-2023 | 1340 CHESTNUT AVENUE, WINTER PARK FL 32789 | $2,200,000 | $526 | $2,352,000 | 4,182 | Single Family Residence | 6/6 | 104 |
| 09-19-2023 | 519 BRECHIN DRIVE, WINTER PARK FL 32792 | $773,000 | $350 | $800,000 | 2,208 | Single Family Residence | 4/4 | 104 |
| 09-18-2023 | 4309 STEED TERRACE, WINTER PARK FL 32792 | $600,000 | $261 | $574,900 | 2,295 | Single Family Residence | 4/4 | 37 |
| 09-15-2023 | 2894 WILD GINGER COURT, WINTER PARK FL 32792 | $1,200,000 | $296 | $1,195,000 | 4,042 | Single Family Residence | 4/4 | 44 |
| 09-15-2023 | 1771 WINCHESTER DRIVE, WINTER PARK FL 32789 | $1,250,000 | $496 | $1,390,000 | 2,516 | Single Family Residence | 4/4 | 23 |
| 09-15-2023 | 1730 GREENWICH AVENUE, WINTER PARK FL 32789 | $2,300,000 | $498 | $2,325,000 | 4,611 | Single Family Residence | 4/5 | 79 |
| 09-15-2023 | 851 MILES AVENUE # 28, WINTER PARK FL 32789 | $239,000 | $295 | $247,000 | 808 | Condominium | 2/1 | 78 |
| 09-15-2023 | 7463 CANFORD COURT # 15, WINTER PARK FL 32792 | $275,000 | $174 | $275,000 | 1,580 | Condominium | 3/3 | 31 |
| 09-15-2023 | 500 N PENNSYLVANIA AVENUE # F, WINTER PARK FL 3278 | $300,000 | $423 | $310,000 | 709 | Condominium | 2/1 | 32 |
| 09-15-2023 | 7419 FIELDCREST AVENUE, WINTER PARK FL 32792 | $345,000 | $282 | $345,000 | 1,221 | Single Family Residence | 3/2 | 30 |
| 09-15-2023 | 3039 TEMPLE TRAIL, WINTER PARK FL 32789 | $780,000 | $376 | $759,900 | 2,070 | Single Family Residence | 4/2 | 63 |
| 09-14-2023 | 1735 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $550,000 | $295 | $579,000 | 1,860 | Single Family Residence | 4/3 | 98 |
| 09-12-2023 | 1725 WALNUT AVENUE, WINTER PARK FL 32789 | $700,000 | $355 | $655,000 | 1,968 | Single Family Residence | 3/3 | 41 |
| 09-11-2023 | 1741 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $575,000 | $400 | $575,000 | 1,434 | Single Family Residence | 3/2 | 13 |
| 09-11-2023 | 3035 GEORGE MASON AVE UNIT C | $99,000 | $180 | $99,000 | 549 | Condominium | 1/1 | 22 |
| 09-08-2023 | 2865 CLEVER LANE, WINTER PARK FL 32792 | $389,990 | $204 | $389,990 | 1,907 | Townhouse | 3/3 | 5 |
| 09-08-2023 | 2869 CLEVER LANE, WINTER PARK FL 32792 | $413,990 | $217 | $418,990 | 1,907 | Townhouse | 3/3 | 151 |
| 09-08-2023 | 536 CORNWALL ROAD, WINTER PARK FL 32792 | $510,000 | $362 | $480,000 | 1,405 | Single Family Residence | 4/2 | 29 |
| 09-08-2023 | 100 S INTERLACHEN AVENUE UNIT 506E | $670,000 | $604 | $699,000 | 1,109 | Condominium | 2/2 | 141 |
| 09-07-2023 | 315 E NEW ENGLAND AVENUE # 23, WINTER PARK FL 3278 | $1,250,000 | $781 | $1,250,000 | 1,599 | Condominium | 2/2 | 30 |
| 09-07-2023 | $1,250,000 | $781 | $1,250,000 | 1,599 | Condominium | 2/2 | 2 | |
| 09-07-2023 | 466 HENKEL CIRCLE, WINTER PARK FL 32789 | $3,500,000 | $792 | $3,750,000 | 4,416 | Single Family Residence | 5/5 | 190 |
| 09-07-2023 | 2224 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $432,000 | $313 | $429,990 | 1,378 | Single Family Residence | 3/2 | 49 |
| 09-06-2023 | 410 GENIUS DRIVE | $2,695,000 | $630 | $2,695,000 | 4,277 | Single Family Residence | 4/5 | 37 |
| 09-06-2023 | 1938 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $300,000 | $239 | $315,000 | 1,253 | Single Family Residence | 3/2 | 62 |
| 09-06-2023 | 7413 BARNACLE COURT, WINTER PARK FL 32792 | $350,000 | $304 | $350,000 | 1,151 | Single Family Residence | 3/2 | 76 |
| 09-01-2023 | 765 VIA LOMBARDY, WINTER PARK FL 32789 | $1,850,000 | $538 | $1,990,000 | 3,437 | Single Family Residence | 5/5 | 49 |
| 09-01-2023 | 1578 LAWNDALE CIRCLE | $340,000 | $264 | $335,000 | 1,286 | Single Family Residence | 2/2 | 38 |
| 09-01-2023 | 1373 PERUVIAN LANE, WINTER PARK FL 32792 | $380,000 | $303 | $380,000 | 1,252 | Single Family Residence | 3/2 | 77 |
| 09-01-2023 | 671 VIA LUGANO, WINTER PARK FL 32789 | $3,800,000 | $539 | $4,500,000 | 7,048 | Single Family Residence | 6/9 | 131 |
| 09-01-2023 | 5609 WINTERBROOK WAY, WINTER PARK FL 32792 | $596,000 | $275 | $623,000 | 2,164 | Single Family Residence | 4/3 | 70 |
| 09-01-2023 | 2216 WOODCREST DRIVE, WINTER PARK FL 32792 | $625,000 | $388 | $625,000 | 1,608 | Single Family Residence | 3/2 | 36 |
| 08-31-2023 | 870 CARVER STREET, WINTER PARK FL 32789 | $290,000 | $272 | $300,000 | 1,064 | Single Family Residence | 3/1 | 95 |
| 08-31-2023 | 1589 SPRINGTIME LOOP, WINTER PARK FL 32792 | $410,000 | $232 | $419,000 | 1,764 | Single Family Residence | 4/2 | 28 |
| 08-31-2023 | 250 CAROLINA AVENUE # 407, WINTER PARK FL 32789 | $530,000 | $459 | $549,000 | 1,153 | Condominium | 2/2 | 149 |
| 08-30-2023 | 2500 LEE ROAD UNIT 233 | $212,000 | $328 | $214,900 | 645 | Condominium | 1/1 | 32 |
| 08-30-2023 | 902 ELLENDALE DRIVE, WINTER PARK FL 32792 | $515,000 | $266 | $515,000 | 1,936 | Single Family Residence | 4/2 | 34 |
| 08-30-2023 | 1936 WHITEHALL DRIVE, WINTER PARK FL 32792 | $679,900 | $384 | $679,900 | 1,769 | Single Family Residence | 3/2 | 26 |
| 08-29-2023 | 2112 SYCAMORE DRIVE, WINTER PARK FL 32789 | $582,000 | $298 | $599,999 | 1,950 | Single Family Residence | 4/3 | 99 |
| 08-28-2023 | 700 MELROSE AVENUE # 33, WINTER PARK FL 32789 | $220,000 | $239 | $229,000 | 917 | Condominium | 1/1 | 116 |
| 08-28-2023 | 2369 FLAMINGO WAY, WINTER PARK FL 32792 | $230,000 | $269 | $230,000 | 854 | Townhouse | 2/1 | 34 |
| 08-28-2023 | 520 KILLARNEY BAY COURT UNIT 2 | $300,000 | $258 | $299,900 | 1,160 | Condominium | 2/2 | 48 |
| 08-28-2023 | 7218 KNOTTYPINE AVENUE, WINTER PARK FL 32792 | $325,000 | $201 | $345,900 | 1,609 | Single Family Residence | 3/2 | 21 |
| 08-28-2023 | 424 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $475,000 | $343 | $500,000 | 1,383 | Single Family Residence | 3/2 | 34 |
| 08-28-2023 | 1690 CYPRESS POINT LANE, WINTER PARK FL 32792 | $770,000 | $300 | $785,000 | 2,560 | Single Family Residence | 4/2 | 39 |
| 08-25-2023 | 1318 MORTON ROAD, WINTER PARK FL 32789 | $1,500,000 | $581 | $1,599,000 | 2,579 | Single Family Residence | 4/4 | 58 |
| 08-25-2023 | 1250 S DENNING DRIVE # 107, WINTER PARK FL 32789 | $190,000 | $288 | $199,000 | 658 | Condominium | 1/1 | 36 |
| 08-25-2023 | 1561 CHESTNUT AVENUE, WINTER PARK FL 32789 | $805,000 | $749,900 | / | 26 | |||
| 08-24-2023 | 3469 ARNEL DRIVE, WINTER PARK FL 32792 | $210,000 | $130 | $210,000 | 1,613 | Single Family Residence | 3/2 | 1 |
| 08-24-2023 | 287 SANDLEWOOD TRAIL # 4, WINTER PARK FL 32789 | $285,000 | $296 | $299,000 | 960 | Condominium | 2/3 | 198 |
| 08-23-2023 | 241 SCOTTSDALE SQUARE # 241, WINTER PARK FL 32792 | $120,000 | $158 | $125,000 | 756 | Condominium | 1/1 | 60 |
| 08-23-2023 | 7904 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $690,000 | $197 | $709,000 | 3,496 | Single Family Residence | 5/4 | 43 |
| 08-21-2023 | 2500 LEE ROAD UNIT 111 | $199,000 | $308 | $199,000 | 645 | Condominium | 1/1 | 99 |
| 08-21-2023 | 846 CABOT COURT, WINTER PARK FL 32792 | $446,000 | $203 | $445,500 | 2,187 | Single Family Residence | 4/2 | 30 |
| 08-18-2023 | 7448 ALOMA AVENUE, WINTER PARK FL 32792 | $975,000 | $272 | $1,100,000 | 3,578 | Retail | / | 87 |
| 08-18-2023 | 161 SCOTTSDALE SQUARE # 161, WINTER PARK FL 32792 | $125,000 | $165 | $135,000 | 756 | Condominium | 1/1 | 84 |
| 08-18-2023 | 1772 CHESTNUT AVENUE, WINTER PARK FL 32789 | $2,150,000 | $558 | $2,195,000 | 3,850 | Single Family Residence | 5/5 | 48 |
| 08-18-2023 | 3004 PATEL DRIVE, WINTER PARK FL 32792 | $205,000 | $175 | $225,000 | 1,166 | 1/2 Duplex | 2/2 | 31 |
| 08-18-2023 | 1428 HOLTS GROVE CIRCLE | $2,050,000 | $489 | $2,300,000 | 4,191 | Single Family Residence | 5/5 | 185 |
| 08-18-2023 | 2526 ROXBURY ROAD, WINTER PARK FL 32789 | $300,000 | $235 | $300,000 | 1,276 | Single Family Residence | 2/1 | 92 |
| 08-18-2023 | 1490 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $450,000 | $239 | $474,900 | 1,878 | Single Family Residence | 3/2 | 54 |
| 08-17-2023 | 1271 PALMER AVENUE, WINTER PARK FL 32789 | $1,875,000 | $623 | $1,875,000 | 3,008 | Single Family Residence | 4/5 | 62 |
| 08-17-2023 | 200 SAINT ANDREWS BOULEVARD # 1902, WINTER PARK FL | $240,000 | $243 | $235,000 | 987 | Condominium | 2/2 | 36 |
| 08-17-2023 | 900 N DENNING DRIVE, WINTER PARK FL 32789 | $350,000 | $207 | $360,000 | 1,690 | Single Family Residence | 4/3 | 186 |
| 08-17-2023 | 1710 PALMER AVENUE, WINTER PARK FL 32789 | $815,000 | $341 | $850,000 | 2,386 | Single Family Residence | 3/3 | 57 |
| 08-16-2023 | 1321 HARMON AVENUE, WINTER PARK FL 32789 | $520,000 | $335 | $520,000 | 1,548 | Duplex | / | 42 |
| 08-15-2023 | 2137 TALMAN COURT, WINTER PARK FL 32792 | $1,637,000 | $298 | $1,637,000 | 5,475 | Single Family Residence | 4/7 | 26 |
| 08-15-2023 | 5460 BRACKEN COURT, WINTER PARK FL 32792 | $317,500 | $264 | $325,000 | 1,200 | Townhouse | 2/3 | 34 |
| 08-15-2023 | 7033 BETTY STREET, WINTER PARK FL 32792 | $480,000 | $266 | $465,000 | 1,804 | Single Family Residence | 4/2 | 40 |
| 08-14-2023 | 7417 DANIEL WEBSTER DRIVE # 2, WINTER PARK FL 3279 | $106,000 | $194 | $114,000 | 546 | Condominium | 1/1 | 45 |
| 08-14-2023 | 102 S VIRGINIA AVENUE # 110, WINTER PARK FL 32789 | $1,590,000 | $420 | $1,795,000 | 3,778 | Condominium | 3/4 | 90 |
| 08-14-2023 | 514 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $460,000 | $300 | $462,000 | 1,529 | Single Family Residence | 3/2 | 57 |
| 08-14-2023 | 2174 SHADYHILL TERRACE, WINTER PARK FL 32792 | $500,000 | $252 | $525,000 | 1,983 | Single Family Residence | 4/2 | 60 |
| 08-14-2023 | 657 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $769,000 | $428 | $769,000 | 1,796 | Single Family Residence | 4/2 | 71 |
| 08-11-2023 | 842 ENGLISH COURT, WINTER PARK FL 32789 | $1,030,000 | $541 | $1,000,000 | 1,903 | Single Family Residence | 3/3 | 26 |
| 08-11-2023 | 422 CAROLINA AVENUE, WINTER PARK FL 32789 | $1,255,000 | $533 | $1,300,000 | 2,351 | Single Family Residence | 4/4 | 36 |
| 08-11-2023 | 3651 N GOLDENROD ROAD # 205, WINTER PARK FL 32792 | $190,000 | $226 | $184,900 | 840 | Condominium | 2/2 | 31 |
| 08-11-2023 | 630 NORTHWOOD CIRCLE, WINTER PARK FL 32789 | $686,000 | $473 | $685,000 | 1,448 | Single Family Residence | 3/2 | 37 |
| 08-10-2023 | $243,000 | $151 | $250,000 | 1,609 | Single Family Residence | 3/2 | 29 | |
| 08-10-2023 | 5528 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $380,000 | $241 | $380,000 | 1,573 | Single Family Residence | 3/2 | 35 |
| 08-10-2023 | 1852 E CHERYL DRIVE, WINTER PARK FL 32792 | $440,000 | $218 | $450,000 | 2,014 | Single Family Residence | 4/2 | 29 |
| 08-09-2023 | 1541 HIGHLAND ROAD, WINTER PARK FL 32789 | $1,156,000 | $496 | $1,150,000 | 2,330 | Single Family Residence | 3/2 | 33 |
| 08-09-2023 | 2500 LEE ROAD UNIT 237 | $169,000 | $262 | $169,000 | 645 | Condominium | 1/1 | 105 |
| 08-08-2023 | 1448 CHAPMAN CIRCLE | $1,295,000 | $470 | $1,295,000 | 2,755 | Single Family Residence | 4/4 | 26 |
| 08-08-2023 | 1750 WINCHESTER DRIVE, WINTER PARK FL 32789 | $1,368,000 | $499 | $1,500,000 | 2,740 | Single Family Residence | 4/4 | 53 |
| 08-07-2023 | 532 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $2,400,000 | $569 | $2,200,000 | 4,214 | Single Family Residence | 5/6 | 622 |
| 08-07-2023 | 1619 ELIZABETHS WALK, WINTER PARK FL 32789 | $1,735,000 | $401 | $2,250,000 | 4,318 | Single Family Residence | 4/4 | 113 |
| 08-07-2023 | 660 W MORSE BOULEVARD, WINTER PARK FL 32789 | $2,240,000 | $681 | $2,345,000 | 3,286 | Townhouse | 3/4 | 158 |
| 08-07-2023 | 1704 W CHERYL DRIVE, WINTER PARK FL 32792 | $430,000 | $213 | $447,999 | 2,017 | Single Family Residence | 4/2 | 35 |
| 08-07-2023 | 1823 DOVER ROAD, WINTER PARK FL 32792 | $490,000 | $271 | $500,000 | 1,808 | Single Family Residence | 4/2 | 58 |
| 08-07-2023 | 627 GILBERT ROAD, WINTER PARK FL 32792 | $584,999 | $272 | $589,999 | 2,148 | Single Family Residence | 4/2 | 77 |
| 08-05-2023 | 1863 LAKE SPIER DR | $1,100,000 | $457 | $1,175,000 | 2,402 | Single Family Residence | 4/3 | 94 |
| 08-04-2023 | 1306 RICHMOND ROAD, WINTER PARK FL 32789 | $1,675,000 | $531 | $1,699,000 | 3,149 | Single Family Residence | 3/3 | 50 |
| 08-04-2023 | 1000 S SEMORAN BOULEVARD # 113, WINTER PARK FL 327 | $220,000 | $219 | $224,000 | 1,003 | Condominium | 2/2 | 73 |
| 08-04-2023 | 200 SAINT ANDREWS BOULEVARD # 712, WINTER PARK FL | $225,000 | $269 | $229,900 | 835 | Condominium | 1/1 | 52 |
| 08-04-2023 | 125 S INTERLACHEN AVENUE # 2, WINTER PARK FL 32789 | $2,325,000 | $716 | $2,450,000 | 3,244 | Townhouse | 3/5 | 164 |
| 08-04-2023 | 1311 VIA TUSCANY, WINTER PARK FL 32789 | $6,000,000 | $545 | $6,900,000 | 10,997 | Single Family Residence | 7/8 | 8 |
| 08-03-2023 | 3901 WOODGLADE COVE, WINTER PARK FL 32792 | $490,000 | $221 | $499,900 | 2,213 | Single Family Residence | 4/3 | 49 |
| 08-02-2023 | 3021 NICHOLSON DRIVE, WINTER PARK FL 32792 | $400,000 | $227 | $410,000 | 1,755 | Single Family Residence | 4/2 | 29 |
| 08-02-2023 | 1431 LAKE FLORENCE WAY, WINTER PARK FL 32792 | $670,000 | $258 | $670,000 | 2,592 | Single Family Residence | 4/3 | 71 |
| 08-01-2023 | 2500 LEE ROAD UNIT 202 | $221,000 | $231 | $229,900 | 956 | Condominium | 2/2 | 48 |
| 08-01-2023 | 200 SAINT ANDREWS BOULEVARD # 1703, WINTER PARK FL | $270,000 | $221 | $275,000 | 1,219 | Condominium | 2/2 | 34 |
| 08-01-2023 | 754 GILBERT ROAD, WINTER PARK FL 32792 | $515,000 | $224 | $524,900 | 2,289 | Single Family Residence | 4/3 | 49 |
| 07-31-2023 | 790 E LAKE SUE AVENUE, WINTER PARK FL 32789 | $1,160,000 | $460 | $1,150,000 | 2,519 | Single Family Residence | 3/2 | 33 |
| 07-31-2023 | 1000 S SEMORAN BOULEVARD # 508, WINTER PARK FL 327 | $187,000 | $178 | $190,000 | 1,049 | Condominium | 2/2 | 46 |
| 07-31-2023 | 2641 CAYMAN WAY, WINTER PARK FL 32792 | $212,500 | $165 | $239,900 | 1,284 | Townhouse | 3/2 | 35 |
| 07-31-2023 | 140 E MORSE BOULEVARD # G, WINTER PARK FL 32789 | $3,200,000 | $950 | $3,400,000 | 3,367 | Condominium | 3/4 | 29 |
| 07-31-2023 | 100 S INTERLACHEN AVENUE UNIT 201 | $965,000 | $556 | $975,000 | 1,734 | Condominium | 3/2 | 118 |
| 07-31-2023 | 100 S VIRGINIA AVENUE # 401, WINTER PARK FL 32789 | $949,000 | $362 | $975,000 | 2,615 | Condominium | 3/3 | 35 |
| 07-28-2023 | 116 SCOTTSDALE SQUARE # 116, WINTER PARK FL 32792 | $140,000 | $137 | $145,000 | 1,020 | Condominium | 2/2 | 95 |
| 07-28-2023 | 7577 DOCKSIDE STREET, WINTER PARK FL 32792 | $362,000 | $290 | $368,500 | 1,245 | Single Family Residence | 3/2 | 127 |
| 07-28-2023 | 1805 MAYWOOD RD, WINTER PARK FL 32792 | $390,000 | $172 | $388,000 | 2,255 | Single Family Residence | 4/2 | 32 |
| 07-28-2023 | 626 CARVELL DRIVE, WINTER PARK FL 32792 | $389,000 | $272 | $389,000 | 1,428 | Single Family Residence | 4/2 | 24 |
| 07-28-2023 | 2068 LEANNE COURT, WINTER PARK FL 32792 | $449,900 | $256 | $449,900 | 1,753 | Single Family Residence | 4/2 | 72 |
| 07-27-2023 | 338 SCOTTSDALE SQUARE # 338, WINTER PARK FL 32792 | $128,000 | $117 | $136,000 | 1,085 | Condominium | 2/2 | 120 |
| 07-27-2023 | 7435 BARNACLE COURT, WINTER PARK FL 32792 | $211,000 | $147 | $175,000 | 1,435 | Single Family Residence | 3/2 | 35 |
| 07-27-2023 | 2502 WINTER PARK ROAD, WINTER PARK FL 32789 | $406,000 | $305 | $375,000 | 1,330 | Single Family Residence | 3/2 | 18 |
| 07-27-2023 | 1868 ERUDITE WAY, WINTER PARK FL 32792 | $431,590 | $226 | $431,590 | 1,907 | Townhouse | 3/3 | 322 |
| 07-27-2023 | 544 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $580,000 | $329 | $610,000 | 1,758 | Single Family Residence | 4/2 | 77 |
| 07-26-2023 | 246 SCOTTSDALE SQUARE # 246, WINTER PARK FL 32792 | $140,000 | $137 | $144,700 | 1,020 | Condominium | 2/2 | 110 |
| 07-26-2023 | 401 N INTERLACHEN AVENUE, WINTER PARK FL 32789 | $1,485,000 | $780 | $1,475,000 | 1,903 | Townhouse | 3/3 | 70 |
| 07-26-2023 | 700 DIXIE PARKWAY, WINTER PARK FL 32789 | $1,540,000 | $703 | $1,495,000 | 2,188 | Single Family Residence | 4/3 | 35 |
| 07-26-2023 | 2356 FLAMINGO WAY, WINTER PARK FL 32792 | $278,000 | $273 | $269,000 | 1,016 | Townhouse | 2/2 | 21 |
| 07-26-2023 | 5210 OHIO STREET, WINTER PARK FL 32792 | $435,000 | $223 | $435,000 | 1,946 | Single Family Residence | 4/3 | 20 |
| 07-25-2023 | 250 W LYMAN AVENUE, WINTER PARK FL 32789 | $1,130,000 | $541 | $1,125,000 | 2,085 | Single Family Residence | 3/3 | 33 |
| 07-25-2023 | 7336 FOREST HILL COURT # 240, WINTER PARK FL 32792 | $214,000 | $216 | $214,000 | 990 | Condominium | 2/2 | 183 |
| 07-24-2023 | 1500 GROVE TERRACE, WINTER PARK FL 32789 | $1,450,000 | $481 | $1,485,000 | 3,010 | Single Family Residence | 3/3 | 49 |
| 07-24-2023 | 290 SCOTTSDALE SQUARE # 290, WINTER PARK FL 32792 | $152,000 | $116 | $169,000 | 1,300 | Condominium | 3/2 | 18 |
| 07-24-2023 | 4944 TANGERINE AVENUE # 4944, WINTER PARK FL 32792 | $215,000 | $203 | $200,000 | 1,059 | Condominium | 2/2 | 104 |
| 07-24-2023 | 2891 CLEVER LANE, WINTER PARK FL 32792 | $394,090 | $206 | $408,590 | 1,907 | Townhouse | 3/3 | 216 |
| 07-24-2023 | 1521 INDIANA AVENUE, WINTER PARK FL 32789 | $440,000 | $387 | $454,500 | 1,136 | Single Family Residence | 2/2 | 34 |
| 07-24-2023 | 2901 CLEVER LANE, WINTER PARK FL 32792 | $460,000 | $258 | $464,790 | 1,782 | Townhouse | 3/3 | 60 |
| 07-24-2023 | 2207 KINDEL AVENUE, WINTER PARK FL 32789 | $650,000 | $454 | $689,000 | 1,431 | Single Family Residence | 3/2 | 160 |
| 07-24-2023 | 1600 ALABAMA DRIVE UNIT 201 | $900,000 | $464 | $975,000 | 1,937 | Condominium | 3/2 | 134 |
| 07-21-2023 | 1572 SUNSET DRIVE, WINTER PARK FL 32789 | $1,080,000 | $411 | $1,150,000 | 2,626 | Single Family Residence | 4/4 | 326 |
| 07-21-2023 | 273 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $180,000 | $265 | $174,900 | 678 | Condominium | 1/1 | 23 |
| 07-21-2023 | 2015 N PARK AVENUE, WINTER PARK FL 32789 | $1,900,000 | $525 | $1,925,000 | 3,617 | Single Family Residence | 4/5 | 80 |
| 07-21-2023 | 7413 BELLE RIVER COURT # 3, WINTER PARK FL 32792 | $240,000 | $208 | $240,000 | 1,151 | Condominium | 3/3 | 33 |
| 07-21-2023 | 1420 HOLTS GROVE CIRCLE | $2,495,000 | $599 | $2,495,000 | 4,159 | Single Family Residence | 4/7 | 24 |
| 07-21-2023 | 5058 SEMINOLE AVENUE, WINTER PARK FL 32792 | $375,000 | $229 | $380,000 | 1,633 | Single Family Residence | 3/2 | 92 |
| 07-21-2023 | 312 FOUNTAIN LANE, WINTER PARK FL 32789 | $455,000 | $340 | $449,900 | 1,337 | Single Family Residence | 3/2 | 149 |
| 07-21-2023 | 3304 OLDE WHARF RUN | $577,000 | $277 | $580,000 | 2,082 | Single Family Residence | 3/2 | 15 |
| 07-21-2023 | 2352 KESTREL PERCH PLACE | $750,000 | $242 | $779,000 | 3,094 | Single Family Residence | 4/4 | 47 |
| 07-20-2023 | 1925 WOODCREST DRIVE, WINTER PARK FL 32792 | $240,000 | $243 | $249,900 | 987 | Condominium | 2/2 | 112 |
| 07-20-2023 | 1834 MAYWOOD ROAD, WINTER PARK FL 32792 | $273,500 | $251 | $289,900 | 1,086 | Single Family Residence | 3/2 | 39 |
| 07-20-2023 | 1887 POINCIANA ROAD, WINTER PARK FL 32792 | $464,000 | $281 | $464,000 | 1,650 | Single Family Residence | 3/2 | 36 |
| 07-20-2023 | 2233 COVENTRY DRIVE, WINTER PARK FL 32792 | $530,000 | $284 | $550,000 | 1,864 | Single Family Residence | 4/3 | 43 |
| 07-20-2023 | 8001 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $589,000 | $259 | $589,000 | 2,267 | Single Family Residence | 4/3 | 42 |
| 07-19-2023 | 722 WARRENTON ROAD, WINTER PARK FL 32792 | $217,000 | $159 | $217,000 | 1,362 | 1/2 Duplex | 2/2 | 1 |
| 07-19-2023 | 1741 HARVEST COVE | $369,000 | $290 | $379,900 | 1,272 | Single Family Residence | 3/2 | 79 |
| 07-18-2023 | 150 LEWFIELD CIRCLE # 150, WINTER PARK FL 32792 | $160,000 | $235 | $165,000 | 678 | Condominium | 1/1 | 118 |
| 07-18-2023 | 236 LEWFIELD CIRCLE # 236, WINTER PARK FL 32792 | $219,000 | $229 | $219,000 | 953 | Condominium | 2/2 | 46 |
| 07-18-2023 | 2905 CLEVER LANE, WINTER PARK FL 32792 | $404,090 | $226 | $404,090 | 1,782 | Townhouse | 3/3 | 16 |
| 07-17-2023 | 154 SCOTTSDALE SQUARE # 154, WINTER PARK FL 32792 | $128,000 | $117 | $140,000 | 1,085 | Condominium | 2/2 | 225 |
| 07-17-2023 | 200 SAINT ANDREWS BOULEVARD UNIT 103 | $195,000 | $233 | $195,000 | 835 | Condominium | 1/1 | 25 |
| 07-17-2023 | 2670 BARBADOS DRIVE, WINTER PARK FL 32792 | $230,000 | $269 | $224,900 | 854 | Townhouse | 2/1 | 82 |
| 07-17-2023 | 915 N KENTUCKY AVENUE, WINTER PARK FL 32789 | $537,400 | $599,999 | / | 229 | |||
| 07-14-2023 | 617 BALMORAL ROAD, WINTER PARK FL 32789 | $1,190,000 | $368 | $1,250,000 | 3,233 | Single Family Residence | 4/3 | 72 |
| 07-14-2023 | 7423 PORTSIDE COURT, WINTER PARK FL 32792 | $375,000 | $233 | $375,000 | 1,606 | Single Family Residence | 3/2 | 30 |
| 07-14-2023 | 1471 HARMON AVENUE, WINTER PARK FL 32789 | $370,000 | $385,000 | / | 43 | |||
| 07-14-2023 | 4548 WHIMBREL PLACE, WINTER PARK FL 32792 | $541,000 | $268 | $499,900 | 2,016 | Single Family Residence | 3/2 | 23 |
| 07-14-2023 | 418 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $600,000 | $300 | $600,000 | 2,000 | Single Family Residence | 3/2 | 51 |
| 07-14-2023 | 546 HOLT AVENUE, WINTER PARK FL 32789 | $725,000 | $476 | $725,000 | 1,520 | Single Family Residence | 3/2 | 28 |
| 07-13-2023 | 2942 BOWER ROAD, WINTER PARK FL 32792 | $739,000 | $321 | $719,900 | 2,301 | Single Family Residence | 4/3 | 36 |
| 07-12-2023 | 234 SCOTTSDALE SQUARE # 234, WINTER PARK FL 32792 | $137,750 | $126 | $145,000 | 1,085 | Condominium | 2/2 | 111 |
| 07-12-2023 | 3019 ANTIQUE OAKS CIRCLE # 124, WINTER PARK FL 327 | $165,000 | $220 | $160,000 | 749 | Condominium | 1/1 | 27 |
| 07-11-2023 | 640 DUNBLANE DRIVE, WINTER PARK FL 32792 | $735,000 | $332 | $776,900 | 2,209 | Single Family Residence | 3/3 | 88 |
| 07-10-2023 | 3069 AARON BURR AVENUE # 4C, WINTER PARK FL 32792 | $114,000 | $193 | $114,000 | 590 | Condominium | 1/1 | 152 |
| 07-10-2023 | 1400 INDIANA AVENUE, WINTER PARK FL 32789 | $600,000 | $292 | $589,000 | 2,054 | Townhouse | 3/3 | 38 |
| 07-10-2023 | 321 ELKHORN COURT, WINTER PARK FL 32792 | $585,000 | $304 | $589,500 | 1,921 | Single Family Residence | 4/3 | 46 |
| 07-07-2023 | 1000 S SEMORAN BOULEVARD # 804, WINTER PARK FL 327 | $215,000 | $204 | $215,000 | 1,049 | Condominium | 2/2 | 149 |
| 07-07-2023 | 722 CARVELL DRIVE, WINTER PARK FL 32792 | $431,000 | $272 | $425,000 | 1,581 | Single Family Residence | 3/2 | 37 |
| 07-07-2023 | 2852 SHERIFF WAY, WINTER PARK FL 32792 | $448,000 | $220 | $450,000 | 2,036 | Single Family Residence | 4/2 | 126 |
| 07-07-2023 | 428 S PHELPS AVENUE, WINTER PARK FL 32789 | $865,000 | $401 | $895,000 | 2,152 | Single Family Residence | 3/2 | 37 |
| 07-06-2023 | 219 SCOTTSDALE SQUARE # 219, WINTER PARK FL 32792 | $113,500 | $144 | $125,000 | 785 | Condominium | 1/1 | 74 |
| 07-06-2023 | 417 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $515,000 | $288 | $534,900 | 1,783 | Single Family Residence | 4/2 | 35 |
| 07-06-2023 | 1782 PINE AVENUE, WINTER PARK FL 32789 | $670,000 | $332 | $685,000 | 2,018 | Single Family Residence | 5/3 | 53 |
| 07-06-2023 | 507 LANGHOLM DRIVE, WINTER PARK FL 32789 | $940,000 | $401 | $985,000 | 2,343 | Single Family Residence | 4/3 | 63 |
| 07-05-2023 | 2038 JEWELL AVENUE, WINTER PARK FL 32789 | $330,000 | $407 | $330,000 | 809 | Single Family Residence | 2/1 | 35 |
| 07-03-2023 | 1618 LOOKOUT LANDING CIRCLE, WINTER PARK FL 32789 | $1,925,000 | $471 | $2,100,000 | 4,080 | Single Family Residence | 4/5 | 74 |
| 07-03-2023 | 1919 CARRIGAN AVENUE, WINTER PARK FL 32792 | $305,000 | $320 | $259,900 | 951 | Single Family Residence | 2/1 | 21 |
| 07-03-2023 | 543 WARRENTON ROAD # 543, WINTER PARK FL 32792 | $284,000 | $206 | $275,000 | 1,374 | Condominium | 3/3 | 21 |
| 06-30-2023 | 7429 DANIEL WEBSTER DRIVE, WINTER PARK FL 32792 | $155,000 | $149 | $159,000 | 1,036 | Condominium | 2/2 | 138 |
| 06-30-2023 | 700 MELROSE AVENUE # 4, WINTER PARK FL 32789 | $170,000 | $232 | $175,000 | 730 | Condominium | 1/1 | 38 |
| 06-30-2023 | 200 SAINT ANDREWS BOULEVARD # 2210, WINTER PARK FL | $250,000 | $253 | $234,900 | 987 | Condominium | 2/2 | 19 |
| 06-30-2023 | 1000 S SEMORAN BOULEVARD # 108, WINTER PARK FL 327 | $250,000 | $171 | $259,999 | 1,457 | Condominium | 3/2 | 213 |
| 06-30-2023 | 1840 VIA GENOA, WINTER PARK FL 32789 | $2,430,000 | $589 | $2,650,000 | 4,120 | Single Family Residence | 4/5 | 57 |
| 06-30-2023 | 700 S MELROSE AVENUE # 2, WINTER PARK FL 32789 | $325,000 | $224 | $350,000 | 1,448 | Condominium | 3/3 | 61 |
| 06-30-2023 | 2538 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $411,000 | $287 | $415,000 | 1,430 | Single Family Residence | 4/2 | 88 |
| 06-30-2023 | 785 VIA LOMBARDY, WINTER PARK FL 32789 | $4,500,000 | $668 | $4,500,000 | 6,736 | Single Family Residence | 5/7 | 12 |
| 06-30-2023 | 528 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $520,000 | $314 | $514,900 | 1,656 | Single Family Residence | 3/2 | 78 |
| 06-29-2023 | 155 E KINGS WAY, WINTER PARK FL 32789 | $1,200,000 | $574 | $1,200,000 | 2,090 | Single Family Residence | 3/2 | 2 |
| 06-29-2023 | 152 LEWFIELD CIRCLE # 152, WINTER PARK FL 32792 | $165,000 | $243 | $165,000 | 678 | Condominium | 1/1 | 57 |
| 06-29-2023 | 1781 PINE AVENUE, WINTER PARK FL 32789 | $1,760,000 | $453 | $2,000,000 | 3,882 | Single Family Residence | 5/5 | 57 |
| 06-29-2023 | 851 MILES AVENUE # 27, WINTER PARK FL 32789 | $235,000 | $290 | $239,000 | 808 | Condominium | 2/1 | 66 |
| 06-29-2023 | 4311 MANDY COURT, WINTER PARK FL 32792 | $510,000 | $237 | $515,000 | 2,146 | Single Family Residence | 3/2 | 46 |
| 06-28-2023 | 1700 PALM AVENUE, WINTER PARK FL 32789 | $2,250,000 | $598 | $2,250,000 | 3,762 | Single Family Residence | 4/5 | 3 |
| 06-28-2023 | 4434 GLENVIEW LANE, WINTER PARK FL 32792 | $450,000 | $227 | $450,000 | 1,982 | Single Family Residence | 4/2 | 35 |
| 06-28-2023 | 643 GILBERT ROAD, WINTER PARK FL 32792 | $483,500 | $221 | $544,000 | 2,185 | Single Family Residence | 4/2 | 81 |
| 06-28-2023 | 1420 LAKE FLORENCE WAY | $790,000 | $217 | $809,900 | 3,636 | Single Family Residence | 5/5 | 119 |
| 06-27-2023 | 200 SAINT ANDREWS BOULEVARD # 3504, WINTER PARK FL | $230,000 | $205 | $237,500 | 1,119 | Condominium | 2/2 | 68 |
| 06-27-2023 | 1408 AUBURN GREEN LOOP, WINTER PARK FL 32792 | $340,000 | $264 | $345,000 | 1,286 | Single Family Residence | 2/2 | 40 |
| 06-27-2023 | 1047 N KENTUCKY AVENUE | $850,000 | $484 | $749,900 | 1,755 | Townhouse | 3/3 | 35 |
| 06-27-2023 | 210 E LAKE SUE AVENUE, WINTER PARK FL 32789 | $812,000 | $314 | $850,000 | 2,582 | Single Family Residence | 5/4 | 41 |
| 06-27-2023 | 375 W WELBOURNE AVENUE # 107, WINTER PARK FL 32789 | $955,000 | $349 | $949,900 | 2,734 | Condominium | 3/4 | 42 |
| 06-26-2023 | 7342 SWALLOW RUN # 7342, WINTER PARK FL 32792 | $165,000 | $213 | $180,000 | 774 | Condominium | 2/2 | 176 |
| 06-26-2023 | 1878 ERUDITE WAY, WINTER PARK FL 32792 | $417,790 | $234 | $422,790 | 1,782 | Townhouse | 3/3 | 236 |
| 06-26-2023 | 1602 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $843,000 | $317 | $849,900 | 2,652 | Single Family Residence | 5/4 | 67 |
| 06-23-2023 | 3390 CEDAR SPRING PLACE # 163, WINTER PARK FL 3279 | $210,000 | $203 | $215,000 | 1,031 | Condominium | 2/3 | 114 |
| 06-23-2023 | 1740 VIA PALERMO, WINTER PARK FL 32789 | $3,850,000 | $732 | $3,995,000 | 5,259 | Single Family Residence | 5/6 | 93 |
| 06-23-2023 | 2104 KILLARNEY DRIVE, WINTER PARK FL 32789 | $420,000 | $289 | $410,000 | 1,450 | Single Family Residence | 3/2 | 16 |
| 06-23-2023 | 1882 ERUDITE WAY, WINTER PARK FL 32792 | $419,090 | $219 | $419,090 | 1,907 | Townhouse | 3/3 | 296 |
| 06-23-2023 | 1736 INDIANA AVENUE, WINTER PARK FL 32789 | $685,000 | $318 | $699,000 | 2,148 | Single Family Residence | 4/3 | 53 |
| 06-23-2023 | 1423 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $743,000 | $416 | $739,000 | 1,785 | Single Family Residence | 3/2 | 23 |
| 06-21-2023 | 512 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,089,925 | $421 | $1,046,925 | 2,585 | Townhouse | 3/3 | 560 |
| 06-21-2023 | 521 CAROLINA AVENUE, WINTER PARK FL 32789 | $1,734,500 | $708 | $1,734,500 | 2,449 | Single Family Residence | 3/3 | 1 |
| 06-20-2023 | 2404 GALLERY VIEW DRIVE # 1, WINTER PARK FL 32792 | $210,000 | $223 | $229,900 | 939 | Condominium | 2/2 | 84 |
| 06-16-2023 | 318 SCOTTSDALE SQUARE # 318, WINTER PARK FL 32792 | $133,000 | $130 | $139,000 | 1,020 | Condominium | 2/2 | 51 |
| 06-16-2023 | 106 SCOTTSDALE SQUARE # 106, WINTER PARK FL 32792 | $160,000 | $128 | $158,000 | 1,250 | Condominium | 3/2 | 38 |
| 06-16-2023 | 203 LEWFIELD CIRCLE # 203, WINTER PARK FL 32792 | $200,000 | $215 | $200,000 | 927 | Condominium | 2/2 | 22 |
| 06-16-2023 | 423 WARRENTON ROAD # 423, WINTER PARK FL 32792 | $300,000 | $257 | $293,500 | 1,163 | Condominium | 2/2 | 81 |
| 06-16-2023 | 7001 JACKMAN BOULEVARD, WINTER PARK FL 32792 | $320,000 | $215 | $330,000 | 1,482 | Single Family Residence | 3/2 | 139 |
| 06-16-2023 | 3113 CROWN JEWEL COURT, WINTER PARK FL 32792 | $366,600 | $260 | $376,000 | 1,408 | Townhouse | 3/3 | 50 |
| 06-16-2023 | 2114 KAROLINA AVENUE, WINTER PARK FL 32789 | $399,000 | $332 | $399,900 | 1,200 | Single Family Residence | 3/1 | 30 |
| 06-16-2023 | 311 E MORSE BOULEVARD # 2, WINTER PARK FL 32789 | $390,000 | $327 | $400,000 | 1,192 | Condominium | 1/1 | 102 |
| 06-16-2023 | 1224 S PENNSYLVANIA AVENUE # 4, WINTER PARK FL 327 | $785,000 | $401 | $765,000 | 1,957 | Condominium | 3/3 | 310 |
| 06-16-2023 | 1640 PALM AVENUE, WINTER PARK FL 32789 | $899,000 | $461 | $899,000 | 1,946 | Single Family Residence | 4/3 | 29 |
| 06-15-2023 | 2325 CHANTILLY AVENUE, WINTER PARK FL 32789 | $1,415,000 | $352 | $1,499,000 | 4,014 | Single Family Residence | 5/6 | 213 |
| 06-15-2023 | 1860 ERUDITE WAY, WINTER PARK FL 32792 | $381,990 | $200 | $407,340 | 1,907 | Townhouse | 3/3 | 225 |
| 06-14-2023 | 2423 VIA SIENNA, WINTER PARK FL 32789 | $1,400,250 | $403 | $1,400,000 | 3,472 | Single Family Residence | 4/4 | 44 |
| 06-14-2023 | 1624 ELIZABETHS WALK | $1,499,000 | $485 | $1,499,000 | 3,085 | Single Family Residence | 5/5 | 34 |
| 06-14-2023 | 2816 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $596,500 | $328 | $600,000 | 1,817 | Single Family Residence | 4/2 | 56 |
| 06-13-2023 | 1600 PALM AVENUE, WINTER PARK FL 32789 | $1,995,000 | $556 | $1,995,000 | 3,585 | Single Family Residence | 4/5 | 2 |
| 06-13-2023 | 1856 ERUDITE WAY, WINTER PARK FL 32792 | $381,990 | $200 | $401,790 | 1,907 | Townhouse | 3/3 | 224 |
| 06-13-2023 | 311 E MORSE BOULEVARD UNIT 6-4 | $415,000 | $338 | $415,000 | 1,227 | Condominium | 1/1 | 40 |
| 06-13-2023 | 943 BUNGALOW AVENUE, WINTER PARK FL 32789 | $525,000 | $438 | $549,000 | 1,197 | Single Family Residence | 3/2 | 193 |
| 06-12-2023 | 1400 S PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $1,100,000 | $491 | $1,185,000 | 2,236 | Single Family Residence | 4/3 | 55 |
| 06-12-2023 | 2619 LAFAYETTE AVE, WINTER PARK FL 32789 | $405,000 | $290 | $425,000 | 1,393 | Single Family Residence | 4/2 | 20 |
| 06-12-2023 | 1769 INDIANA AVENUE # D, WINTER PARK FL 32789 | $420,000 | $259 | $429,000 | 1,616 | Condominium | 3/3 | 81 |
| 06-09-2023 | 1060 VIA MERANO COURT, WINTER PARK FL 32789 | $1,550,000 | $415 | $1,550,000 | 3,726 | Single Family Residence | 5/5 | 43 |
| 06-09-2023 | 7102 EASTER STREET, WINTER PARK FL 32792 | $268,200 | $240 | $239,000 | 1,114 | Single Family Residence | 3/1 | 43 |
| 06-09-2023 | 669 GRENADINE COURT # 669, WINTER PARK FL 32792 | $235,000 | $226 | $239,900 | 1,037 | Condominium | 2/2 | 118 |
| 06-09-2023 | 5161 LAZY OAKS DRIVE # 5161, WINTER PARK FL 32792 | $259,000 | $209 | $259,000 | 1,236 | Condominium | 2/3 | 36 |
| 06-09-2023 | 2144 SYCAMORE DRIVE, WINTER PARK FL 32789 | $401,000 | $285 | $350,000 | 1,405 | Single Family Residence | 3/2 | 50 |
| 06-09-2023 | 4940 ARDMORE DRIVE, WINTER PARK FL 32792 | $377,500 | $241 | $375,000 | 1,560 | Single Family Residence | 3/2 | 36 |
| 06-09-2023 | 2321 SHADOWLAND LOOP, WINTER PARK FL 32792 | $455,000 | $259 | $469,000 | 1,755 | Townhouse | 3/3 | 43 |
| 06-08-2023 | 5492 PEACO PLACE, WINTER PARK FL 32792 | $290,000 | $269 | $290,000 | 1,078 | 1/2 Duplex | 3/2 | 114 |
| 06-07-2023 | 2808 AMSDEN ROAD, WINTER PARK FL 32792 | $515,000 | $254 | $515,000 | 2,020 | Single Family Residence | 3/4 | 55 |
| 06-06-2023 | 514 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,189,382 | $460 | $1,098,625 | 2,585 | Townhouse | 3/3 | 460 |
| 06-06-2023 | 3221 CROWN JEWEL COURT, WINTER PARK FL 32792 | $350,000 | $248 | $370,000 | 1,406 | Townhouse | 3/3 | 155 |
| 06-06-2023 | 7034 ACORN COURT, WINTER PARK FL 32792 | $425,000 | $204 | $425,000 | 2,076 | Single Family Residence | 4/2 | 41 |
| 06-05-2023 | 149 LEWFIELD CIRCLE # 149, WINTER PARK FL 32792 | $170,000 | $250 | $170,000 | 678 | Condominium | 1/1 | 43 |
| 06-05-2023 | 1715 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $287,000 | $217 | $279,000 | 1,319 | Townhouse | 2/2 | 18 |
| 06-05-2023 | 2613 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $399,000 | $361 | $399,000 | 1,104 | Single Family Residence | 2/1 | 28 |
| 06-05-2023 | 7130 CITRUS AVENUE, WINTER PARK FL 32792 | $475,000 | $266 | $485,000 | 1,784 | Single Family Residence | 4/2 | 103 |
| 06-05-2023 | 1936 WHITEHALL DRIVE, WINTER PARK FL 32792 | $500,000 | $282 | $525,000 | 1,769 | Single Family Residence | 3/2 | 133 |
| 06-05-2023 | 2220 COVENTRY DRIVE, WINTER PARK FL 32792 | $571,000 | $216 | $581,500 | 2,633 | Single Family Residence | 3/3 | 39 |
| 06-05-2023 | 1585 CHESTNUT AVENUE, WINTER PARK FL 32789 | $989,000 | $408 | $989,000 | 2,420 | Single Family Residence | 4/3 | 54 |
| 06-02-2023 | 3173 CROWN JEWEL COURT, WINTER PARK FL 32792 | $355,000 | $252 | $370,000 | 1,408 | Townhouse | 3/3 | 71 |
| 06-02-2023 | 336 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $450,000 | $289 | $400,000 | 1,554 | Single Family Residence | 3/2 | 18 |
| 06-02-2023 | 840 W COMSTOCK AVENUE, WINTER PARK FL 32789 | $450,000 | $450,000 | / | 444 | |||
| 06-02-2023 | 1464 BROAD WING LANE, WINTER PARK FL 32792 | $490,000 | $212 | $510,000 | 2,308 | Townhouse | 3/3 | 47 |
| 06-02-2023 | 200 CAROLINA AVENUE # 402, WINTER PARK FL 32789 | $625,000 | $462 | $649,000 | 1,350 | Condominium | 3/2 | 122 |
| 06-02-2023 | 436 BALMORAL ROAD, WINTER PARK FL 32789 | $750,000 | $375 | $749,000 | 1,998 | Single Family Residence | 4/2 | 29 |
| 06-02-2023 | 3065 GEORGE MASON AVENUE # 2, WINTER PARK FL 32792 | $95,000 | $180 | $95,000 | 525 | Condominium | 1/1 | 30 |
| 06-01-2023 | 1404 BORDER DRIVE, WINTER PARK FL 32789 | $1,075,000 | $429 | $1,150,000 | 2,505 | Single Family Residence | 4/4 | 206 |
| 06-01-2023 | 4464 TUSCANY ISLAND COURT, WINTER PARK FL 32792 | $1,300,000 | $281 | $1,375,000 | 4,625 | Single Family Residence | 4/5 | 121 |
| 06-01-2023 | 1691 PALM AVENUE, WINTER PARK FL 32789 | $1,825,000 | $593 | $1,800,000 | 3,075 | Single Family Residence | 4/4 | 50 |
| 06-01-2023 | 1761 INDIANA AVENUE # F, WINTER PARK FL 32789 | $413,000 | $258 | $413,000 | 1,598 | Townhouse | 3/3 | 5 |
| 06-01-2023 | 1757 INDIANA AVENUE # G, WINTER PARK FL 32789 | $420,000 | $259 | $420,000 | 1,616 | Townhouse | 3/3 | 5 |
| 06-01-2023 | 1871 BISCAYNE DRIVE, WINTER PARK FL 32789 | $527,000 | $248 | $500,000 | 2,120 | Single Family Residence | 4/3 | 50 |
| 06-01-2023 | 1822 TEMPLE DRIVE, WINTER PARK FL 32789 | $687,000 | $330 | $699,000 | 2,079 | Single Family Residence | 3/3 | 295 |
| 05-31-2023 | 100 S INTERLACHEN AVENUE UNIT 301C | $1,107,000 | $675 | $1,150,000 | 1,639 | Condominium | 3/2 | 56 |
| 05-31-2023 | 851 MILES AVENUE # 15, WINTER PARK FL 32789 | $235,500 | $291 | $244,800 | 808 | Condominium | 2/1 | 125 |
| 05-31-2023 | 1841 BISCAYNE DRIVE, WINTER PARK FL 32789 | $285,000 | $413 | $275,000 | 690 | Single Family Residence | 2/1 | 13 |
| 05-31-2023 | 2529 FRANKLIN AVENUE, WINTER PARK FL 32789 | $355,000 | $276 | $350,000 | 1,284 | Single Family Residence | 3/2 | 24 |
| 05-31-2023 | 3343 ELLWOOD COURT, WINTER PARK FL 32792 | $462,000 | $262 | $445,000 | 1,762 | Single Family Residence | 3/2 | 42 |
| 05-31-2023 | 654 FRIAR ROAD, WINTER PARK FL 32792 | $550,000 | $310 | $550,000 | 1,772 | Single Family Residence | 3/2 | 10 |
| 05-31-2023 | 250 CAROLINA AVENUE # 303, WINTER PARK FL 32789 | $610,000 | $467 | $610,000 | 1,305 | Condominium | 2/2 | 1 |
| 05-31-2023 | 1232 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $661,500 | $367 | $675,000 | 1,798 | Single Family Residence | 3/2 | 42 |
| 05-30-2023 | 1664 TREMONT LANE, WINTER PARK FL 32792 | $325,000 | $252 | $335,000 | 1,286 | Single Family Residence | 2/2 | 65 |
| 05-30-2023 | 7541 GLENMOOR LANE, WINTER PARK FL 32792 | $519,000 | $226 | $519,000 | 2,288 | Single Family Residence | 4/2 | 58 |
| 05-27-2023 | 500 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,212,835 | $454 | $1,079,730 | 2,666 | Townhouse | 3/3 | 535 |
| 05-26-2023 | 2011 N PARK AVENUE, WINTER PARK FL 32789 | $1,950,000 | $556 | $1,980,000 | 3,502 | Single Family Residence | 4/4 | 164 |
| 05-26-2023 | 255 STIRLING AVENUE, WINTER PARK FL 32789 | $2,100,000 | $577 | $2,200,000 | 3,635 | Single Family Residence | 4/4 | 80 |
| 05-26-2023 | 652 GRENADINE COURT S, WINTER PARK FL 32792 | $241,000 | $232 | $240,000 | 1,037 | Condominium | 2/2 | 31 |
| 05-26-2023 | 523 WARRENTON ROAD # 523, WINTER PARK FL 32792 | $280,000 | $240 | $285,000 | 1,163 | Condominium | 2/2 | 24 |
| 05-26-2023 | 3148 RAIDERS RUN # 1, WINTER PARK FL 32792 | $417,000 | $298 | $409,900 | 1,398 | Single Family Residence | 3/2 | 33 |
| 05-26-2023 | 2755 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $486,000 | $304 | $475,000 | 1,595 | Single Family Residence | 4/2 | 37 |
| 05-26-2023 | 1270 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $505,000 | $307 | $530,000 | 1,644 | Single Family Residence | 3/2 | 65 |
| 05-26-2023 | 1034 S KENTUCKY AVENUE, WINTER PARK FL 32789 | $689,000 | $378 | $689,000 | 1,820 | Townhouse | 3/3 | 25 |
| 05-25-2023 | 1756 HOLLYWOOD AVE, WINTER PARK FL 32789 | $1,000,000 | $422 | $1,199,999 | 2,366 | Single Family Residence | 4/3 | 23 |
| 05-25-2023 | 112 LEWFIELD CIRCLE # 112, WINTER PARK FL 32792 | $202,000 | $211 | $195,000 | 953 | Condominium | 2/2 | 35 |
| 05-25-2023 | 865 S PENNSYLVANIA AVENUE | $684,000 | $486 | $700,000 | 1,407 | Single Family Residence | 3/2 | 85 |
| 05-25-2023 | 656 RANDY LANE, WINTER PARK FL 32789 | $715,000 | $347 | $725,000 | 2,060 | Single Family Residence | 3/2 | 64 |
| 05-25-2023 | 408 LANGHOLM DRIVE | $770,000 | $448 | $760,000 | 1,715 | Single Family Residence | 3/2 | 42 |
| 05-24-2023 | 1115 N PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $2,450,000 | $685 | $2,595,000 | 3,576 | Single Family Residence | 4/5 | 34 |
| 05-24-2023 | 1327 FOUNTAIN HILLS COURT, WINTER PARK FL 32792 | $650,000 | $252 | $650,000 | 2,575 | Single Family Residence | 4/3 | 36 |
| 05-24-2023 | 100 S VIRGINIA AVENUE # 316, WINTER PARK FL 32789 | $965,000 | $371 | $990,000 | 2,599 | Condominium | 3/3 | 204 |
| 05-23-2023 | 166 LEWFIELD CIR # 166, WINTER PARK FL 32792 | $165,000 | $243 | $167,000 | 678 | Condominium | 1/1 | 47 |
| 05-22-2023 | 316 SCOTTSDALE SQUARE # 316, WINTER PARK FL 32792 | $100,000 | $92 | $145,000 | 1,085 | Condominium | 2/2 | 64 |
| 05-22-2023 | 1580 GROVE TERRACE, WINTER PARK FL 32789 | $1,580,000 | $370 | $1,580,000 | 4,264 | Single Family Residence | 5/5 | 257 |
| 05-22-2023 | 192 LEWFIELD CIRCLE # 192, WINTER PARK FL 32792 | $163,000 | $240 | $169,000 | 678 | Condominium | 1/1 | 35 |
| 05-22-2023 | 1086 AZALEA LANE # 1, WINTER PARK FL 32789 | $589,000 | $331 | $589,000 | 1,776 | Condominium | 3/2 | 39 |
| 05-19-2023 | 1500 GAY ROAD UNIT 3C | $236,500 | $230 | $236,500 | 1,026 | Condominium | 2/2 | 143 |
| 05-19-2023 | 2279 ISLAND RUN, WINTER PARK FL 32792 | $290,000 | $225 | $290,000 | 1,284 | Townhouse | 3/2 | 82 |
| 05-19-2023 | 200 SAINT ANDREWS BOULEVARD # 1203, WINTER PARK FL | $293,455 | $221 | $295,000 | 1,322 | Condominium | 3/2 | 31 |
| 05-19-2023 | 1901 AZALEA AVENUE, WINTER PARK FL 32792 | $303,000 | $337 | $310,000 | 897 | Single Family Residence | 2/1 | 60 |
| 05-19-2023 | 654 SELKIRK DRIVE, WINTER PARK FL 32792 | $410,000 | $405,000 | / | 49 | |||
| 05-19-2023 | 2460 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $415,000 | $284 | $419,900 | 1,461 | Single Family Residence | 4/2 | 65 |
| 05-18-2023 | 2500 LEE ROAD UNIT 210 | $169,000 | $262 | $169,000 | 645 | Condominium | 1/1 | 35 |
| 05-18-2023 | 4932 TANGERINE AVENUE # 4932, WINTER PARK FL 32792 | $174,900 | $229 | $174,900 | 763 | Condominium | 1/1 | 31 |
| 05-18-2023 | 4790 TANGERINE AVENUE # 4790, WINTER PARK FL 32792 | $207,300 | $195 | $210,000 | 1,058 | Condominium | 2/2 | 39 |
| 05-18-2023 | 1224 PARK GREEN PLACE, WINTER PARK FL 32789 | $345,000 | $222 | $350,000 | 1,552 | Townhouse | 3/2 | 49 |
| 05-17-2023 | 1870 LAUREL ROAD, WINTER PARK FL 32789 | $2,252,500 | $558 | $2,250,000 | 4,036 | Single Family Residence | 4/5 | 36 |
| 05-17-2023 | 7337 CEDAR CREEK COURT # 75, WINTER PARK FL 32792 | $230,000 | $223 | $229,999 | 1,031 | Townhouse | 2/3 | 72 |
| 05-17-2023 | 621 TRINIDAD COURT # 621, WINTER PARK FL 32792 | $239,900 | $231 | $239,900 | 1,037 | Condominium | 2/2 | 37 |
| 05-16-2023 | 1944 HOUNDSLAKE DRIVE, WINTER PARK FL 32792 | $397,000 | $204 | $400,000 | 1,938 | Single Family Residence | 3/2 | 79 |
| 05-16-2023 | 1762 CHESTNUT AVENUE, WINTER PARK FL 32789 | $820,000 | $465 | $850,000 | 1,760 | Single Family Residence | 3/2 | 82 |
| 05-15-2023 | 1017 VIA TUSCANY OAKS WAY, WINTER PARK FL 32789 | $1,925,000 | $455 | $1,995,000 | 4,230 | Single Family Residence | 5/6 | 108 |
| 05-15-2023 | 610 GENIUS DRIVE | $3,190,000 | $613 | $3,290,000 | 5,196 | Single Family Residence | 5/6 | 68 |
| 05-15-2023 | 4400 TUSCANY ISLAND COURT | $3,700,000 | $512 | $3,850,000 | 7,226 | Single Family Residence | 4/7 | 112 |
| 05-15-2023 | 7909 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $675,000 | $193 | $725,000 | 3,496 | Single Family Residence | 5/4 | 147 |
| 05-12-2023 | 1809 HARLAND PARK DRIVE, WINTER PARK FL 32789 | $1,550,000 | $423 | $1,599,000 | 3,660 | Single Family Residence | 4/4 | 64 |
| 05-12-2023 | 1120 PALMER AVE, WINTER PARK FL 32789 | $1,600,000 | $478 | $1,695,000 | 3,341 | Single Family Residence | 3/4 | 88 |
| 05-12-2023 | 735 WARRENTON ROAD, WINTER PARK FL 32792 | $285,000 | $238 | $250,000 | 1,196 | 1/2 Duplex | 3/2 | 22 |
| 05-12-2023 | 7325 WALNUT AVENUE, WINTER PARK FL 32792 | $350,000 | $147 | $350,000 | 2,379 | Single Family Residence | 4/2 | 23 |
| 05-12-2023 | 5311 CYPRESS DRIVE, WINTER PARK FL 32792 | $420,600 | $299 | $419,900 | 1,403 | Single Family Residence | 3/2 | 45 |
| 05-12-2023 | 3630 HAWTHORNE LANE, WINTER PARK FL 32792 | $439,900 | $267 | $439,900 | 1,645 | Single Family Residence | 3/2 | 44 |
| 05-12-2023 | 1607 LITTLE WREN LANE, WINTER PARK FL 32792 | $476,250 | $206 | $475,000 | 2,308 | Townhouse | 3/3 | 59 |
| 05-11-2023 | 1931 LAUREL ROAD | $1,500,000 | $476 | $1,525,000 | 3,150 | Single Family Residence | 4/4 | 35 |
| 05-11-2023 | 2522 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $2,100,000 | $600 | $2,190,000 | 3,500 | Single Family Residence | 4/4 | 216 |
| 05-11-2023 | 2114 BISCAYNE DRIVE, WINTER PARK FL 32789 | $373,000 | $291 | $384,900 | 1,279 | Single Family Residence | 3/1 | 43 |
| 05-09-2023 | 1416 ASTER COURT, WINTER PARK FL 32792 | $535,000 | $281 | $539,990 | 1,898 | Single Family Residence | 5/3 | 97 |
| 05-08-2023 | 7417 DANIEL WEBSTER DRIVE # 3, WINTER PARK FL 3279 | $105,000 | $192 | $110,000 | 546 | Condominium | /1 | 63 |
| 05-08-2023 | 2343 VERSAILLES AVENUE, WINTER PARK FL 32789 | $1,700,000 | $526 | $1,750,000 | 3,227 | Single Family Residence | 4/4 | 60 |
| 05-08-2023 | 723 MONMOUTH WAY, WINTER PARK FL 32792 | $725,000 | $299 | $725,000 | 2,423 | Single Family Residence | 5/3 | 40 |
| 05-05-2023 | 1913 SYCAMORE DRIVE, WINTER PARK FL 32789 | $1,425,000 | $455 | $1,475,000 | 3,130 | Single Family Residence | 4/5 | 133 |
| 05-05-2023 | 195 CORTLAND AVENUE, WINTER PARK FL 32789 | $1,425,000 | $472 | $1,475,000 | 3,018 | Single Family Residence | 3/4 | 51 |
| 05-05-2023 | 1338 PERUVIAN LANE, WINTER PARK FL 32792 | $294,000 | $278 | $299,000 | 1,056 | Single Family Residence | 3/2 | 46 |
| 05-05-2023 | 3152 DWARF PINE AVENUE, WINTER PARK FL 32792 | $365,000 | $231 | $349,999 | 1,578 | Single Family Residence | 3/2 | 26 |
| 05-05-2023 | 3031 NORTHWOOD BOULEVARD, WINTER PARK FL 32789 | $415,000 | $337 | $415,000 | 1,230 | Single Family Residence | 3/1 | 12 |
| 05-05-2023 | 1941 NATALEN ROAD, WINTER PARK FL 32792 | $375,000 | $242 | $425,000 | 1,547 | Single Family Residence | 3/2 | 198 |
| 05-05-2023 | 425 BALMORAL ROAD, WINTER PARK FL 32789 | $880,000 | $456 | $775,000 | 1,929 | Single Family Residence | 3/2 | 17 |
| 05-04-2023 | 1918 SUMMERFIELD ROAD | $1,175,000 | $359 | $1,300,000 | 3,269 | Single Family Residence | 5/5 | 43 |
| 05-04-2023 | 700 MELROSE AVENUE # 1, WINTER PARK FL 32789 | $239,000 | $303 | $239,000 | 787 | Condominium | 1/1 | 1 |
| 05-04-2023 | 1551 LAUREL ROAD | $4,500,000 | $855 | $4,595,000 | 5,258 | Single Family Residence | 4/6 | 30 |
| 05-03-2023 | 232 SANDLEWOOD TRAIL # 4, WINTER PARK FL 32789 | $327,000 | $297 | $334,000 | 1,098 | Condominium | 2/3 | 20 |
| 05-03-2023 | 5639 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $350,000 | $312 | $359,900 | 1,120 | Single Family Residence | 3/2 | 106 |
| 05-03-2023 | 1164 DODD ROAD, WINTER PARK FL 32792 | $560,000 | $197 | $560,000 | 2,840 | Single Family Residence | 5/4 | 112 |
| 05-02-2023 | 1531 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $389,500 | $236 | $394,500 | 1,647 | Single Family Residence | 3/2 | 48 |
| 05-02-2023 | 640 DOUGLAS AVENUE, WINTER PARK FL 32789 | $467,000 | $364 | $419,000 | 1,280 | Single Family Residence | 3/2 | 34 |
| 05-02-2023 | 1240 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $750,000 | $357 | $765,000 | 2,096 | Single Family Residence | 3/2 | 27 |
| 05-01-2023 | 2747 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $520,000 | $323 | $535,000 | 1,608 | Single Family Residence | 3/2 | 77 |
| 05-01-2023 | 620 DUNBLANE DRIVE, WINTER PARK FL 32792 | $850,000 | $412 | $850,000 | 2,059 | Single Family Residence | 4/3 | 31 |
| 04-28-2023 | 3054 GEORGE MASON AVENUE # 8, WINTER PARK FL 32792 | $145,000 | $140 | $150,000 | 1,035 | Condominium | 2/2 | 127 |
| 04-28-2023 | 4916 TANGERINE AVE, WINTER PARK FL 32792 | $239,900 | $226 | $239,900 | 1,058 | Condominium | 2/2 | 25 |
| 04-28-2023 | 1408 VIBURNUM LANE, WINTER PARK FL 32792 | $318,000 | $233 | $299,900 | 1,362 | Single Family Residence | 3/2 | 32 |
| 04-28-2023 | 5347 N ORANGE AVENUE, WINTER PARK FL 32792 | $350,000 | $245 | $350,000 | 1,427 | Single Family Residence | 4/2 | 59 |
| 04-28-2023 | 1768 MILLER AVENUE, WINTER PARK FL 32789 | $340,000 | $331 | $375,000 | 1,025 | Duplex | 2/2 | 54 |
| 04-28-2023 | 3340 BALSAM DR, WINTER PARK FL 32792 | $412,000 | $289 | $412,000 | 1,424 | Single Family Residence | 3/2 | 36 |
| 04-28-2023 | 2811 WOODSIDE AVENUE, WINTER PARK FL 32789 | $380,000 | $223 | $430,000 | 1,703 | Single Family Residence | 3/2 | 73 |
| 04-28-2023 | 1796 E CHERYL DRIVE, WINTER PARK FL 32792 | $450,000 | $236 | $446,900 | 1,906 | Single Family Residence | 3/2 | 70 |
| 04-28-2023 | 1213 DENSMORE DRIVE, WINTER PARK FL 32792 | $510,000 | $220 | $499,500 | 2,318 | Single Family Residence | 4/2 | 30 |
| 04-28-2023 | 230 S RANGER BOULEVARD, WINTER PARK FL 32792 | $565,000 | $244 | $569,500 | 2,309 | Single Family Residence | 3/2 | 72 |
| 04-28-2023 | 636 DUNBLANE DRIVE, WINTER PARK FL 32792 | $622,000 | $344 | $625,000 | 1,803 | Single Family Residence | 3/3 | 1 |
| 04-28-2023 | 2843 EASTERN PARKWAY, WINTER PARK FL 32789 | $639,000 | $377 | $639,000 | 1,692 | Single Family Residence | 3/2 | 45 |
| 04-27-2023 | $1,235,000 | $594 | $1,235,000 | 2,079 | Single Family Residence | 4/3 | 1 | |
| 04-27-2023 | $1,235,000 | $1,235,000 | / | 2 | ||||
| 04-27-2023 | 1209 SHARON PLACE, WINTER PARK FL 32789 | $1,235,000 | $1,397,000 | / | 308 | |||
| 04-27-2023 | 1209 SHARON PLACE, WINTER PARK FL 32789 | $1,235,000 | $594 | $1,397,000 | 2,079 | Single Family Residence | 4/3 | 308 |
| 04-27-2023 | 204 LEWFIELD CIRCLE # 204, WINTER PARK FL 32792 | $209,000 | $225 | $200,000 | 927 | Condominium | 2/2 | 41 |
| 04-27-2023 | 677 DEPUGH STREET, WINTER PARK FL 32789 | $365,000 | $390,000 | / | 331 | |||
| 04-27-2023 | 677 DEPUGH STREET, WINTER PARK FL 32789 | $365,000 | $268 | $390,000 | 1,358 | Single Family Residence | 3/1 | 311 |
| 04-27-2023 | 227 GENIUS DRIVE | $4,750,000 | $627 | $4,950,000 | 7,568 | Single Family Residence | 5/7 | 291 |
| 04-26-2023 | 1252 VIA DEL MAR, WINTER PARK FL 32789 | $3,550,000 | $859 | $3,550,000 | 4,131 | Single Family Residence | 5/6 | 41 |
| 04-26-2023 | 1810 ALICE AVENUE, WINTER PARK FL 32792 | $387,500 | $341 | $399,900 | 1,136 | Single Family Residence | 2/2 | 56 |
| 04-26-2023 | 2461 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $395,000 | $265 | $400,000 | 1,487 | Single Family Residence | 3/2 | 44 |
| 04-26-2023 | 1820 VIBURNUM LANE, WINTER PARK FL 32792 | $499,999 | $172 | $499,999 | 2,906 | Single Family Residence | 5/3 | 71 |
| 04-25-2023 | 1265 PARK POINTE LANE, WINTER PARK FL 32789 | $820,000 | $357 | $815,000 | 2,295 | Single Family Residence | 4/3 | 26 |
| 04-25-2023 | 202 LONGBRANCH COURT, WINTER PARK FL 32792 | $850,000 | $297 | $850,000 | 2,855 | Single Family Residence | 4/4 | 34 |
| 04-24-2023 | 1949 KILLARNEY DRIVE | $2,525,000 | $524 | $2,999,000 | 4,817 | Single Family Residence | 4/5 | 67 |
| 04-24-2023 | 206 BALFOUR DRIVE # 6, WINTER PARK FL 32792 | $370,000 | $302 | $370,000 | 1,225 | Condominium | 2/2 | 42 |
| 04-24-2023 | 4033 TENITA DRIVE, WINTER PARK FL 32792 | $550,000 | $272 | $559,000 | 2,022 | Single Family Residence | 4/2 | 32 |
| 04-21-2023 | 266 W LYMAN AVENUE, WINTER PARK FL 32789 | $1,090,000 | $545 | $1,095,000 | 2,000 | Townhouse | 3/3 | 34 |
| 04-21-2023 | 1368 HIBISCUS AVENUE, WINTER PARK FL 32789 | $1,010,000 | $421 | $1,135,000 | 2,394 | Single Family Residence | 4/3 | 53 |
| 04-21-2023 | 1250 S DENNING DRIVE # 203, WINTER PARK FL 32789 | $255,000 | $280 | $260,000 | 908 | Condominium | 2/2 | 50 |
| 04-21-2023 | 2961 CLEVER LANE, WINTER PARK FL 32792 | $381,990 | $200 | $381,990 | 1,907 | Townhouse | 3/3 | 208 |
| 04-21-2023 | 3464 ATHENA DRIVE, WINTER PARK FL 32792 | $425,000 | $253 | $425,000 | 1,674 | Single Family Residence | 4/2 | 53 |
| 04-21-2023 | 1300 BLUE STEM LANE, WINTER PARK FL 32792 | $655,000 | $254 | $655,000 | 2,577 | Single Family Residence | 4/4 | 74 |
| 04-21-2023 | 826 W LYMAN AVENUE, WINTER PARK FL 32789 | $915,000 | $500 | $900,000 | 1,828 | Single Family Residence | 3/3 | 35 |
| 04-19-2023 | 518 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,164,083 | $450 | $1,046,925 | 2,585 | Townhouse | 3/3 | 497 |
| 04-19-2023 | 2957 CLEVER LANE, WINTER PARK FL 32792 | $412,190 | $216 | $412,190 | 1,907 | Townhouse | 3/3 | 206 |
| 04-19-2023 | 418 GILBERT ROAD, WINTER PARK FL 32792 | $400,000 | $212 | $450,000 | 1,880 | Single Family Residence | 4/3 | 65 |
| 04-19-2023 | 1530 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $615,000 | $204 | $664,900 | 3,011 | Single Family Residence | 5/3 | 213 |
| 04-18-2023 | 1144 N PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $1,299,999 | $566 | $1,299,000 | 2,296 | Single Family Residence | 2/3 | 19 |
| 04-18-2023 | 241 E FAWSETT ROAD, WINTER PARK FL 32789 | $1,650,000 | $337 | $1,650,000 | 4,884 | Single Family Residence | 5/7 | 1 |
| 04-18-2023 | 1813 GIPSON GREEN LANE, WINTER PARK FL 32789 | $1,600,000 | $1,799,932 | / | 215 | |||
| 04-18-2023 | 1795 KILLARNEY DRIVE | $3,550,000 | $813 | $3,700,000 | 4,363 | Single Family Residence | 4/5 | 104 |
| 04-17-2023 | 1441 CARDINAL COURT, WINTER PARK FL 32789 | $3,395,000 | $836 | $3,395,000 | 4,060 | Single Family Residence | 4/6 | 40 |
| 04-17-2023 | 3035 MOSS VALLEY PLACE, WINTER PARK FL 32792 | $360,000 | $273 | $340,000 | 1,316 | Single Family Residence | 3/2 | 34 |
| 04-17-2023 | 2819 AMBERGATE ROAD, WINTER PARK FL 32792 | $360,048 | $218 | $350,000 | 1,650 | Single Family Residence | 4/2 | 13 |
| 04-17-2023 | 2621 ALOMA AVENUE, WINTER PARK FL 32792 | $389,000 | $320 | $389,000 | 1,215 | Single Family Residence | 3/2 | 38 |
| 04-17-2023 | 1420 ALOMA AVENUE, WINTER PARK FL 32789 | $760,000 | $323 | $799,900 | 2,350 | Single Family Residence | 2/3 | 219 |
| 04-17-2023 | 942 POINCIANA LANE, WINTER PARK FL 32789 | $850,000 | $361 | $995,000 | 2,350 | Single Family Residence | 3/3 | 69 |
| 04-15-2023 | 280 SCOTTSDALE SQUARE # 280, WINTER PARK FL 32792 | $130,000 | $119 | $144,900 | 1,085 | Condominium | 2/2 | 64 |
| 04-14-2023 | 715 VIA LUGANO, WINTER PARK FL 32789 | $3,850,000 | $523 | $3,850,000 | 7,349 | Single Family Residence | 6/8 | 4 |
| 04-14-2023 | 5319 PINE LILY CIRCLE, WINTER PARK FL 32792 | $610,000 | $269 | $615,000 | 2,265 | Single Family Residence | 4/2 | 68 |
| 04-13-2023 | 2965 CLEVER LANE, WINTER PARK FL 32792 | $425,390 | $238 | $401,990 | 1,782 | Townhouse | 3/3 | 200 |
| 04-12-2023 | 516 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,188,432 | $445 | $1,153,050 | 2,666 | Townhouse | 3/3 | 405 |
| 04-12-2023 | 1761 GREENWICH AVENUE, WINTER PARK FL 32789 | $1,350,000 | $358 | $1,250,000 | 3,770 | Single Family Residence | 6/5 | 22 |
| 04-12-2023 | 1694 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $405,000 | $308 | $415,000 | 1,314 | Single Family Residence | 3/2 | 142 |
| 04-12-2023 | 782 S PENNSYLVANIA AVENUE # 1, WINTER PARK FL 3278 | $625,000 | $265 | $650,000 | 2,354 | Townhouse | 3/3 | 226 |
| 04-11-2023 | 2581 SALISBURY BLVD BOULEVARD, WINTER PARK FL 3278 | $345,000 | $305 | $345,000 | 1,128 | Single Family Residence | 2/1 | 62 |
| 04-10-2023 | 2314 INAGUA WAY, WINTER PARK FL 32792 | $245,000 | $240 | $245,000 | 1,020 | Townhouse | 2/2 | 36 |
| 04-10-2023 | 1064 HOWELL BRANCH ROAD | $2,525,000 | $391 | $2,900,000 | 6,452 | Single Family Residence | 5/5 | 298 |
| 04-10-2023 | 2430 CHANTILLY AVENUE, WINTER PARK FL 32789 | $367,000 | $423 | $345,000 | 867 | Single Family Residence | 2/1 | 25 |
| 04-10-2023 | 2126 WOODCREST DRIVE, WINTER PARK FL 32792 | $397,500 | $228 | $445,000 | 1,741 | Single Family Residence | 3/2 | 243 |
| 04-10-2023 | 1793 PINEVIEW CIRCLE, WINTER PARK FL 32792 | $460,000 | $308 | $469,900 | 1,492 | Single Family Residence | 3/2 | 49 |
| 04-10-2023 | 1451 CAVENDISH ROAD, WINTER PARK FL 32789 | $400,000 | $278 | $485,000 | 1,437 | Single Family Residence | 3/2 | 67 |
| 04-10-2023 | 311 E MORSE BOULEVARD UNIT 4-4 | $640,000 | $380 | $640,000 | 1,682 | Condominium | 2/2 | 18 |
| 04-07-2023 | 1300 BUCKINGHAM ROAD, WINTER PARK FL 32789 | $640,000 | $335 | $659,900 | 1,910 | Single Family Residence | 3/3 | 132 |
| 04-06-2023 | 5405 JUSTINE WAY, WINTER PARK FL 32792 | $370,000 | $296 | $380,000 | 1,247 | Single Family Residence | 3/2 | 242 |
| 04-05-2023 | 361 BELOIT AVENUE, WINTER PARK FL 32789 | $1,500,000 | $537 | $1,475,000 | 2,793 | Single Family Residence | 3/3 | 86 |
| 04-05-2023 | 1016 TUSCANY PLACE | $1,479,000 | $469 | $1,479,000 | 3,151 | Single Family Residence | 5/4 | 62 |
| 04-05-2023 | 851 MILES AVENUE # 13, WINTER PARK FL 32789 | $187,000 | $231 | $200,000 | 808 | Condominium | 2/1 | 59 |
| 04-05-2023 | 1513 VIBURNUM LANE, WINTER PARK FL 32792 | $325,000 | $239 | $325,000 | 1,356 | Single Family Residence | 3/2 | 252 |
| 04-05-2023 | 1541 HIGHLAND ROAD, WINTER PARK FL 32789 | $850,000 | $364 | $899,000 | 2,330 | Single Family Residence | 3/2 | 149 |
| 04-05-2023 | 1541 HIGHLAND ROAD, WINTER PARK FL 32789 | $850,000 | $899,000 | / | 149 | |||
| 04-04-2023 | 168 SCOTTSDALE SQUARE # 168, WINTER PARK FL 32792 | $158,000 | $126 | $165,900 | 1,250 | Condominium | 3/2 | 29 |
| 04-04-2023 | 700 MELROSE AVENUE # 33, WINTER PARK FL 32789 | $279,000 | $259 | $249,000 | 1,074 | Condominium | 2/2 | 33 |
| 04-03-2023 | 502 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,050,000 | $406 | $1,050,000 | 2,585 | Townhouse | 3/3 | 396 |
| 04-03-2023 | 1863 MEADOWGOLD LANE, WINTER PARK FL 32792 | $400,000 | $239 | $400,000 | 1,672 | Single Family Residence | 3/2 | 62 |
| 04-02-2023 | 7421 DANIEL WEBSTER DRIVE # B, WINTER PARK FL 3279 | $159,000 | $154 | $159,000 | 1,030 | Condominium | 2/2 | 55 |
| 03-31-2023 | 1050 VIA MERANO COURT, WINTER PARK FL 32789 | $1,350,001 | $515 | $1,250,000 | 2,617 | Single Family Residence | 4/3 | 61 |
| 03-31-2023 | 243 SCOTTSDALE SQUARE # 243, WINTER PARK FL 32792 | $120,000 | $117 | $128,000 | 1,020 | Condominium | 2/2 | 64 |
| 03-31-2023 | 4842 TANGERINE AVENUE # 4842, WINTER PARK FL 32792 | $195,000 | $261 | $195,000 | 747 | Condominium | 1/1 | 29 |
| 03-31-2023 | 2500 LEE ROAD Unit 136 | $195,000 | $229 | $200,000 | 851 | Condominium | 2/1 | 71 |
| 03-31-2023 | 239 LEWFIELD CIR # 239, WINTER PARK FL 32792 | $198,000 | $207 | $200,000 | 953 | Condominium | 2/2 | 70 |
| 03-31-2023 | 2471 HARBOUR WAY, WINTER PARK FL 32792 | $240,000 | $236 | $234,777 | 1,013 | Townhouse | 2/2 | 22 |
| 03-31-2023 | 4965 N PALM AVENUE, WINTER PARK FL 32792 | $353,000 | $314 | $374,000 | 1,124 | Office | / | 248 |
| 03-31-2023 | 3431 AUSTRALIAN CIRCLE, WINTER PARK FL 32792 | $424,000 | $184 | $458,000 | 2,300 | Single Family Residence | 3/2 | 187 |
| 03-31-2023 | 4444 STEED TERRACE, WINTER PARK FL 32792 | $437,000 | $226 | $460,000 | 1,928 | Single Family Residence | 4/2 | 86 |
| 03-31-2023 | 1552 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $500,750 | $286 | $539,500 | 1,749 | Single Family Residence | 3/2 | 190 |
| 03-31-2023 | 4038 TENITA DRIVE, WINTER PARK FL 32792 | $549,000 | $263 | $599,900 | 2,082 | Single Family Residence | 3/2 | 87 |
| 03-30-2023 | 7101 GREEN NEEDLE DRIVE, WINTER PARK FL 32792 | $378,900 | $278 | $379,900 | 1,362 | Single Family Residence | 3/2 | 19 |
| 03-30-2023 | 2823 AMBERGATE ROAD, WINTER PARK FL 32792 | $450,000 | $270 | $450,000 | 1,663 | Single Family Residence | 4/2 | 51 |
| 03-30-2023 | 2810 FITZOOTH DRIVE, WINTER PARK FL 32792 | $485,000 | $272 | $485,000 | 1,777 | Single Family Residence | 4/2 | 45 |
| 03-29-2023 | 7732 FERNBROOK WAY, WINTER PARK FL 32792 | $308,000 | $231 | $323,000 | 1,332 | Townhouse | 3/3 | 123 |
| 03-28-2023 | 2417 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $365,000 | $440 | $375,000 | 829 | Single Family Residence | 2/1 | 142 |
| 03-28-2023 | 2417 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $365,000 | $375,000 | / | 142 | |||
| 03-28-2023 | 1760 OAKHURST AVENUE, WINTER PARK FL 32789 | $740,000 | $372 | $750,000 | 1,989 | Single Family Residence | 3/3 | 414 |
| 03-27-2023 | 191 SCOTTSDALE SQUARE # 191, WINTER PARK FL 32792 | $118,000 | $150 | $125,000 | 785 | Condominium | 1/1 | 19 |
| 03-27-2023 | 1742 TEMPLE DRIVE, WINTER PARK FL 32789 | $1,650,000 | $482 | $1,750,000 | 3,418 | Single Family Residence | 4/5 | 42 |
| 03-27-2023 | 356 FLEET ROAD, WINTER PARK FL 32792 | $546,000 | $294 | $569,000 | 1,853 | Single Family Residence | 3/3 | 35 |
| 03-27-2023 | 2119 BLOSSOM LANE | $875,000 | $345 | $899,999 | 2,529 | Single Family Residence | 4/2 | 209 |
| 03-24-2023 | 1920 WOODCREST DRIVE # 17, WINTER PARK FL 32792 | $146,500 | $190 | $182,784 | 768 | Condominium | 1/1 | 72 |
| 03-24-2023 | 3267 OAK LAKE PLACE # 3267, WINTER PARK FL 32792 | $200,000 | $193 | $209,900 | 1,031 | Condominium | 2/3 | 127 |
| 03-24-2023 | 1519 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $277,500 | $167 | $277,500 | 1,652 | Townhouse | 2/3 | 119 |
| 03-24-2023 | 2067 LEANNE COURT, WINTER PARK FL 32792 | $382,500 | $246 | $375,000 | 1,551 | Single Family Residence | 3/2 | 38 |
| 03-24-2023 | 690 N NEW YORK AVENUE, WINTER PARK FL 32789 | $4,100,000 | $836 | $4,600,000 | 4,901 | Single Family Residence | 4/5 | 73 |
| 03-23-2023 | 2829 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $325,000 | $268 | $335,000 | 1,210 | Single Family Residence | 2/2 | 51 |
| 03-23-2023 | 1879 VIBURNUM LANE, WINTER PARK FL 32792 | $355,000 | $289 | $378,000 | 1,227 | Single Family Residence | 3/2 | 238 |
| 03-23-2023 | 2008 NATALEN ROAD | $500,000 | $285 | $515,000 | 1,754 | Single Family Residence | 3/2 | 57 |
| 03-22-2023 | 1180 N NEW YORK AVENUE, WINTER PARK FL 32789 | $3,295,000 | $882 | $3,295,000 | 3,734 | Single Family Residence | 4/5 | 35 |
| 03-22-2023 | 1936 SUMMERFIELD ROAD | $428,600 | $285 | $425,000 | 1,503 | Single Family Residence | 3/2 | 29 |
| 03-21-2023 | 3651 N GOLDENROD ROAD # D, WINTER PARK FL 32792 | $195,000 | $232 | $210,000 | 840 | Condominium | 2/2 | 51 |
| 03-21-2023 | 700 MELROSE AVENUE # J24, WINTER PARK FL 32789 | $225,000 | $227 | $225,000 | 987 | Condominium | 1/1 | 48 |
| 03-21-2023 | 5498 PEACO PLACE, WINTER PARK FL 32792 | $235,000 | $242 | $245,000 | 968 | 1/2 Duplex | 2/1 | 93 |
| 03-21-2023 | 7792 FERNBROOK WAY, WINTER PARK FL 32792 | $250,000 | $187 | $250,000 | 1,332 | Townhouse | 3/3 | 46 |
| 03-21-2023 | 1420 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $350,000 | $172 | $389,900 | 2,031 | Single Family Residence | 3/2 | 177 |
| 03-21-2023 | 4353 STEED TERRACE, WINTER PARK FL 32792 | $585,000 | $257 | $575,000 | 2,275 | Single Family Residence | 4/2 | 61 |
| 03-21-2023 | 1331 SUFFOLK ROAD, WINTER PARK FL 32789 | $578,000 | $383 | $589,900 | 1,508 | Single Family Residence | 3/2 | 50 |
| 03-20-2023 | 2250 VENETIAN WAY | $950,000 | $520 | $1,200,000 | 1,824 | Single Family Residence | 3/2 | 60 |
| 03-20-2023 | 2250 VENETIAN WAY, WINTER PARK FL 32789 | $950,000 | $1,200,000 | / | 60 | |||
| 03-20-2023 | 1901 PALMER AVENUE, WINTER PARK FL 32792 | $405,000 | $347 | $420,000 | 1,165 | Single Family Residence | 3/1 | 154 |
| 03-20-2023 | 367 FITZHUGH ROAD, WINTER PARK FL 32792 | $830,000 | $371 | $885,000 | 2,234 | Single Family Residence | 4/3 | 195 |
| 03-17-2023 | 1636 ELIZABETHS WALK, WINTER PARK FL 32789 | $1,975,000 | $578 | $1,975,000 | 3,412 | Single Family Residence | 4/5 | 50 |
| 03-17-2023 | 5309 N WOODCREST DRIVE, WINTER PARK FL 32792 | $481,000 | $276 | $477,500 | 1,740 | Single Family Residence | 3/2 | 59 |
| 03-16-2023 | 7500 GLENMOOR LANE, WINTER PARK FL 32792 | $448,000 | $227 | $450,000 | 1,967 | Single Family Residence | 3/2 | 228 |
| 03-16-2023 | 2818 FITZOOTH DRIVE, WINTER PARK FL 32792 | $624,000 | $245 | $639,000 | 2,542 | Single Family Residence | 3/2 | 50 |
| 03-15-2023 | 678 TRINIDAD COURT, WINTER PARK FL 32792 | $165,000 | $217 | $165,000 | 759 | Condominium | 1/1 | 30 |
| 03-15-2023 | 7460 SWALLOW RUN # 42, WINTER PARK FL 32792 | $191,000 | $139 | $189,000 | 1,365 | Condominium | 2/2 | 62 |
| 03-15-2023 | 252 LEWFIELD CIRCLE # 252, WINTER PARK FL 32792 | $192,500 | $207 | $195,000 | 927 | Condominium | 2/2 | 57 |
| 03-15-2023 | 1451 BROAD WING LANE, WINTER PARK FL 32792 | $459,000 | $261 | $475,000 | 1,755 | Townhouse | 3/3 | 49 |
| 03-15-2023 | 2817 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $617,000 | $282 | $620,000 | 2,183 | Single Family Residence | 4/4 | 47 |
| 03-14-2023 | 7529 COMPASS DRIVE, WINTER PARK FL 32792 | $440,000 | $282 | $439,990 | 1,555 | Single Family Residence | 4/2 | 139 |
| 03-13-2023 | 1780 VIA PALERMO, WINTER PARK FL 32789 | $3,250,000 | $689 | $3,250,000 | 4,711 | Single Family Residence | 6/6 | 414 |
| 03-13-2023 | 1300 FORMOSA AVENUE, WINTER PARK FL 32789 | $364,900 | $400 | $364,900 | 912 | Single Family Residence | 3/1 | 96 |
| 03-13-2023 | 3039 TEMPLE TRAIL, WINTER PARK FL 32789 | $735,000 | $355 | $729,000 | 2,070 | Single Family Residence | 4/2 | 32 |
| 03-10-2023 | 510 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,608,786 | $389 | $1,599,000 | 4,130 | Single Family Residence | 4/4 | 457 |
| 03-10-2023 | 1588 GARDENIA COURT, WINTER PARK FL 32792 | $365,000 | $219 | $330,000 | 1,660 | Single Family Residence | 4/2 | 23 |
| 03-10-2023 | 2601 AMSDEN ROAD, WINTER PARK FL 32792 | $365,000 | $309 | $375,000 | 1,181 | Single Family Residence | 3/2 | 149 |
| 03-10-2023 | 1926 E HAMPTON CIRCLE, WINTER PARK FL 32792 | $430,000 | $226 | $440,000 | 1,900 | Single Family Residence | 3/2 | 127 |
| 03-10-2023 | 1545 INDIANA AVENUE # A, WINTER PARK FL 32789 | $505,000 | $314 | $523,500 | 1,606 | Condominium | 3/3 | 56 |
| 03-09-2023 | 335 BELOIT AVENUE, WINTER PARK FL 32789 | $1,100,000 | $454 | $1,150,000 | 2,420 | Single Family Residence | 3/2 | 38 |
| 03-09-2023 | 419 W MORSE BOULEVARD, WINTER PARK FL 32789 | $1,900,000 | $627 | $1,900,000 | 3,027 | Townhouse | 3/4 | 63 |
| 03-09-2023 | 439 ELLENDALE DRIVE, WINTER PARK FL 32792 | $335,000 | $165 | $325,000 | 2,028 | Single Family Residence | 3/3 | 13 |
| 03-09-2023 | 2144 N HAMPTON CIRCLE, WINTER PARK FL 32792 | $381,000 | $218 | $391,000 | 1,745 | Single Family Residence | 3/3 | 322 |
| 03-09-2023 | 2825 FITZOOTH DRIVE # 6, WINTER PARK FL 32792 | $625,000 | $265 | $610,000 | 2,356 | Single Family Residence | 4/3 | 40 |
| 03-09-2023 | 4041 YACHT CT, WINTER PARK FL 32792 | $675,000 | $292 | $645,000 | 2,309 | Single Family Residence | 5/3 | 17 |
| 03-09-2023 | $725,000 | $294 | $725,000 | 2,461 | Single Family Residence | 4/2 | 1 | |
| 03-08-2023 | 3001 NORTHWOOD BOULEVARD, WINTER PARK FL 32789 | $726,000 | $308 | $686,000 | 2,354 | Single Family Residence | 4/2 | 20 |
| 03-07-2023 | 1157 TOM GURNEY DRIVE, WINTER PARK FL 32789 | $2,100,000 | $490 | $2,350,000 | 4,285 | Single Family Residence | 5/6 | 181 |
| 03-07-2023 | 1702 GLENRIDGE WAY | $582,500 | $317 | $679,000 | 1,832 | Townhouse | 2/2 | 211 |
| 03-07-2023 | 345 W WELBOURNE AVENUE # 104, WINTER PARK FL 32789 | $931,625 | $340 | $975,000 | 2,734 | Condominium | 3/4 | 211 |
| 03-06-2023 | 2500 LEE ROAD UNIT 211 | $180,000 | $279 | $184,900 | 645 | Condominium | 1/1 | 94 |
| 03-06-2023 | 453 WARRENTON ROAD # 453, WINTER PARK FL 32792 | $275,000 | $263 | $279,900 | 1,043 | Condominium | 2/2 | 47 |
| 03-06-2023 | 1957 NOTTINGDALE LANE, WINTER PARK FL 32792 | $339,000 | $287 | $320,000 | 1,179 | Single Family Residence | 3/2 | 47 |
| 03-06-2023 | 1292 ALABAMA DRIVE | $3,750,000 | $839 | $3,900,000 | 4,467 | Single Family Residence | 5/5 | 27 |
| 03-04-2023 | $362,000 | $332 | $375,000 | 1,088 | Business | / | 45 | |
| 03-04-2023 | 1620 ORANGE AVENUE, WINTER PARK FL 32789 | $375,000 | $308 | $378,000 | 1,214 | Single Family Residence | 2/2 | 102 |
| 03-03-2023 | 2559 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $337,000 | $249 | $325,000 | 1,353 | Single Family Residence | 3/2 | 37 |
| 03-03-2023 | 2258 POINCIANA ROAD, WINTER PARK FL 32792 | $520,000 | $257 | $519,900 | 2,019 | Single Family Residence | 4/3 | 32 |
| 03-03-2023 | 1248 S PENNSYLVANIA AVENUE # 7, WINTER PARK FL 327 | $760,000 | $388 | $779,900 | 1,957 | Condominium | 3/3 | 108 |
| 03-02-2023 | 1131 DENTON ROAD, WINTER PARK FL 32792 | $445,000 | $312 | $445,000 | 1,422 | Single Family Residence | 4/2 | 281 |
| 03-01-2023 | 418 GENIUS DRIVE | $3,050,000 | $648 | $3,200,000 | 4,700 | Single Family Residence | 5/5 | 23 |
| 03-01-2023 | 2408 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $460,000 | $198 | $469,987 | 2,312 | Townhouse | 3/3 | 87 |
| 03-01-2023 | 564 S RANGER BOULEVARD, WINTER PARK FL 32792 | $725,000 | $301 | $725,000 | 2,407 | Single Family Residence | 4/3 | 57 |
| 02-28-2023 | 603 ELLEN DRIVE | $1,250,000 | $441 | $1,250,000 | 2,830 | Single Family Residence | 4/5 | 419 |
| 02-28-2023 | 315 E NEW ENGLAND AVENUE # 10, WINTER PARK FL 3278 | $1,850,000 | $946 | $1,800,000 | 1,955 | Condominium | 3/2 | 13 |
| 02-28-2023 | 1401 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $440,000 | $264 | $450,000 | 1,661 | Single Family Residence | 3/2 | 107 |
| 02-28-2023 | 1523 LITTLE WREN LANE, WINTER PARK FL 32792 | $475,000 | $199 | $485,000 | 2,378 | Townhouse | 3/3 | 19 |
| 02-28-2023 | 1858 BARKER DR, WINTER PARK FL 32789 | $547,000 | $353 | $597,900 | 1,548 | Single Family Residence | 3/2 | 166 |
| 02-28-2023 | 1647 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $625,000 | $252 | $625,000 | 2,472 | Single Family Residence | 3/2 | 160 |
| 02-28-2023 | 1790 HOLLYWOOD AVENUE, WINTER PARK FL 32789 | $680,000 | $489 | $698,500 | 1,388 | Single Family Residence | 2/2 | 36 |
| 02-28-2023 | 3048 TEMPLE TRAIL, WINTER PARK FL 32789 | $730,000 | $299 | $719,900 | 2,436 | Single Family Residence | 3/2 | 51 |
| 02-28-2023 | $7,000,000 | $1,301 | $7,200,000 | 5,377 | Single Family Residence | 4/5 | 5 | |
| 02-28-2023 | 1455 W FAIRBANKS AVENUE, WINTER PARK FL 32789 | $850,000 | $508 | $925,000 | 1,672 | Office | / | 54 |
| 02-26-2023 | 460 CLARENDON AVENUE, WINTER PARK FL 32789 | $1,550,000 | $454 | $1,550,000 | 3,412 | Single Family Residence | 5/5 | 639 |
| 02-24-2023 | 7119 IVY COURT, WINTER PARK FL 32792 | $403,000 | $230 | $409,000 | 1,746 | Single Family Residence | 3/2 | 33 |
| 02-24-2023 | 1526 BROAD WING LANE, WINTER PARK FL 32792 | $439,000 | $223 | $439,000 | 1,964 | Townhouse | 3/3 | 150 |
| 02-24-2023 | 1114 WASHINGTON AVENUE # 3, WINTER PARK FL 32789 | $440,000 | $299 | $450,000 | 1,468 | Condominium | 2/3 | 38 |
| 02-24-2023 | 5303 PINE LILY CIRCLE, WINTER PARK FL 32792 | $618,000 | $272 | $618,000 | 2,265 | Single Family Residence | 3/2 | 87 |
| 02-24-2023 | 1841 WINTER PARK ROAD, WINTER PARK FL 32789 | $772,000 | $314 | $799,900 | 2,452 | Single Family Residence | 3/2 | 102 |
| 02-23-2023 | 2840 CADY WAY, WINTER PARK FL 32792 | $375,000 | $266 | $395,000 | 1,407 | Single Family Residence | 3/2 | 35 |
| 02-22-2023 | 3264 HIDDEN GROVE LANE # 80, WINTER PARK FL 32792 | $229,800 | $222 | $229,800 | 1,031 | Townhouse | 2/3 | 69 |
| 02-22-2023 | 1847 MEADOWGOLD LANE, WINTER PARK FL 32792 | $439,900 | $257 | $439,900 | 1,708 | Single Family Residence | 4/3 | 75 |
| 02-21-2023 | 103 SCOTTSDALE SQUARE # 103, WINTER PARK FL 32792 | $128,000 | $125 | $134,900 | 1,020 | Condominium | 2/2 | 46 |
| 02-21-2023 | 250 HAMPDEN PLACE | $1,200,000 | $470 | $1,349,000 | 2,548 | Single Family Residence | 3/3 | 47 |
| 02-21-2023 | 508 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,660,000 | $401 | $1,652,000 | 4,130 | Single Family Residence | 4/4 | 587 |
| 02-21-2023 | 1520 MIZELL AVENUE | $1,850,000 | $408 | $1,999,000 | 4,526 | Single Family Residence | 5/5 | 62 |
| 02-21-2023 | 5122 N WOODCREST DRIVE, WINTER PARK FL 32792 | $415,000 | $276 | $408,600 | 1,499 | Single Family Residence | 4/2 | 154 |
| 02-21-2023 | 322 N PHELPS AVENUE, WINTER PARK FL 32789 | $665,000 | $423 | $679,900 | 1,570 | Single Family Residence | 2/2 | 107 |
| 02-17-2023 | 315 E NEW ENGLAND AVENUE # 14, WINTER PARK FL 3278 | $1,180,000 | $779 | $1,175,000 | 1,514 | Condominium | 2/2 | 18 |
| 02-17-2023 | 1741 PALMER AVENUE, WINTER PARK FL 32789 | $1,250,000 | $531 | $1,250,000 | 2,351 | Single Family Residence | 3/3 | 15 |
| 02-17-2023 | 1901 HEATHWOOD DRIVE, WINTER PARK FL 32792 | $435,000 | $277 | $445,000 | 1,565 | Single Family Residence | 3/2 | 151 |
| 02-17-2023 | 631 CALLAHAN STREET, WINTER PARK FL 32789 | $515,000 | $294 | $515,000 | 1,751 | Single Family Residence | 3/2 | 318 |
| 02-17-2023 | 1712 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $652,500 | $309 | $660,000 | 2,111 | Single Family Residence | 4/2 | 96 |
| 02-15-2023 | 1695 LEE ROAD # A104, WINTER PARK FL 32789 | $162,000 | $183 | $162,000 | 881 | Condominium | 2/1 | 43 |
| 02-15-2023 | 236 BALFOUR DRIVE # 21, WINTER PARK FL 32792 | $344,000 | $267 | $349,000 | 1,287 | Condominium | 2/2 | 58 |
| 02-14-2023 | 200 OAKWOOD WAY, WINTER PARK FL 32789 | $3,275,000 | $749 | $3,275,000 | 4,370 | Single Family Residence | 5/6 | 2 |
| 02-14-2023 | 2630 AMSDEN ROAD, WINTER PARK FL 32792 | $305,000 | $199 | $350,000 | 1,528 | Single Family Residence | 3/2 | 114 |
| 02-13-2023 | 521 GARFIELD AVENUE, WINTER PARK FL 32789 | $1,150,000 | $473 | $1,200,000 | 2,430 | Single Family Residence | 3/3 | 61 |
| 02-13-2023 | 2813 NORTHWOOD BOULEVARD, WINTER PARK FL 32789 | $1,500,000 | $435 | $1,550,000 | 3,444 | Single Family Residence | 4/4 | 143 |
| 02-13-2023 | 1381 RIDGEWOOD AVE., WINTER PARK FL 32789 | $444,375 | $453 | $495,000 | 980 | Single Family Residence | 2/1 | 63 |
| 02-13-2023 | 701 NORTHWOOD CIRCLE, WINTER PARK FL 32789 | $580,000 | $345 | $599,000 | 1,681 | Single Family Residence | 4/2 | 58 |
| 02-10-2023 | 700 MELROSE AVENUE # 23, WINTER PARK FL 32789 | $220,000 | $279 | $225,000 | 787 | Condominium | 1/1 | 36 |
| 02-10-2023 | 1831 IVY LANE, WINTER PARK FL 32792 | $330,000 | $295 | $339,900 | 1,116 | Single Family Residence | 3/1 | 58 |
| 02-10-2023 | 640 N PARK AVENUE # 31, WINTER PARK FL 32789 | $415,000 | $474 | $435,000 | 875 | Condominium | 1/1 | 44 |
| 02-10-2023 | 2112 FOSGATE DRIVE, WINTER PARK FL 32789 | $889,000 | $376 | $899,000 | 2,360 | Single Family Residence | 4/3 | 58 |
| 02-08-2023 | 2071 TEMPLE DRIVE, WINTER PARK FL 32789 | $629,512 | $333 | $650,000 | 1,889 | Single Family Residence | 3/2 | 34 |
| 02-07-2023 | 850 E LAKE SUE AVENUE, WINTER PARK FL 32789 | $3,250,000 | $611 | $3,250,000 | 5,317 | Single Family Residence | 5/6 | 22 |
| 02-07-2023 | 3025 DIKEWOOD COURT, WINTER PARK FL 32792 | $340,000 | $229 | $340,000 | 1,479 | Single Family Residence | 3/2 | 31 |
| 02-07-2023 | 7016 HAMMOCK WAY, WINTER PARK FL 32792 | $509,000 | $259 | $509,000 | 1,958 | Single Family Residence | 4/2 | 167 |
| 02-03-2023 | 315 E NEW ENGLAND AVENUE # 9, WINTER PARK FL 32789 | $1,250,000 | $763 | $1,250,000 | 1,637 | Condominium | 2/2 | 4 |
| 02-03-2023 | 1005 S PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $1,412,500 | $429 | $1,425,000 | 3,287 | Townhouse | 3/3 | 110 |
| 02-03-2023 | 2644 PASSAMONTE DRIVE # 7C, WINTER PARK FL 32792 | $335,000 | $215 | $350,000 | 1,554 | Townhouse | 3/3 | 56 |
| 02-03-2023 | 5225 ALBERT DRIVE, WINTER PARK FL 32792 | $378,500 | $220 | $400,000 | 1,716 | Single Family Residence | 3/2 | 95 |
| 02-02-2023 | 2218 FOSGATE DRIVE, WINTER PARK FL 32789 | $1,245,000 | $393 | $1,299,000 | 3,160 | Single Family Residence | 4/4 | 105 |
| 02-02-2023 | 1911 WOODCREST DRIVE # A, WINTER PARK FL 32792 | $255,000 | $258 | $265,000 | 987 | Condominium | 2/2 | 70 |
| 02-01-2023 | 1920 WOODCREST DRIVE # 7, WINTER PARK FL 32792 | $218,000 | $228 | $252,714 | 955 | Condominium | 2/2 | 86 |
| 02-01-2023 | 2828 CASA ALOMA WAY # 600, WINTER PARK FL 32792 | $275,000 | $192 | $280,000 | 1,431 | Office | / | 112 |
| 01-31-2023 | 1007 S PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $1,516,000 | $453 | $1,425,000 | 3,345 | Townhouse | 3/3 | 78 |
| 01-31-2023 | 1387 MERRYDALE WAY, WINTER PARK FL 32792 | $493,990 | $241 | $493,990 | 2,042 | Townhouse | 3/3 | 9 |
| 01-31-2023 | 1721 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $830,000 | $258 | $825,000 | 3,215 | Single Family Residence | 4/3 | 169 |
| 01-30-2023 | 1843 BARKER DRIVE, WINTER PARK FL 32789 | $500,000 | $294 | $519,900 | 1,697 | Single Family Residence | 3/2 | 144 |
| 01-27-2023 | 1050 KEYES AVENUE, WINTER PARK FL 32789 | $1,945,000 | $560 | $2,000,000 | 3,473 | Single Family Residence | 4/5 | 29 |
| 01-27-2023 | 5157 LAZY OAKS DRIVE, WINTER PARK FL 32792 | $250,000 | $248 | $255,000 | 1,008 | Condominium | 2/2 | 52 |
| 01-27-2023 | 5205 N INDIANA AVENUE, WINTER PARK FL 32792 | $367,000 | $305 | $384,000 | 1,202 | Single Family Residence | 3/2 | 161 |
| 01-27-2023 | 1905 BONANZA COURT, WINTER PARK FL 32792 | $454,900 | $256 | $454,900 | 1,774 | Single Family Residence | 4/2 | 96 |
| 01-27-2023 | 1567 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $469,500 | $207 | $469,500 | 2,266 | Single Family Residence | 3/3 | 115 |
| 01-27-2023 | 7875 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $490,000 | $216 | $525,000 | 2,268 | Single Family Residence | 4/3 | 187 |
| 01-26-2023 | 224 OVERLOOK ROAD, WINTER PARK FL 32789 | $494,000 | $353 | $499,000 | 1,399 | Single Family Residence | 2/2 | 101 |
| 01-25-2023 | 1695 LEE ROAD # B109, WINTER PARK FL 32789 | $127,000 | $199 | $134,900 | 638 | Condominium | 1/1 | 58 |
| 01-24-2023 | 3005 GEORGE MASON AVENUE # B, WINTER PARK FL 32792 | $204,000 | $150 | $200,000 | 1,356 | Condominium | 3/2 | 139 |
| 01-24-2023 | 5212 LAZY OAKS DRIVE # 5212, WINTER PARK FL 32792 | $265,000 | $214 | $259,000 | 1,236 | Condominium | 2/3 | 40 |
| 01-24-2023 | 106 S INTERLACHEN AVENUE UNIT 516 | $670,000 | $528 | $699,000 | 1,267 | Condominium | 2/2 | 88 |
| 01-20-2023 | 2390 DOMINICA RUN, WINTER PARK FL 32792 | $230,000 | $186 | $230,000 | 1,235 | Townhouse | 2/2 | 52 |
| 01-20-2023 | 151 OAKWOOD WAY, WINTER PARK FL 32789 | $2,425,000 | $587 | $2,425,000 | 4,129 | Single Family Residence | 4/5 | 3 |
| 01-20-2023 | 638 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $465,000 | $290 | $485,000 | 1,599 | Single Family Residence | 3/2 | 65 |
| 01-19-2023 | 140 LEWFIELD CIRCLE # 140, WINTER PARK FL 32792 | $160,000 | $235 | $160,000 | 678 | Condominium | 1/1 | 38 |
| 01-18-2023 | 1499 ALOMA AVENUE, WINTER PARK FL 32789 | $631,900 | $278 | $699,000 | 2,270 | Single Family Residence | 4/2 | 106 |
| 01-17-2023 | 5118 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $370,000 | $318 | $389,990 | 1,160 | Single Family Residence | 3/1 | 89 |
| 01-17-2023 | 2701 NORRIS AVENUE, WINTER PARK FL 32789 | $450,000 | $325 | $499,000 | 1,382 | Single Family Residence | 3/1 | 181 |
| 01-17-2023 | 1750 VIA TUSCANY, WINTER PARK FL 32789 | $5,500,000 | $719 | $5,795,000 | 7,644 | Single Family Residence | 6/8 | 76 |
| 01-17-2023 | 632 LANGHOLM DRIVE, WINTER PARK FL 32789 | $600,000 | $333 | $649,000 | 1,799 | Single Family Residence | 3/2 | 137 |
| 01-16-2023 | 192 SCOTTSDALE SQUARE # 192, WINTER PARK FL 32792 | $133,000 | $122 | $140,000 | 1,085 | Condominium | 2/2 | 49 |
| 01-13-2023 | 704 W COMSTOCK AVENUE, WINTER PARK FL 32789 | $1,375,000 | $414 | $1,395,000 | 3,314 | Single Family Residence | 3/5 | 73 |
| 01-12-2023 | 1420 ONECO AVENUE, WINTER PARK FL 32789 | $1,100,000 | $449 | $1,199,990 | 2,446 | Single Family Residence | 4/4 | 147 |
| 01-09-2023 | 1564 LITTLE WREN LANE, WINTER PARK FL 32792 | $474,000 | $235 | $480,000 | 2,010 | Townhouse | 3/3 | 110 |
| 01-06-2023 | 2277 ISLAND RUN, WINTER PARK FL 32792 | $225,000 | $263 | $225,000 | 854 | Townhouse | 2/1 | 85 |
| 01-06-2023 | 1971 KAROLINA AVENUE, WINTER PARK FL 32789 | $360,000 | $321 | $369,900 | 1,120 | Single Family Residence | 2/1 | 65 |
| 01-06-2023 | 2412 BEMAN COURT, WINTER PARK FL 32792 | $575,000 | $217 | $599,900 | 2,644 | Single Family Residence | 4/3 | 60 |
| 01-06-2023 | 1550 GRAND ROAD, WINTER PARK FL 32792 | $878,950 | $391 | $870,000 | 2,243 | Single Family Residence | 4/2 | 616 |
| 01-06-2023 | 3075 AARON BURR AVENUE # 8, WINTER PARK FL 32792 | $88,000 | $163 | $90,000 | 537 | Condominium | 1/1 | 26 |
| 01-05-2023 | 326 SCOTTSDALE SQUARE # 326, WINTER PARK FL 32792 | $112,000 | $103 | $145,000 | 1,085 | Condominium | 2/2 | 42 |
| 01-05-2023 | 1800 E CHERYL DRIVE, WINTER PARK FL 32792 | $455,000 | $262 | $455,000 | 1,736 | Single Family Residence | 4/2 | 163 |
| 01-05-2023 | 1570 ONECO AVENUE, WINTER PARK FL 32789 | $840,000 | $493 | $840,000 | 1,703 | Single Family Residence | 3/2 | 54 |
| 01-04-2023 | 7308 SWALLOW RUN UNIT 7308 | $177,500 | $226 | $175,000 | 784 | Condominium | 2/2 | 48 |
| 01-04-2023 | 2896 EUSTON ROAD, WINTER PARK FL 32789 | $320,000 | $229 | $335,000 | 1,392 | Single Family Residence | 3/2 | 24 |
| 01-04-2023 | 3620 JONQUIL LANE, WINTER PARK FL 32792 | $466,000 | $282 | $476,000 | 1,647 | Single Family Residence | 4/2 | 171 |
| 01-03-2023 | 5206 LAZY OAKS DRIVE # 5206, WINTER PARK FL 32792 | $285,000 | $230 | $295,500 | 1,236 | Condominium | 2/3 | 69 |
| 01-03-2023 | 470 W COMSTOCK AVENUE, WINTER PARK FL 32789 | $450,000 | $450,000 | / | 294 | |||
| 01-02-2023 | 1931 W FAIRBANKS AVENUE, WINTER PARK FL 32789 | $1,300,000 | $602 | $1,500,000 | 2,158 | Business | / | 148 |
| 01-01-2023 | 7422 WYNNEWOOD SQUARE # 196, WINTER PARK FL 32792 | $210,000 | $188 | $210,000 | 1,117 | Condominium | 3/2 | 68 |
| 12-30-2022 | 164 SCOTTSDALE SQUARE # 164, WINTER PARK FL 32792 | $126,000 | $123 | $132,900 | 1,020 | Condominium | 2/2 | 67 |
| 12-30-2022 | 700 MELROSE AVE # 23, WINTER PARK FL 32789 | $245,000 | $228 | $255,000 | 1,074 | Condominium | 2/2 | 159 |
| 12-30-2022 | 1337 PERUVIAN LANE, WINTER PARK FL 32792 | $299,900 | $223 | $299,900 | 1,340 | Single Family Residence | 3/2 | 64 |
| 12-30-2022 | 2231 ELSINORE AVENUE, WINTER PARK FL 32792 | $341,000 | $248 | $365,000 | 1,370 | Single Family Residence | 3/2 | 179 |
| 12-30-2022 | 5356 MELLOW PALM WAY, WINTER PARK FL 32792 | $527,000 | $243 | $529,000 | 2,167 | Single Family Residence | 3/2 | 28 |
| 12-30-2022 | 185 SYLVAN BOULEVARD, WINTER PARK FL 32789 | $675,000 | $675,000 | / | 2 | |||
| 12-29-2022 | 850 VIRGINIA DRIVE, WINTER PARK FL 32789 | $1,120,000 | $354 | $1,245,000 | 3,155 | Single Family Residence | 5/4 | 65 |
| 12-29-2022 | 200 SAINT ANDREWS BOULEVARD # 1805, WINTER PARK FL | $236,900 | $194 | $249,900 | 1,219 | Condominium | 2/2 | 25 |
| 12-29-2022 | 690 DUNBAR STREET, WINTER PARK FL 32789 | $340,000 | $400 | $348,500 | 850 | Single Family Residence | 2/1 | 16 |
| 12-29-2022 | 2149 LAKE DRIVE, WINTER PARK FL 32789 | $725,000 | $343 | $750,000 | 2,110 | Single Family Residence | 4/3 | 227 |
| 12-28-2022 | 4842 TANGERINE AVENUE # 4842, WINTER PARK FL 32792 | $170,000 | $227 | $175,000 | 747 | Condominium | 1/1 | 57 |
| 12-28-2022 | 2322 WOODCREST DRIVE, WINTER PARK FL 32792 | $586,000 | $348 | $595,000 | 1,681 | Single Family Residence | 4/2 | 84 |
| 12-27-2022 | 5049 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $1,100,000 | $246 | $1,100,000 | 4,462 | Single Family Residence | 4/5 | 145 |
| 12-27-2022 | 2512 LEEWARD WAY, WINTER PARK FL 32792 | $200,000 | $196 | $230,000 | 1,020 | Townhouse | 2/2 | 44 |
| 12-27-2022 | 1400 CLAY STREET, WINTER PARK FL 32789 | $305,000 | $285 | $309,999 | 1,069 | Single Family Residence | 2/1 | 100 |
| 12-27-2022 | 1507 CLEMATIS LANE, WINTER PARK FL 32792 | $300,000 | $170 | $330,000 | 1,756 | Single Family Residence | 3/2 | 19 |
| 12-27-2022 | 2641 CARVELL COURT, WINTER PARK FL 32792 | $340,000 | $159 | $350,000 | 2,126 | Single Family Residence | 4/2 | 131 |
| 12-27-2022 | 1621 PURITAN AVENUE, WINTER PARK FL 32792 | $330,000 | $186 | $360,000 | 1,765 | Single Family Residence | 4/2 | 47 |
| 12-27-2022 | 1224 DENTON ROAD, WINTER PARK FL 32792 | $420,000 | $249 | $399,000 | 1,682 | Single Family Residence | 4/2 | 224 |
| 12-25-2022 | 3322 NETHERWOOD DRIVE, WINTER PARK FL 32792 | $215,000 | $181 | $224,900 | 1,182 | 1/2 Duplex | 2/2 | 26 |
| 12-22-2022 | 1664 MEADOWGOLD COURT, WINTER PARK FL 32792 | $389,000 | $257 | $409,900 | 1,510 | Single Family Residence | 3/2 | 111 |
| 12-22-2022 | 1450 GENE STREET, WINTER PARK FL 32789 | $442,300 | $212 | $475,000 | 2,080 | Single Family Residence | 3/3 | 429 |
| 12-22-2022 | 1450 GENE STREET, WINTER PARK FL 32789 | $442,300 | $212 | $475,000 | 2,080 | Mixed Use | / | 331 |
| 12-21-2022 | 2012 HOWARD DRIVE, WINTER PARK FL 32789 | $1,031,000 | $439 | $1,029,000 | 2,344 | Single Family Residence | 3/2 | 38 |
| 12-21-2022 | 200 SAINT ANDREWS BOULEVARD # 2501, WINTER PARK FL | $280,000 | $219 | $280,000 | 1,275 | Condominium | 3/2 | 50 |
| 12-21-2022 | 506 W SWOOPE AVENUE, WINTER PARK FL 32789 | $969,325 | $374 | $969,375 | 2,585 | Townhouse | 3/3 | 420 |
| 12-20-2022 | 504 W SWOOPE AVENUE, WINTER PARK FL 32789 | $1,008,150 | $390 | $1,008,150 | 2,585 | Townhouse | 3/3 | 331 |
| 12-20-2022 | 759 S RANGER BOULEVARD, WINTER PARK FL 32792 | $640,000 | $272 | $649,000 | 2,349 | Single Family Residence | 4/3 | 47 |
| 12-19-2022 | 200 SAINT ANDREWS BOULEVARD # 1808, WINTER PARK FL | $255,000 | $201 | $275,900 | 1,266 | Condominium | 2/2 | 53 |
| 12-16-2022 | 161 SCOTTSDALE SQUARE # 161, WINTER PARK FL 32792 | $100,000 | $132 | $105,000 | 756 | Condominium | 1/1 | 58 |
| 12-16-2022 | 558 GENIUS DRIVE | $2,415,000 | $535 | $2,500,000 | 4,509 | Single Family Residence | 4/5 | 44 |
| 12-16-2022 | 200 SAINT ANDREWS BOULEVARD # 2904, WINTER PARK FL | $255,000 | $209 | $255,000 | 1,219 | Townhouse | 2/2 | 151 |
| 12-16-2022 | 3382 BOUGAINVILLEA DRIVE, WINTER PARK FL 32792 | $325,000 | $205 | $329,900 | 1,578 | Single Family Residence | 3/2 | 50 |
| 12-16-2022 | 1926 LINDEN ROAD, WINTER PARK FL 32792 | $468,000 | $243 | $479,000 | 1,920 | Single Family Residence | 4/3 | 127 |
| 12-16-2022 | 212 BLOSSOM LANE, WINTER PARK FL 32789 | $460,000 | $259 | $485,000 | 1,771 | Single Family Residence | 3/2 | 57 |
| 12-15-2022 | 7429 BELLE RIVER COURT # 15, WINTER PARK FL 32792 | $220,000 | $196 | $220,000 | 1,117 | Condominium | 3/2 | 49 |
| 12-15-2022 | 196 BALFOUR DRIVE # 4, WINTER PARK FL 32792 | $325,000 | $252 | $345,000 | 1,287 | Condominium | 2/2 | 42 |
| 12-15-2022 | 1475 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $665,529 | $370 | $725,000 | 1,797 | Single Family Residence | 3/3 | 58 |
| 12-15-2022 | 1240 S PENNSYLVANIA AVENUE UNIT 6 | $825,000 | $421 | $870,000 | 1,957 | Condominium | 3/3 | 49 |
| 12-14-2022 | 1633 PINE AVENUE, WINTER PARK FL 32789 | $1,250,000 | $503 | $1,150,000 | 2,481 | Single Family Residence | 4/4 | 28 |
| 12-14-2022 | 2929 ANTIQUE OAKS CIRCLE # 56, WINTER PARK FL 3279 | $159,888 | $213 | $169,900 | 749 | Condominium | 1/1 | 65 |
| 12-14-2022 | 1250 S DENNING DRIVE # 109, WINTER PARK FL 32789 | $199,000 | $302 | $209,900 | 658 | Condominium | 1/1 | 127 |
| 12-14-2022 | 620 GAINES WAY, WINTER PARK FL 32789 | $2,985,000 | $641 | $3,200,000 | 4,652 | Single Family Residence | 5/6 | 69 |
| 12-13-2022 | 1060 N LAKEMONT AVENUE, WINTER PARK FL 32792 | $315,000 | $298 | $315,000 | 1,056 | Single Family Residence | 3/2 | 103 |
| 12-13-2022 | 1245 W FAIRBANKS AVENUE, WINTER PARK FL 32789 | $7,995,000 | $392 | $7,995,000 | 20,384 | Office | / | 1 |
| 12-12-2022 | 1551 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $359,900 | $232 | $359,900 | 1,546 | Single Family Residence | 3/3 | 182 |
| 12-09-2022 | 1321 SUFFOLK ROAD, WINTER PARK FL 32789 | $305,000 | $317 | $340,000 | 961 | Single Family Residence | 2/1 | 46 |
| 12-09-2022 | 629 SELKIRK DRIVE, WINTER PARK FL 32792 | $600,000 | $248 | $599,000 | 2,416 | Single Family Residence | 4/3 | 50 |
| 12-08-2022 | 1520 HIGHLAND ROAD, WINTER PARK FL 32789 | $2,300,000 | $487 | $2,400,000 | 4,720 | Single Family Residence | 5/7 | 45 |
| 12-08-2022 | 1223 HARDING STREET, WINTER PARK FL 32789 | $2,600,000 | $603 | $2,595,000 | 4,309 | Single Family Residence | 4/6 | 91 |
| 12-06-2022 | 668 SAINT JOHNS COURT, WINTER PARK FL 32792 | $210,000 | $202 | $210,000 | 1,037 | Condominium | 2/2 | 28 |
| 12-06-2022 | 1000 S SEMORAN BOULEVARD # 819, WINTER PARK FL 327 | $219,700 | $219 | $219,700 | 1,003 | Condominium | 2/2 | 35 |
| 12-05-2022 | 811 DOUGLAS AVENUE, WINTER PARK FL 32789 | $335,000 | $314 | $390,000 | 1,066 | Single Family Residence | 3/2 | 218 |
| 12-05-2022 | 1702 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $423,000 | $294 | $475,000 | 1,435 | Single Family Residence | 3/2 | 31 |
| 12-01-2022 | 700 MELROSE AVENUE # 4, WINTER PARK FL 32789 | $225,000 | $227 | $225,000 | 987 | Condominium | 1/1 | 31 |
| 12-01-2022 | 1840 BISCAYNE DRIVE | $280,000 | $381 | $299,000 | 734 | Single Family Residence | 2/1 | 60 |
| 11-30-2022 | 617 CALLAHAN STREET, WINTER PARK FL 32789 | $340,000 | $399 | $395,000 | 852 | Single Family Residence | 2/1 | 168 |
| 11-30-2022 | 1364 BLUE STEM LANE, WINTER PARK FL 32792 | $609,000 | $284 | $630,000 | 2,138 | Single Family Residence | 4/4 | 90 |
| 11-30-2022 | 443 BROADVIEW AVENUE, WINTER PARK FL 32789 | $885,000 | $315 | $929,000 | 2,803 | Single Family Residence | 4/3 | 105 |
| 11-29-2022 | 100 S INTERLACHEN AVENUE UNIT 501C | $1,200,000 | $685 | $1,200,000 | 1,750 | Condominium | 2/2 | 20 |
| 11-29-2022 | 3204 NETHERWOOD DRIVE, WINTER PARK FL 32792 | $220,000 | $208 | $215,000 | 1,056 | Villa | 2/1 | 29 |
| 11-29-2022 | 715 DOUGLAS AVENUE, WINTER PARK FL 32789 | $225,000 | $280,000 | / | 518 | |||
| 11-29-2022 | 912 FAIRWAY DR, WINTER PARK FL 32792 | $420,000 | $204 | $429,999 | 2,058 | Single Family Residence | 4/2 | 77 |
| 11-28-2022 | 700 MELROSE AVENUE # K22, WINTER PARK FL 32789 | $200,000 | $259 | $200,000 | 772 | Condominium | 1/1 | 47 |
| 11-28-2022 | 151 N ORLANDO AVENUE UNIT 118 | $212,000 | $298 | $229,000 | 710 | Condominium | 2/1 | 32 |
| 11-28-2022 | 1984 JAPONICA ROAD, WINTER PARK FL 32792 | $499,000 | $248 | $499,000 | 2,011 | Single Family Residence | 4/2 | 54 |
| 11-27-2022 | 2258 POINCIANA ROAD, WINTER PARK FL 32792 | $307,000 | $152 | $307,000 | 2,019 | Single Family Residence | 4/2 | 1 |
| 11-22-2022 | 5528 ALBERT DRIVE, WINTER PARK FL 32792 | $375,500 | $250 | $374,900 | 1,500 | Single Family Residence | 4/2 | 36 |
| 11-22-2022 | 1128 WASHINGTON AVENUE # 10, WINTER PARK FL 32789 | $430,000 | $253 | $459,900 | 1,693 | Condominium | 3/3 | 109 |
| 11-22-2022 | 217 E CANTON AVENUE # 217, WINTER PARK FL 32789 | $485,000 | $458 | $495,000 | 1,057 | Condominium | 2/2 | 47 |
| 11-22-2022 | 1304 BLUE STEM LANE | $601,924 | $233 | $601,924 | 2,582 | Single Family Residence | 4/4 | 2 |
| 11-22-2022 | 325 PARK NORTH COURT, WINTER PARK FL 32789 | $925,000 | $342 | $950,000 | 2,702 | Single Family Residence | 3/3 | 131 |
| 11-21-2022 | 1217 CARVELL DRIVE, WINTER PARK FL 32792 | $375,000 | $250 | $375,000 | 1,498 | Single Family Residence | 3/2 | 60 |
| 11-21-2022 | 220 BLOSSOM LANE, WINTER PARK FL 32789 | $387,500 | $176 | $475,000 | 2,193 | Single Family Residence | 3/2 | 80 |
| 11-18-2022 | 1946 STRATHAVEN ROAD, WINTER PARK FL 32792 | $410,000 | $195 | $425,000 | 2,102 | Single Family Residence | 3/2 | 46 |
| 11-17-2022 | 680 GRENADINE COURT, WINTER PARK FL 32792 | $145,000 | $191 | $150,000 | 759 | Condominium | 1/1 | 45 |
| 11-17-2022 | 3270 OAK LAKE PLACE # 141, WINTER PARK FL 32792 | $230,000 | $199 | $235,000 | 1,151 | Condominium | 3/3 | 108 |
| 11-17-2022 | 2600 EUSTON ROAD, WINTER PARK FL 32789 | $499,000 | $158 | $499,000 | 3,145 | Single Family Residence | 6/3 | 62 |
| 11-17-2022 | 151 N ORLANDO AVENUE UNIT 212 | $580,000 | $309 | $598,000 | 1,875 | Condominium | 3/2 | 337 |
| 11-17-2022 | 2839 LION HEART ROAD, WINTER PARK FL 32792 | $670,000 | $277 | $675,000 | 2,417 | Single Family Residence | 4/3 | 64 |
| 11-17-2022 | 541 MELROSE AVENUE | $699,000 | $388 | $699,000 | 1,801 | Townhouse | 3/3 | 42 |
| 11-16-2022 | 7034 EASTER STREET, WINTER PARK FL 32792 | $140,000 | $149 | $145,000 | 936 | Mobile Home | 2/1 | 27 |
| 11-16-2022 | 2020 CORNELL AVENUE, WINTER PARK FL 32789 | $305,000 | $241 | $315,000 | 1,263 | Duplex | 3/2 | 144 |
| 11-15-2022 | 2406 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $369,000 | $223 | $379,000 | 1,649 | Single Family Residence | 3/2 | 56 |
| 11-14-2022 | 315 E NEW ENGLAND AVENUE # 23, WINTER PARK FL 3278 | $1,050,000 | $656 | $1,125,000 | 1,599 | Condominium | 2/2 | 43 |
| 11-14-2022 | 174 LEWFIELD CIRCLE # 174, WINTER PARK FL 32792 | $160,000 | $235 | $165,000 | 678 | Condominium | 1/1 | 32 |
| 11-14-2022 | 2348 WELLINGTON BOULEVARD, WINTER PARK FL 32789 | $338,000 | $212 | $375,000 | 1,594 | Single Family Residence | 3/2 | 27 |
| 11-14-2022 | 2184 CRANDON AVE, WINTER PARK FL 32789 | $411,500 | $237 | $424,900 | 1,734 | Single Family Residence | 3/2 | 40 |
| 11-14-2022 | 1049 N KENTUCKY AVENUE, WINTER PARK FL 32789 | $685,000 | $394 | $685,000 | 1,737 | Townhouse | 3/3 | 50 |
| 11-11-2022 | 1695 LEE ROAD # A111, WINTER PARK FL 32789 | $172,000 | $195 | $185,000 | 881 | Condominium | 2/1 | 41 |
| 11-10-2022 | 1251 RICHMOND ROAD | $1,510,000 | $417 | $1,595,000 | 3,613 | Single Family Residence | 3/4 | 84 |
| 11-10-2022 | 2862 KINGS DEER ROAD, WINTER PARK FL 32792 | $485,000 | $275 | $500,000 | 1,763 | Single Family Residence | 3/2 | 42 |
| 11-09-2022 | 780 ARJAY WAY, WINTER PARK FL 32789 | $1,370,000 | $427 | $1,599,999 | 3,205 | Single Family Residence | 5/5 | 78 |
| 11-09-2022 | 1920 WOODCREST DRIVE # 9, WINTER PARK FL 32792 | $240,000 | $237 | $225,000 | 1,010 | Condominium | 2/2 | 51 |
| 11-09-2022 | 2000 WHITEHALL DRIVE, WINTER PARK FL 32792 | $664,000 | $364 | $664,000 | 1,820 | Single Family Residence | 3/2 | 146 |
| 11-09-2022 | 616 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $616,000 | $360 | $695,000 | 1,708 | Single Family Residence | 4/3 | 139 |
| 11-08-2022 | 1920 CARRIGAN AVENUE, WINTER PARK FL 32792 | $235,000 | $213 | $249,900 | 1,100 | Single Family Residence | 3/2 | 69 |
| 11-04-2022 | 1635 HIGHLAND ROAD, WINTER PARK FL 32789 | $2,890,000 | $668 | $2,890,000 | 4,325 | Single Family Residence | 5/6 | 177 |
| 11-03-2022 | 1741 W CHERYL DRIVE, WINTER PARK FL 32792 | $440,000 | $283 | $440,000 | 1,550 | Single Family Residence | 3/2 | 64 |
| 11-03-2022 | 2686 BANCHORY ROAD, WINTER PARK FL 32792 | $490,000 | $295 | $469,000 | 1,656 | Single Family Residence | 3/2 | 42 |
| 11-03-2022 | 775 MCINTYRE AVENUE # 9, WINTER PARK FL 32789 | $550,000 | $268 | $560,000 | 2,052 | Condominium | 3/3 | 57 |
| 11-03-2022 | 301 GLENRIDGE WAY, WINTER PARK FL 32789 | $793,000 | $409 | $795,000 | 1,935 | Single Family Residence | 3/2 | 44 |
| 11-02-2022 | 4477 GABRIELLA LANE, WINTER PARK FL 32792 | $590,000 | $260 | $650,000 | 2,263 | Single Family Residence | 4/3 | 53 |
| 11-01-2022 | 1466 ALABAMA DRIVE, WINTER PARK FL 32789 | $2,650,000 | $722 | $2,995,000 | 3,668 | Single Family Residence | 4/5 | 68 |
| 11-01-2022 | 130 KILLARNEY BAY COURT UNIT 5-3 | $386,500 | $251 | $399,000 | 1,536 | Condominium | 2/3 | 47 |
| 11-01-2022 | 350 CAROLINA AVENUE # 103, WINTER PARK FL 32789 | $725,000 | $373 | $725,000 | 1,941 | Condominium | 2/2 | 15 |
| 10-31-2022 | 5227 SEMINOLE AVENUE, WINTER PARK FL 32792 | $260,000 | $323 | $286,000 | 804 | Single Family Residence | 3/1 | 103 |
| 10-28-2022 | 200 SAINT ANDREWS BOULEVARD # 608, WINTER PARK FL | $205,000 | $258 | $209,000 | 793 | Condominium | 1/1 | 28 |
| 10-28-2022 | 700 MELROSE AVENUE # M, WINTER PARK FL 32789 | $195,000 | $267 | $219,900 | 730 | Condominium | 1/1 | 75 |
| 10-28-2022 | 1915 WOODCREST DRIVE # D, WINTER PARK FL 32792 | $221,000 | $223 | $225,000 | 987 | Condominium | 2/2 | 72 |
| 10-28-2022 | 664 GRENADINE COURT, WINTER PARK FL 32792 | $230,000 | $170 | $245,000 | 1,350 | Condominium | 3/2 | 113 |
| 10-28-2022 | 1483 CHILEAN LANE, WINTER PARK FL 32792 | $305,000 | $308 | $310,000 | 989 | Single Family Residence | 3/2 | 53 |
| 10-28-2022 | 502 GENIUS DRIVE | $3,000,000 | $633 | $3,150,000 | 4,735 | Single Family Residence | 6/5 | 263 |
| 10-28-2022 | 1312 BLUE STEM LANE, WINTER PARK FL 32792 | $586,055 | $266 | $586,055 | 2,197 | Single Family Residence | 4/3 | 5 |
| 10-27-2022 | 200 SAINT ANDREWS BOULEVARD # 2705, WINTER PARK FL | $200,000 | $203 | $204,900 | 983 | Condominium | 2/2 | 36 |
| 10-27-2022 | 200 SAINT ANDREWS BOULEVARD # 3608, WINTER PARK FL | $255,000 | $209 | $257,000 | 1,219 | Condominium | 2/2 | 36 |
| 10-27-2022 | 3220 CROWN JEWEL COURT, WINTER PARK FL 32792 | $375,000 | $266 | $380,000 | 1,408 | Townhouse | 3/3 | 49 |
| 10-27-2022 | 7433 DANIEL WEBSTER DRIVE # 18, WINTER PARK FL 327 | $90,000 | $163 | $88,000 | 549 | Condominium | 1/1 | 22 |
| 10-26-2022 | 2879 NAPLES DRIVE, WINTER PARK FL 32789 | $330,000 | $252 | $330,000 | 1,306 | Single Family Residence | 3/2 | 140 |
| 10-26-2022 | 1719 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $345,000 | $260 | $357,750 | 1,323 | Single Family Residence | 3/2 | 145 |
| 10-26-2022 | 311 E MORSE BLVD BOULEVARD UNIT 3-5 | $610,000 | $389 | $629,000 | 1,567 | Condominium | 2/2 | 41 |
| 10-25-2022 | 330 SCOTTSDALE SQUARE # 330, WINTER PARK FL 32792 | $139,000 | $136 | $144,900 | 1,020 | Condominium | 2/2 | 68 |
| 10-25-2022 | 7453 DANIEL WEBSTER DRIVE # 5e, WINTER PARK FL 327 | $158,000 | $148 | $149,900 | 1,063 | Condominium | 2/2 | 40 |
| 10-25-2022 | 3319 ROYAL STREET, WINTER PARK FL 32792 | $240,000 | $200 | $220,000 | 1,197 | 1/2 Duplex | 3/2 | 63 |
| 10-24-2022 | 7436 WOODBURN COURT # 27, WINTER PARK FL 32792 | $195,000 | $189 | $200,000 | 1,031 | Condominium | 2/3 | 109 |
| 10-21-2022 | 277 SCOTTSDALE SQUARE # 277, WINTER PARK FL 32792 | $126,000 | $123 | $134,900 | 1,020 | Condominium | 2/2 | 107 |
| 10-21-2022 | 7707 COUNTRY PLACE, WINTER PARK FL 32792 | $249,000 | $233 | $255,000 | 1,068 | Villa | 2/2 | 71 |
| 10-21-2022 | 1188 SAWMILL COURT, WINTER PARK FL 32792 | $360,000 | $308 | $370,000 | 1,168 | Single Family Residence | 3/2 | 16 |
| 10-21-2022 | 311 E MORSE BOULEVARD UNIT 6-4 | $394,000 | $321 | $399,000 | 1,227 | Condominium | 1/1 | 117 |
| 10-20-2022 | 367 HOLT AVENUE, WINTER PARK FL 32789 | $470,000 | $380 | $449,000 | 1,234 | Single Family Residence | 3/2 | 14 |
| 10-20-2022 | 2126 N HAMPTON CIRCLE, WINTER PARK FL 32792 | $455,000 | $260 | $470,000 | 1,745 | Single Family Residence | 3/2 | 36 |
| 10-20-2022 | 2418 EUSTON ROAD, WINTER PARK FL 32789 | $465,000 | $227 | $499,000 | 2,048 | Single Family Residence | 3/3 | 114 |
| 10-19-2022 | 2437 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $470,000 | $217 | $489,000 | 2,156 | Townhouse | 3/3 | 72 |
| 10-18-2022 | 138 DETMAR DRIVE, WINTER PARK FL 32789 | $1,750,000 | $322 | $1,945,000 | 5,430 | Single Family Residence | 6/8 | 714 |
| 10-18-2022 | 2354 FLAMINGO WAY, WINTER PARK FL 32792 | $297,500 | $189 | $297,500 | 1,568 | Single Family Residence | 3/2 | 65 |
| 10-18-2022 | 5242 TANGERINE AVENUE, WINTER PARK FL 32792 | $410,000 | $232 | $405,000 | 1,764 | Single Family Residence | 4/2 | 104 |
| 10-18-2022 | 640 N PARK AVENUE # 28, WINTER PARK FL 32789 | $435,000 | $807 | $500,000 | 539 | Condominium | 1/1 | 204 |
| 10-18-2022 | 1602 ALABAMA DRIVE UNIT 304 | $700,000 | $562 | $750,000 | 1,245 | Condominium | 2/2 | 191 |
| 10-17-2022 | 1718 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $312,000 | $286 | $305,000 | 1,090 | Single Family Residence | 3/2 | 33 |
| 10-17-2022 | 5416 ALBERT DRIVE, WINTER PARK FL 32792 | $456,000 | $215 | $430,000 | 2,113 | Single Family Residence | 4/2 | 40 |
| 10-17-2022 | 2488 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $455,000 | $197 | $459,000 | 2,308 | Townhouse | 3/3 | 45 |
| 10-14-2022 | 617 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $1,745,500 | $495 | $1,819,000 | 3,523 | Single Family Residence | 5/5 | 159 |
| 10-14-2022 | 443 WARRENTON ROAD # 443, WINTER PARK FL 32792 | $270,000 | $225 | $280,000 | 1,200 | Condominium | 3/2 | 50 |
| 10-13-2022 | 7418 GRAND AVENUE, WINTER PARK FL 32792 | $380,000 | $312 | $384,900 | 1,216 | Single Family Residence | 3/2 | 126 |
| 10-13-2022 | 2536 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $420,000 | $208 | $415,000 | 2,018 | Single Family Residence | 4/2 | 86 |
| 10-13-2022 | 8412 COMMANDER COVE | $439,000 | $266 | $439,000 | 1,647 | Single Family Residence | 3/3 | 51 |
| 10-13-2022 | 540 OLOLU DRIVE | $820,000 | $736 | $839,900 | 1,114 | Single Family Residence | 2/2 | 50 |
| 10-12-2022 | 5630 S LAKE BURKETT LANE | $975,000 | $406 | $1,025,000 | 2,400 | Single Family Residence | 5/4 | 173 |
| 10-12-2022 | 315 E NEW ENGLAND AVENUE # 8, WINTER PARK FL 32789 | $1,050,000 | $654 | $1,200,000 | 1,605 | Condominium | 2/2 | 65 |
| 10-12-2022 | 301 RIPPLING LANE | $1,150,000 | $311 | $1,275,000 | 3,694 | Single Family Residence | 4/5 | 182 |
| 10-12-2022 | 2500 LEE ROAD UNIT 142 | $199,000 | $233 | $199,000 | 851 | Condominium | 2/1 | 76 |
| 10-12-2022 | 3172 CROWN JEWEL COURT, WINTER PARK FL 32792 | $370,000 | $263 | $370,000 | 1,406 | Townhouse | 3/3 | 89 |
| 10-12-2022 | 312 FOUNTAIN LANE, WINTER PARK FL 32789 | $300,000 | $224 | $410,000 | 1,337 | Single Family Residence | 3/2 | 155 |
| 10-11-2022 | 2624 EXUMA WAY, WINTER PARK FL 32792 | $233,000 | $255 | $224,900 | 912 | Townhouse | 2/1 | 26 |
| 10-11-2022 | 607 ELLEN DRIVE | $290,000 | $299,000 | / | 156 | |||
| 10-11-2022 | 3130 LOWNDES DRIVE, WINTER PARK FL 32792 | $390,000 | $325 | $395,000 | 1,200 | Single Family Residence | 3/2 | 110 |
| 10-11-2022 | 5315 N LAKE BURKETT LANE | $450,000 | $205 | $449,000 | 2,188 | Single Family Residence | 4/3 | 69 |
| 10-11-2022 | 423 LONDON ROAD, WINTER PARK FL 32792 | $425,000 | $138 | $490,000 | 3,072 | Single Family Residence | 3/3 | 88 |
| 10-07-2022 | 622 PENN PLACE, WINTER PARK FL 32789 | $825,000 | $298 | $1,050,000 | 2,767 | Single Family Residence | 3/3 | 149 |
| 10-07-2022 | 142 SCOTTSDALE SQUARE # 142, WINTER PARK FL 32792 | $115,000 | $105 | $125,000 | 1,085 | Condominium | 2/2 | 89 |
| 10-07-2022 | 145 SCOTTSDALE SQUARE # 145, WINTER PARK FL 32792 | $138,000 | $135 | $150,000 | 1,020 | Condominium | 2/2 | 75 |
| 10-07-2022 | 1491 W FAIRBANKS AVENUE, WINTER PARK FL 32789 | $1,100,000 | $433 | $1,600,000 | 2,536 | Office | / | 219 |
| 10-07-2022 | 2650 EUSTON ROAD, WINTER PARK FL 32789 | $346,000 | $176 | $396,000 | 1,961 | Single Family Residence | 4/2 | 366 |
| 10-07-2022 | 269 BLOSSOM LANE, WINTER PARK FL 32789 | $440,000 | $264 | $445,000 | 1,666 | Single Family Residence | 3/2 | 87 |
| 10-07-2022 | 1680 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $455,000 | $242 | $459,900 | 1,878 | Single Family Residence | 3/2 | 82 |
| 10-07-2022 | 645 MINNESOTA AVENUE, WINTER PARK FL 32789 | $475,000 | $344 | $475,000 | 1,380 | Single Family Residence | 3/2 | 85 |
| 10-07-2022 | 645 MINNESOTA AVENUE, WINTER PARK FL 32789 | $475,000 | $475,000 | / | 85 | |||
| 10-07-2022 | 1409 SUNSET DRIVE, WINTER PARK FL 32789 | $435,000 | $467 | $475,000 | 931 | Single Family Residence | 2/1 | 102 |
| 10-07-2022 | 710 W WEBSTER AVENUE, WINTER PARK FL 32789 | $490,000 | $415 | $495,000 | 1,178 | Single Family Residence | 3/2 | 36 |
| 10-07-2022 | 311 E MORSE BOULEVARD UNIT 6-1 | $565,000 | $379 | $599,000 | 1,488 | Condominium | 2/2 | 169 |
| 10-06-2022 | 2398 DOMINICA RUN, WINTER PARK FL 32792 | $249,900 | $193 | $249,900 | 1,290 | Townhouse | 2/2 | 55 |
| 10-06-2022 | 2538 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $320,000 | $223 | $300,000 | 1,430 | Single Family Residence | 4/2 | 17 |
| 10-06-2022 | 2212 FAIRGLENN WAY, WINTER PARK FL 32792 | $454,900 | $201 | $454,900 | 2,258 | Single Family Residence | 4/3 | 57 |
| 10-05-2022 | 5091 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $1,450,000 | $439 | $1,450,000 | 3,300 | Single Family Residence | 3/4 | 44 |
| 10-05-2022 | 280 E LAKE SUE AVENUE, WINTER PARK FL 32789 | $1,789,900 | $523 | $1,789,900 | 3,422 | Single Family Residence | 5/4 | 104 |
| 10-05-2022 | 1918 LOCH BERRY ROAD, WINTER PARK FL 32792 | $535,000 | $308 | $528,000 | 1,737 | Single Family Residence | 4/2 | 73 |
| 10-05-2022 | 3329 BENNINGTON COURT, WINTER PARK FL 32792 | $570,000 | $232 | $589,900 | 2,453 | Single Family Residence | 4/3 | 56 |
| 10-04-2022 | 1405 CHAPMAN CIRCLE, WINTER PARK FL 32789 | $1,250,000 | $427 | $1,316,250 | 2,925 | Single Family Residence | 3/4 | 44 |
| 10-04-2022 | 4806 TANGERINE AVENUE # 4806, WINTER PARK FL 32792 | $200,000 | $189 | $199,900 | 1,058 | Condominium | 2/2 | 31 |
| 10-04-2022 | 151 N ORLANDO AVENUE UNIT 102 | $252,000 | $354 | $259,000 | 710 | Condominium | 2/1 | 65 |
| 10-04-2022 | 7101 GREEN NEEDLE DRIVE, WINTER PARK FL 32792 | $264,000 | $195 | $285,000 | 1,352 | Single Family Residence | 3/2 | 116 |
| 10-04-2022 | 1131 VIA LUGANO, WINTER PARK FL 32789 | $3,005,000 | $527 | $3,250,000 | 5,701 | Single Family Residence | 4/5 | 158 |
| 10-04-2022 | 3904 WOODGLADE COVE, WINTER PARK FL 32792 | $415,000 | $200 | $420,000 | 2,072 | Single Family Residence | 4/2 | 54 |
| 10-04-2022 | 617 S PHELPS AVENUE, WINTER PARK FL 32789 | $796,000 | $375 | $789,100 | 2,118 | Single Family Residence | 3/2 | 47 |
| 10-04-2022 | 1336 SUNSET DRIVE, WINTER PARK FL 32789 | $1,037,500 | $379 | $995,000 | 2,732 | Single Family Residence | 4/3 | 48 |
| 10-03-2022 | 640 PENN PLACE, WINTER PARK FL 32789 | $2,075,000 | $509 | $2,049,000 | 4,074 | Single Family Residence | 4/3 | 53 |
| 10-03-2022 | 472 FLETCHER PLACE, WINTER PARK FL 32789 | $2,125,000 | $495 | $2,100,000 | 4,286 | Single Family Residence | 4/5 | 102 |
| 10-03-2022 | 3410 HAMLET LOOP | $382,500 | $258 | $385,000 | 1,482 | Single Family Residence | 3/3 | 27 |
| 10-03-2022 | 541 W CANTON AVENUE, WINTER PARK FL 32789 | $515,000 | $582 | $539,000 | 884 | Single Family Residence | 2/1 | 155 |
| 10-03-2022 | 541 W CANTON AVENUE, WINTER PARK FL 32789 | $515,000 | $539,000 | / | 154 | |||
| 10-03-2022 | 2204 FAIRGLENN WAY, WINTER PARK FL 32792 | $540,000 | $229 | $575,000 | 2,358 | Single Family Residence | 4/2 | 33 |
| 10-03-2022 | 640 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $749,000 | $360 | $749,900 | 2,080 | Single Family Residence | 4/2 | 60 |
| 09-30-2022 | 126 SCOTTSDALE SQUARE # 126, WINTER PARK FL 32792 | $140,000 | $129 | $150,000 | 1,085 | Condominium | 2/2 | 133 |
| 09-30-2022 | 1829 HARLAND PARK DRIVE | $1,610,000 | $474 | $1,550,000 | 3,393 | Single Family Residence | 5/4 | 31 |
| 09-30-2022 | 1875 BISCAYNE DRIVE, WINTER PARK FL 32789 | $385,000 | $280 | $399,000 | 1,375 | Single Family Residence | 3/2 | 71 |
| 09-30-2022 | 1418 LONE FEATHER TRAIL, WINTER PARK FL 32792 | $555,428 | $252 | $555,428 | 2,197 | Single Family Residence | 4/3 | 13 |
| 09-28-2022 | 2138 BLOSSOM LANE, WINTER PARK FL 32789 | $485,000 | $297 | $485,000 | 1,629 | Single Family Residence | 3/2 | 42 |
| 09-27-2022 | 662 CALLAHAN STREET, WINTER PARK FL 32789 | $306,000 | $360 | $329,000 | 850 | Single Family Residence | 2/1 | 72 |
| 09-26-2022 | 2407 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $1,500,000 | $478 | $1,590,000 | 3,133 | Single Family Residence | 5/5 | 79 |
| 09-26-2022 | 2310 INAGUA WAY, WINTER PARK FL 32792 | $230,000 | $225 | $230,000 | 1,020 | Townhouse | 2/2 | 67 |
| 09-26-2022 | 2780 LAKE HOWELL LANE | $2,895,000 | $475 | $2,995,000 | 6,090 | Single Family Residence | 8/6 | 187 |
| 09-26-2022 | 3604/3606 LEANNE COURT, WINTER PARK FL 32792 | $415,000 | $198 | $449,999 | 2,094 | Duplex | 6/4 | 89 |
| 09-26-2022 | 1368 HIBISCUS AVENUE, WINTER PARK FL 32789 | $700,000 | $313 | $700,000 | 2,230 | Single Family Residence | 4/3 | 13 |
| 09-23-2022 | 1000 S SEMORAN BOULEVARD # 412, WINTER PARK FL 327 | $140,000 | $180 | $135,000 | 776 | Condominium | 1/1 | 39 |
| 09-23-2022 | 4858 SEMINOLE AVENUE, WINTER PARK FL 32792 | $278,000 | $211 | $289,900 | 1,313 | Single Family Residence | 2/2 | 51 |
| 09-23-2022 | 5517 JUSTINE WAY, WINTER PARK FL 32792 | $351,000 | $270 | $339,900 | 1,300 | Single Family Residence | 3/2 | 36 |
| 09-23-2022 | 760 DOUGLAS AVENUE, WINTER PARK FL 32789 | $400,000 | $299 | $400,000 | 1,334 | Single Family Residence | 3/1 | 41 |
| 09-23-2022 | 1361 HEAVENLY COVE, WINTER PARK FL 32792 | $775,000 | $254 | $785,000 | 3,044 | Single Family Residence | 4/3 | 37 |
| 09-23-2022 | 667 DUNBLANE DRIVE, WINTER PARK FL 32792 | $770,000 | $381 | $799,000 | 2,017 | Single Family Residence | 3/2 | 41 |
| 09-22-2022 | 617 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $650,000 | $304 | $650,000 | 2,134 | Single Family Residence | 4/4 | 43 |
| 09-21-2022 | 1695 LEE ROAD # E115, WINTER PARK FL 32789 | $180,000 | $156 | $180,000 | 1,149 | Condominium | 3/2 | 29 |
| 09-21-2022 | 5660 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $360,000 | $321 | $359,900 | 1,120 | Single Family Residence | 3/2 | 92 |
| 09-21-2022 | 2234 KING CHARLES COURT, WINTER PARK FL 32792 | $470,000 | $276 | $455,000 | 1,697 | Single Family Residence | 4/2 | 35 |
| 09-20-2022 | 2723 ALOMA AVENUE, WINTER PARK FL 32792 | $312,000 | $249 | $325,000 | 1,252 | Single Family Residence | 3/2 | 47 |
| 09-20-2022 | 2019 STRATHAVEN ROAD, WINTER PARK FL 32792 | $505,000 | $225 | $525,000 | 2,241 | Single Family Residence | 4/3 | 86 |
| 09-19-2022 | 363 HENKEL CIRCLE, WINTER PARK FL 32789 | $1,050,000 | $371 | $1,195,000 | 2,829 | Single Family Residence | 5/3 | 82 |
| 09-19-2022 | 602 GENIUS DRIVE | $2,295,000 | $523 | $2,350,000 | 4,388 | Single Family Residence | 5/5 | 53 |
| 09-16-2022 | 3011 GEORGE MASON AVENUE # 3, WINTER PARK FL 32792 | $178,995 | $169 | $178,995 | 1,056 | Condominium | 2/2 | 56 |
| 09-16-2022 | 200 SAINT ANDREWS BOULEVARD # 908, WINTER PARK FL | $190,000 | $239 | $190,000 | 793 | Condominium | 1/1 | 29 |
| 09-16-2022 | 1711 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $282,000 | $193 | $270,000 | 1,460 | Townhouse | 2/2 | 36 |
| 09-16-2022 | 7542 CRANES CREEK COURT, WINTER PARK FL 32792 | $324,000 | $220 | $324,000 | 1,471 | Townhouse | 3/3 | 3 |
| 09-16-2022 | 1712 LOOKOUT LANDING CIRCLE | $3,500,000 | $675 | $3,400,000 | 5,179 | Single Family Residence | 5/7 | 71 |
| 09-16-2022 | 2625 ALOMA AVENUE, WINTER PARK FL 32792 | $450,000 | $284 | $460,000 | 1,584 | Single Family Residence | 3/3 | 39 |
| 09-16-2022 | 1583 ORANGE AVENUE, WINTER PARK FL 32789 | $500,000 | $334 | $525,000 | 1,495 | Single Family Residence | 3/2 | 81 |
| 09-16-2022 | 1421 SUNSET DRIVE, WINTER PARK FL 32789 | $650,000 | $388 | $697,500 | 1,672 | Single Family Residence | 3/4 | 61 |
| 09-15-2022 | 1000 S SEMORAN BOULEVARD # 703, WINTER PARK FL 327 | $157,000 | $213 | $164,900 | 735 | Condominium | 1/1 | 130 |
| 09-15-2022 | 7732 FERNBROOK WAY, WINTER PARK FL 32792 | $182,000 | $136 | $175,000 | 1,332 | Townhouse | 3/3 | 17 |
| 09-15-2022 | 1807 LINDEN ROAD, WINTER PARK FL 32792 | $330,000 | $290 | $330,000 | 1,135 | Single Family Residence | 3/1 | 114 |
| 09-15-2022 | 3137 CROWN JEWEL COURT, WINTER PARK FL 32792 | $371,500 | $263 | $375,000 | 1,408 | Townhouse | 3/3 | 56 |
| 09-15-2022 | 5153 ARDMORE DRIVE, WINTER PARK FL 32792 | $432,000 | $255 | $419,000 | 1,689 | Single Family Residence | 4/2 | 31 |
| 09-15-2022 | 233 CAMBRIDGE BOULEVARD, WINTER PARK FL 32789 | $510,000 | $356 | $499,990 | 1,432 | Single Family Residence | 3/2 | 36 |
| 09-15-2022 | 8077 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $680,000 | $211 | $675,000 | 3,215 | Single Family Residence | 4/4 | 51 |
| 09-14-2022 | 214 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $220,000 | $169 | $225,000 | 1,300 | Condominium | 2/3 | 40 |
| 09-14-2022 | 178 BALFOUR DRIVE # 5, WINTER PARK FL 32792 | $320,000 | $292 | $315,000 | 1,094 | Condominium | 2/2 | 29 |
| 09-14-2022 | 619 ELLENDALE DRIVE, WINTER PARK FL 32792 | $370,000 | $272 | $380,000 | 1,356 | Single Family Residence | 3/2 | 65 |
| 09-13-2022 | 2511 PASSAMONTE DRIVE # 4C, WINTER PARK FL 32792 | $326,000 | $209 | $345,900 | 1,554 | Condominium | 3/3 | 63 |
| 09-12-2022 | 4814 TANGERINE AVENUE # 4814, WINTER PARK FL 32792 | $200,000 | $189 | $195,000 | 1,058 | Condominium | 2/2 | 81 |
| 09-12-2022 | 2013 PONDEROSA AVENUE, WINTER PARK FL 32792 | $350,000 | $253 | $355,000 | 1,378 | Single Family Residence | 4/2 | 82 |
| 09-09-2022 | 2300 BARBADOS DRIVE, WINTER PARK FL 32792 | $225,000 | $180 | $235,000 | 1,250 | Townhouse | 2/3 | 23 |
| 09-09-2022 | 690 OSCEOLA AVENUE UNIT 502 | $295,000 | $210 | $349,900 | 1,400 | Condominium | 2/2 | 124 |
| 09-09-2022 | 3437 BOWMAN DRIVE, WINTER PARK FL 32792 | $350,000 | $261 | $369,000 | 1,336 | Single Family Residence | 3/2 | 47 |
| 09-09-2022 | 306 FOUNTAIN LANE, WINTER PARK FL 32789 | $383,000 | $305 | $383,000 | 1,255 | Single Family Residence | 3/2 | 43 |
| 09-09-2022 | 5230 ARDMORE DRIVE, WINTER PARK FL 32792 | $415,000 | $236 | $425,000 | 1,755 | Single Family Residence | 4/2 | 51 |
| 09-09-2022 | 2372 SHADOWLAND LOOP, WINTER PARK FL 32792 | $435,000 | $247 | $440,000 | 1,755 | Townhouse | 3/3 | 39 |
| 09-09-2022 | 2811 WILL O TH GREEN, WINTER PARK FL 32792 | $445,000 | $300 | $450,000 | 1,483 | Single Family Residence | 4/2 | 36 |
| 09-09-2022 | 3138 LOWNDES DRIVE, WINTER PARK FL 32792 | $450,000 | $257 | $460,000 | 1,749 | Single Family Residence | 4/2 | 36 |
| 09-08-2022 | 1796 E CHERYL DRIVE, WINTER PARK FL 32792 | $340,000 | $178 | $350,000 | 1,906 | Single Family Residence | 3/2 | 11 |
| 09-08-2022 | 3336 ELLWOOD COURT, WINTER PARK FL 32792 | $426,000 | $306 | $425,000 | 1,391 | Single Family Residence | 3/2 | 28 |
| 09-07-2022 | 3651 N GOLDENROD ROAD # B107, WINTER PARK FL 32792 | $185,000 | $196 | $199,000 | 940 | Condominium | 2/2 | 270 |
| 09-07-2022 | 2308 DUNBURY COURT, WINTER PARK FL 32792 | $417,000 | $252 | $437,000 | 1,651 | Single Family Residence | 4/2 | 51 |
| 09-07-2022 | 2563 FIFESHIRE DRIVE, WINTER PARK FL 32792 | $445,000 | $201 | $500,000 | 2,212 | Single Family Residence | 4/3 | 146 |
| 09-07-2022 | 1800 MIZELL AVENUE, WINTER PARK FL 32789 | $775,000 | $475 | $775,000 | 1,630 | Single Family Residence | 3/2 | 35 |
| 09-06-2022 | $3,400,000 | $817 | $3,400,000 | 4,160 | Townhouse | 3/5 | 1 | |
| 09-06-2022 | 125 S INTERLACHEN AVE. # 1, WINTER PARK FL 32789 | $3,400,000 | $817 | $3,450,000 | 4,160 | Townhouse | 3/5 | 68 |
| 09-06-2022 | 1550 INDIANA AVENUE, WINTER PARK FL 32789 | $388,000 | $375 | $399,900 | 1,032 | Single Family Residence | 3/2 | 46 |
| 09-06-2022 | 7536 VILLAGE GREEN DRIVE, WINTER PARK FL 32792 | $495,000 | $300 | $492,000 | 1,647 | Single Family Residence | 3/2 | 56 |
| 09-05-2022 | 4872 TANGERINE AVENUE # 4872, WINTER PARK FL 32792 | $170,000 | $225 | $149,900 | 753 | Condominium | 1/1 | 78 |
| 09-01-2022 | 3053 GEORGE MASON AVENUE # 8, WINTER PARK FL 32792 | $148,000 | $143 | $145,000 | 1,030 | Condominium | 2/2 | 44 |
| 09-01-2022 | 450 OLOLU DRIVE, WINTER PARK FL 32789 | $1,599,999 | $320 | $1,599,900 | 4,988 | Single Family Residence | 5/6 | 360 |
| 09-01-2022 | 1768 MEADOWGOLD LANE, WINTER PARK FL 32792 | $355,000 | $297 | $359,900 | 1,192 | Single Family Residence | 3/2 | 59 |
| 09-01-2022 | 2145 LAKE DRIVE # 26, WINTER PARK FL 32789 | $425,000 | $251 | $450,000 | 1,693 | Single Family Residence | 3/2 | 66 |
| 08-31-2022 | 2707 EASTERN PARKWAY, WINTER PARK FL 32789 | $1,295,000 | $470 | $1,374,900 | 2,750 | Single Family Residence | 4/4 | 47 |
| 08-31-2022 | 147 S INTERLACHEN AVENUE # 101, WINTER PARK FL 327 | $2,100,000 | $633 | $1,995,000 | 3,317 | Condominium | 4/5 | 69 |
| 08-31-2022 | 1250 S DENNING DRIVE # 125, WINTER PARK FL 32789 | $212,000 | $236 | $212,000 | 898 | Condominium | 2/2 | 18 |
| 08-31-2022 | 2612 PASSAMONTE DRIVE # 8C, WINTER PARK FL 32792 | $325,000 | $209 | $335,000 | 1,554 | Condominium | 3/3 | 25 |
| 08-31-2022 | 1320 N LAKEMONT AVENUE, WINTER PARK FL 32792 | $375,000 | $347 | $380,000 | 1,079 | Single Family Residence | 3/1 | 35 |
| 08-31-2022 | 2500 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $355,000 | $225 | $389,000 | 1,576 | Single Family Residence | 3/2 | 99 |
| 08-31-2022 | 7616 UNIVERSITY GARDEN DRIVE, WINTER PARK FL 32792 | $673,000 | $206 | $675,000 | 3,266 | Triplex | 6/7 | 30 |
| 08-30-2022 | 151 N ORLANDO AVENUE UNIT 207 | $225,000 | $316 | $230,000 | 710 | Condominium | 2/1 | 40 |
| 08-30-2022 | 2265 S LEE ROAD # 205A, WINTER PARK FL 32789 | $239,000 | $210 | $249,000 | 1,134 | Mixed Use | / | 90 |
| 08-30-2022 | 200 SAINT ANDREWS BOULEVARD # 3308, WINTER PARK FL | $250,000 | $197 | $289,990 | 1,266 | Condominium | 2/2 | 65 |
| 08-30-2022 | 2248 ELSINORE AVENUE, WINTER PARK FL 32792 | $360,000 | $231 | $375,000 | 1,557 | Single Family Residence | 4/3 | 233 |
| 08-29-2022 | 1814 PINEVIEW CIRCLE, WINTER PARK FL 32792 | $450,000 | $269 | $475,000 | 1,669 | Single Family Residence | 3/2 | 60 |
| 08-26-2022 | 1229 PARK GREEN PLACE, WINTER PARK FL 32789 | $311,000 | $208 | $299,900 | 1,495 | Townhouse | 2/2 | 37 |
| 08-26-2022 | 5031 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $400,000 | $282 | $400,000 | 1,416 | Single Family Residence | 3/2 | 53 |
| 08-26-2022 | 2855 CADY WAY, WINTER PARK FL 32792 | $505,000 | $290 | $525,000 | 1,736 | Single Family Residence | 3/2 | 64 |
| 08-25-2022 | 664 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $476,000 | $252 | $424,900 | 1,882 | Single Family Residence | 3/2 | 21 |
| 08-25-2022 | 792 W SWOOPE AVENUE # 4, WINTER PARK FL 32789 | $835,000 | $349 | $849,900 | 2,389 | Single Family Residence | 4/4 | 77 |
| 08-25-2022 | 266 W LYMAN AVENUE, WINTER PARK FL 32789 | $980,000 | $490 | $995,000 | 2,000 | Townhouse | 3/3 | 21 |
| 08-24-2022 | 1595 LITTLE WREN LANE, WINTER PARK FL 32792 | $480,000 | $202 | $489,000 | 2,376 | Townhouse | 3/3 | 91 |
| 08-24-2022 | 4473 GABRIELLA LANE, WINTER PARK FL 32792 | $515,000 | $188 | $550,000 | 2,730 | Single Family Residence | 4/3 | 36 |
| 08-24-2022 | 213 SCOTTSDALE SQUARE # 213, WINTER PARK FL 32792 | $97,000 | $123 | $99,000 | 785 | Condominium | 1/1 | 51 |
| 08-23-2022 | 296 LEWFIELD CIRCLE # 296, WINTER PARK FL 32792 | $160,000 | $235 | $160,000 | 678 | Condominium | 1/1 | 40 |
| 08-23-2022 | 2309 DEVON COURT, WINTER PARK FL 32789 | $310,000 | $245 | $329,900 | 1,264 | Single Family Residence | 2/1 | 96 |
| 08-23-2022 | 301 CORNWALL ROAD, WINTER PARK FL 32792 | $512,000 | $310 | $537,000 | 1,648 | Single Family Residence | 3/2 | 44 |
| 08-23-2022 | 1321 BLUE STEM LANE, WINTER PARK FL 32792 | $642,623 | $292 | $642,623 | 2,197 | Single Family Residence | 4/3 | 9 |
| 08-22-2022 | 750 KILLARNEY BAY COURT UNIT 1 | $300,000 | $263 | $315,000 | 1,140 | Condominium | 2/2 | 81 |
| 08-22-2022 | 770 JULIAN STREET, WINTER PARK FL 32789 | $445,000 | $294 | $449,900 | 1,512 | Single Family Residence | 3/3 | 41 |
| 08-22-2022 | 3810 WATERVIEW LOOP, WINTER PARK FL 32792 | $420,000 | $245 | $455,000 | 1,708 | Single Family Residence | 3/2 | 120 |
| 08-22-2022 | 350 CAROLINA AVENUE # 103, WINTER PARK FL 32789 | $705,000 | $363 | $689,000 | 1,941 | Condominium | 2/2 | 39 |
| 08-19-2022 | 1347 CHAPMAN CIRCLE | $1,205,000 | $412 | $1,275,000 | 2,922 | Single Family Residence | 4/4 | 43 |
| 08-19-2022 | 664 OSCEOLA AVENUE UNIT 302 | $1,800,000 | $662 | $1,999,000 | 2,715 | Condominium | 3/4 | 64 |
| 08-19-2022 | 2561 ROXBURY ROAD, WINTER PARK FL 32789 | $305,000 | $342 | $289,000 | 890 | Single Family Residence | 2/1 | 37 |
| 08-19-2022 | 535 N INTERLACHEN AVENUE # 307, WINTER PARK FL 327 | $465,000 | $480 | $485,000 | 968 | Condominium | 2/2 | 101 |
| 08-19-2022 | 300 CAROLINA AVENUE # 206, WINTER PARK FL 32789 | $700,000 | $536 | $700,000 | 1,305 | Condominium | 2/2 | 15 |
| 08-18-2022 | 611 SAINT JOHNS COURT # 611, WINTER PARK FL 32792 | $206,600 | $184 | $204,900 | 1,120 | Condominium | 2/2 | 28 |
| 08-18-2022 | 1401 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $345,000 | $207 | $335,000 | 1,661 | Single Family Residence | 3/2 | 37 |
| 08-17-2022 | 5503 ALBERT DRIVE, WINTER PARK FL 32792 | $367,500 | $269 | $365,000 | 1,366 | Single Family Residence | 4/2 | 42 |
| 08-17-2022 | 5140 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $418,000 | $272 | $418,000 | 1,536 | Single Family Residence | 4/2 | 164 |
| 08-17-2022 | 233 LINCOLNSHIRE, WINTER PARK FL 32792 | $495,000 | $221 | $485,000 | 2,236 | Single Family Residence | 4/2 | 114 |
| 08-16-2022 | 427 W MORSE BOULEVARD, WINTER PARK FL 32789 | $1,800,000 | $594 | $1,900,000 | 3,027 | Townhouse | 3/4 | 60 |
| 08-16-2022 | 7478 CANFORD COURT # 11, WINTER PARK FL 32792 | $230,000 | $165 | $239,500 | 1,393 | Condominium | 2/2 | 61 |
| 08-15-2022 | 664 PENN PLACE, WINTER PARK FL 32789 | $1,100,000 | $421 | $1,149,000 | 2,607 | Single Family Residence | 3/3 | 60 |
| 08-15-2022 | 7555 CRANES CREEK COURT, WINTER PARK FL 32792 | $316,000 | $214 | $310,000 | 1,471 | Townhouse | 3/3 | 39 |
| 08-15-2022 | 8422 COMMANDER COVE | $465,000 | $262 | $445,000 | 1,770 | Single Family Residence | 4/3 | 33 |
| 08-15-2022 | 283 N RANGER BOULEVARD, WINTER PARK FL 32792 | $549,000 | $356 | $549,000 | 1,542 | Single Family Residence | 3/2 | 52 |
| 08-12-2022 | 240 CAMBRIDGE BOULEVARD, WINTER PARK FL 32789 | $499,000 | $306 | $505,000 | 1,630 | Single Family Residence | 3/2 | 131 |
| 08-12-2022 | 689 S LAKEMONT AVENUE, WINTER PARK FL 32792 | $569,000 | $335 | $569,900 | 1,698 | Single Family Residence | 3/3 | 96 |
| 08-12-2022 | 743 LONDON ROAD, WINTER PARK FL 32792 | $643,000 | $303 | $649,000 | 2,121 | Single Family Residence | 4/2 | 51 |
| 08-11-2022 | 2709 EASTHAM ROAD, WINTER PARK FL 32792 | $384,000 | $317 | $389,000 | 1,209 | Single Family Residence | 3/2 | 118 |
| 08-10-2022 | 343 SCOTTSDALE SQUARE # 343, WINTER PARK FL 32792 | $110,000 | $107 | $120,000 | 1,020 | Condominium | 2/2 | 24 |
| 08-10-2022 | 200 ST ANDREWS BOULEVARD # 1307, WINTER PARK FL 32 | $265,000 | $222 | $254,000 | 1,190 | Condominium | 3/2 | 23 |
| 08-10-2022 | 220 KILLARNEY BAY COURT UNIT 2 | $317,000 | $278 | $300,000 | 1,140 | Condominium | 2/2 | 28 |
| 08-10-2022 | 1411 NORFOLK AVENUE, WINTER PARK FL 32789 | $450,000 | $317 | $469,900 | 1,417 | Single Family Residence | 3/1 | 71 |
| 08-10-2022 | 2812 BANCHORY ROAD, WINTER PARK FL 32792 | $521,000 | $272 | $499,999 | 1,914 | Single Family Residence | 3/2 | 34 |
| 08-09-2022 | 128 SANDLEWOOD TRAIL # 6, WINTER PARK FL 32789 | $260,000 | $229 | $265,000 | 1,133 | Condominium | 2/3 | 40 |
| 08-09-2022 | 2500 LEE ROAD UNIT 226 | $265,000 | $277 | $269,900 | 956 | Condominium | 2/2 | 76 |
| 08-08-2022 | 2032 TEMPLE DRIVE, WINTER PARK FL 32789 | $1,345,000 | $458 | $1,350,000 | 2,931 | Single Family Residence | 4/4 | 60 |
| 08-08-2022 | 1802 STONEHURST ROAD, WINTER PARK FL 32789 | $1,600,000 | $434 | $1,695,000 | 3,681 | Single Family Residence | 4/4 | 73 |
| 08-08-2022 | 7913 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $545,000 | $272 | $549,000 | 2,003 | Single Family Residence | 4/2 | 39 |
| 08-05-2022 | 315 E NEW ENGLAND AVENUE # 5, WINTER PARK FL 32789 | $2,350,000 | $719 | $2,350,000 | 3,266 | Condominium | 3/4 | 42 |
| 08-05-2022 | 1989 BISCAYNE DRIVE, WINTER PARK FL 32789 | $386,500 | $317 | $400,000 | 1,219 | Single Family Residence | 2/2 | 75 |
| 08-05-2022 | 1541 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $430,000 | $284 | $415,000 | 1,513 | Single Family Residence | 3/3 | 50 |
| 08-05-2022 | 2330 WESTMINSTER CT, WINTER PARK FL 32789 | $530,000 | $160 | $575,000 | 3,296 | Single Family Residence | 4/3 | 58 |
| 08-05-2022 | 1770 ANZLE AVENUE, WINTER PARK FL 32789 | $575,000 | $282 | $599,000 | 2,032 | Single Family Residence | 3/2 | 113 |
| 08-03-2022 | 1540 LAUREL RD, WINTER PARK FL 32789 | $2,599,000 | $449 | $2,599,000 | 5,782 | Single Family Residence | 5/7 | 48 |
| 08-02-2022 | 2000 SHADYHILL TERRACE, WINTER PARK FL 32792 | $485,000 | $240 | $485,000 | 2,015 | Single Family Residence | 4/3 | 34 |
| 08-01-2022 | 605 ELLEN DRIVE | $245,000 | $245,000 | / | 221 | |||
| 08-01-2022 | 1811 ASTER DRIVE, WINTER PARK FL 32792 | $343,000 | $220 | $313,990 | 1,554 | Single Family Residence | 3/2 | 39 |
| 07-29-2022 | 655 TRINIDAD COURT, WINTER PARK FL 32792 | $166,000 | $218 | $155,000 | 759 | Condominium | 1/1 | 22 |
| 07-29-2022 | 7729 COUNTRY PLACE # 4, WINTER PARK FL 32792 | $235,000 | $220 | $244,900 | 1,068 | Condominium | 2/2 | 42 |
| 07-29-2022 | 200 SAINT ANDREWS BOULEVARD # 2808, WINTER PARK FL | $235,000 | $208 | $245,900 | 1,127 | Condominium | 2/2 | 64 |
| 07-29-2022 | 2287 ISLAND RUN, WINTER PARK FL 32792 | $275,000 | $214 | $275,000 | 1,284 | Townhouse | 3/2 | 37 |
| 07-29-2022 | 595 OLOLU DRIVE, WINTER PARK FL 32789 | $295,000 | $404 | $310,000 | 729 | Single Family Residence | 2/1 | 36 |
| 07-29-2022 | 7140 GREEN NEEDLE DRIVE, WINTER PARK FL 32792 | $376,000 | $268 | $369,000 | 1,398 | Single Family Residence | 3/2 | 46 |
| 07-29-2022 | 1831 WILLOW LANE, WINTER PARK FL 32792 | $370,000 | $202 | $399,900 | 1,830 | Single Family Residence | 3/3 | 58 |
| 07-29-2022 | $570,549 | $259 | $570,549 | 2,197 | Single Family Residence | 4/3 | 5 | |
| 07-29-2022 | 2416 WINTER PARK ROAD, WINTER PARK FL 32789 | $685,000 | $407 | $685,000 | 1,680 | Single Family Residence | 3/2 | 89 |
| 07-28-2022 | 2653 EASTHAM ROAD, WINTER PARK FL 32792 | $410,000 | $265 | $410,000 | 1,542 | Single Family Residence | 3/2 | 42 |
| 07-28-2022 | 2025 SHADYHILL TERRACE, WINTER PARK FL 32792 | $485,000 | $244 | $495,000 | 1,983 | Single Family Residence | 4/2 | 49 |
| 07-28-2022 | 7884 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $570,000 | $245 | $589,000 | 2,319 | Single Family Residence | 4/3 | 83 |
| 07-27-2022 | 624 WARRENTON ROAD, WINTER PARK FL 32792 | $280,000 | $205 | $298,000 | 1,365 | Villa | 3/2 | 24 |
| 07-27-2022 | 104 SANDLEWOOD TRAIL # 6, WINTER PARK FL 32789 | $299,900 | $312 | $299,900 | 959 | Condominium | 2/3 | 40 |
| 07-26-2022 | 612 BALFOUR DRIVE, WINTER PARK FL 32792 | $375,000 | $249 | $374,900 | 1,504 | Single Family Residence | 3/2 | 370 |
| 07-26-2022 | 7314 FIELDCREST AVENUE, WINTER PARK FL 32792 | $387,000 | $280 | $405,000 | 1,382 | Single Family Residence | 3/2 | 18 |
| 07-26-2022 | 1840 MEADOWGOLD LANE, WINTER PARK FL 32792 | $435,000 | $254 | $435,000 | 1,708 | Single Family Residence | 3/3 | 33 |
| 07-26-2022 | 5008 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $935,000 | $345 | $975,000 | 2,710 | Single Family Residence | 5/4 | 69 |
| 07-25-2022 | 212 LEWFIELD CIRCLE # 212, WINTER PARK FL 32792 | $180,000 | $194 | $175,000 | 927 | Condominium | 2/2 | 15 |
| 07-25-2022 | 151 N ORLANDO AVENUE UNIT 137 | $230,000 | $323 | $215,000 | 710 | Condominium | 2/1 | 39 |
| 07-25-2022 | 7308 FOREST HILL COURT # 232, WINTER PARK FL 32792 | $215,000 | $208 | $215,000 | 1,031 | Condominium | 2/3 | 81 |
| 07-25-2022 | 1705 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $316,000 | $289 | $301,400 | 1,090 | Single Family Residence | 3/2 | 39 |
| 07-25-2022 | 5179 POINSETTA AVENUE, WINTER PARK FL 32792 | $340,000 | $270 | $345,000 | 1,259 | Single Family Residence | 3/2 | 55 |
| 07-22-2022 | 245 LEWFIELD CIRCLE # 245, WINTER PARK FL 32792 | $205,000 | $221 | $189,900 | 927 | Condominium | 2/2 | 22 |
| 07-22-2022 | 623 GRENADINE COURT # 623, WINTER PARK FL 32792 | $195,000 | $188 | $195,000 | 1,037 | Condominium | 2/2 | 44 |
| 07-22-2022 | 1208 SHARON PLACE, WINTER PARK FL 32789 | $2,900,000 | $603 | $2,850,000 | 4,802 | Single Family Residence | 4/5 | 70 |
| 07-22-2022 | 2588 LAKE HOWELL LANE, WINTER PARK FL 32792 | $475,000 | $241 | $459,900 | 1,969 | Single Family Residence | 4/2 | 134 |
| 07-22-2022 | 2745 WILL O TH GREEN, WINTER PARK FL 32792 | $505,000 | $314 | $495,000 | 1,608 | Single Family Residence | 4/2 | 49 |
| 07-22-2022 | 349 BECKETT COURT, WINTER PARK FL 32792 | $520,000 | $281 | $520,000 | 1,850 | Single Family Residence | 4/3 | 59 |
| 07-22-2022 | 3071 GEORGE MASON AVENUE # D, WINTER PARK FL 32792 | $106,000 | $193 | $99,000 | 549 | Condominium | 1/1 | 29 |
| 07-21-2022 | 331 E READING WAY, WINTER PARK FL 32789 | $1,599,000 | $475 | $1,599,000 | 3,361 | Single Family Residence | 4/5 | 59 |
| 07-21-2022 | 193 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $235,000 | $180 | $225,000 | 1,300 | Townhouse | 2/3 | 37 |
| 07-21-2022 | 623 SAINT JOHNS COURT # 623, WINTER PARK FL 32792 | $232,500 | $207 | $230,000 | 1,120 | Condominium | 2/2 | 35 |
| 07-21-2022 | 2551 PASSAMONTE DRIVE # 5, WINTER PARK FL 32792 | $300,000 | $163 | $315,000 | 1,837 | Condominium | 3/3 | 63 |
| 07-21-2022 | 505 W CANTON AVENUE, WINTER PARK FL 32789 | $1,000,000 | $425 | $875,000 | 2,349 | Townhouse | 3/3 | 373 |
| 07-20-2022 | 710 WARRENTON ROAD, WINTER PARK FL 32792 | $275,000 | $201 | $260,000 | 1,362 | 1/2 Duplex | 2/2 | 83 |
| 07-20-2022 | 2312 BONANZA AVENUE, WINTER PARK FL 32792 | $366,575 | $208 | $349,900 | 1,756 | Single Family Residence | 4/2 | 28 |
| 07-20-2022 | 1561 NOTTINGHAM DRIVE, WINTER PARK FL 32792 | $453,000 | $238 | $443,000 | 1,900 | Single Family Residence | 4/2 | 35 |
| 07-19-2022 | 5309 N WOODCREST DRIVE, WINTER PARK FL 32792 | $230,000 | $127 | $290,000 | 1,807 | Single Family Residence | 3/2 | 1 |
| 07-19-2022 | 3339 BALSAM DRIVE, WINTER PARK FL 32792 | $398,000 | $275 | $398,000 | 1,447 | Single Family Residence | 3/2 | 34 |
| 07-19-2022 | 4887 SEMINOLE AVE AVENUE, WINTER PARK FL 32792 | $400,000 | $177 | $415,000 | 2,256 | Single Family Residence | 4/3 | 42 |
| 07-18-2022 | 700 MELROSE AVENUE # K, WINTER PARK FL 32789 | $235,000 | $304 | $239,900 | 772 | Condominium | 1/1 | 29 |
| 07-18-2022 | 1788 E CHERYL DRIVE, WINTER PARK FL 32792 | $510,000 | $293 | $495,000 | 1,740 | Single Family Residence | 4/2 | 62 |
| 07-15-2022 | 169 LEWFIELD CIRCLE # 169, WINTER PARK FL 32792 | $145,000 | $213 | $150,000 | 678 | Condominium | 1/1 | 59 |
| 07-15-2022 | 5118 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $250,000 | $215 | $250,000 | 1,160 | Single Family Residence | 2/1 | 47 |
| 07-15-2022 | 635 ROUGHBEARD ROAD, WINTER PARK FL 32792 | $575,000 | $223 | $575,000 | 2,577 | Single Family Residence | 5/3 | 45 |
| 07-14-2022 | 2500 LEE ROAD UNIT 134 | $190,000 | $294 | $185,000 | 645 | Condominium | 1/1 | 17 |
| 07-14-2022 | 2376 DOMINICA RUN, WINTER PARK FL 32792 | $295,000 | $229 | $305,000 | 1,284 | Townhouse | 3/2 | 49 |
| 07-14-2022 | 2904 ABBEY COURT, WINTER PARK FL 32792 | $476,000 | $293 | $475,000 | 1,622 | Single Family Residence | 3/2 | 36 |
| 07-14-2022 | 1730 PALM AVENUE, WINTER PARK FL 32789 | $700,000 | $472 | $675,000 | 1,480 | Single Family Residence | 3/2 | 29 |
| 07-14-2022 | 7797 BROKEN ARROW TRAIL | $785,000 | $308 | $799,995 | 2,548 | Single Family Residence | 4/2 | 70 |
| 07-12-2022 | 1670 SPRUCE AVENUE, WINTER PARK FL 32789 | $1,315,000 | $357 | $1,350,000 | 3,680 | Single Family Residence | 5/4 | 88 |
| 07-12-2022 | 3458 ARBUTUS LANE, WINTER PARK FL 32792 | $395,000 | $205 | $424,990 | 1,919 | Single Family Residence | 4/3 | 53 |
| 07-12-2022 | 1737 W CHERYL DRIVE, WINTER PARK FL 32792 | $435,000 | $210 | $425,000 | 2,062 | Single Family Residence | 4/2 | 40 |
| 07-11-2022 | 1470 GLENCOE ROAD, WINTER PARK FL 32789 | $1,457,500 | $463 | $1,495,000 | 3,142 | Single Family Residence | 5/4 | 46 |
| 07-11-2022 | 2413 ANTILLES DRIVE, WINTER PARK FL 32792 | $300,000 | $207 | $274,999 | 1,446 | Townhouse | 3/2 | 47 |
| 07-11-2022 | 1429 INDIANA AVENUE, WINTER PARK FL 32789 | $740,000 | $381 | $739,900 | 1,939 | Single Family Residence | 3/3 | 123 |
| 07-11-2022 | 393 SYLVAN DRIVE, WINTER PARK FL 32789 | $800,000 | $450 | $775,000 | 1,776 | Single Family Residence | 3/3 | 38 |
| 07-08-2022 | 232 SCOTTSDALE SQUARE # 232, WINTER PARK FL 32792 | $152,000 | $140 | $158,000 | 1,085 | Condominium | 2/2 | 176 |
| 07-08-2022 | 850 W CANTON AVENUE, WINTER PARK FL 32789 | $345,000 | $327 | $349,000 | 1,053 | Single Family Residence | 2/1 | 29 |
| 07-08-2022 | 1830 LINDEN ROAD, WINTER PARK FL 32792 | $368,000 | $309 | $365,000 | 1,188 | Single Family Residence | 3/2 | 29 |
| 07-08-2022 | 943 BUNGALOW AVENUE, WINTER PARK FL 32789 | $405,000 | $338 | $410,000 | 1,197 | Single Family Residence | 3/2 | 99 |
| 07-08-2022 | 1956 KING ARTHURS COURT, WINTER PARK FL 32792 | $433,000 | $277 | $455,000 | 1,562 | Single Family Residence | 3/2 | 30 |
| 07-08-2022 | 701 DENTON ROAD, WINTER PARK FL 32792 | $470,000 | $257 | $475,000 | 1,828 | Single Family Residence | 3/2 | 60 |
| 07-08-2022 | 2351 WESTMINSTER COURT, WINTER PARK FL 32789 | $500,000 | $318 | $499,900 | 1,568 | Single Family Residence | 3/2 | 37 |
| 07-08-2022 | 5279 PINE LILY CIRCLE | $552,000 | $238 | $550,000 | 2,313 | Single Family Residence | 3/3 | 37 |
| 07-08-2022 | 103 CORNWALL ROAD, WINTER PARK FL 32792 | $621,000 | $272 | $649,900 | 2,280 | Single Family Residence | 4/3 | 30 |
| 07-08-2022 | 1835 TEMPLE DRIVE, WINTER PARK FL 32789 | $970,000 | $512 | $974,000 | 1,894 | Single Family Residence | 4/2 | 37 |
| 07-07-2022 | 5131 ARDMORE DRIVE, WINTER PARK FL 32792 | $427,600 | $293 | $424,900 | 1,455 | Single Family Residence | 3/2 | 42 |
| 07-07-2022 | 1364 HEAVENLY COVE, WINTER PARK FL 32792 | $690,000 | $246 | $700,000 | 2,800 | Single Family Residence | 4/3 | 57 |
| 07-06-2022 | 3355 RIVER VIEW WAY # 42, WINTER PARK FL 32792 | $201,000 | $203 | $210,000 | 990 | Condominium | 2/2 | 41 |
| 07-06-2022 | 100 STIRLING AVENUE | $2,150,000 | $532 | $2,250,000 | 4,038 | Single Family Residence | 5/4 | 56 |
| 07-06-2022 | 1386 CLEMATIS LANE, WINTER PARK FL 32792 | $320,000 | $221 | $314,900 | 1,442 | Single Family Residence | 3/2 | 35 |
| 07-06-2022 | $400,000 | $240 | $400,000 | 1,665 | Single Family Residence | 4/2 | 1 | |
| 07-06-2022 | 1352 HEAVENLY COVE, WINTER PARK FL 32792 | $675,000 | $238 | $679,000 | 2,825 | Single Family Residence | 4/3 | 42 |
| 07-06-2022 | 350 CAROLINA AVENUE # D, WINTER PARK FL 32789 | $755,000 | $321 | $775,000 | 2,347 | Condominium | 2/2 | 37 |
| 07-05-2022 | 1450 SUFFOLK ROAD, WINTER PARK FL 32789 | $430,000 | $275 | $442,000 | 1,559 | Single Family Residence | 2/3 | 58 |
| 07-01-2022 | 1442 PALM AVENUE, WINTER PARK FL 32789 | $1,200,000 | $332 | $1,225,000 | 3,611 | Single Family Residence | 5/6 | 71 |
| 07-01-2022 | 1770 OAKHURST AVENUE, WINTER PARK FL 32789 | $1,925,000 | $528 | $1,995,000 | 3,640 | Single Family Residence | 5/5 | 92 |
| 07-01-2022 | 1000 S SEMORAN BOULEVARD, WINTER PARK FL 32792 | $245,000 | $157 | $248,500 | 1,554 | Dock-Rackominium | 3/2 | 38 |
| 07-01-2022 | 7583 LODGE POLE TRAIL, WINTER PARK FL 32792 | $417,100 | $215 | $399,900 | 1,936 | Single Family Residence | 4/2 | 22 |
| 07-01-2022 | 1350 PELHAM ROAD, WINTER PARK FL 32789 | $469,000 | $401 | $469,000 | 1,169 | Single Family Residence | 3/1 | 58 |
| 07-01-2022 | 1020 MINNESOTA AVE # 11, WINTER PARK FL 32789 | $397,500 | $198 | $475,000 | 2,000 | Condominium | 3/4 | 46 |
| 07-01-2022 | 1421 LONE FEATHER TRAIL, WINTER PARK FL 32792 | $534,261 | $268 | $534,261 | 1,989 | Single Family Residence | 3/4 | 7 |
| 06-30-2022 | 2345 CHANTILLY AVENUE, WINTER PARK FL 32789 | $1,275,000 | $411 | $1,295,000 | 3,102 | Single Family Residence | 4/4 | 42 |
| 06-30-2022 | 7401 DANIEL WEBSTER DRIVE # 4, WINTER PARK FL 3279 | $156,000 | $141 | $160,000 | 1,104 | Condominium | 2/2 | 16 |
| 06-30-2022 | 720 KILLARNEY BAY COURT UNIT 6 | $350,000 | $307 | $350,000 | 1,140 | Condominium | 2/2 | 36 |
| 06-30-2022 | 2103 BISCAYNE DRIVE, WINTER PARK FL 32789 | $401,200 | $314 | $399,000 | 1,275 | Single Family Residence | 3/1 | 50 |
| 06-30-2022 | 2011 SYCAMORE DRIVE, WINTER PARK FL 32789 | $400,000 | $251 | $400,000 | 1,593 | Single Family Residence | 4/2 | 33 |
| 06-30-2022 | 4887 N MAGNOLIA AVENUE, WINTER PARK FL 32792 | $429,900 | $219 | $429,900 | 1,955 | Single Family Residence | 4/3 | 49 |
| 06-30-2022 | 1136 WASHINGTON AVENUE # 14, WINTER PARK FL 32789 | $574,900 | $339 | $574,900 | 1,693 | Townhouse | 3/3 | 35 |
| 06-30-2022 | 1308 LINDENWOOD LN, WINTER PARK FL 32792 | $675,000 | $303 | $624,900 | 2,227 | Single Family Residence | 4/3 | 36 |
| 06-30-2022 | 1636 LAWNDALE CIRCLE | $750,000 | $404 | $724,999 | 1,856 | Single Family Residence | 3/3 | 77 |
| 06-28-2022 | 181 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $175,000 | $258 | $165,000 | 678 | Condominium | 1/1 | 19 |
| 06-28-2022 | 3117 RAIDERS RUN, WINTER PARK FL 32792 | $405,000 | $197 | $429,000 | 2,047 | Single Family Residence | 5/3 | 28 |
| 06-28-2022 | 2812 SCARLET ROAD, WINTER PARK FL 32792 | $444,750 | $263 | $459,900 | 1,685 | Single Family Residence | 4/2 | 54 |
| 06-28-2022 | 2700 CADY WAY, WINTER PARK FL 32792 | $550,000 | $293 | $560,000 | 1,876 | Single Family Residence | 4/2 | 43 |
| 06-27-2022 | 1640 CHESTNUT AVENUE, WINTER PARK FL 32789 | $1,360,000 | $533 | $1,399,000 | 2,550 | Single Family Residence | 4/5 | 25 |
| 06-27-2022 | 200 SAINT ANDREWS BOULEVARD # 1708, WINTER PARK FL | $240,000 | $189 | $239,000 | 1,266 | Condominium | 2/2 | 33 |
| 06-27-2022 | 1920 MAGNOLIA AVENUE, WINTER PARK FL 32792 | $305,000 | $227 | $300,000 | 1,340 | Single Family Residence | 3/2 | 40 |
| 06-27-2022 | 3529 AUSTRALIAN CIRCLE, WINTER PARK FL 32792 | $387,000 | $308 | $389,000 | 1,255 | Single Family Residence | 3/2 | 39 |
| 06-27-2022 | 690 S LAKEMONT AVENUE, WINTER PARK FL 32792 | $599,900 | $316 | $599,900 | 1,897 | Single Family Residence | 4/3 | 54 |
| 06-27-2022 | 332 N PHELPS AVENUE, WINTER PARK FL 32789 | $750,000 | $477 | $750,000 | 1,570 | Single Family Residence | 3/2 | 34 |
| 06-24-2022 | 2601 WESTERN PARKWAY, WINTER PARK FL 32789 | $1,425,000 | $477 | $1,400,000 | 2,986 | Single Family Residence | 4/4 | 50 |
| 06-24-2022 | 1200 PARK GREEN PLACE, WINTER PARK FL 32789 | $325,000 | $246 | $300,000 | 1,318 | Townhouse | 3/2 | 45 |
| 06-24-2022 | 7133 TIMBER DRIVE, WINTER PARK FL 32792 | $365,000 | $325 | $365,000 | 1,121 | Single Family Residence | 2/2 | 30 |
| 06-24-2022 | 1927 NOTTINGHAM DRIVE, WINTER PARK FL 32792 | $425,000 | $273 | $425,000 | 1,554 | Single Family Residence | 4/2 | 44 |
| 06-24-2022 | 102 S RANGER BOULEVARD, WINTER PARK FL 32792 | $460,000 | $264 | $450,000 | 1,740 | Single Family Residence | 4/2 | 30 |
| 06-24-2022 | 4031 QUENITA DRIVE, WINTER PARK FL 32792 | $476,000 | $217 | $469,000 | 2,186 | Single Family Residence | 4/3 | 39 |
| 06-24-2022 | 1319 HEAVENLY COVE, WINTER PARK FL 32792 | $905,000 | $221 | $919,000 | 4,088 | Single Family Residence | 4/4 | 24 |
| 06-23-2022 | 1695 LEE ROAD # E101, WINTER PARK FL 32789 | $173,000 | $150 | $175,000 | 1,149 | Condominium | 3/2 | 37 |
| 06-23-2022 | 2450 ROXBURY ROAD, WINTER PARK FL 32789 | $265,000 | $248 | $240,000 | 1,068 | Single Family Residence | 2/1 | 35 |
| 06-23-2022 | 4594 WHIMBREL PLACE, WINTER PARK FL 32792 | $470,000 | $204 | $467,900 | 2,303 | Single Family Residence | 3/2 | 113 |
| 06-22-2022 | 618 SAINT JOHNS COURT, WINTER PARK FL 32792 | $205,000 | $197 | $199,900 | 1,037 | Condominium | 2/2 | 37 |
| 06-22-2022 | 2854 ROUEN AVENUE, WINTER PARK FL 32789 | $305,000 | $311 | $320,000 | 980 | Single Family Residence | 3/2 | 48 |
| 06-22-2022 | 2068 HOUNDSLAKE DRIVE, WINTER PARK FL 32792 | $386,000 | $300 | $385,000 | 1,284 | Single Family Residence | 3/2 | 31 |
| 06-22-2022 | 344 STARLING ROAD, WINTER PARK FL 32789 | $430,000 | $319 | $449,900 | 1,345 | Single Family Residence | 2/2 | 33 |
| 06-21-2022 | 189 LEWFIELD CIRCLE # 189, WINTER PARK FL 32792 | $160,000 | $235 | $149,800 | 678 | Condominium | 1/1 | 112 |
| 06-21-2022 | 606 GRENADINE COURT # 606, WINTER PARK FL 32792 | $240,000 | $177 | $240,000 | 1,350 | Condominium | 3/2 | 14 |
| 06-21-2022 | 7510 AZUREBROOK COURT, WINTER PARK FL 32792 | $355,000 | $216 | $355,000 | 1,642 | Single Family Residence | 3/2 | 1 |
| 06-21-2022 | 3131 CROWN JEWEL COURT, WINTER PARK FL 32792 | $370,500 | $256 | $369,999 | 1,442 | Townhouse | 3/3 | 49 |
| 06-21-2022 | 3046 MOSS VALLEY PLACE, WINTER PARK FL 32792 | $394,000 | $266 | $375,000 | 1,479 | Single Family Residence | 3/2 | 27 |
| 06-20-2022 | 3273 FERNDELL DRIVE, WINTER PARK FL 32792 | $428,600 | $300 | $399,000 | 1,424 | Single Family Residence | 3/2 | 33 |
| 06-20-2022 | 1952 KING ARTHURS COURT, WINTER PARK FL 32792 | $487,000 | $277 | $470,000 | 1,754 | Single Family Residence | 4/2 | 29 |
| 06-17-2022 | 616 PENN PLACE, WINTER PARK FL 32789 | $1,335,000 | $403 | $1,325,000 | 3,308 | Single Family Residence | 3/4 | 57 |
| 06-17-2022 | 1861 TAYLOR AVENUE, WINTER PARK FL 32789 | $1,589,183 | $504 | $1,460,000 | 3,150 | Single Family Residence | 5/5 | 385 |
| 06-17-2022 | 1667 WALNUT AVENUE, WINTER PARK FL 32789 | $1,900,000 | $537 | $1,789,000 | 3,535 | Single Family Residence | 4/4 | 14 |
| 06-17-2022 | 441 CLAY STREET, WINTER PARK FL 32789 | $307,000 | $292 | $305,000 | 1,048 | Duplex | / | 39 |
| 06-17-2022 | 653 BALFOUR DRIVE, WINTER PARK FL 32792 | $369,500 | $294 | $369,500 | 1,255 | Single Family Residence | 3/2 | 84 |
| 06-17-2022 | 5125 ARDMORE DRIVE, WINTER PARK FL 32792 | $390,000 | $315 | $375,000 | 1,235 | Single Family Residence | 3/2 | 37 |
| 06-17-2022 | 3325 ATHENA DRIVE, WINTER PARK FL 32792 | $430,000 | $252 | $399,500 | 1,703 | Single Family Residence | 4/2 | 31 |
| 06-17-2022 | 1527 LITTLE WREN LANE, WINTER PARK FL 32792 | $482,000 | $236 | $475,000 | 2,042 | Townhouse | 3/3 | 50 |
| 06-17-2022 | 2819 BANCHORY ROAD, WINTER PARK FL 32792 | $610,000 | $204 | $599,900 | 2,980 | Single Family Residence | 4/4 | 47 |
| 06-17-2022 | 1465 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $577,500 | $371 | $600,000 | 1,554 | Single Family Residence | 2/2 | 36 |
| 06-16-2022 | 1701 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $270,000 | $184 | $249,999 | 1,460 | Townhouse | 2/2 | 27 |
| 06-16-2022 | 4890 N MAGNOLIA AVENUE, WINTER PARK FL 32792 | $535,000 | $258 | $525,000 | 2,071 | Single Family Residence | 3/2 | 56 |
| 06-16-2022 | 1325 BLUE STEM LANE, WINTER PARK FL 32792 | $589,327 | $268 | $589,327 | 2,197 | Single Family Residence | 4/3 | 6 |
| 06-15-2022 | 1320 LAKE KNOWLES CIRCLE, WINTER PARK FL 32789 | $1,389,375 | $505 | $1,500,000 | 2,750 | Single Family Residence | 2/3 | 59 |
| 06-15-2022 | 654 SELKIRK DRIVE, WINTER PARK FL 32792 | $390,000 | $389,000 | / | 24 | |||
| 06-15-2022 | 2156 BONANZA AVENUE, WINTER PARK FL 32792 | $455,000 | $314 | $435,000 | 1,447 | Single Family Residence | 3/2 | 43 |
| 06-15-2022 | 1710 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $505,000 | $311 | $499,000 | 1,619 | Single Family Residence | 3/2 | 47 |
| 06-14-2022 | 1513 LAWNDALE CIRCLE, WINTER PARK FL 32792 | $324,000 | $287 | $324,000 | 1,126 | Single Family Residence | 2/2 | 3 |
| 06-14-2022 | 3520 BALSAM DRIVE, WINTER PARK FL 32792 | $377,750 | $257 | $350,000 | 1,468 | Single Family Residence | 4/2 | 47 |
| 06-14-2022 | 5399 JUSTINE WAY, WINTER PARK FL 32792 | $375,000 | $245 | $359,000 | 1,530 | Single Family Residence | 3/2 | 35 |
| 06-14-2022 | 1245 HOWELL POINT | $4,750,000 | $726 | $4,750,000 | 6,540 | Single Family Residence | 7/7 | 47 |
| 06-14-2022 | 355 CAMBRIDGE BOULEVARD, WINTER PARK FL 32789 | $475,000 | $239 | $484,900 | 1,985 | Single Family Residence | 4/3 | 196 |
| 06-13-2022 | 533 COUNTRY CLUB DRIVE | $1,400,000 | $475 | $1,250,000 | 2,942 | Single Family Residence | 4/4 | 75 |
| 06-13-2022 | 1453 LYNDALE BOULEVARD, WINTER PARK FL 32789 | $1,200,000 | $364 | $1,250,000 | 3,292 | Single Family Residence | 4/3 | 87 |
| 06-11-2022 | $128,000 | $117 | $135,000 | 1,085 | Condominium | 2/2 | 97 | |
| 06-10-2022 | 7331 FOREST HILL COURT # 222, WINTER PARK FL 32792 | $235,000 | $227 | $220,000 | 1,031 | Condominium | 2/3 | 37 |
| 06-10-2022 | 2404 GALLERY VIEW DRIVE # 6, WINTER PARK FL 32792 | $245,000 | $271 | $245,000 | 902 | Condominium | 2/2 | 50 |
| 06-10-2022 | 1621 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $327,000 | $275 | $325,900 | 1,187 | Single Family Residence | 3/2 | 29 |
| 06-10-2022 | 430 KILLARNEY BAY COURT UNIT 3 | $364,900 | $255 | $359,900 | 1,428 | Condominium | 2/3 | 60 |
| 06-10-2022 | 690 CALLAHAN STREET, WINTER PARK FL 32789 | $485,000 | $293 | $495,000 | 1,653 | Single Family Residence | 4/2 | 114 |
| 06-09-2022 | 1524 SPRINGTIME LOOP | $389,500 | $284 | $369,000 | 1,368 | Single Family Residence | 3/2 | 49 |
| 06-09-2022 | 1736 INDIANA AVENUE, WINTER PARK FL 32789 | $677,500 | $315 | $674,900 | 2,148 | Single Family Residence | 4/3 | 71 |
| 06-07-2022 | 2531 PASSAMONTE DRIVE # 4H, WINTER PARK FL 32792 | $349,900 | $195 | $349,900 | 1,790 | Condominium | 3/3 | 34 |
| 06-07-2022 | 2244 COVENTRY DRIVE, WINTER PARK FL 32792 | $426,600 | $298 | $400,000 | 1,430 | Single Family Residence | 3/2 | 26 |
| 06-07-2022 | 1518 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $440,000 | $207 | $450,000 | 2,121 | Single Family Residence | 3/3 | 50 |
| 06-07-2022 | 640 N PARK AVENUE # 27, WINTER PARK FL 32789 | $529,000 | $616 | $499,500 | 858 | Condominium | 2/2 | 26 |
| 06-07-2022 | 1488 ASTER COURT | $650,000 | $320 | $650,000 | 2,031 | Single Family Residence | 3/2 | 25 |
| 06-06-2022 | 580 OLOLU DRIVE | $1,340,000 | $476 | $1,428,400 | 2,812 | Single Family Residence | 3/3 | 235 |
| 06-06-2022 | 137 CORNWALL ROAD, WINTER PARK FL 32792 | $468,600 | $296 | $450,000 | 1,580 | Single Family Residence | 4/2 | 19 |
| 06-06-2022 | 2107 STAUNTON AVENUE, WINTER PARK FL 32789 | $489,000 | $365 | $459,900 | 1,337 | Single Family Residence | 3/2 | 28 |
| 06-06-2022 | 7740 LAKE DAWN DR, WINTER PARK FL 32792 | $645,087 | $258 | $649,900 | 2,495 | Single Family Residence | 5/3 | 32 |
| 06-03-2022 | 3651 N GOLDENROD ROAD # D201, WINTER PARK FL 32792 | $177,000 | $210 | $177,500 | 840 | Condominium | 2/2 | 32 |
| 06-03-2022 | 1370 PLACE PICARDY, WINTER PARK FL 32789 | $2,000,000 | $380 | $2,150,000 | 5,263 | Single Family Residence | 6/6 | 8 |
| 06-03-2022 | 2655 EXUMA WAY, WINTER PARK FL 32792 | $310,000 | $241 | $310,000 | 1,284 | Townhouse | 3/2 | 2 |
| 06-03-2022 | 920 N LAKEMONT AVENUE, WINTER PARK FL 32792 | $590,000 | $228 | $590,000 | 2,580 | Single Family Residence | 4/4 | 74 |
| 06-03-2022 | 2172 TEMPLE DRIVE, WINTER PARK FL 32789 | $650,000 | $405 | $599,900 | 1,601 | Single Family Residence | 3/2 | 22 |
| 06-03-2022 | 501 W CANTON AVENUE, WINTER PARK FL 32789 | $875,000 | $372 | $875,000 | 2,349 | Townhouse | 3/3 | 325 |
| 06-03-2022 | 242 W LYMAN AVENUE, WINTER PARK FL 32789 | $965,000 | $482 | $975,000 | 2,000 | Townhouse | 3/3 | 29 |
| 06-03-2022 | 503 W CANTON AVENUE, WINTER PARK FL 32789 | $985,011 | $424 | $975,000 | 2,319 | Townhouse | 3/3 | 325 |
| 06-03-2022 | 250 W LYMAN AVENUE, WINTER PARK FL 32789 | $995,000 | $497 | $995,000 | 2,000 | Townhouse | 3/3 | 60 |
| 06-02-2022 | 1689 CLEMATIS LANE, WINTER PARK FL 32792 | $390,000 | $280 | $390,000 | 1,392 | Single Family Residence | 3/2 | 36 |
| 06-02-2022 | 4420 STEED TERRACE, WINTER PARK FL 32792 | $630,000 | $263 | $599,000 | 2,387 | Single Family Residence | 4/4 | 42 |
| 06-02-2022 | 922 GARDEN DRIVE, WINTER PARK FL 32789 | $704,000 | $330 | $719,000 | 2,131 | Single Family Residence | 3/3 | 84 |
| 06-01-2022 | 1821 LEGION DRIVE, WINTER PARK FL 32789 | $1,742,000 | $419 | $1,749,000 | 4,154 | Single Family Residence | 5/5 | 31 |
| 06-01-2022 | 200 SAINT ANDREWS BOULEVARD # 3708, WINTER PARK FL | $250,000 | $197 | $239,000 | 1,266 | Condominium | 2/2 | 35 |
| 06-01-2022 | 5030 OAK HILL DRIVE, WINTER PARK FL 32792 | $335,000 | $342 | $299,000 | 978 | Single Family Residence | 3/2 | 55 |
| 06-01-2022 | 682 S LAKEMONT AVENUE, WINTER PARK FL 32792 | $569,000 | $337 | $569,000 | 1,685 | Single Family Residence | 4/2 | 78 |
| 06-01-2022 | 2686 MERRIE OAKS ROAD, WINTER PARK FL 32792 | $560,500 | $301 | $572,000 | 1,857 | Single Family Residence | 3/2 | 92 |
| 05-31-2022 | 2061 TEMPLE DRIVE, WINTER PARK FL 32789 | $1,875,000 | $478 | $1,875,000 | 3,922 | Single Family Residence | 4/6 | 124 |
| 05-31-2022 | 7487 CANFORD CT # 5, WINTER PARK FL 32792 | $247,500 | $153 | $225,000 | 1,611 | Condominium | 3/3 | 23 |
| 05-31-2022 | 4976 TANGERINE AVENUE, WINTER PARK FL 32792 | $380,600 | $238 | $360,000 | 1,594 | Single Family Residence | 3/2 | 47 |
| 05-31-2022 | 704 CORNWALL ROAD, WINTER PARK FL 32792 | $481,000 | $277 | $450,000 | 1,735 | Single Family Residence | 4/2 | 27 |
| 05-31-2022 | 7985 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $590,000 | $260 | $565,000 | 2,267 | Single Family Residence | 4/3 | 55 |
| 05-31-2022 | 1706 SARONG PLACE, WINTER PARK FL 32792 | $785,000 | $238 | $700,000 | 3,285 | Single Family Residence | 4/4 | 55 |
| 05-28-2022 | 507 W CANTON AVENUE, WINTER PARK FL 32789 | $875,000 | $377 | $875,000 | 2,319 | Townhouse | 3/3 | 319 |
| 05-27-2022 | 2500 LEE ROAD UNIT 121 | $160,000 | $248 | $160,000 | 645 | Condominium | 1/1 | 106 |
| 05-27-2022 | 3319 ELLWOOD COURT, WINTER PARK FL 32792 | $392,000 | $253 | $392,000 | 1,546 | Single Family Residence | 4/2 | 204 |
| 05-27-2022 | 1001 ANCHORAGE COURT, WINTER PARK FL 32789 | $6,100,000 | $660 | $6,495,000 | 9,233 | Single Family Residence | 5/7 | 1 |
| 05-27-2022 | 935 GARDEN DRIVE, WINTER PARK FL 32789 | $690,000 | $337 | $660,000 | 2,042 | Single Family Residence | 4/2 | 26 |
| 05-27-2022 | 1891 LAKE SPIER DRIVE | $840,000 | $372 | $819,900 | 2,255 | Single Family Residence | 4/3 | 106 |
| 05-26-2022 | 721 CALLAHAN STREET, WINTER PARK FL 32789 | $500,000 | $356 | $520,000 | 1,403 | Single Family Residence | 3/2 | 51 |
| 05-26-2022 | 1930 FORREST ROAD, WINTER PARK FL 32789 | $1,028,000 | $430 | $900,000 | 2,390 | Single Family Residence | 4/3 | 36 |
| 05-25-2022 | 7440 WOODBURN COURT # 28, WINTER PARK FL 32792 | $240,000 | $232 | $220,000 | 1,031 | Condominium | 2/3 | 41 |
| 05-25-2022 | 2688 GRANADA RUN, WINTER PARK FL 32792 | $281,000 | $191 | $249,900 | 1,467 | Townhouse | 3/2 | 35 |
| 05-25-2022 | 1056 HOWELL BRANCH ROAD | $2,787,500 | $679 | $2,875,000 | 4,100 | Single Family Residence | 4/5 | 56 |
| 05-24-2022 | 2413 WINTER PARK ROAD, WINTER PARK FL 32789 | $750,000 | $502 | $725,000 | 1,494 | Single Family Residence | 3/2 | 33 |
| 05-24-2022 | 2413 WINTER PARK ROAD, WINTER PARK FL 32789 | $750,000 | $725,000 | / | 33 | |||
| 05-23-2022 | 492 FLETCHER PLACE, WINTER PARK FL 32789 | $1,210,000 | $414 | $1,200,000 | 2,918 | Single Family Residence | 4/4 | 70 |
| 05-23-2022 | 209 LEWFIELD CIRCLE # 209, WINTER PARK FL 32792 | $188,000 | $202 | $150,000 | 927 | Condominium | 2/2 | 26 |
| 05-23-2022 | 228 SCOTTSDALE SQUARE # 228, WINTER PARK FL 32792 | $165,000 | $132 | $169,000 | 1,250 | Condominium | 3/2 | 47 |
| 05-23-2022 | 1570 HILLCREST AVENUE, WINTER PARK FL 32789 | $1,602,000 | $513 | $1,750,000 | 3,120 | Single Family Residence | 4/4 | 58 |
| 05-20-2022 | 3246 HEATHERBROOK COURT, WINTER PARK FL 32792 | $350,000 | $249 | $349,000 | 1,403 | Single Family Residence | 3/2 | 15 |
| 05-20-2022 | 1947 SUMMERFIELD ROAD, WINTER PARK FL 32792 | $400,000 | $281 | $400,000 | 1,422 | 3/2 | 4 | |
| 05-20-2022 | 7603 GLENMOOR LANE, WINTER PARK FL 32792 | $450,000 | $283 | $449,000 | 1,585 | Single Family Residence | 3/2 | 37 |
| 05-20-2022 | 428 SELKIRK DRIVE, WINTER PARK FL 32792 | $560,000 | $314 | $549,900 | 1,782 | Single Family Residence | 4/3 | 36 |
| 05-20-2022 | 716 ROUGHBEARD ROAD, WINTER PARK FL 32792 | $649,000 | $281 | $649,000 | 2,308 | Single Family Residence | 4/3 | 57 |
| 05-18-2022 | 1627 ORANGE AVENUE, WINTER PARK FL 32789 | $474,900 | $364 | $479,000 | 1,302 | Single Family Residence | 3/2 | 55 |
| 05-18-2022 | 2825 MULFORD AVENUE, WINTER PARK FL 32789 | $539,700 | $432 | $525,000 | 1,249 | Single Family Residence | 2/2 | 29 |
| 05-17-2022 | 3057 AARON BURR AVENUE # 2, WINTER PARK FL 32792 | $145,000 | $136 | $140,000 | 1,066 | Condominium | 2/2 | 26 |
| 05-17-2022 | 1434 MICHIGAN AVENUE, WINTER PARK FL 32789 | $310,000 | $341 | $325,000 | 908 | Single Family Residence | 2/1 | 134 |
| 05-17-2022 | 1305 HEAVENLY COVE, WINTER PARK FL 32792 | $775,000 | $292 | $745,000 | 2,654 | Single Family Residence | 4/3 | 36 |
| 05-16-2022 | 4768 TANGERINE AVENUE # 4768, WINTER PARK FL 32792 | $162,000 | $215 | $147,500 | 753 | Condominium | 1/1 | 25 |
| 05-16-2022 | 3651 N GOLDENROD ROAD # 102, WINTER PARK FL 32792 | $180,000 | $214 | $149,900 | 840 | Condominium | 2/2 | 18 |
| 05-16-2022 | 4824 TANGERINE AVENUE # 4824, WINTER PARK FL 32792 | $250,000 | $185 | $249,000 | 1,345 | Condominium | 3/3 | 32 |
| 05-14-2022 | 2935 FITZOOTH DRIVE, WINTER PARK FL 32792 | $515,000 | $224 | $500,000 | 2,299 | Single Family Residence | 3/2 | 24 |
| 05-13-2022 | 123 LEWFIELD CIRCLE # 123, WINTER PARK FL 32792 | $130,000 | $191 | $125,000 | 678 | Condominium | 1/1 | 37 |
| 05-13-2022 | 3259 OAK LAKE PLACE # 133, WINTER PARK FL 32792 | $200,500 | $174 | $189,900 | 1,151 | Townhouse | 3/3 | 41 |
| 05-13-2022 | 843 W SWOOPE AVENUE, WINTER PARK FL 32789 | $435,000 | $353 | $425,000 | 1,232 | Single Family Residence | 3/2 | 31 |
| 05-13-2022 | 1777 INDIANA AVENUE # B, WINTER PARK FL 32789 | $460,000 | $287 | $425,000 | 1,598 | Townhouse | 3/3 | 56 |
| 05-13-2022 | 694 DUNBLANE DRIVE, WINTER PARK FL 32792 | $675,000 | $376 | $649,900 | 1,793 | Single Family Residence | 3/2 | 29 |
| 05-12-2022 | 789 S PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $1,300,000 | $676 | $1,300,000 | 1,921 | Single Family Residence | 2/3 | 52 |
| 05-12-2022 | 2417 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $295,000 | $355 | $305,000 | 829 | Single Family Residence | 2/1 | 59 |
| 05-12-2022 | 238 BALFOUR DRIVE # 22, WINTER PARK FL 32792 | $336,000 | $274 | $310,000 | 1,225 | Condominium | 2/2 | 42 |
| 05-12-2022 | 648 W WEBSTER AVENUE, WINTER PARK FL 32789 | $430,000 | $211 | $499,000 | 2,034 | Single Family Residence | 4/2 | 32 |
| 05-12-2022 | 1126 WASHINGTON AVENUE # A, WINTER PARK FL 32789 | $525,000 | $319 | $525,000 | 1,641 | Condominium | 3/3 | 36 |
| 05-10-2022 | 4332 STEED TERRACE, WINTER PARK FL 32792 | $430,000 | $194 | $400,000 | 2,206 | Single Family Residence | 4/3 | 222 |
| 05-09-2022 | 200 SAINT ANDREWS BOULEVARD # 903, WINTER PARK FL | $215,000 | $257 | $229,000 | 835 | Condominium | 1/1 | 26 |
| 05-09-2022 | 1250 S DENNING DRIVE # 105, WINTER PARK FL 32789 | $265,000 | $291 | $239,900 | 908 | Condominium | 2/2 | 21 |
| 05-09-2022 | 2419 GALLERY VIEW DRIVE UNIT 6 | $257,000 | $255 | $265,000 | 1,004 | Condominium | 2/2 | 47 |
| 05-09-2022 | 4983 TANGERINE AVENUE, WINTER PARK FL 32792 | $397,000 | $237 | $399,900 | 1,674 | Single Family Residence | 3/2 | 55 |
| 05-06-2022 | 3054 GEORGE MASON AVENUE # 7, WINTER PARK FL 32792 | $140,000 | $135 | $140,000 | 1,035 | Condominium | 2/2 | 58 |
| 05-06-2022 | 3422 BOWMAN DRIVE, WINTER PARK FL 32792 | $433,000 | $258 | $400,000 | 1,675 | Single Family Residence | 3/2 | 37 |
| 05-06-2022 | 3125 RAIDERS RUN, WINTER PARK FL 32792 | $415,000 | $181 | $400,000 | 2,285 | Single Family Residence | 4/3 | 65 |
| 05-05-2022 | 2127 LAKE DRIVE, WINTER PARK FL 32789 | $476,000 | $334 | $465,000 | 1,424 | Single Family Residence | 3/2 | 60 |
| 05-05-2022 | 1381 CANTERBURY ROAD, WINTER PARK FL 32789 | $549,000 | $301 | $549,000 | 1,819 | Single Family Residence | 3/2 | 15 |
| 05-04-2022 | 625 N INTERLACHEN AVENUE # A, WINTER PARK FL 32789 | $1,050,000 | $611 | $1,050,000 | 1,718 | Condominium | 2/2 | 27 |
| 05-04-2022 | 191 SCOTTSDALE SQUARE # 191, WINTER PARK FL 32792 | $119,000 | $151 | $119,000 | 785 | Condominium | 1/1 | 48 |
| 05-04-2022 | 777 GREEN OAKS COURT, WINTER PARK FL 32789 | $1,250,000 | $395 | $1,343,000 | 3,162 | Single Family Residence | 5/3 | 29 |
| 05-04-2022 | 3382 CEDAR SPRINGS PLACE # 153, WINTER PARK FL 327 | $225,000 | $195 | $229,950 | 1,151 | Townhouse | 3/3 | 24 |
| 05-04-2022 | 520 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $507,500 | $314 | $517,000 | 1,616 | Single Family Residence | 3/2 | 100 |
| 05-03-2022 | 1035 N KENTUCKY AVENUE, WINTER PARK FL 32789 | $1,395,000 | $467 | $1,475,000 | 2,983 | Single Family Residence | 4/3 | 47 |
| 05-03-2022 | 353 ELKHORN COURT, WINTER PARK FL 32792 | $540,000 | $301 | $550,000 | 1,793 | Single Family Residence | 4/2 | 47 |
| 05-02-2022 | 4772 TANGERINE AVENUE # 4772, WINTER PARK FL 32792 | $159,000 | $150 | $144,000 | 1,058 | Condominium | 2/2 | 25 |
| 05-02-2022 | 3366 AUSTRALIAN CIRCLE, WINTER PARK FL 32792 | $330,000 | $233 | $299,900 | 1,415 | Single Family Residence | 3/2 | 28 |
| 05-02-2022 | 1945 POINCIANA ROAD, WINTER PARK FL 32792 | $425,000 | $260 | $418,888 | 1,632 | Single Family Residence | 3/2 | 32 |
| 05-02-2022 | 1841 LOCH BERRY ROAD, WINTER PARK FL 32789 | $757,000 | $409 | $749,000 | 1,848 | Single Family Residence | 3/2 | 1 |
| 04-29-2022 | 1580 ONECO AVE, WINTER PARK FL 32789 | $1,275,000 | $500 | $1,250,000 | 2,548 | Single Family Residence | 4/4 | 67 |
| 04-29-2022 | 143 SCOTTSDALE SQUARE # 143, WINTER PARK FL 32792 | $140,000 | $137 | $130,000 | 1,020 | Condominium | 2/2 | 32 |
| 04-29-2022 | 455 MELROSE AVENUE | $1,255,000 | $415 | $1,350,000 | 3,022 | Single Family Residence | 4/4 | 57 |
| 04-29-2022 | 1850 CAROLLEE LANE, WINTER PARK FL 32789 | $1,450,000 | $447 | $1,450,000 | 3,239 | Single Family Residence | 5/5 | 52 |
| 04-29-2022 | 334 SCOTTSDALE SQUARE # 334, WINTER PARK FL 32792 | $140,000 | $112 | $150,000 | 1,250 | Condominium | 3/2 | 29 |
| 04-29-2022 | 543 GENIUS DRIVE | $1,469,813 | $402 | $1,540,000 | 3,651 | Single Family Residence | 4/4 | 64 |
| 04-29-2022 | 7332 FOREST HILL COURT # 239, WINTER PARK FL 32792 | $180,000 | $181 | $170,000 | 990 | Condominium | 2/2 | 29 |
| 04-29-2022 | 1250 S DENNING DRIVE # 116, WINTER PARK FL 32789 | $245,000 | $269 | $239,900 | 908 | Condominium | 2/2 | 37 |
| 04-29-2022 | 2350 FLAMINGO WAY, WINTER PARK FL 32792 | $305,000 | $170 | $299,000 | 1,787 | Townhouse | 3/2 | 95 |
| 04-29-2022 | 243 ORANGE TERRACE DRIVE, WINTER PARK FL 32789 | $345,000 | $292 | $335,000 | 1,178 | Single Family Residence | 3/1 | 44 |
| 04-29-2022 | 5398 JUSTINE WAY, WINTER PARK FL 32792 | $381,000 | $272 | $375,000 | 1,398 | Single Family Residence | 3/2 | 43 |
| 04-29-2022 | 2077 PONDEROSA AVENUE, WINTER PARK FL 32792 | $419,000 | $236 | $380,000 | 1,770 | Single Family Residence | 4/2 | 40 |
| 04-29-2022 | 2837 KINGS DEER ROAD, WINTER PARK FL 32792 | $405,000 | $254 | $395,000 | 1,593 | Single Family Residence | 3/2 | 19 |
| 04-29-2022 | 984 MAYFIELD AVENUE, WINTER PARK FL 32789 | $3,995,000 | $735 | $3,995,000 | 5,429 | Single Family Residence | 4/6 | 54 |
| 04-29-2022 | 1682 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $502,500 | $362 | $499,000 | 1,387 | Single Family Residence | 4/2 | 15 |
| 04-29-2022 | 2717 BOWER ROAD, WINTER PARK FL 32792 | $530,000 | $287 | $499,900 | 1,843 | Single Family Residence | 4/2 | 78 |
| 04-29-2022 | 8140 LAZY BEAR LANE, WINTER PARK FL 32792 | $545,000 | $295 | $539,000 | 1,843 | Single Family Residence | 4/2 | 9 |
| 04-29-2022 | 805 W CANTON AVENUE, WINTER PARK FL 32789 | $964,500 | $430 | $897,000 | 2,241 | Single Family Residence | 3/3 | 58 |
| 04-28-2022 | 225 SCOTTSDALE SQUARE # 225, WINTER PARK FL 32792 | $133,000 | $130 | $135,000 | 1,020 | Condominium | 2/2 | 57 |
| 04-28-2022 | 200 SAINT ANDREWS BOULEVARD # 503, WINTER PARK FL | $190,000 | $227 | $187,500 | 835 | Condominium | 1/1 | 57 |
| 04-28-2022 | 7486 CANFORD COURT # 7, WINTER PARK FL 32792 | $224,900 | $142 | $224,900 | 1,580 | Townhouse | 3/3 | 15 |
| 04-28-2022 | 2174 SUSSEX ROAD, WINTER PARK FL 32792 | $427,000 | $196 | $395,000 | 2,175 | Single Family Residence | 4/2 | 39 |
| 04-28-2022 | 7016 HAMMOCK WAY, WINTER PARK FL 32792 | $405,000 | $207 | $400,000 | 1,950 | Single Family Residence | 4/2 | 33 |
| 04-27-2022 | 2430 VENETIAN WAY | $2,245,000 | $448 | $2,245,000 | 5,005 | Single Family Residence | 6/6 | 1 |
| 04-27-2022 | 1300 FORMOSA AVENUE, WINTER PARK FL 32789 | $230,000 | $252 | $265,000 | 912 | Single Family Residence | 2/1 | 146 |
| 04-27-2022 | 1442 LONE FEATHER TRAIL, WINTER PARK FL 32792 | $478,332 | $217 | $478,332 | 2,197 | 4/3 | 26 | |
| 04-26-2022 | 2156 TALMAN COURT, WINTER PARK FL 32792 | $1,750,000 | $225 | $1,750,000 | 7,762 | Single Family Residence | 5/8 | 459 |
| 04-26-2022 | 501 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $932,087 | $308 | $890,000 | 3,024 | Single Family Residence | 5/3 | 554 |
| 04-25-2022 | 5312 POINSETTA AVENUE, WINTER PARK FL 32792 | $315,000 | $249 | $315,000 | 1,263 | Single Family Residence | 3/2 | 53 |
| 04-25-2022 | 733 FRIAR ROAD, WINTER PARK FL 32792 | $488,000 | $265 | $489,900 | 1,838 | Single Family Residence | 3/2 | 33 |
| 04-22-2022 | 104 SANDLEWOOD TRAIL # 6, WINTER PARK FL 32789 | $221,000 | $230 | $215,000 | 959 | Condominium | 2/3 | 37 |
| 04-22-2022 | 7702 COUNTRY PLACE # 10, WINTER PARK FL 32792 | $220,000 | $178 | $220,000 | 1,230 | Condominium | 3/2 | 39 |
| 04-22-2022 | 1610 CHESTNUT AVENUE, WINTER PARK FL 32789 | $900,000 | $427 | $929,900 | 2,106 | Single Family Residence | 3/3 | 52 |
| 04-21-2022 | 7340 SWALLOW RUN # 7340, WINTER PARK FL 32792 | $155,000 | $193 | $149,900 | 802 | Condominium | 2/2 | 43 |
| 04-21-2022 | 543 GILBERT ROAD, WINTER PARK FL 32792 | $530,000 | $267 | $500,000 | 1,981 | Single Family Residence | 4/3 | 35 |
| 04-20-2022 | 1786 CLEMATIS LANE, WINTER PARK FL 32792 | $312,000 | $226 | $299,900 | 1,380 | Single Family Residence | 3/2 | 41 |
| 04-20-2022 | 2818 ROUEN AVENUE, WINTER PARK FL 32789 | $457,000 | $348 | $450,000 | 1,310 | Single Family Residence | 3/2 | 27 |
| 04-20-2022 | 737 S RANGER BOULEVARD, WINTER PARK FL 32792 | $662,000 | $296 | $649,000 | 2,229 | Single Family Residence | 4/3 | 49 |
| 04-19-2022 | 5618 WINTERBROOK WAY, WINTER PARK FL 32792 | $750,000 | $261 | $740,000 | 2,866 | Single Family Residence | 5/4 | 46 |
| 04-18-2022 | 145 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $126,000 | $185 | $110,000 | 678 | Condominium | 1/1 | 31 |
| 04-18-2022 | 1841 GOODRICH AVENUE, WINTER PARK FL 32789 | $385,000 | $387 | $449,000 | 993 | Single Family Residence | 2/1 | 70 |
| 04-18-2022 | 1261 ARLINGTON PLACE, WINTER PARK FL 32789 | $740,000 | $311 | $749,000 | 2,375 | Townhouse | 3/3 | 47 |
| 04-15-2022 | 1000 S SEMORAN BOULEVARD # 703, WINTER PARK FL 327 | $125,000 | $170 | $120,000 | 735 | Condominium | 1/1 | 18 |
| 04-15-2022 | 331 N PHELPS AVENUE, WINTER PARK FL 32789 | $1,135,000 | $359 | $1,200,000 | 3,154 | Single Family Residence | 4/5 | 90 |
| 04-15-2022 | 168 LEWFIELD CIRCLE # 168, WINTER PARK FL 32792 | $146,000 | $215 | $135,000 | 678 | Condominium | 1/1 | 26 |
| 04-15-2022 | $220,000 | $196 | $239,900 | 1,120 | Single Family Residence | 2/2 | 36 | |
| 04-15-2022 | 100 E ROCKWOOD WAY, WINTER PARK FL 32789 | $2,500,000 | $580 | $2,500,000 | 4,304 | 4/6 | 2 | |
| 04-15-2022 | 3435 BALSAM DRIVE, WINTER PARK FL 32792 | $350,000 | $231 | $339,900 | 1,510 | Single Family Residence | 2/2 | 35 |
| 04-15-2022 | 3454 BOWMAN DRIVE, WINTER PARK FL 32792 | $400,000 | $261 | $375,000 | 1,530 | Single Family Residence | 3/2 | 29 |
| 04-15-2022 | 1737 INDIANA AVENUE, WINTER PARK FL 32789 | $485,000 | $529,000 | / | 121 | |||
| 04-15-2022 | 1551 NORFOLK AVENUE, WINTER PARK FL 32789 | $660,000 | $240 | $649,000 | 2,740 | Single Family Residence | 5/3 | 247 |
| 04-15-2022 | 368 SYLVAN DRIVE, WINTER PARK FL 32789 | $740,000 | $449 | $685,000 | 1,647 | Single Family Residence | 3/2 | 43 |
| 04-14-2022 | 101 S NEW YORK AVENUE # 312, WINTER PARK FL 32789 | $1,560,000 | $501 | $1,585,000 | 3,112 | Condominium | 3/4 | 71 |
| 04-14-2022 | 200 SAINT ANDREWS BOULEVARD # 2012, WINTER PARK FL | $220,000 | $196 | $220,000 | 1,119 | Condominium | 2/2 | 89 |
| 04-14-2022 | 2612 EXUMA WAY, WINTER PARK FL 32792 | $260,000 | $254 | $279,000 | 1,020 | Townhouse | 2/2 | 28 |
| 04-14-2022 | 2110 KAROLINA AVENUE, WINTER PARK FL 32789 | $525,000 | $307 | $499,900 | 1,708 | Single Family Residence | 4/2 | 37 |
| 04-14-2022 | 1333 BLUE STEM LANE, WINTER PARK FL 32792 | $544,999 | $211 | $544,999 | 2,582 | 4/4 | 6 | |
| 04-13-2022 | 2344 FLAMINGO WAY, WINTER PARK FL 32792 | $305,000 | $198 | $299,900 | 1,536 | Townhouse | 3/2 | 59 |
| 04-13-2022 | 2551 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $385,000 | $221 | $374,900 | 1,735 | Single Family Residence | 3/2 | 27 |
| 04-12-2022 | 2030 FORREST ROAD, WINTER PARK FL 32789 | $1,350,000 | $342 | $1,299,000 | 3,942 | Single Family Residence | 4/3 | 56 |
| 04-12-2022 | 1725 CLEMATIS LANE, WINTER PARK FL 32792 | $258,000 | $197 | $299,900 | 1,308 | Single Family Residence | 3/2 | 49 |
| 04-12-2022 | 4947 ARDMORE DRIVE, WINTER PARK FL 32792 | $403,200 | $231 | $380,000 | 1,741 | Single Family Residence | 3/3 | 20 |
| 04-12-2022 | 1599 LITTLE WREN LANE, WINTER PARK FL 32792 | $471,000 | $226 | $469,900 | 2,076 | Townhouse | 3/3 | 35 |
| 04-12-2022 | 1729 MICHIGAN AVENUE, WINTER PARK FL 32789 | $520,000 | $336 | $490,000 | 1,546 | Single Family Residence | 3/3 | 49 |
| 04-12-2022 | 1600 ALABAMA DRIVE UNIT 101 | $890,000 | $606 | $890,000 | 1,467 | Condominium | 2/2 | 302 |
| 04-11-2022 | 5118 ARDMORE DRIVE, WINTER PARK FL 32792 | $403,000 | $274 | $403,000 | 1,467 | Single Family Residence | 3/2 | 151 |
| 04-08-2022 | 114 SCOTTSDALE SQUARE # 114, WINTER PARK FL 32792 | $131,500 | $121 | $129,000 | 1,085 | Condominium | 2/2 | 21 |
| 04-08-2022 | 1879 VIBURNUM LANE, WINTER PARK FL 32792 | $289,000 | $235 | $269,000 | 1,227 | Single Family Residence | 3/2 | 27 |
| 04-08-2022 | 2521 ROXBURY ROAD, WINTER PARK FL 32789 | $335,000 | $274 | $325,000 | 1,220 | Single Family Residence | 2/1 | 30 |
| 04-08-2022 | 4595 WHIMBREL PLACE, WINTER PARK FL 32792 | $480,000 | $232 | $449,000 | 2,063 | Single Family Residence | 3/2 | 16 |
| 04-07-2022 | 3162 PATEL DRIVE, WINTER PARK FL 32792 | $280,000 | $237 | $275,000 | 1,180 | Single Family Residence | 3/2 | 22 |
| 04-07-2022 | 1131 DENTON ROAD, WINTER PARK FL 32792 | $360,000 | $253 | $369,900 | 1,422 | Single Family Residence | 4/2 | 18 |
| 04-07-2022 | 8073 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $580,000 | $250 | $579,000 | 2,319 | Single Family Residence | 4/3 | 316 |
| 04-06-2022 | 367 FITZHUGH ROAD, WINTER PARK FL 32792 | $270,000 | $300,000 | / | 38 | |||
| 04-06-2022 | 2739 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $500,000 | $327 | $485,000 | 1,528 | Single Family Residence | 3/2 | 33 |
| 04-05-2022 | 913 MOSS LANE, WINTER PARK FL 32789 | $710,000 | $376 | $700,000 | 1,887 | Single Family Residence | 3/2 | 41 |
| 04-04-2022 | 336 BLUE HERON DRIVE | $1,100,000 | $627 | $1,190,000 | 1,754 | Single Family Residence | 3/3 | 159 |
| 04-04-2022 | 4770 TANGERINE AVENUE # 4770, WINTER PARK FL 32792 | $155,000 | $205 | $140,000 | 753 | Condominium | 1/1 | 19 |
| 04-04-2022 | 1707 NOTTINGHAM DRIVE, WINTER PARK FL 32792 | $410,000 | $232 | $365,000 | 1,767 | Single Family Residence | 4/2 | 34 |
| 04-04-2022 | 1364 WESTDALE AVENUE, WINTER PARK FL 32792 | $380,000 | $215 | $380,000 | 1,764 | Single Family Residence | 3/2 | 52 |
| 04-04-2022 | 690 N NEW YORK AVENUE, WINTER PARK FL 32789 | $3,990,000 | $814 | $3,990,000 | 4,901 | Single Family Residence | 4/5 | 350 |
| 04-04-2022 | 1802 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $751,000 | $415 | $699,000 | 1,808 | Single Family Residence | 3/3 | 39 |
| 04-01-2022 | 2935 ANTIQUE OAKS CIRCLE # 64, WINTER PARK FL 3279 | $202,500 | $198 | $202,500 | 1,018 | Condominium | 2/2 | 57 |
| 04-01-2022 | 5112 TANGERINE AVENUE, WINTER PARK FL 32792 | $412,000 | $236 | $416,000 | 1,745 | Single Family Residence | 4/2 | 47 |
| 04-01-2022 | 1835 BISCAYNE DRIVE, WINTER PARK FL 32789 | $463,000 | $252 | $439,000 | 1,837 | Duplex | / | 50 |
| 04-01-2022 | 2245 FAIRGLENN WAY, WINTER PARK FL 32792 | $715,000 | $255 | $675,000 | 2,801 | Single Family Residence | 4/3 | 37 |
| 03-31-2022 | 130 SCOTTSDALE SQUARE # 130, WINTER PARK FL 32792 | $140,000 | $137 | $130,000 | 1,020 | Condominium | 2/2 | 29 |
| 03-31-2022 | 5152 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $290,000 | $194 | $349,000 | 1,490 | Single Family Residence | 3/2 | 51 |
| 03-31-2022 | 5152 Lake Howell RD | $290,000 | $194 | $349,000 | 1,490 | Single Family Residence | 3/2 | 49 |
| 03-31-2022 | 427 ELLENDALE DRIVE, WINTER PARK FL 32792 | $376,900 | $272 | $379,900 | 1,384 | Single Family Residence | 3/2 | 49 |
| 03-31-2022 | 2183 CRANDON AVENUE, WINTER PARK FL 32789 | $400,000 | $333 | $399,900 | 1,200 | Duplex | / | 44 |
| 03-31-2022 | 2360 SHADOWLAND LOOP, WINTER PARK FL 32792 | $447,000 | $215 | $430,000 | 2,076 | Townhouse | 3/4 | 37 |
| 03-31-2022 | 786 S PENNSYLVANIA AVENUE # 2, WINTER PARK FL 3278 | $642,500 | $272 | $649,900 | 2,354 | Condominium | 3/3 | 51 |
| 03-31-2022 | 1627 MIZELL AVENUE, WINTER PARK FL 32789 | $755,000 | $464 | $749,000 | 1,625 | Single Family Residence | 3/1 | 42 |
| 03-31-2022 | 7309 DANIEL WEBSTER DRIVE # 2, WINTER PARK FL 3279 | $93,000 | $173 | $98,500 | 537 | Quadruplex | / | 21 |
| 03-31-2022 | 7309 DANIEL WEBSTER DRIVE # 2b, WINTER PARK FL 327 | $93,000 | $173 | $98,500 | 537 | Condominium | 1/1 | 25 |
| 03-31-2022 | 7390 ALOMA AVENUE, WINTER PARK FL 32792 | $950,000 | $292 | $999,999 | 3,244 | Retail | / | 277 |
| 03-30-2022 | 5219 ALBERT DRIVE, WINTER PARK FL 32792 | $374,000 | $299 | $359,900 | 1,247 | Single Family Residence | 3/2 | 94 |
| 03-30-2022 | 738 S RANGER BOULEVARD, WINTER PARK FL 32792 | $675,000 | $290 | $649,900 | 2,327 | Single Family Residence | 4/3 | 70 |
| 03-29-2022 | 1706 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $291,000 | $245 | $305,000 | 1,187 | Single Family Residence | 3/2 | 139 |
| 03-29-2022 | 1880 MEADOWGOLD LANE, WINTER PARK FL 32792 | $400,000 | $292 | $379,900 | 1,368 | Single Family Residence | 3/2 | 36 |
| 03-29-2022 | 1690 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $450,000 | $239 | $449,000 | 1,878 | Single Family Residence | 4/2 | 28 |
| 03-29-2022 | 4175 BEAR GULLY ROAD, WINTER PARK FL 32792 | $445,300 | $262 | $459,999 | 1,696 | Single Family Residence | 3/2 | 73 |
| 03-28-2022 | 2222 AZALEA PLACE, WINTER PARK FL 32789 | $2,550,000 | $534 | $2,699,000 | 4,768 | Single Family Residence | 5/8 | 43 |
| 03-28-2022 | 677 W SWOOPE AVENUE, WINTER PARK FL 32789 | $315,000 | $417 | $315,000 | 754 | Single Family Residence | 2/1 | 342 |
| 03-28-2022 | 1319 BUCKINGHAM ROAD, WINTER PARK FL 32789 | $475,000 | $394 | $449,000 | 1,204 | Single Family Residence | 2/1 | 33 |
| 03-28-2022 | 102 S INTERLACHEN AVENUE UNIT 411F | $475,000 | $527 | $475,000 | 901 | Condominium | 2/1 | 18 |
| 03-28-2022 | 2521 EUSTON ROAD, WINTER PARK FL 32789 | $579,000 | $252 | $549,900 | 2,296 | Single Family Residence | 4/3 | 19 |
| 03-25-2022 | 620 MONTEGO BAY COURT # 620, WINTER PARK FL 32792 | $221,000 | $197 | $199,500 | 1,120 | Condominium | 2/2 | 21 |
| 03-25-2022 | 5515 ALBERT DRIVE, WINTER PARK FL 32792 | $420,000 | $273 | $420,000 | 1,533 | Single Family Residence | 4/2 | 57 |
| 03-25-2022 | 2246 KING HENRYS COURT, WINTER PARK FL 32792 | $429,900 | $164 | $429,900 | 2,609 | Single Family Residence | 4/3 | 194 |
| 03-25-2022 | 519 DUNBLANE DRIVE, WINTER PARK FL 32792 | $450,000 | $304 | $450,000 | 1,479 | Single Family Residence | 3/2 | 31 |
| 03-25-2022 | 4013 QUENITA DRIVE, WINTER PARK FL 32792 | $465,000 | $199 | $465,000 | 2,327 | Single Family Residence | 4/3 | 44 |
| 03-25-2022 | 1360 FORMOSA AVENUE, WINTER PARK FL 32789 | $490,000 | $259 | $490,000 | 1,890 | / | 7 | |
| 03-24-2022 | 1871 MEADOWGOLD LANE, WINTER PARK FL 32792 | $390,000 | $252 | $369,000 | 1,546 | Single Family Residence | 3/3 | 24 |
| 03-24-2022 | 236 BLOSSOM LANE | $434,000 | $286 | $429,900 | 1,514 | Single Family Residence | 3/2 | 36 |
| 03-24-2022 | 1821 ANZLE AVENUE, WINTER PARK FL 32789 | $720,000 | $328 | $729,900 | 2,195 | Single Family Residence | 5/4 | 57 |
| 03-23-2022 | 210 SCOTTSDALE SQUARE # 210, WINTER PARK FL 32792 | $130,000 | $119 | $139,900 | 1,085 | Condominium | 2/2 | 98 |
| 03-23-2022 | 820 W CANTON AVENUE, WINTER PARK FL 32789 | $368,000 | $386 | $450,000 | 952 | Single Family Residence | 2/1 | 57 |
| 03-23-2022 | 820 W CANTON AVENUE, WINTER PARK FL 32789 | $368,000 | $450,000 | / | 57 | |||
| 03-22-2022 | 1560 LAWNDALE CIRCLE | $377,000 | $266 | $365,000 | 1,415 | Single Family Residence | 3/2 | 41 |
| 03-22-2022 | 1268 FORMOSA AVENUE # 8, WINTER PARK FL 32789 | $483,900 | $249 | $483,900 | 1,937 | Townhouse | 3/4 | 68 |
| 03-21-2022 | 1000 S SEMORAN BOULEVARD # 414, WINTER PARK FL 327 | $118,000 | $152 | $104,994 | 776 | Condominium | 1/1 | 22 |
| 03-21-2022 | 278 SCOTTSDALE SQUARE # 278, WINTER PARK FL 32792 | $122,000 | $119 | $125,000 | 1,020 | Condominium | 2/2 | 46 |
| 03-21-2022 | 1631 ONECO AVENUE, WINTER PARK FL 32789 | $1,576,500 | $451 | $1,599,900 | 3,488 | Single Family Residence | 5/5 | 183 |
| 03-21-2022 | 1000 S SEMORAN BLVD # 807, WINTER PARK FL 32792 | $163,000 | $162 | $165,000 | 1,003 | Condominium | 2/2 | 48 |
| 03-21-2022 | 3651 N GOLDENROD ROAD # B102, WINTER PARK FL 32792 | $172,000 | $204 | $169,000 | 840 | Condominium | 2/2 | 25 |
| 03-21-2022 | 1384 WESTDALE AVENUE, WINTER PARK FL 32792 | $330,000 | $200 | $320,000 | 1,648 | Single Family Residence | 3/2 | 25 |
| 03-21-2022 | 2834 CHANTILLY AVE | $384,450 | $330 | $339,000 | 1,165 | Single Family Residence | 3/2 | 25 |
| 03-21-2022 | 5560 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $326,000 | $242 | $370,000 | 1,346 | Single Family Residence | 3/2 | 59 |
| 03-20-2022 | 214 SCOTTSDALE SQUARE # 214, WINTER PARK FL 32792 | $144,000 | $132 | $149,000 | 1,085 | Condominium | 2/2 | 94 |
| 03-19-2022 | 2138 LAKE DRIVE | $3,000,000 | $580 | $3,000,000 | 5,171 | Single Family Residence | 4/4 | 44 |
| 03-18-2022 | 200 SAINT ANDREWS BOULEVARD # 807, WINTER PARK FL | $218,000 | $194 | $220,000 | 1,119 | Condominium | 2/2 | 75 |
| 03-18-2022 | 362 SYLVAN DRIVE, WINTER PARK FL 32789 | $535,000 | $261 | $525,000 | 2,047 | Single Family Residence | 3/2 | 26 |
| 03-18-2022 | 151 STIRLING AVENUE, WINTER PARK FL 32789 | $925,000 | $393 | $850,000 | 2,352 | Single Family Residence | 3/2 | 15 |
| 03-17-2022 | 420 SYLVAN DRIVE, WINTER PARK FL 32789 | $960,000 | $359 | $1,025,000 | 2,673 | Single Family Residence | 3/4 | 179 |
| 03-17-2022 | $960,000 | $358 | $1,025,000 | 2,676 | Single Family Residence | 3/4 | 2 | |
| 03-17-2022 | 315 E NEW ENGLAND AVENUE # 2, WINTER PARK FL 32789 | $1,993,000 | $608 | $2,100,000 | 3,276 | Condominium | 3/4 | 42 |
| 03-17-2022 | 609 GALLERY DRIVE # B204, WINTER PARK FL 32792 | $225,000 | $251 | $225,000 | 893 | Condominium | 2/2 | 64 |
| 03-17-2022 | 2747 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $500,000 | $310 | $475,000 | 1,608 | Single Family Residence | 3/2 | 57 |
| 03-17-2022 | 315 BALFOUR DRIVE, WINTER PARK FL 32792 | $490,000 | $180 | $520,000 | 2,721 | Duplex | / | 119 |
| 03-16-2022 | 2471 ALOMA AVENUE, WINTER PARK FL 32792 | $1,225,000 | $324 | $1,295,000 | 3,770 | Office | / | 155 |
| 03-15-2022 | 1851/1861 GOODRICH AVENUE, WINTER PARK FL 32789 | $800,000 | $552 | $1,080,000 | 1,449 | Office | / | 131 |
| 03-15-2022 | 4559 WHIMBREL PLACE | $1,200,000 | $352 | $1,250,000 | 3,400 | Single Family Residence | 5/4 | 58 |
| 03-15-2022 | 1402 INDIANA AVENUE, WINTER PARK FL 32789 | $490,000 | $266 | $465,000 | 1,836 | Townhouse | 3/3 | 47 |
| 03-14-2022 | xxx FAIRVIEW & GROVE AVENUE, WINTER PARK FL 32789 | $1,300,000 | $264 | $1,350,000 | 4,918 | Office | / | 176 |
| 03-14-2022 | 1810 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $340,000 | $205 | $314,999 | 1,656 | Single Family Residence | 3/3 | 81 |
| 03-14-2022 | 1379 CHILEAN LANE, WINTER PARK FL 32792 | $365,000 | $266 | $373,100 | 1,371 | Single Family Residence | 3/2 | 40 |
| 03-14-2022 | 776 S PENNSYLVANIA AVENUE # 4, WINTER PARK FL 3278 | $715,000 | $348 | $715,000 | 2,051 | Townhouse | 3/3 | 32 |
| 03-14-2022 | 633 S PHELPS AVE, WINTER PARK FL 32789 | $780,000 | $825,000 | / | 28 | |||
| 03-11-2022 | 185 LEWFIELD CIRCLE # 185, WINTER PARK FL 32792 | $125,000 | $184 | $125,000 | 678 | Condominium | 1/1 | 27 |
| 03-11-2022 | 1920 WOODCREST DRIVE # 15, WINTER PARK FL 32792 | $255,000 | $252 | $250,000 | 1,010 | Condominium | 2/2 | 39 |
| 03-11-2022 | 5169 LAZY OAKS DRIVE # 5169, WINTER PARK FL 32792 | $252,000 | $163 | $250,000 | 1,538 | Townhouse | 2/3 | 51 |
| 03-11-2022 | 3557 AUSTRALIAN CIRCLE, WINTER PARK FL 32792 | $360,000 | $290 | $350,000 | 1,240 | Single Family Residence | 3/2 | 43 |
| 03-11-2022 | 1915 NATALEN ROAD, WINTER PARK FL 32792 | $431,000 | $297 | $415,000 | 1,450 | Single Family Residence | 3/2 | 30 |
| 03-11-2022 | 700 VIA LUGANO ROAD | $4,515,000 | $4,515,000 | / | 8 | |||
| 03-11-2022 | 1280 FORMOSA AVENUE # 10, WINTER PARK FL 32789 | $463,900 | $239 | $463,900 | 1,937 | Townhouse | 3/4 | 53 |
| 03-11-2022 | 1541 SPRINGTIME LOOP, WINTER PARK FL 32792 | $490,000 | $246 | $480,000 | 1,989 | Single Family Residence | 4/3 | 24 |
| 03-11-2022 | 2918 BANCHORY ROAD, WINTER PARK FL 32792 | $520,100 | $267 | $499,000 | 1,942 | Single Family Residence | 4/3 | 63 |
| 03-11-2022 | 632 LONDON ROAD, WINTER PARK FL 32792 | $575,000 | $262 | $575,000 | 2,190 | Single Family Residence | 4/3 | 14 |
| 03-10-2022 | 311 E MORSE BOULEVARD # 3, WINTER PARK FL 32789 | $1,025,000 | $444 | $1,050,000 | 2,304 | Condominium | 2/2 | 49 |
| 03-10-2022 | 1550 DODD ROAD | $1,175,000 | $225 | $1,250,000 | 5,220 | Single Family Residence | 4/6 | 258 |
| 03-10-2022 | 2021 HARMON AVENUE, WINTER PARK FL 32789 | $435,000 | $229 | $425,000 | 1,897 | Single Family Residence | 3/2 | 42 |
| 03-08-2022 | 2860 WILL O TH GREEN STREET, WINTER PARK FL 32792 | $440,000 | $335 | $425,000 | 1,312 | Single Family Residence | 3/2 | 20 |
| 03-08-2022 | 1946 KING ARTHURS COURT, WINTER PARK FL 32792 | $451,000 | $280 | $449,000 | 1,607 | Single Family Residence | 3/2 | 132 |
| 03-08-2022 | 1292 FORMOSA AVENUE # 12, WINTER PARK FL 32789 | $510,000 | $263 | $499,900 | 1,937 | Townhouse | 3/4 | 154 |
| 03-07-2022 | 7429 DANIEL WEBSTER DRIVE, WINTER PARK FL 32792 | $125,000 | $120 | $114,900 | 1,036 | Condominium | 2/2 | 24 |
| 03-07-2022 | 1000 S SEMORAN BOULEVARD # 406, WINTER PARK FL 327 | $120,000 | $154 | $129,900 | 776 | Condominium | 1/1 | 29 |
| 03-07-2022 | 600 MONTEGO BAY COURT # 600, WINTER PARK FL 32792 | $175,000 | $168 | $170,000 | 1,037 | Condominium | 2/2 | 19 |
| 03-07-2022 | 1508 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $397,500 | $216 | $368,000 | 1,840 | Single Family Residence | 3/3 | 33 |
| 03-07-2022 | 5101 ORANGE AVENUE, WINTER PARK FL 32792 | $393,000 | $204 | $389,000 | 1,922 | Single Family Residence | 6/2 | 64 |
| 03-07-2022 | 1238 FORMOSA AVENUE # 3, WINTER PARK FL 32789 | $472,700 | $244 | $472,700 | 1,937 | Townhouse | 3/4 | 53 |
| 03-07-2022 | 516 S PHELPS AVENUE, WINTER PARK FL 32789 | $585,000 | $294 | $600,000 | 1,986 | Single Family Residence | 3/2 | 22 |
| 03-04-2022 | 1259 ESSEX ROAD, WINTER PARK FL 32789 | $1,199,000 | $508 | $1,199,000 | 2,360 | Single Family Residence | 4/3 | 1 |
| 03-04-2022 | 700 MELROSE AVENUE # 31, WINTER PARK FL 32789 | $260,000 | $320 | $229,900 | 810 | Condominium | 1/1 | 29 |
| 03-04-2022 | 720 W WEBSTER AVENUE, WINTER PARK FL 32789 | $385,000 | $283 | $385,000 | 1,356 | 3/2 | 1 | |
| 03-04-2022 | 1262 FORMOSA AVENUE # 7, WINTER PARK FL 32789 | $475,000 | $245 | $475,000 | 1,937 | Townhouse | 3/4 | 106 |
| 03-04-2022 | 260 RIPPLING LANE, WINTER PARK FL 32789 | $635,000 | $291 | $635,000 | 2,179 | Single Family Residence | 3/2 | 74 |
| 03-03-2022 | 1360 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $437,000 | $217 | $449,000 | 2,006 | Single Family Residence | 4/2 | 65 |
| 03-03-2022 | 1226 FORMOSA AVENUE # 1, WINTER PARK FL 32789 | $459,900 | $237 | $469,900 | 1,934 | Townhouse | 3/4 | 218 |
| 03-03-2022 | $549,500 | $216 | $549,500 | 2,535 | Single Family Residence | 4/3 | 33 | |
| 03-02-2022 | 1624 ROUNDELAY LANE, WINTER PARK FL 32789 | $1,400,000 | $296 | $1,450,000 | 4,720 | Single Family Residence | 5/4 | 93 |
| 03-02-2022 | 1956 BISCAYNE DRIVE, WINTER PARK FL 32789 | $285,000 | $194 | $295,000 | 1,469 | Single Family Residence | 3/2 | 20 |
| 03-02-2022 | 648 DUNBAR STREET, WINTER PARK FL 32789 | $335,000 | $394 | $315,000 | 850 | Single Family Residence | 2/1 | 27 |
| 03-02-2022 | 2040 JEWELL AVENUE, WINTER PARK FL 32789 | $400,000 | $333 | $400,000 | 1,200 | Triplex | / | 155 |
| 03-02-2022 | 1286 FORMOSA AVENUE # 11, WINTER PARK FL 32789 | $463,900 | $239 | $463,900 | 1,937 | Townhouse | 3/4 | 45 |
| 03-01-2022 | 690 OSCEOLA AVENUE UNIT 504 | $1,540,000 | $770 | $1,589,000 | 1,998 | Condominium | 3/3 | 76 |
| 03-01-2022 | 3651 N GOLDENROD ROAD # 208, WINTER PARK FL 32792 | $145,000 | $172 | $165,000 | 840 | Condominium | 2/2 | 76 |
| 03-01-2022 | 4078 SCARLET IRIS PLACE, WINTER PARK FL 32792 | $1,975,000 | $250 | $2,250,000 | 7,895 | Single Family Residence | 4/6 | 103 |
| 03-01-2022 | 769 W LYMAN AVENUE, WINTER PARK FL 32789 | $320,000 | $349,900 | / | 170 | |||
| 03-01-2022 | 2817 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $350,000 | $272 | $349,900 | 1,285 | Single Family Residence | 3/2 | 47 |
| 03-01-2022 | 7431 PORTSIDE COURT, WINTER PARK FL 32792 | $355,000 | $245 | $385,000 | 1,448 | Single Family Residence | 3/2 | 26 |
| 03-01-2022 | 532 S RANGER BOULEVARD, WINTER PARK FL 32792 | $417,600 | $196 | $475,880 | 2,120 | Single Family Residence | 5/3 | 243 |
| 02-28-2022 | 688 N NEW YORK AVENUE, WINTER PARK FL 32789 | $1,175,000 | $1,175,000 | / | 59 | |||
| 02-28-2022 | 1680 CHESTNUT AVE, WINTER PARK FL 32789 | $1,600,000 | $514 | $1,600,000 | 3,110 | Single Family Residence | 4/5 | 13 |
| 02-28-2022 | 5475 BRACKEN COURT, WINTER PARK FL 32792 | $265,000 | $176 | $274,900 | 1,499 | Townhouse | 3/4 | 53 |
| 02-28-2022 | 5127 OAK HILL DRIVE, WINTER PARK FL 32792 | $353,000 | $230 | $334,900 | 1,532 | Single Family Residence | 3/2 | 26 |
| 02-28-2022 | 3220 SHADY PINE AVENUE, WINTER PARK FL 32792 | $372,990 | $238 | $345,000 | 1,563 | Single Family Residence | 3/2 | 12 |
| 02-28-2022 | 2754 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $400,000 | $227 | $430,000 | 1,760 | Single Family Residence | 3/2 | 77 |
| 02-28-2022 | 1250 FORMOSA AVENUE # 5, WINTER PARK FL 32789 | $452,500 | $233 | $452,500 | 1,937 | Townhouse | 3/4 | 124 |
| 02-28-2022 | 1232 FORMOSA AVENUE # 2, WINTER PARK FL 32789 | $459,900 | $237 | $459,900 | 1,937 | Townhouse | 3/4 | 35 |
| 02-28-2022 | 1256 FORMOSA AVENUE # 6, WINTER PARK FL 32789 | $472,500 | $243 | $472,500 | 1,937 | Townhouse | 3/4 | 214 |
| 02-28-2022 | 535 N INTERLACHEN AVENUE # 203, WINTER PARK FL 327 | $471,000 | $477 | $479,000 | 986 | Condominium | 2/2 | 38 |
| 02-28-2022 | 1274 FORMOSA AVENUE # 9, WINTER PARK FL 32789 | $485,000 | $250 | $483,900 | 1,937 | Townhouse | 3/4 | 45 |
| 02-25-2022 | 291 SCOTTSDALE SQUARE # 291, WINTER PARK FL 32792 | $115,000 | $146 | $119,000 | 785 | Condominium | 1/1 | 24 |
| 02-25-2022 | 675 TRINIDAD COURT, WINTER PARK FL 32792 | $173,000 | $154 | $168,000 | 1,120 | Townhouse | 2/2 | 38 |
| 02-25-2022 | 151 N ORLANDO AVENUE UNIT 238 | $251,000 | $326 | $219,900 | 768 | Condominium | 2/1 | 31 |
| 02-25-2022 | 2057 POINCIANA RD, WINTER PARK FL 32792 | $357,500 | $219 | $355,000 | 1,630 | Single Family Residence | 3/2 | 100 |
| 02-25-2022 | 955 MINNESOTA AVENUE, WINTER PARK FL 32789 | $420,000 | $311 | $390,000 | 1,349 | Single Family Residence | 3/1 | 35 |
| 02-24-2022 | 4762 TANGERINE AVENUE # 4762, WINTER PARK FL 32792 | $180,000 | $140 | $175,000 | 1,281 | Townhouse | 2/2 | 36 |
| 02-24-2022 | 7128 BETTY STREET, WINTER PARK FL 32792 | $376,000 | $241 | $390,300 | 1,560 | Single Family Residence | 3/2 | 45 |
| 02-24-2022 | 3621 OAK VISTA LANE, WINTER PARK FL 32792 | $435,000 | $204 | $415,000 | 2,124 | Single Family Residence | 3/2 | 36 |
| 02-24-2022 | 2408 WINTER PARK ROAD, WINTER PARK FL 32789 | $465,000 | $360 | $475,000 | 1,291 | Single Family Residence | 3/2 | 42 |
| 02-24-2022 | 2257 HOWARD DRIVE, WINTER PARK FL 32789 | $500,000 | $259 | $525,000 | 1,925 | Single Family Residence | 4/2 | 152 |
| 02-23-2022 | 1930 ASTER DRIVE, WINTER PARK FL 32792 | $415,000 | $252 | $399,999 | 1,645 | Single Family Residence | 3/2 | 43 |
| 02-23-2022 | 5140 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $411,000 | $234 | $435,000 | 1,752 | Single Family Residence | 4/2 | 68 |
| 02-23-2022 | 624 MONMOUTH WAY, WINTER PARK FL 32792 | $617,000 | $195 | $685,000 | 3,155 | Single Family Residence | 5/4 | 29 |
| 02-22-2022 | 1430 ALOMA AVENUE | $1,210,000 | $423 | $1,289,000 | 2,855 | Single Family Residence | 3/3 | 117 |
| 02-22-2022 | 668 SAINT JOHNS COURT, WINTER PARK FL 32792 | $172,000 | $165 | $172,000 | 1,037 | 2/2 | 2 | |
| 02-22-2022 | 3043 MOSS VALLEY PLACE, WINTER PARK FL 32792 | $330,700 | $237 | $315,000 | 1,394 | Single Family Residence | 3/3 | 48 |
| 02-22-2022 | 2828 SCARLET ROAD, WINTER PARK FL 32792 | $440,000 | $283 | $425,000 | 1,550 | Single Family Residence | 3/2 | 42 |
| 02-22-2022 | 502 GILBERT ROAD, WINTER PARK FL 32792 | $590,000 | $318 | $557,000 | 1,854 | Single Family Residence | 3/2 | 38 |
| 02-21-2022 | 200 SAINT ANDREWS BOULEVARD # 502, WINTER PARK FL | $185,500 | $255 | $185,500 | 727 | Condominium | 1/1 | 40 |
| 02-21-2022 | 5592 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $379,999 | $229 | $379,999 | 1,658 | Single Family Residence | 3/2 | 61 |
| 02-18-2022 | 3351 RIVER VIEW WAY # 41, WINTER PARK FL 32792 | $160,000 | $161 | $160,000 | 990 | Condominium | 2/2 | 80 |
| 02-18-2022 | 2500 LEE ROAD UNIT 144 | $160,000 | $248 | $170,000 | 645 | Condominium | 1/1 | 74 |
| 02-18-2022 | 1520 MIZELL AVENUE | $1,750,000 | $387 | $1,795,000 | 4,516 | Single Family Residence | 5/5 | 163 |
| 02-18-2022 | 128 OAK GROVE ROAD, WINTER PARK FL 32789 | $293,000 | $253 | $289,900 | 1,156 | Single Family Residence | 3/2 | 23 |
| 02-18-2022 | 2632 PASSAMONTE DRIVE # 7F, WINTER PARK FL 32792 | $315,000 | $166 | $345,000 | 1,892 | Townhouse | 3/3 | 53 |
| 02-18-2022 | 1791 TAYLOR AVENUE, WINTER PARK FL 32789 | $580,000 | $533 | $499,000 | 1,087 | Single Family Residence | 3/1 | 19 |
| 02-18-2022 | 1712 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $505,000 | $265 | $520,000 | 1,899 | Single Family Residence | 3/2 | 44 |
| 02-18-2022 | 1712 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $505,000 | $520,000 | / | 43 | |||
| 02-17-2022 | $225,000 | $386 | $225,000 | 582 | Condominium | 1/1 | 16 | |
| 02-16-2022 | 409 LANGHOLM DRIVE, WINTER PARK FL 32789 | $1,630,000 | $434 | $1,590,000 | 3,751 | Single Family Residence | 4/5 | 70 |
| 02-16-2022 | 3220 OAK LAWN PLACE # 210, WINTER PARK FL 32792 | $183,000 | $158 | $179,990 | 1,151 | Condominium | 3/3 | 35 |
| 02-16-2022 | 1319 N NEW YORK AVENUE, WINTER PARK FL 32789 | $1,900,000 | $379 | $1,900,000 | 5,010 | Single Family Residence | 4/4 | 1 |
| 02-16-2022 | 1915 CARRIGAN AVENUE, WINTER PARK FL 32792 | $333,000 | $219 | $340,000 | 1,520 | Single Family Residence | 3/1 | 35 |
| 02-15-2022 | 1695 LEE ROAD # D113, WINTER PARK FL 32789 | $130,000 | $147 | $129,999 | 881 | Condominium | 2/1 | 30 |
| 02-15-2022 | 200 SAINT ANDREWS BOULEVARD # 1806, WINTER PARK FL | $235,000 | $192 | $247,500 | 1,219 | Condominium | 2/2 | 27 |
| 02-15-2022 | 1350 PELHAM ROAD, WINTER PARK FL 32789 | $325,000 | $278 | $374,900 | 1,169 | Single Family Residence | 3/1 | 58 |
| 02-15-2022 | 2750 SCARLET ROAD, WINTER PARK FL 32792 | $485,000 | $291 | $479,900 | 1,662 | Single Family Residence | 4/2 | 43 |
| 02-14-2022 | 543 COUNTRY CLUB DRIVE | $234,000 | $235,000 | / | 665 | |||
| 02-14-2022 | 501 COUNTRY CLUB DRIVE | $284,000 | $285,000 | / | 665 | |||
| 02-14-2022 | 633 HUNTINGTON AVENUE # 633, WINTER PARK FL 32789 | $318,000 | $257 | $324,900 | 1,234 | Condominium | 2/3 | 133 |
| 02-14-2022 | 3528 BALSAM DRIVE, WINTER PARK FL 32792 | $360,000 | $224 | $349,990 | 1,605 | Single Family Residence | 3/2 | 18 |
| 02-14-2022 | 2106 BISCAYNE DRIVE, WINTER PARK FL 32789 | $455,000 | $296 | $435,000 | 1,533 | Single Family Residence | 3/2 | 18 |
| 02-14-2022 | 327 ELKHORN COURT, WINTER PARK FL 32792 | $589,900 | $299 | $589,900 | 1,968 | Single Family Residence | 4/3 | 34 |
| 02-14-2022 | 1820 MONDRIAN CIRCLE | $680,000 | $301 | $719,000 | 2,252 | Townhouse | 3/4 | 28 |
| 02-14-2022 | 195 SCOTTSDALE SQUARE # 195, WINTER PARK FL 32792 | $75,000 | $125 | $82,000 | 600 | Condominium | /1 | 104 |
| 02-11-2022 | 1691 PALM AVENUE, WINTER PARK FL 32789 | $1,450,000 | $471 | $1,695,000 | 3,075 | Single Family Residence | 4/4 | 82 |
| 02-11-2022 | 1000 S SEMORAN BOULEVARD # 104, WINTER PARK FL 327 | $205,000 | $131 | $199,990 | 1,554 | Condominium | 3/2 | 17 |
| 02-11-2022 | 1554 MINNESOTA AVENUE, WINTER PARK FL 32789 | $315,000 | $417 | $314,900 | 754 | Single Family Residence | 2/1 | 78 |
| 02-11-2022 | 1122 DENTON ROAD, WINTER PARK FL 32792 | $449,000 | $275 | $429,000 | 1,628 | Single Family Residence | 4/2 | 24 |
| 02-11-2022 | 678 DEPUGH STREET, WINTER PARK FL 32789 | $624,500 | $321 | $639,900 | 1,940 | Single Family Residence | 4/3 | 37 |
| 02-11-2022 | 1510 GROVE TERRACE, WINTER PARK FL 32789 | $750,000 | $472 | $699,000 | 1,586 | Single Family Residence | 2/2 | 30 |
| 02-11-2022 | $750,000 | $472 | $750,000 | 1,586 | Single Family Residence | 2/2 | 1 | |
| 02-10-2022 | 1531 GROVE TERRACE, WINTER PARK FL 32789 | $1,084,000 | $442 | $1,050,000 | 2,451 | Single Family Residence | 4/3 | 36 |
| 02-10-2022 | 2628 EXUMA WAY, WINTER PARK FL 32792 | $231,500 | $198 | $225,000 | 1,166 | Townhouse | 2/1 | 42 |
| 02-10-2022 | 3610 HAWTHORNE LANE, WINTER PARK FL 32792 | $367,000 | $222 | $339,000 | 1,647 | Single Family Residence | 4/2 | 24 |
| 02-10-2022 | 7045 HAMMOCK WAY, WINTER PARK FL 32792 | $375,000 | $237 | $369,000 | 1,577 | Single Family Residence | 3/2 | 16 |
| 02-10-2022 | 2554 FORFARSHIRE DRIVE, WINTER PARK FL 32792 | $465,000 | $299 | $455,000 | 1,551 | Single Family Residence | 3/2 | 32 |
| 02-09-2022 | 200 SAINT ANDREWS BOULEVARD # 1603, WINTER PARK FL | $195,000 | $173 | $195,000 | 1,127 | Condominium | 2/2 | 51 |
| 02-09-2022 | 511 W CANTON AVENUE, WINTER PARK FL 32789 | $3,800,000 | $426 | $4,900,000 | 8,910 | Single Family Residence | 5/7 | 67 |
| 02-07-2022 | 1180 WHITESELL DRIVE, WINTER PARK FL 32789 | $975,000 | $524 | $1,000,000 | 1,859 | Single Family Residence | 3/2 | 4 |
| 02-07-2022 | 198 LEWFIELD CIRCLE # 198, WINTER PARK FL 32792 | $189,000 | $149 | $189,000 | 1,268 | Condominium | 3/2 | 55 |
| 02-04-2022 | 3045 AARON BURR AVENUE # 11, WINTER PARK FL 32792 | $160,000 | $150 | $155,000 | 1,062 | Condominium | 2/2 | 24 |
| 02-04-2022 | RIDDLE DRIVE, WINTER PARK FL 32789 | $180,000 | $182,000 | / | 520 | |||
| 02-04-2022 | 2651 EXUMA WAY, WINTER PARK FL 32792 | $240,500 | $157 | $239,900 | 1,528 | Townhouse | 3/2 | 29 |
| 02-04-2022 | 2281 ISLAND RUN, WINTER PARK FL 32792 | $247,000 | $242 | $245,000 | 1,020 | Townhouse | 2/2 | 71 |
| 02-04-2022 | $265,000 | $235 | $299,900 | 1,125 | Single Family Residence | 3/2 | 35 | |
| 02-04-2022 | 648 CALLAHAN STREET, WINTER PARK FL 32789 | $335,000 | $350,000 | / | 86 | |||
| 02-04-2022 | 1905 SUMMERFIELD ROAD, WINTER PARK FL 32792 | $460,000 | $310 | $450,000 | 1,480 | Single Family Residence | 3/2 | 15 |
| 02-04-2022 | 657 BRECHIN DRIVE, WINTER PARK FL 32792 | $470,000 | $319 | $487,000 | 1,472 | Single Family Residence | 3/2 | 66 |
| 02-04-2022 | 2723 RIDDLE DRIVE, WINTER PARK FL 32789 | $580,000 | $301 | $589,000 | 1,925 | Single Family Residence | 4/2 | 58 |
| 02-03-2022 | 1123 DENTON ROAD, WINTER PARK FL 32792 | $367,500 | $180 | $387,500 | 2,040 | Single Family Residence | 4/3 | 122 |
| 02-03-2022 | 4963 N PINE AVENUE, WINTER PARK FL 32792 | $403,000 | $192 | $420,000 | 2,096 | Business | / | 102 |
| 02-03-2022 | 1584 LITTLE WREN LANE, WINTER PARK FL 32792 | $420,000 | $176 | $427,000 | 2,378 | Townhouse | 3/3 | 231 |
| 02-03-2022 | 690 OSCEOLA AVENUE UNIT 205 | $475,000 | $558 | $475,000 | 850 | Condominium | 1/1 | 1 |
| 02-02-2022 | 301 BELOIT AVENUE, WINTER PARK FL 32789 | $1,300,000 | $468 | $1,695,000 | 2,774 | Single Family Residence | 3/3 | 71 |
| 02-02-2022 | 3364 RIVER VIEW WAY # 51, WINTER PARK FL 32792 | $170,000 | $164 | $175,000 | 1,031 | Condominium | 2/3 | 22 |
| 02-02-2022 | 2427 DOMINICA RUN, WINTER PARK FL 32792 | $270,000 | $149 | $225,000 | 1,803 | Townhouse | 3/2 | 31 |
| 02-02-2022 | 1506 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $260,000 | $157 | $270,000 | 1,652 | Townhouse | 3/2 | 134 |
| 02-02-2022 | 690 OSCEOLA AVENUE UNIT 204 | $600,000 | $522 | $489,500 | 1,148 | Condominium | 2/2 | 305 |
| 02-02-2022 | 8147 LAZY BEAR LANE, WINTER PARK FL 32792 | $568,300 | $220 | $569,000 | 2,572 | Single Family Residence | 4/3 | 43 |
| 02-01-2022 | 3318 ROYAL STREET, WINTER PARK FL 32792 | $245,000 | $206 | $239,000 | 1,185 | 1/2 Duplex | 3/2 | 26 |
| 02-01-2022 | 912 CARVELL DRIVE, WINTER PARK FL 32792 | $410,000 | $254 | $400,000 | 1,614 | Single Family Residence | 3/2 | 21 |
| 01-31-2022 | 155 LEWFIELD CIRCLE # 155, WINTER PARK FL 32792 | $118,000 | $174 | $114,900 | 678 | Condominium | 1/1 | 40 |
| 01-31-2022 | 1009 VIA TUSCANY OAKS WAY, WINTER PARK FL 32789 | $1,535,000 | $415 | $1,550,000 | 3,692 | Single Family Residence | 4/5 | 1 |
| 01-31-2022 | 1725 SPRUCE AVENUE, WINTER PARK FL 32789 | $1,985,000 | $508 | $1,995,000 | 3,904 | Single Family Residence | 5/5 | 60 |
| 01-31-2022 | 1920 WOODCREST DRIVE # 10, WINTER PARK FL 32792 | $225,000 | $222 | $225,000 | 1,010 | Condominium | 2/2 | 54 |
| 01-31-2022 | 2844 SCARLET ROAD, WINTER PARK FL 32792 | $412,284 | $273 | $399,900 | 1,508 | Single Family Residence | 4/2 | 29 |
| 01-31-2022 | 641 DOUGLAS AVENUE, WINTER PARK FL 32789 | $412,500 | $425,000 | / | 120 | |||
| 01-31-2022 | 671 DOUGLAS AVENUE, WINTER PARK FL 32789 | $412,500 | $425,000 | / | 120 | |||
| 01-31-2022 | 913 CAMELLIA AVENUE, WINTER PARK FL 32789 | $445,000 | $320 | $449,900 | 1,389 | Single Family Residence | 3/3 | 74 |
| 01-28-2022 | 741 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $435,000 | $206 | $400,000 | 2,104 | Single Family Residence | 4/2 | 292 |
| 01-28-2022 | 1445 PELICAN BAY TRAIL, WINTER PARK FL 32792 | $415,000 | $225 | $429,900 | 1,844 | Single Family Residence | 3/2 | 80 |
| 01-28-2022 | 2205 HAWICK LANE, WINTER PARK FL 32792 | $430,000 | $241 | $430,000 | 1,778 | Townhouse | 3/3 | 114 |
| 01-28-2022 | 660 NORTHWOOD CIRCLE, WINTER PARK FL 32789 | $620,000 | $308 | $687,500 | 2,008 | Single Family Residence | 5/3 | 51 |
| 01-28-2022 | 648 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $740,000 | $348 | $749,900 | 2,125 | Single Family Residence | 4/3 | 66 |
| 01-27-2022 | 2224 VENETIAN WAY | $1,500,000 | $408 | $1,590,000 | 3,673 | Single Family Residence | 4/4 | 143 |
| 01-27-2022 | 7457 WYNNEWOOD SQUARE # 184, WINTER PARK FL 32792 | $185,000 | $160 | $181,900 | 1,151 | Condominium | 3/3 | 62 |
| 01-27-2022 | 3506 BALSAM DRIVE, WINTER PARK FL 32792 | $320,000 | $257 | $300,000 | 1,243 | Single Family Residence | 3/2 | 25 |
| 01-27-2022 | $455,000 | $229 | $455,000 | 1,983 | Single Family Residence | 4/3 | 5 | |
| 01-27-2022 | $455,000 | $200 | $465,000 | 2,274 | Single Family Residence | 4/3 | 103 | |
| 01-27-2022 | 224 OVERLOOK ROAD, WINTER PARK FL 32789 | $450,000 | $321 | $499,000 | 1,399 | Single Family Residence | 2/2 | 77 |
| 01-27-2022 | 1808 BARKER DR DRIVE, WINTER PARK FL 32789 | $499,900 | $250 | $499,900 | 1,994 | Single Family Residence | 4/3 | 71 |
| 01-26-2022 | 7027 CITRUS POINT COURT, WINTER PARK FL 32792 | $390,000 | $260 | $388,900 | 1,495 | Single Family Residence | 3/2 | 62 |
| 01-25-2022 | 3056 NICHOLSON DRIVE, WINTER PARK FL 32792 | $400,000 | $186 | $419,000 | 2,144 | Single Family Residence | 4/3 | 110 |
| 01-25-2022 | 1635 HIGHLAND ROAD | $599,900 | $351 | $599,900 | 1,706 | Single Family Residence | 3/2 | 92 |
| 01-25-2022 | 102 S INTERLACHEN AVENUE UNIT 206 | $600,000 | $541 | $619,000 | 1,109 | Condominium | 2/2 | 20 |
| 01-24-2022 | 419 W MORSE BOULEVARD, WINTER PARK FL 32789 | $1,760,000 | $581 | $1,850,000 | 3,027 | Townhouse | 3/4 | 40 |
| 01-24-2022 | 1995 BENTWOOD DRIVE, WINTER PARK FL 32792 | $415,000 | $244 | $425,000 | 1,700 | Single Family Residence | 3/2 | 74 |
| 01-24-2022 | 2420 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $863,000 | $307 | $887,000 | 2,811 | Single Family Residence | 4/4 | 238 |
| 01-21-2022 | 234 SCOTTSDALE SQUARE # 234, WINTER PARK FL 32792 | $127,000 | $117 | $125,990 | 1,085 | Condominium | 2/2 | 20 |
| 01-21-2022 | 5420 FERROL DRIVE, WINTER PARK FL 32792 | $328,000 | $263 | $335,000 | 1,247 | Single Family Residence | 3/2 | 52 |
| 01-21-2022 | 106 S INTERLACHEN AVENUE UNIT 516 | $519,000 | $454 | $519,000 | 1,143 | Condominium | 2/2 | 36 |
| 01-20-2022 | 3446 BOWMAN DRIVE, WINTER PARK FL 32792 | $359,000 | $249 | $345,000 | 1,438 | Single Family Residence | 3/2 | 26 |
| 01-20-2022 | 2369 SHADOWLAND LOOP, WINTER PARK FL 32792 | $387,500 | $220 | $400,000 | 1,756 | Townhouse | 3/3 | 42 |
| 01-19-2022 | 461 S VIRGINIA AVENUE, WINTER PARK FL 32789 | $300,000 | $400,000 | / | 48 | |||
| 01-19-2022 | 445 S VIRGINIA AVENUE, WINTER PARK FL 32789 | $535,000 | $424 | $400,000 | 1,260 | Single Family Residence | 3/2 | 48 |
| 01-19-2022 | 313 SCOTTSDALE SQUARE # 313, WINTER PARK FL 32792 | $76,000 | $96 | $80,900 | 785 | Condominium | 1/1 | 148 |
| 01-18-2022 | 7706 COUNTRY PLACE # 8, WINTER PARK FL 32792 | $210,000 | $170 | $225,000 | 1,230 | Condominium | 3/2 | 44 |
| 01-18-2022 | 1570 BRYAN AVENUE, WINTER PARK FL 32789 | $2,830,000 | $611 | $2,850,000 | 4,627 | Single Family Residence | 6/7 | 250 |
| 01-18-2022 | 1732 HARVEST COVE, WINTER PARK FL 32792 | $369,000 | $241 | $381,000 | 1,528 | Single Family Residence | 3/2 | 142 |
| 01-18-2022 | 2424 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $420,000 | $176 | $430,000 | 2,378 | Townhouse | 3/3 | 78 |
| 01-18-2022 | 1729 MICHIGAN AVENUE, WINTER PARK FL 32789 | $460,800 | $298 | $475,000 | 1,546 | Single Family Residence | 3/3 | 132 |
| 01-18-2022 | 2902 BANCHORY ROAD, WINTER PARK FL 32792 | $685,000 | $262 | $674,990 | 2,612 | Single Family Residence | 4/3 | 17 |
| 01-14-2022 | 315 E NEW ENGLAND AVENUE # 24, WINTER PARK FL 3278 | $1,110,000 | $733 | $1,195,000 | 1,514 | Condominium | 2/2 | 78 |
| 01-14-2022 | 2929 ANTIQUE OAKS CIRCLE # 53, WINTER PARK FL 3279 | $87,000 | $116 | $124,900 | 749 | Condominium | 1/1 | 340 |
| 01-14-2022 | 3651 N GOLDENROD ROAD # B102, WINTER PARK FL 32792 | $128,000 | $152 | $159,000 | 840 | Condominium | 2/2 | 122 |
| 01-14-2022 | 5043 GOLDENROD PLACE ROAD, WINTER PARK FL 32792 | $314,000 | $232 | $305,000 | 1,350 | Single Family Residence | 3/2 | 44 |
| 01-14-2022 | 3212 SHADY PINE AVE, WINTER PARK FL 32792 | $366,000 | $217 | $369,900 | 1,680 | Single Family Residence | 4/2 | 23 |
| 01-14-2022 | 1820 VIBURNUM LANE, WINTER PARK FL 32792 | $420,000 | $190 | $420,000 | 2,202 | Single Family Residence | 4/3 | 1 |
| 01-14-2022 | 4552 WHIMBREL PLACE, WINTER PARK FL 32792 | $480,000 | $195 | $509,000 | 2,454 | Single Family Residence | 4/3 | 57 |
| 01-13-2022 | 275 SANDLEWOOD TRAIL # 1, WINTER PARK FL 32789 | $226,000 | $235 | $215,000 | 959 | Condominium | 2/3 | 46 |
| 01-12-2022 | 7777 FERNBROOK WAY, WINTER PARK FL 32792 | $218,000 | $199 | $229,000 | 1,092 | Townhouse | 2/2 | 120 |
| 01-12-2022 | 2948 FITZOOTH DRIVE, WINTER PARK FL 32792 | $545,000 | $236 | $499,900 | 2,301 | Single Family Residence | 4/3 | 36 |
| 01-11-2022 | 174 SCOTTSDALE SQUARE # 174, WINTER PARK FL 32792 | $115,000 | $105 | $115,000 | 1,085 | Condominium | 2/2 | 33 |
| 01-11-2022 | 3364 RIVER VIEW WAY # 51, WINTER PARK FL 32792 | $145,000 | $140 | $150,000 | 1,031 | Condominium | 2/3 | 14 |
| 01-11-2022 | 1427 BROAD WING LANE, WINTER PARK FL 32792 | $430,000 | $180 | $425,000 | 2,378 | Townhouse | 3/3 | 33 |
| 01-10-2022 | 1411 NORFOLK AVENUE, WINTER PARK FL 32789 | $307,500 | $207 | $307,500 | 1,480 | 3/1 | 11 | |
| 01-10-2022 | 2336 SHADOWLAND LOOP, WINTER PARK FL 32792 | $439,000 | $214 | $429,000 | 2,042 | Townhouse | 3/3 | 54 |
| 01-07-2022 | 157 SCOTTSDALE SQUARE # 157, WINTER PARK FL 32792 | $137,000 | $134 | $139,900 | 1,020 | Condominium | 2/2 | 63 |
| 01-07-2022 | 200 SAINT ANDREWS BOULEVARD # 304, WINTER PARK FL | $147,000 | $185 | $159,000 | 793 | Condominium | 1/1 | 49 |
| 01-07-2022 | 3282 OAK LAKE PLACE # 122, WINTER PARK FL 32792 | $160,000 | $161 | $169,000 | 990 | Condominium | 2/2 | 23 |
| 01-07-2022 | 4115 N GOLDENROD ROAD, WINTER PARK FL 32792 | $290,000 | $190 | $270,000 | 1,520 | Single Family Residence | 2/2 | 36 |
| 01-07-2022 | 3120 NICHOLSON DRIVE, WINTER PARK FL 32792 | $340,000 | $176 | $340,000 | 1,930 | Single Family Residence | 4/3 | 51 |
| 01-07-2022 | 880 N LAKEMONT AVENUE, WINTER PARK FL 32792 | $422,000 | $298 | $421,999 | 1,414 | Single Family Residence | 3/2 | 72 |
| 01-06-2022 | RIDDLE DRIVE, WINTER PARK FL 32789 | $175,000 | $182,000 | / | 491 | |||
| 01-06-2022 | 1800 GLADIOLAS DRIVE, WINTER PARK FL 32792 | $320,000 | $193 | $350,000 | 1,650 | Single Family Residence | 3/2 | 35 |
| 01-06-2022 | 694 DUNBLANE DRIVE, WINTER PARK FL 32792 | $389,000 | $216 | $399,000 | 1,793 | Single Family Residence | 3/2 | 70 |
| 01-06-2022 | 2241 SHADOWLAND LOOP, WINTER PARK FL 32792 | $402,000 | $204 | $406,000 | 1,964 | Townhouse | 3/3 | 36 |
| 01-05-2022 | 1760 LOOKOUT LANDING CIRCLE, WINTER PARK FL 32789 | $1,560,000 | $396 | $1,560,000 | 3,931 | 5/5 | 2 | |
| 01-05-2022 | 2237 ELSINORE AVENUE, WINTER PARK FL 32792 | $294,000 | $294 | $275,000 | 1,000 | Single Family Residence | 3/1 | 49 |
| 01-05-2022 | 2626 AMBERGATE ROAD, WINTER PARK FL 32792 | $300,000 | $262 | $300,000 | 1,143 | 3/1 | 5 | |
| 01-05-2022 | 1109 DENTON ROAD, WINTER PARK FL 32792 | $310,000 | $222 | $320,000 | 1,396 | Single Family Residence | 3/2 | 21 |
| 01-05-2022 | 826 GUTHRIE COURT, WINTER PARK FL 32792 | $430,000 | $242 | $429,000 | 1,776 | Single Family Residence | 4/2 | 35 |
| 01-04-2022 | 551 COUNTRY CLUB DRIVE | $1,250,000 | $423 | $1,299,900 | 2,950 | Single Family Residence | 4/5 | 208 |
| 01-04-2022 | 1550 BRYAN AVENUE, WINTER PARK FL 32789 | $2,200,000 | $485 | $2,195,000 | 4,532 | Single Family Residence | 5/7 | 62 |
| 01-04-2022 | 190 BALFOUR DRIVE # 1, WINTER PARK FL 32792 | $238,000 | $194 | $250,000 | 1,225 | Condominium | 2/2 | 82 |
| 01-04-2022 | 240 N PHELPS AVENUE, WINTER PARK FL 32789 | $430,000 | $445,000 | / | 133 | |||
| 01-04-2022 | 350 CAROLINA AVENUE # 305, WINTER PARK FL 32789 | $460,000 | $297 | $479,000 | 1,544 | Condominium | 2/2 | 109 |
| 01-03-2022 | 1409 CHAPMAN CIRCLE | $1,119,000 | $367 | $1,119,000 | 3,043 | Single Family Residence | 3/4 | 144 |
| 12-31-2021 | 7314 FIELDCREST AVENUE, WINTER PARK FL 32792 | $250,000 | $210 | $225,000 | 1,188 | Single Family Residence | 3/2 | 30 |
| 12-31-2021 | 1008 N PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $2,295,000 | $650 | $2,295,000 | 3,530 | Single Family Residence | 4/5 | 88 |
| 12-31-2021 | 700 MELROSE AVENUE # 23, WINTER PARK FL 32789 | $240,000 | $223 | $240,000 | 1,074 | 2/2 | 5 | |
| 12-30-2021 | 3158 SHADY PINE AVENUE, WINTER PARK FL 32792 | $335,000 | $207 | $368,900 | 1,615 | Single Family Residence | 4/2 | 39 |
| 12-30-2021 | 7627 LODGE POLE TRAIL, WINTER PARK FL 32792 | $381,000 | $169 | $375,000 | 2,251 | Single Family Residence | 3/2 | 37 |
| 12-30-2021 | 133 SCOTTSDALE SQUARE # 133, WINTER PARK FL 32792 | $77,000 | $98 | $79,000 | 785 | Condominium | 1/1 | 106 |
| 12-29-2021 | 1800 TAYLOR AVENUE, WINTER PARK FL 32789 | $1,085,000 | $432 | $1,085,000 | 2,508 | Single Family Residence | 2/3 | 44 |
| 12-29-2021 | 3217 OAK LAWN PLACE # 211, WINTER PARK FL 32792 | $180,000 | $161 | $180,000 | 1,117 | Condominium | 3/2 | 52 |
| 12-29-2021 | 310 S RANGER BOULEVARD, WINTER PARK FL 32792 | $450,000 | $252 | $430,000 | 1,782 | Single Family Residence | 3/2 | 41 |
| 12-28-2021 | 315 E NEW ENGLAND AVENUE # 13, WINTER PARK FL 3278 | $950,000 | $594 | $1,000,000 | 1,599 | Condominium | 2/2 | 98 |
| 12-28-2021 | 1520 MAGNOLIA AVENUE, WINTER PARK FL 32789 | $1,285,000 | $393 | $1,324,900 | 3,262 | Single Family Residence | 4/4 | 105 |
| 12-28-2021 | 920 CARVELL DRIVE, WINTER PARK FL 32792 | $410,000 | $205 | $389,950 | 1,996 | Single Family Residence | 4/2 | 283 |
| 12-28-2021 | 1165 WASHINGTON AVENUE # B, WINTER PARK FL 32789 | $500,000 | $263 | $500,000 | 1,900 | Condominium | 3/2 | 89 |
| 12-27-2021 | 292 LEWFIELD CIRCLE # 292, WINTER PARK FL 32792 | $110,500 | $162 | $100,000 | 678 | Condominium | 1/1 | 46 |
| 12-27-2021 | 200 SAINT ANDREWS BOULEVARD # 1208, WINTER PARK FL | $219,000 | $165 | $229,000 | 1,322 | Condominium | 3/2 | 46 |
| 12-27-2021 | 693 MINNESOTA AVENUE # 693, WINTER PARK FL 32789 | $354,900 | $341 | $354,900 | 1,038 | Condominium | 2/2 | 29 |
| 12-23-2021 | 1331 MERRYDALE WAY, WINTER PARK FL 32792 | $432,614 | $181 | $432,614 | 2,378 | 3/3 | 15 | |
| 12-23-2021 | 1860 ANZLE AVENUE, WINTER PARK FL 32789 | $555,000 | $250 | $555,000 | 2,214 | Mixed Use | / | 112 |
| 12-23-2021 | 208 BREWER AVENUE, WINTER PARK FL 32789 | $695,000 | $305 | $685,000 | 2,273 | Single Family Residence | 4/4 | 64 |
| 12-23-2021 | 737 N CAPEN AVENUE, WINTER PARK FL 32789 | $700,000 | $362 | $732,000 | 1,930 | Single Family Residence | 3/2 | 66 |
| 12-22-2021 | 261 E CANTON AVENUE # 261, WINTER PARK FL 32789 | $320,000 | $436 | $325,000 | 733 | Condominium | 1/1 | 128 |
| 12-22-2021 | 741 FRIAR ROAD, WINTER PARK FL 32792 | $500,000 | $253 | $450,000 | 1,970 | Single Family Residence | 4/3 | 21 |
| 12-22-2021 | 1453 LONE FEATHER TRAIL, WINTER PARK FL 32792 | $525,970 | $203 | $525,970 | 2,582 | 4/4 | 2 | |
| 12-22-2021 | 690 OSCEOLA AVENUE UNIT 607 | $799,000 | $474 | $849,000 | 1,683 | Condominium | 3/3 | 69 |
| 12-21-2021 | 4887 SEMINOLE AVE, WINTER PARK FL 32792 | $175,000 | $77 | $262,600 | 2,256 | Single Family Residence | 4/3 | 117 |
| 12-20-2021 | 1180 TOM GURNEY DRIVE, WINTER PARK FL 32789 | $2,845,000 | $660 | $2,800,000 | 4,309 | Single Family Residence | 4/5 | 39 |
| 12-20-2021 | 674 W MORSE BOULEVARD, WINTER PARK FL 32789 | $3,200,000 | $728 | $3,150,000 | 4,390 | Single Family Residence | 4/5 | 47 |
| 12-20-2021 | 1708 W CHERYL DRIVE, WINTER PARK FL 32792 | $312,500 | $171 | $349,999 | 1,818 | Single Family Residence | 4/2 | 50 |
| 12-17-2021 | 127 LEWFIELD CIRCLE # 127, WINTER PARK FL 32792 | $113,000 | $166 | $115,000 | 678 | Condominium | 1/1 | 100 |
| 12-17-2021 | 200 SAINT ANDREWS BOULEVARD # 2612, WINTER PARK FL | $208,000 | $185 | $215,000 | 1,119 | Condominium | 2/2 | 47 |
| 12-17-2021 | 3320 ROYAL STREET, WINTER PARK FL 32792 | $236,000 | $199 | $235,000 | 1,185 | 1/2 Duplex | 3/2 | 37 |
| 12-17-2021 | 1705 MICHIGAN AVENUE, WINTER PARK FL 32789 | $218,000 | $386 | $249,000 | 564 | Single Family Residence | 2/1 | 50 |
| 12-17-2021 | 1331 COLLEGE POINT, WINTER PARK FL 32789 | $2,470,000 | $2,575,000 | / | 143 | |||
| 12-17-2021 | 3073 BLUEBROOK DRIVE, WINTER PARK FL 32792 | $313,000 | $219 | $323,900 | 1,426 | Single Family Residence | 3/2 | 138 |
| 12-17-2021 | 7619 GLENMOOR LANE, WINTER PARK FL 32792 | $315,000 | $227 | $335,000 | 1,387 | Single Family Residence | 3/2 | 85 |
| 12-17-2021 | 1491 CLEMATIS LANE, WINTER PARK FL 32792 | $370,000 | $171 | $369,999 | 2,157 | Single Family Residence | 4/2 | 77 |
| 12-17-2021 | 1652 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $383,800 | $256 | $389,900 | 1,498 | Single Family Residence | 3/2 | 93 |
| 12-17-2021 | 1773 INDIANA AVENUE # C, WINTER PARK FL 32789 | $399,000 | $246 | $415,000 | 1,616 | Townhouse | 3/3 | 58 |
| 12-17-2021 | 2631 ROXBURY ROAD, WINTER PARK FL 32789 | $425,000 | $243 | $420,000 | 1,742 | Duplex | / | 34 |
| 12-17-2021 | 1424 CAVENDISH ROAD, WINTER PARK FL 32789 | $445,000 | $393 | $435,000 | 1,132 | Single Family Residence | 2/1 | 30 |
| 12-17-2021 | 1457 LONE FEATHER TRAIL, WINTER PARK FL 32792 | $464,921 | $180 | $464,921 | 2,582 | 4/4 | 4 | |
| 12-17-2021 | 1352 BLUE STEM LANE, WINTER PARK FL 32792 | $515,278 | $202 | $515,278 | 2,542 | 4/4 | 30 | |
| 12-17-2021 | 2050 SHARON ROAD, WINTER PARK FL 32789 | $780,000 | $422 | $739,900 | 1,845 | Single Family Residence | 3/2 | 39 |
| 12-17-2021 | 134 DETMAR DRIVE, WINTER PARK FL 32789 | $880,000 | $264 | $899,000 | 3,333 | Single Family Residence | 4/4 | 123 |
| 12-17-2021 | 1620 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $900,000 | $229 | $999,900 | 3,915 | Single Family Residence | 3/4 | 99 |
| 12-16-2021 | 116 SCOTTSDALE SQUARE # 116, WINTER PARK FL 32792 | $100,000 | $98 | $107,500 | 1,020 | Condominium | 2/2 | 113 |
| 12-16-2021 | 317 PARK NORTH COURT, WINTER PARK FL 32789 | $1,279,000 | $443 | $1,279,000 | 2,882 | Single Family Residence | 4/3 | 63 |
| 12-16-2021 | 7445 DANIEL WEBSTER DRIVE # 1, WINTER PARK FL 3279 | $155,000 | $142 | $155,000 | 1,085 | Condominium | 2/3 | 112 |
| 12-16-2021 | 1740 SUMMERLAND AVENUE, WINTER PARK FL 32789 | $1,947,430 | $470 | $2,000,000 | 4,136 | Single Family Residence | 5/7 | 86 |
| 12-16-2021 | 128 OAK GROVE ROAD, WINTER PARK FL 32789 | $250,000 | $216 | $275,000 | 1,156 | Single Family Residence | 3/2 | 34 |
| 12-16-2021 | 1504 CLEMATIS LANE, WINTER PARK FL 32792 | $323,000 | $259 | $323,000 | 1,245 | Single Family Residence | 3/2 | 16 |
| 12-16-2021 | 1415 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $940,000 | $274 | $949,000 | 3,427 | Single Family Residence | 4/4 | 50 |
| 12-15-2021 | 3833 FERN GULLY COVE, WINTER PARK FL 32792 | $120,000 | $145,900 | / | 126 | |||
| 12-15-2021 | 300 FOUNTAIN LANE, WINTER PARK FL 32789 | $449,000 | $258 | $459,000 | 1,736 | Single Family Residence | 3/3 | 57 |
| 12-15-2021 | 2812 WOODSIDE AVENUE, WINTER PARK FL 32789 | $490,000 | $266 | $490,000 | 1,842 | Single Family Residence | 3/2 | 30 |
| 12-14-2021 | 1641 ONECO AVENUE, WINTER PARK FL 32789 | $1,665,000 | $423 | $1,750,000 | 3,934 | Single Family Residence | 5/6 | 29 |
| 12-13-2021 | 662 OSCEOLA AVENUE UNIT 201 | $1,950,000 | $851 | $2,095,000 | 2,290 | Condominium | 3/4 | 143 |
| 12-13-2021 | 250 CAROLINA AVENUE # 402, WINTER PARK FL 32789 | $483,000 | $324 | $535,000 | 1,488 | Condominium | 2/2 | 53 |
| 12-10-2021 | 1644 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $375,000 | $360 | $385,000 | 1,040 | Single Family Residence | 2/1 | 52 |
| 12-10-2021 | 1901 SUMMERFIELD ROAD, WINTER PARK FL 32792 | $450,000 | $268 | $450,000 | 1,675 | Single Family Residence | 3/2 | 72 |
| 12-09-2021 | 248 SCOTTSDALE SQUARE # 248, WINTER PARK FL 32792 | $157,000 | $125 | $159,900 | 1,250 | Condominium | 3/2 | 35 |
| 12-09-2021 | 4048 WATERVIEW LOOP, WINTER PARK FL 32792 | $320,000 | $191 | $320,000 | 1,670 | Single Family Residence | 3/2 | 22 |
| 12-08-2021 | 246 SCOTTSDALE SQ # 246, WINTER PARK FL 32792 | $113,000 | $110 | $120,000 | 1,020 | Condominium | 2/2 | 26 |
| 12-08-2021 | 260 SCOTTSDALE SQUARE # 260, WINTER PARK FL 32792 | $127,000 | $117 | $139,900 | 1,085 | Condominium | 2/2 | 37 |
| 12-08-2021 | 642 BALFOUR DRIVE, WINTER PARK FL 32792 | $299,500 | $212 | $314,900 | 1,412 | Single Family Residence | 3/2 | 108 |
| 12-08-2021 | 5317 CYPRESS DRIVE, WINTER PARK FL 32792 | $369,900 | $292 | $369,000 | 1,263 | Single Family Residence | 3/2 | 50 |
| 12-08-2021 | 556 S RANGER BOULEVARD, WINTER PARK FL 32792 | $449,000 | $240 | $449,000 | 1,870 | Single Family Residence | 4/2 | 104 |
| 12-08-2021 | 134 SCOTTSDALE SQUARE # 134, WINTER PARK FL 32792 | $99,000 | $79 | $99,000 | 1,250 | Condominium | 3/2 | 131 |
| 12-07-2021 | 604 MONTEGO BAY COURT, WINTER PARK FL 32792 | $165,000 | $147 | $179,995 | 1,120 | Condominium | 2/2 | 34 |
| 12-07-2021 | 2601 ANTILLES DRIVE, WINTER PARK FL 32792 | $257,000 | $177 | $250,000 | 1,448 | Townhouse | 3/2 | 41 |
| 12-06-2021 | 2649 EXUMA WAY, WINTER PARK FL 32792 | $257,000 | $142 | $257,900 | 1,803 | Townhouse | 3/2 | 119 |
| 12-06-2021 | 2822 AMBERGATE ROAD, WINTER PARK FL 32792 | $375,000 | $284 | $379,900 | 1,319 | Single Family Residence | 3/2 | 35 |
| 12-06-2021 | 2680 FITZHUGH ROAD, WINTER PARK FL 32792 | $530,000 | $256 | $525,000 | 2,064 | Single Family Residence | 4/3 | 41 |
| 12-06-2021 | 282 SCOTTSDALE SQUARE # 282, WINTER PARK FL 32792 | $75,000 | $99 | $75,000 | 756 | Condominium | 1/1 | 27 |
| 12-03-2021 | 1024 TUSCANY PLACE, WINTER PARK FL 32789 | $1,150,000 | $335 | $1,150,000 | 3,423 | Single Family Residence | 4/4 | 5 |
| 12-03-2021 | 1752 CHESTNUT AVENUE, WINTER PARK FL 32789 | $1,365,000 | $422 | $1,350,000 | 3,228 | Single Family Residence | 4/5 | 72 |
| 12-03-2021 | 234 LEWFIELD CIRCLE # 234, WINTER PARK FL 32792 | $168,500 | $176 | $168,500 | 953 | Condominium | 2/2 | 52 |
| 12-03-2021 | 4912 TANGERINE AVENUE # 4912, WINTER PARK FL 32792 | $170,000 | $160 | $170,000 | 1,058 | Condominium | 2/2 | 34 |
| 12-03-2021 | 1133 PARK GREEN PLACE, WINTER PARK FL 32789 | $292,000 | $178 | $300,000 | 1,639 | Townhouse | 2/2 | 51 |
| 12-03-2021 | 2429 PASSAMONTE DRIVE # 20, WINTER PARK FL 32792 | $305,000 | $161 | $300,000 | 1,893 | Townhouse | 3/3 | 43 |
| 12-03-2021 | 521 CAROLINA AVENUE, WINTER PARK FL 32789 | $450,000 | $280 | $475,000 | 1,602 | Single Family Residence | 4/2 | 191 |
| 12-03-2021 | 185 SYLVAN BOULEVARD, WINTER PARK FL 32789 | $565,650 | $565,650 | / | 1 | |||
| 12-03-2021 | 1550 GROVE TERRACE, WINTER PARK FL 32789 | $555,000 | $372 | $599,000 | 1,488 | Single Family Residence | 2/2 | 58 |
| 12-03-2021 | 1427 INDIANA AVENUE, WINTER PARK FL 32789 | $699,900 | $360 | $699,900 | 1,939 | Single Family Residence | 3/3 | 114 |
| 12-02-2021 | 265 SCOTTSDALE SQUARE # 265, WINTER PARK FL 32792 | $120,000 | $117 | $120,000 | 1,020 | Condominium | 2/2 | 40 |
| 12-02-2021 | 615 ELLENDALE DRIVE, WINTER PARK FL 32792 | $305,000 | $216 | $309,000 | 1,410 | Single Family Residence | 3/2 | 91 |
| 12-02-2021 | 2715 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $376,200 | $240 | $418,000 | 1,565 | Single Family Residence | 3/2 | 133 |
| 12-02-2021 | 1469 LONE FEATHER TRAIL, WINTER PARK FL 32792 | $529,100 | $204 | $529,100 | 2,589 | 4/8 | 30 | |
| 12-01-2021 | 2238 HAWICK LANE # 2238, WINTER PARK FL 32792 | $415,000 | $233 | $425,000 | 1,775 | Townhouse | 3/3 | 93 |
| 11-30-2021 | 334 SCOTTSDALE SQUARE # 334, WINTER PARK FL 32792 | $130,000 | $104 | $135,000 | 1,250 | Condominium | 3/2 | 93 |
| 11-30-2021 | 2368 BARBADOS DRIVE, WINTER PARK FL 32792 | $225,000 | $175 | $225,000 | 1,284 | Townhouse | 3/2 | 41 |
| 11-30-2021 | 2218 KING RICHARDS COURT, WINTER PARK FL 32792 | $350,000 | $224 | $350,000 | 1,562 | Single Family Residence | 3/2 | 69 |
| 11-30-2021 | 5050 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $449,000 | $353 | $449,900 | 1,269 | Single Family Residence | 3/2 | 75 |
| 11-30-2021 | 629 BALFOUR DRIVE, WINTER PARK FL 32792 | $620,000 | $196 | $589,000 | 3,156 | Single Family Residence | 4/3 | 41 |
| 11-29-2021 | 214 SCOTTSDALE SQUARE # 214, WINTER PARK FL 32792 | $110,000 | $101 | $115,000 | 1,085 | Condominium | 2/2 | 30 |
| 11-29-2021 | 628 PENN PLACE, WINTER PARK FL 32789 | $1,200,000 | $357 | $1,225,000 | 3,356 | Single Family Residence | 4/4 | 77 |
| 11-29-2021 | 1223 HARDING STREET, WINTER PARK FL 32789 | $1,925,000 | $446 | $2,000,000 | 4,309 | Single Family Residence | 5/6 | 26 |
| 11-24-2021 | 1357 BLUE STEM LANE, WINTER PARK FL 32792 | $500,000 | $282 | $500,000 | 1,770 | 4/3 | 20 | |
| 11-24-2021 | 1361 BLUE STEM LANE, WINTER PARK FL 32792 | $569,888 | $220 | $569,888 | 2,582 | 4/4 | 10 | |
| 11-24-2021 | 4068 TENITA DRIVE, WINTER PARK FL 32792 | $574,900 | $210 | $574,900 | 2,732 | Single Family Residence | 4/4 | 63 |
| 11-24-2021 | 106 S INTERLACHEN AVENUE UNIT 316 | $780,000 | $555 | $798,000 | 1,405 | Condominium | 2/2 | 69 |
| 11-23-2021 | 5415 PEACO PLACE, WINTER PARK FL 32792 | $255,000 | $226 | $259,900 | 1,124 | 1/2 Duplex | 3/2 | 32 |
| 11-23-2021 | 1726 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $283,000 | $258 | $299,000 | 1,096 | Single Family Residence | 3/2 | 61 |
| 11-22-2021 | 2313 DUNBURY CT, WINTER PARK FL 32792 | $310,100 | $276 | $310,000 | 1,120 | Single Family Residence | 3/2 | 36 |
| 11-22-2021 | 465 GENIUS DRIVE | $3,290,000 | $529 | $3,290,000 | 6,215 | Single Family Residence | 5/6 | 87 |
| 11-22-2021 | 807 HUNTINGTON COURT, WINTER PARK FL 32789 | $350,000 | $291 | $379,000 | 1,202 | Townhouse | 2/3 | 109 |
| 11-22-2021 | 4345 STEED TERRACE, WINTER PARK FL 32792 | $490,000 | $207 | $495,000 | 2,363 | Single Family Residence | 4/2 | 32 |
| 11-22-2021 | 2322 WOODCREST DRIVE, WINTER PARK FL 32792 | $580,000 | $345 | $600,000 | 1,681 | Single Family Residence | 4/2 | 32 |
| 11-19-2021 | 2443 VIA SIENNA, WINTER PARK FL 32789 | $1,211,000 | $499 | $1,099,000 | 2,424 | Single Family Residence | 4/3 | 60 |
| 11-19-2021 | 1503 SUMMERLAND AVENUE, WINTER PARK FL 32789 | $1,700,000 | $378 | $1,750,000 | 4,487 | Single Family Residence | 4/5 | 106 |
| 11-19-2021 | $236,100 | $152 | $236,000 | 1,545 | Townhouse | 3/3 | 45 | |
| 11-19-2021 | 120 LONGBRANCH ROAD, WINTER PARK FL 32792 | $768,000 | $233 | $800,000 | 3,284 | Single Family Residence | 5/4 | 43 |
| 11-19-2021 | 1475 GROVE TERRACE | $940,000 | $443 | $935,000 | 2,120 | Single Family Residence | 3/3 | 33 |
| 11-19-2021 | 1475 GROVE TERRACE | $940,000 | $935,000 | / | 33 | |||
| 11-18-2021 | 200 SAINT ANDREWS BOULEVARD # 401, WINTER PARK FL | $128,000 | $176 | $135,500 | 727 | Condominium | 1/1 | 32 |
| 11-18-2021 | 2715 ALOMA AVENUE, WINTER PARK FL 32792 | $340,000 | $213 | $340,000 | 1,595 | Single Family Residence | 3/2 | 186 |
| 11-18-2021 | 2629 ALOMA AVENUE, WINTER PARK FL 32792 | $360,000 | $284 | $359,500 | 1,264 | Single Family Residence | 3/2 | 36 |
| 11-18-2021 | 2106 SHADYHILL TERRACE, WINTER PARK FL 32792 | $440,000 | $221 | $424,900 | 1,983 | Single Family Residence | 4/2 | 58 |
| 11-17-2021 | 3203 CROWN JEWEL CT, WINTER PARK FL 32792 | $291,000 | $206 | $289,900 | 1,406 | Townhouse | 3/3 | 34 |
| 11-17-2021 | 1421 PELICAN BAY TRAIL | $450,000 | $166 | $450,000 | 2,700 | Single Family Residence | 4/2 | 42 |
| 11-16-2021 | 200 SAINT ANDREWS BOULEVARD # 2107, WINTER PARK FL | $189,900 | $169 | $189,900 | 1,119 | Condominium | 2/2 | 47 |
| 11-16-2021 | 210 KILLARNEY BAY COURT COURT UNIT 6-1 | $279,900 | $245 | $279,900 | 1,140 | Condominium | 2/2 | 11 |
| 11-16-2021 | 2021 SUSSEX ROAD, WINTER PARK FL 32792 | $450,000 | $213 | $450,000 | 2,110 | Single Family Residence | 4/2 | 13 |
| 11-16-2021 | 730 VIA LUGANO, WINTER PARK FL 32789 | $4,250,000 | $660 | $4,500,000 | 6,430 | Single Family Residence | 5/9 | 6 |
| 11-16-2021 | 4027 GILDER ROSE PLACE, WINTER PARK FL 32792 | $785,000 | $233 | $765,000 | 3,369 | Single Family Residence | 4/5 | 76 |
| 11-15-2021 | 2500 LEE ROAD UNIT 236 | $175,000 | $205 | $185,000 | 851 | Condominium | 2/1 | 41 |
| 11-15-2021 | 2102 BONANZA AVENUE, WINTER PARK FL 32792 | $339,900 | $233 | $339,900 | 1,458 | Single Family Residence | 3/2 | 41 |
| 11-15-2021 | 1945 HOUNDSLAKE DRIVE, WINTER PARK FL 32792 | $350,000 | $283 | $349,900 | 1,233 | Single Family Residence | 3/2 | 40 |
| 11-15-2021 | 1851 ASTER DRIVE, WINTER PARK FL 32792 | $390,000 | $195 | $389,900 | 1,992 | Single Family Residence | 3/2 | 34 |
| 11-15-2021 | 609 CARVELL DRIVE, WINTER PARK FL 32792 | $390,000 | $240 | $414,900 | 1,622 | Single Family Residence | 4/2 | 88 |
| 11-15-2021 | 531 BRECHIN DRIVE, WINTER PARK FL 32792 | $430,000 | $279 | $425,000 | 1,540 | Single Family Residence | 3/2 | 39 |
| 11-15-2021 | 100 S INTERLACHEN AVENUE UNIT 507F | $469,000 | $520 | $469,000 | 901 | Condominium | 2/2 | 34 |
| 11-15-2021 | 1324 INDIANA AVENUE, WINTER PARK FL 32789 | $485,000 | $286 | $475,000 | 1,692 | Single Family Residence | 4/3 | 139 |
| 11-15-2021 | 1562 SUNSET DRIVE, WINTER PARK FL 32789 | $635,000 | $390 | $635,000 | 1,628 | Single Family Residence | 2/3 | 46 |
| 11-12-2021 | 299 LEWFIELD CIRCLE # 299, WINTER PARK FL 32792 | $109,000 | $160 | $119,900 | 678 | Condominium | 1/1 | 62 |
| 11-12-2021 | 606 SAINT JOHNS COURT, WINTER PARK FL 32792 | $175,000 | $156 | $175,000 | 1,120 | Condominium | 2/2 | 39 |
| 11-12-2021 | 3217 DWARF PINE AVENUE, WINTER PARK FL 32792 | $339,900 | $242 | $339,900 | 1,402 | Single Family Residence | 3/2 | 41 |
| 11-12-2021 | 5009 TANGERINE AVENUE, WINTER PARK FL 32792 | $338,000 | $189 | $344,900 | 1,784 | Single Family Residence | 4/2 | 78 |
| 11-12-2021 | 2039 LINDEN ROAD, WINTER PARK FL 32792 | $405,000 | $225 | $425,000 | 1,800 | Single Family Residence | 3/2 | 59 |
| 11-12-2021 | 2051 LYNWOOD LN, WINTER PARK FL 32789 | $535,000 | $235 | $550,000 | 2,269 | Single Family Residence | 3/3 | 71 |
| 11-12-2021 | 159 BURKS CIRCLE, WINTER PARK FL 32789 | $585,000 | $233 | $599,000 | 2,508 | Single Family Residence | 4/3 | 58 |
| 11-12-2021 | 774 S PENNSYLVANIA AVENUE | $720,000 | $305 | $719,000 | 2,354 | Townhouse | 3/3 | 44 |
| 11-11-2021 | 433 LAKEVIEW AVENUE, WINTER PARK FL 32789 | $555,000 | $288 | $549,000 | 1,925 | Single Family Residence | 3/2 | 23 |
| 11-10-2021 | 1021 LINCOLN CIRCLE, WINTER PARK FL 32789 | $1,100,000 | $481 | $1,150,000 | 2,284 | Single Family Residence | 3/3 | 147 |
| 11-10-2021 | 2500 LEE ROAD # 111, WINTER PARK FL 32789 | $150,000 | $232 | $150,000 | 645 | 1/1 | 1 | |
| 11-10-2021 | 5222 POINSETTA AVENUE, WINTER PARK FL 32792 | $320,000 | $166 | $310,000 | 1,925 | Single Family Residence | 3/2 | 63 |
| 11-10-2021 | 814 HAMILTON PLACE COURT, WINTER PARK FL 32789 | $800,000 | $275 | $824,900 | 2,907 | Single Family Residence | 4/4 | 65 |
| 11-10-2021 | 1591 CARDINAL COURT, WINTER PARK FL 32789 | $960,000 | $272 | $995,000 | 3,523 | Single Family Residence | 4/3 | 121 |
| 11-08-2021 | 7748 FERNBROOK WAY, WINTER PARK FL 32792 | $222,500 | $203 | $230,000 | 1,092 | Townhouse | 2/2 | 39 |
| 11-08-2021 | $285,000 | $229 | $308,000 | 1,240 | Single Family Residence | 3/2 | 27 | |
| 11-08-2021 | 1378 PELHAM ROAD, WINTER PARK FL 32789 | $405,000 | $368 | $425,000 | 1,100 | Single Family Residence | 2/1 | 82 |
| 11-08-2021 | 5610 WINTERBROOK WAY, WINTER PARK FL 32792 | $449,000 | $226 | $449,000 | 1,978 | Single Family Residence | 3/2 | 71 |
| 11-08-2021 | 3047 TEMPLE TRAIL, WINTER PARK FL 32789 | $620,000 | $271 | $625,000 | 2,281 | Single Family Residence | 4/2 | 33 |
| 11-05-2021 | 3318 YOUNG STREET, WINTER PARK FL 32792 | $350,000 | $164 | $350,000 | 2,127 | Single Family Residence | 4/2 | 43 |
| 11-05-2021 | 1904 HEATHWOOD DRIVE, WINTER PARK FL 32792 | $386,900 | $195 | $379,900 | 1,978 | Single Family Residence | 3/3 | 57 |
| 11-04-2021 | 246 SCOTTSDALE SQUARE # 246, WINTER PARK FL 32792 | $95,000 | $93 | $107,000 | 1,020 | Condominium | 2/2 | 86 |
| 11-04-2021 | 2856 CADY WAY, WINTER PARK FL 32792 | $435,000 | $314 | $437,500 | 1,385 | Single Family Residence | 3/2 | 34 |
| 11-04-2021 | 1235 PARK POINTE LANE, WINTER PARK FL 32789 | $582,500 | $223 | $599,900 | 2,608 | Single Family Residence | 4/3 | 58 |
| 11-03-2021 | 640 OSCEOLA AVENUE | $1,080,000 | $400 | $1,120,000 | 2,696 | Condominium | 3/3 | 104 |
| 11-03-2021 | 2613 ANTILLES DRIVE, WINTER PARK FL 32792 | $230,000 | $179 | $224,990 | 1,284 | Townhouse | 3/2 | 34 |
| 11-03-2021 | 1465 LONE FEATHER TRAIL, WINTER PARK FL 32792 | $509,799 | $197 | $509,799 | 2,582 | Single Family Residence | 4/4 | 7 |
| 11-03-2021 | 731 W CANTON AVENUE, WINTER PARK FL 32789 | $682,500 | $390 | $698,000 | 1,748 | Single Family Residence | 3/3 | 158 |
| 11-02-2021 | 446 MELROSE AVENUE | $1,260,000 | $477 | $1,175,000 | 2,640 | Single Family Residence | 4/2 | 85 |
| 11-02-2021 | 200 SAINT ANDREWS BOULEVARD # 2904, WINTER PARK FL | $180,000 | $147 | $165,000 | 1,219 | Condominium | 2/2 | 19 |
| 11-02-2021 | 1219 LINDENWOOD LANE, WINTER PARK FL 32792 | $400,000 | $244 | $395,000 | 1,633 | Single Family Residence | 3/2 | 29 |
| 11-02-2021 | 1003 S KENTUCKY AVENUE, WINTER PARK FL 32789 | $486,000 | $269 | $486,000 | 1,803 | Townhouse | 3/3 | 197 |
| 11-02-2021 | 408 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $799,000 | $299 | $799,000 | 2,668 | Single Family Residence | 5/4 | 50 |
| 11-01-2021 | 660 OSCEOLA AVENUE UNIT 101 | $1,700,000 | $626 | $1,699,000 | 2,714 | Condominium | 3/4 | 56 |
| 11-01-2021 | 1471 HARMON AVENUE, WINTER PARK FL 32789 | $285,000 | $227 | $310,000 | 1,252 | Single Family Residence | 2/1 | 14 |
| 11-01-2021 | 904 CARVELL DRIVE, WINTER PARK FL 32792 | $330,000 | $182 | $349,900 | 1,810 | Single Family Residence | 3/2 | 40 |
| 11-01-2021 | 1792 KILLARNEY DRIVE, WINTER PARK FL 32789 | $599,000 | $264 | $599,000 | 2,264 | Single Family Residence | 4/3 | 53 |
| 11-01-2021 | 915 GARDEN DRIVE, WINTER PARK FL 32789 | $650,000 | $264 | $675,000 | 2,456 | Single Family Residence | 3/3 | 130 |
| 11-01-2021 | 247 W LYMAN AVENUE, WINTER PARK FL 32789 | $880,000 | $540 | $850,000 | 1,628 | Single Family Residence | 4/3 | 29 |
| 10-30-2021 | 640 N PARK AVENUE # 27, WINTER PARK FL 32789 | $390,000 | $454 | $390,000 | 858 | Condominium | 2/2 | 1 |
| 10-29-2021 | 2910 REEF KNOT PLACE | $1,440,000 | $394 | $1,495,000 | 3,652 | Single Family Residence | 5/5 | 36 |
| 10-29-2021 | 7326 CEDAR CREEK COURT # 59, WINTER PARK FL 32792 | $162,000 | $157 | $169,900 | 1,031 | Condominium | 2/3 | 59 |
| 10-29-2021 | 160 SANDLEWOOD TRAIL # 4, WINTER PARK FL 32789 | $217,000 | $192 | $218,000 | 1,130 | Condominium | 2/3 | 163 |
| 10-29-2021 | 7420 BARNACLE COURT, WINTER PARK FL 32792 | $305,000 | $265 | $310,000 | 1,147 | Single Family Residence | 3/2 | 67 |
| 10-29-2021 | 7432 GRAND AVENUE, WINTER PARK FL 32792 | $310,000 | $270 | $310,000 | 1,147 | Single Family Residence | 3/2 | 30 |
| 10-29-2021 | 557 HERITAGE BOULEVARD, WINTER PARK FL 32792 | $328,000 | $257 | $345,000 | 1,275 | Single Family Residence | 3/2 | 35 |
| 10-29-2021 | 2125 N HAMPTON CIRCLE, WINTER PARK FL 32792 | $427,600 | $250 | $429,000 | 1,710 | Single Family Residence | 3/2 | 171 |
| 10-29-2021 | 728 ROUGHBEARD ROAD, WINTER PARK FL 32792 | $480,000 | $248 | $480,000 | 1,931 | Single Family Residence | 4/3 | 121 |
| 10-29-2021 | 2409 SUMMERFIELD ROAD, WINTER PARK FL 32792 | $471,000 | $239 | $539,000 | 1,966 | Single Family Residence | 3/2 | 129 |
| 10-29-2021 | 1875 STAUNTON AVENUE, WINTER PARK FL 32789 | $550,000 | $270 | $550,000 | 2,036 | Single Family Residence | 4/2 | 40 |
| 10-29-2021 | 1411/1413 INDIANA AVENUE, WINTER PARK FL 32789 | $525,000 | $240 | $595,000 | 2,180 | Duplex | / | 75 |
| 10-28-2021 | 1055 S KENTUCKY AVENUE, WINTER PARK FL 32789 | $1,000,000 | $198 | $1,100,000 | 5,032 | Quadruplex | / | 130 |
| 10-28-2021 | 2440 ROXBURY ROAD, WINTER PARK FL 32789 | $350,000 | $203 | $350,000 | 1,721 | Single Family Residence | 3/2 | 28 |
| 10-28-2021 | 739 ROUGHBEARD ROAD, WINTER PARK FL 32792 | $495,000 | $225 | $475,000 | 2,194 | Single Family Residence | 5/3 | 57 |
| 10-28-2021 | 2127 BLOSSOM LANE | $680,000 | $315 | $649,900 | 2,158 | Single Family Residence | 3/3 | 64 |
| 10-27-2021 | 171 OAK GROVE ROAD, WINTER PARK FL 32789 | $285,000 | $243 | $279,900 | 1,170 | Single Family Residence | 3/2 | 35 |
| 10-27-2021 | 5219 ALBERT DRIVE, WINTER PARK FL 32792 | $322,000 | $258 | $345,000 | 1,247 | Single Family Residence | 3/2 | 63 |
| 10-27-2021 | 1389 SAWGRASS COURT, WINTER PARK FL 32792 | $515,000 | $246 | $523,900 | 2,093 | Single Family Residence | 3/2 | 63 |
| 10-26-2021 | 1618 LOOKOUT LANDING CIRCLE, WINTER PARK FL 32789 | $1,410,000 | $345 | $1,495,000 | 4,080 | Single Family Residence | 4/4 | 78 |
| 10-26-2021 | 7532 AZUREBROOK COURT, WINTER PARK FL 32792 | $320,000 | $228 | $320,000 | 1,402 | Single Family Residence | 3/2 | 41 |
| 10-26-2021 | 2830 MULFORD AVENUE, WINTER PARK FL 32789 | $710,000 | $338 | $673,800 | 2,097 | Single Family Residence | 4/3 | 40 |
| 10-26-2021 | 1393 HEAVENLY COVE, WINTER PARK FL 32792 | $699,000 | $246 | $699,000 | 2,836 | Single Family Residence | 4/3 | 82 |
| 10-25-2021 | 302 LEWFIELD CIRCLE # 302, WINTER PARK FL 32792 | $112,000 | $165 | $119,990 | 678 | Condominium | 1/1 | 18 |
| 10-25-2021 | 1813 GIPSON GREEN LANE, WINTER PARK FL 32789 | $1,300,000 | $1,300,000 | / | 67 | |||
| 10-25-2021 | 2101 OAKHURST AVENUE, WINTER PARK FL 32792 | $360,000 | $198 | $369,900 | 1,812 | Single Family Residence | 3/2 | 71 |
| 10-22-2021 | 629 PENN PLACE, WINTER PARK FL 32789 | $1,233,000 | $369 | $1,250,000 | 3,340 | Single Family Residence | 3/3 | 57 |
| 10-22-2021 | 512 FLETCHER PLACE, WINTER PARK FL 32789 | $1,935,000 | $398 | $1,945,000 | 4,860 | Single Family Residence | 5/6 | 32 |
| 10-22-2021 | 2219 AZALEA PLACE | $3,090,000 | $462 | $3,299,000 | 6,683 | Single Family Residence | 6/8 | 112 |
| 10-22-2021 | 827 DENSMORE DRIVE, WINTER PARK FL 32792 | $339,000 | $251 | $339,000 | 1,349 | Single Family Residence | 4/2 | 30 |
| 10-22-2021 | 3826 WATERVIEW LOOP, WINTER PARK FL 32792 | $400,000 | $234 | $389,900 | 1,704 | Single Family Residence | 3/3 | 26 |
| 10-22-2021 | 417 CARVELL DRIVE, WINTER PARK FL 32792 | $399,500 | $219 | $398,000 | 1,823 | Single Family Residence | 4/3 | 77 |
| 10-22-2021 | 777 S DENNING DRIVE # B, WINTER PARK FL 32789 | $499,000 | $300 | $524,999 | 1,661 | Townhouse | 3/3 | 152 |
| 10-22-2021 | 529 COUNTRY CLUB DRIVE | $929,000 | $328 | $979,900 | 2,829 | Single Family Residence | 4/5 | 103 |
| 10-21-2021 | 1510 ONECO AVENUE, WINTER PARK FL 32789 | $1,175,000 | $484 | $1,175,000 | 2,426 | Single Family Residence | 3/4 | 7 |
| 10-21-2021 | 2583 PASSAMONTE DRIVE # 6E, WINTER PARK FL 32792 | $290,000 | $157 | $290,000 | 1,837 | Townhouse | 3/3 | 30 |
| 10-21-2021 | 657 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $592,000 | $222 | $590,000 | 2,663 | Single Family Residence | 4/3 | 35 |
| 10-21-2021 | 1726 PALMER AVENUE, WINTER PARK FL 32789 | $989,000 | $309 | $989,000 | 3,199 | Single Family Residence | 4/4 | 38 |
| 10-20-2021 | 740 KILLARNEY BAY COURT UNIT 3 | $329,000 | $214 | $339,000 | 1,536 | Condominium | 2/3 | 27 |
| 10-18-2021 | 2420 EUSTON ROAD, WINTER PARK FL 32789 | $325,000 | $349 | $325,000 | 931 | Single Family Residence | 2/1 | 68 |
| 10-18-2021 | 1537 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $500,000 | $160 | $498,000 | 3,116 | Single Family Residence | 4/3 | 43 |
| 10-15-2021 | 4962 TANGERINE AVENUE # 4962, WINTER PARK FL 32792 | $135,000 | $179 | $135,000 | 753 | Condominium | 1/1 | 23 |
| 10-15-2021 | 1217 HARDING STREET, WINTER PARK FL 32789 | $1,700,000 | $566 | $1,750,000 | 3,002 | Single Family Residence | 4/5 | 116 |
| 10-15-2021 | 2118 BONANZA AVENUE, WINTER PARK FL 32792 | $330,000 | $216 | $340,000 | 1,526 | Single Family Residence | 3/2 | 38 |
| 10-15-2021 | 2860 WILL O TH GREEN, WINTER PARK FL 32792 | $400,000 | $304 | $409,900 | 1,312 | Single Family Residence | 3/2 | 55 |
| 10-15-2021 | 1564 INDIANA AVENUE, WINTER PARK FL 32789 | $451,000 | $309 | $450,000 | 1,456 | Single Family Residence | 3/2 | 43 |
| 10-15-2021 | 1832 PINEVIEW CIRCLE, WINTER PARK FL 32792 | $425,000 | $380 | $464,900 | 1,116 | Single Family Residence | 3/2 | 306 |
| 10-15-2021 | 1832 PINEVIEW CIR, WINTER PARK FL 32792 | $425,000 | $464,900 | / | 306 | |||
| 10-15-2021 | 1312 FOUNTAIN HILLS COURT, WINTER PARK FL 32792 | $600,000 | $233 | $600,000 | 2,575 | Single Family Residence | 4/3 | 107 |
| 10-14-2021 | 1698 CYPRESS POINT LANE, WINTER PARK FL 32792 | $465,000 | $275 | $450,000 | 1,689 | Single Family Residence | 3/2 | 38 |
| 10-13-2021 | 1918 SUMMERFIELD ROAD | $980,000 | $299 | $1,090,000 | 3,269 | Single Family Residence | 5/5 | 83 |
| 10-13-2021 | 3358 CEDAR SPRINGS PLACE # 159, WINTER PARK FL 327 | $135,500 | $131 | $159,900 | 1,031 | Condominium | 2/3 | 28 |
| 10-12-2021 | 2107 STAUNTON AVENUE, WINTER PARK FL 32789 | $240,000 | $179 | $265,000 | 1,337 | Single Family Residence | 3/1 | 29 |
| 10-12-2021 | 3448 ASTORIA COURT, WINTER PARK FL 32792 | $338,000 | $217 | $349,000 | 1,556 | Single Family Residence | 4/2 | 72 |
| 10-12-2021 | 1475 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $680,000 | $456 | $699,000 | 1,491 | Single Family Residence | 3/2 | 89 |
| 10-12-2021 | 1475 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $680,000 | $699,000 | / | 89 | |||
| 10-11-2021 | 641 NORTHWOOD CIRCLE, WINTER PARK FL 32789 | $250,000 | $319,900 | / | 301 | |||
| 10-08-2021 | 1811 LAURELTON HALL LANE, WINTER PARK FL 32789 | $1,245,000 | $328 | $1,299,000 | 3,787 | Single Family Residence | 5/5 | 97 |
| 10-08-2021 | 216 BALFOUR DRIVE # 11, WINTER PARK FL 32792 | $281,500 | $185 | $279,000 | 1,520 | Condominium | 3/2 | 22 |
| 10-08-2021 | 8413 COMMANDER COVE | $350,000 | $238 | $350,000 | 1,468 | Single Family Residence | 3/3 | 1 |
| 10-08-2021 | 633 S PHELPS AVENUE, WINTER PARK FL 32789 | $650,000 | $325 | $674,900 | 1,996 | Single Family Residence | 3/2 | 24 |
| 10-08-2021 | 2872 OLD CASTLE DRIVE | $880,000 | $208 | $924,900 | 4,227 | Single Family Residence | 4/5 | 59 |
| 10-07-2021 | 1860 VIA CONTESSA, WINTER PARK FL 32789 | $1,800,000 | $262 | $1,895,000 | 6,854 | Single Family Residence | 7/6 | 63 |
| 10-07-2021 | 1557 NOTTINGHAM DRIVE, WINTER PARK FL 32792 | $260,000 | $173 | $320,000 | 1,496 | Single Family Residence | 3/2 | 56 |
| 10-06-2021 | 1746 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $305,000 | $223 | $298,000 | 1,365 | Single Family Residence | 3/2 | 118 |
| 10-06-2021 | 2619 AMBERGATE ROAD, WINTER PARK FL 32792 | $330,000 | $268 | $339,000 | 1,227 | Single Family Residence | 3/2 | 49 |
| 10-05-2021 | 1000 S SEMORAN BOULEVARD # 708, WINTER PARK FL 327 | $97,000 | $125 | $104,900 | 776 | Condominium | 1/1 | 67 |
| 10-05-2021 | 3243 FOREST OAKS COURT # 117, WINTER PARK FL 32792 | $139,500 | $140 | $139,000 | 990 | Condominium | 2/2 | 27 |
| 10-05-2021 | 843 W SWOOPE AVENUE, WINTER PARK FL 32789 | $289,000 | $234 | $339,900 | 1,232 | Single Family Residence | 3/2 | 139 |
| 10-05-2021 | 3463 ARNEL DRIVE, WINTER PARK FL 32792 | $340,000 | $194 | $350,000 | 1,750 | Single Family Residence | 3/2 | 62 |
| 10-05-2021 | 2405 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $378,000 | $192 | $374,900 | 1,964 | Townhouse | 3/3 | 83 |
| 10-04-2021 | 4144 WATERVIEW LOOP, WINTER PARK FL 32792 | $440,000 | $242 | $419,900 | 1,811 | Single Family Residence | 3/3 | 17 |
| 10-04-2021 | 212 N RANGER BOULEVARD, WINTER PARK FL 32792 | $440,000 | $272 | $439,900 | 1,615 | Single Family Residence | 4/2 | 47 |
| 10-04-2021 | 1417 PELICAN BAY TRAIL, WINTER PARK FL 32792 | $489,000 | $178 | $499,900 | 2,738 | Single Family Residence | 4/3 | 81 |
| 10-04-2021 | 1461 PALM AVENUE, WINTER PARK FL 32789 | $515,000 | $349 | $535,000 | 1,474 | Single Family Residence | 3/1 | 19 |
| 10-04-2021 | 3039 TEMPLE TRAIL, WINTER PARK FL 32789 | $635,000 | $306 | $625,000 | 2,070 | Single Family Residence | 4/2 | 34 |
| 10-04-2021 | 460 W LYMAN AVENUE, WINTER PARK FL 32789 | $670,000 | $699,000 | / | 193 | |||
| 10-02-2021 | 1841 GOODRICH AVENUE, WINTER PARK FL 32789 | $280,000 | $255 | $325,000 | 1,095 | Single Family Residence | 3/1 | 51 |
| 10-02-2021 | 799 ENGLISH COURT, WINTER PARK FL 32789 | $689,000 | $329 | $689,900 | 2,091 | Single Family Residence | 3/3 | 62 |
| 10-01-2021 | 830 JUANITA RAEL, WINTER PARK FL 32789 | $1,060,000 | $322 | $1,080,000 | 3,282 | Single Family Residence | 4/4 | 62 |
| 10-01-2021 | 1701 WALNUT AVENUE, WINTER PARK FL 32789 | $1,300,000 | $340 | $1,349,000 | 3,819 | Single Family Residence | 4/4 | 50 |
| 10-01-2021 | 200 SAINT ANDREWS BOULEVARD # 612, WINTER PARK FL | $141,500 | $169 | $148,000 | 835 | Condominium | 1/1 | 102 |
| 10-01-2021 | 2870 CHANTILLY AVENUE, WINTER PARK FL 32789 | $286,000 | $234 | $290,000 | 1,220 | Single Family Residence | 3/2 | 57 |
| 10-01-2021 | 3606 MANGO CT, WINTER PARK FL 32792 | $297,500 | $216 | $294,999 | 1,373 | Single Family Residence | 3/2 | 51 |
| 10-01-2021 | 2819 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $370,000 | $258 | $375,000 | 1,430 | Single Family Residence | 3/2 | 51 |
| 09-30-2021 | 335 BELOIT AVENUE, WINTER PARK FL 32789 | $1,000,000 | $413 | $1,000,000 | 2,420 | Single Family Residence | 3/2 | 16 |
| 09-30-2021 | 1171 VIA LUGANO, WINTER PARK FL 32789 | $1,225,000 | $420 | $1,225,000 | 2,916 | 3/4 | 28 | |
| 09-30-2021 | 4059 COOL WATER COURT | $1,050,000 | $316 | $1,250,000 | 3,318 | Single Family Residence | 5/3 | 105 |
| 09-30-2021 | 668 MONTEGO BAY COURT # 668, WINTER PARK FL 32792 | $174,990 | $168 | $174,990 | 1,037 | Condominium | 2/2 | 26 |
| 09-30-2021 | 3605 MANGO COURT, WINTER PARK FL 32792 | $295,000 | $224 | $299,000 | 1,316 | Single Family Residence | 4/2 | 65 |
| 09-30-2021 | 913 CAMELLIA AVENUE, WINTER PARK FL 32789 | $309,000 | $253 | $309,000 | 1,221 | Single Family Residence | 3/2 | 49 |
| 09-30-2021 | 5623 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $315,000 | $281 | $325,000 | 1,120 | Single Family Residence | 3/2 | 37 |
| 09-30-2021 | 5409 ALBERT DRIVE, WINTER PARK FL 32792 | $359,500 | $242 | $355,000 | 1,483 | Single Family Residence | 3/2 | 45 |
| 09-30-2021 | 346 S RANGER BOULEVARD, WINTER PARK FL 32792 | $374,000 | $234 | $385,000 | 1,592 | Single Family Residence | 3/2 | 69 |
| 09-30-2021 | 426 GILBERT ROAD, WINTER PARK FL 32792 | $440,000 | $265 | $434,900 | 1,658 | Single Family Residence | 4/2 | 50 |
| 09-30-2021 | 223 E CANTON AVENUE # 223, WINTER PARK FL 32789 | $510,000 | $490 | $510,000 | 1,040 | Condominium | 2/2 | 18 |
| 09-30-2021 | 1721 LAUREL ROAD, WINTER PARK FL 32789 | $605,000 | $585,000 | / | 18 | |||
| 09-30-2021 | 117 SCOTTSDALE SQUARE # 117, WINTER PARK FL 32792 | $80,000 | $101 | $75,000 | 785 | Condominium | 1/1 | 43 |
| 09-30-2021 | 1725 PINE AVENUE, WINTER PARK FL 32789 | $769,100 | $246 | $835,000 | 3,125 | Single Family Residence | 4/4 | 70 |
| 09-29-2021 | 1121 WHITESELL DRIVE, WINTER PARK FL 32789 | $2,230,000 | $449 | $2,230,000 | 4,964 | Single Family Residence | 4/7 | 8 |
| 09-29-2021 | 850 GEORGIA AVENUE, WINTER PARK FL 32789 | $2,900,000 | $626 | $2,900,000 | 4,627 | Single Family Residence | 4/6 | 48 |
| 09-29-2021 | 1932 HOUNDSLAKE DRIVE, WINTER PARK FL 32792 | $260,000 | $155 | $329,900 | 1,671 | Single Family Residence | 3/2 | 116 |
| 09-29-2021 | 104 LONGBRANCH ROAD, WINTER PARK FL 32792 | $580,000 | $197 | $580,000 | 2,937 | Single Family Residence | 4/2 | 60 |
| 09-28-2021 | 1211 VIA ESTRELLA, WINTER PARK FL 32789 | $1,994,000 | $719 | $1,994,000 | 2,770 | Single Family Residence | 4/3 | 21 |
| 09-28-2021 | 5492 PEACO PLACE, WINTER PARK FL 32792 | $241,900 | $224 | $259,900 | 1,078 | 1/2 Duplex | 3/2 | 125 |
| 09-28-2021 | 1840 ANZLE AVENUE, WINTER PARK FL 32789 | $312,000 | $330,000 | / | 26 | |||
| 09-28-2021 | 4405 GLENMOOR COURT, WINTER PARK FL 32792 | $515,000 | $254 | $514,900 | 2,023 | Single Family Residence | 4/3 | 41 |
| 09-27-2021 | 340 FLEET ROAD, WINTER PARK FL 32792 | $344,900 | $249 | $344,900 | 1,381 | Single Family Residence | 2/2 | 38 |
| 09-27-2021 | 454 SHOREVIEW AVENUE, WINTER PARK FL 32789 | $335,650 | $307 | $349,900 | 1,092 | Single Family Residence | 2/2 | 45 |
| 09-27-2021 | 5213 ARDMORE DRIVE, WINTER PARK FL 32792 | $350,000 | $213 | $360,000 | 1,640 | Single Family Residence | 3/3 | 39 |
| 09-27-2021 | 5575 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $365,000 | $258 | $365,000 | 1,414 | Single Family Residence | 3/2 | 109 |
| 09-27-2021 | 103 CORNWALL ROAD, WINTER PARK FL 32792 | $390,000 | $187 | $400,000 | 2,085 | Single Family Residence | 3/2 | 74 |
| 09-27-2021 | 724 MONMOUTH WAY, WINTER PARK FL 32792 | $455,000 | $160 | $470,000 | 2,832 | Single Family Residence | 4/2 | 119 |
| 09-27-2021 | 5259 PINE LILY CIRCLE, WINTER PARK FL 32792 | $529,000 | $187 | $539,900 | 2,822 | Single Family Residence | 4/4 | 108 |
| 09-26-2021 | 1011 ORANGE AVE, WINTER PARK FL 32789 | $1,480,000 | $458 | $1,590,000 | 3,228 | Retail | / | 69 |
| 09-24-2021 | 948 POINCIANA LANE | $1,449,000 | $387 | $1,459,000 | 3,740 | Single Family Residence | 4/4 | 52 |
| 09-24-2021 | 7338 SWALLOW RUN # 7338, WINTER PARK FL 32792 | $150,000 | $193 | $150,000 | 774 | Condominium | 2/2 | 50 |
| 09-24-2021 | 2500 LEE ROAD UNIT 216 | $205,000 | $215 | $215,000 | 950 | Condominium | 2/1 | 36 |
| 09-24-2021 | 210 VIRGINIA DRIVE, WINTER PARK FL 32789 | $2,080,000 | $554 | $2,400,000 | 3,749 | Single Family Residence | 5/7 | 229 |
| 09-24-2021 | 5039 FERNCREST DRIVE, WINTER PARK FL 32792 | $319,990 | $278 | $319,990 | 1,150 | Single Family Residence | 3/2 | 58 |
| 09-24-2021 | 682 S LAKEMONT AVENUE, WINTER PARK FL 32792 | $341,800 | $202 | $360,000 | 1,685 | Single Family Residence | 4/2 | 43 |
| 09-24-2021 | 1423 ONECO AVENUE, WINTER PARK FL 32789 | $425,000 | $491 | $425,000 | 864 | Single Family Residence | 2/1 | 37 |
| 09-24-2021 | 2830 LION HEART ROAD, WINTER PARK FL 32792 | $440,000 | $244 | $425,000 | 1,802 | Single Family Residence | 3/2 | 37 |
| 09-23-2021 | 543 SHEPHERD AVENUE, WINTER PARK FL 32789 | $1,075,000 | $289 | $1,149,500 | 3,707 | Single Family Residence | 4/4 | 170 |
| 09-23-2021 | 730 KILLARNEY BAY COURT UNIT 4 | $309,900 | $201 | $309,900 | 1,536 | Condominium | 2/3 | 40 |
| 09-23-2021 | 1881 CAROLLEE LANE, WINTER PARK FL 32789 | $410,000 | $304 | $415,000 | 1,345 | Single Family Residence | 3/2 | 476 |
| 09-23-2021 | 7876 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $485,000 | $213 | $485,000 | 2,267 | Single Family Residence | 4/2 | 49 |
| 09-23-2021 | 1690 CYPRESS POINT LANE, WINTER PARK FL 32792 | $650,000 | $253 | $649,700 | 2,560 | Single Family Residence | 4/2 | 54 |
| 09-23-2021 | 532 DUNBLANE DRIVE, WINTER PARK FL 32792 | $900,000 | $297 | $875,000 | 3,024 | Single Family Residence | 5/3 | 501 |
| 09-22-2021 | 632 MONTEGO BAY COURT # 632, WINTER PARK FL 32792 | $181,000 | $174 | $172,500 | 1,037 | Condominium | 2/2 | 50 |
| 09-22-2021 | 5472 BRACKEN COURT, WINTER PARK FL 32792 | $205,000 | $187 | $225,000 | 1,092 | Townhouse | 2/2 | 38 |
| 09-21-2021 | 200 SAINT ANDREWS BOULEVARD # 1808, WINTER PARK FL | $225,000 | $177 | $225,000 | 1,266 | Condominium | 2/2 | 34 |
| 09-20-2021 | 140 E ROCKWOOD WAY, WINTER PARK FL 32789 | $1,047,000 | $296 | $1,099,000 | 3,531 | Single Family Residence | 4/5 | 90 |
| 09-20-2021 | 1705 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $275,000 | $250 | $280,000 | 1,096 | Single Family Residence | 3/2 | 60 |
| 09-20-2021 | 7143 GROVE AVENUE, WINTER PARK FL 32792 | $360,000 | $240 | $399,900 | 1,495 | Single Family Residence | 3/2 | 137 |
| 09-17-2021 | 1000 S SEMORAN BOULEVARD # 303, WINTER PARK FL 327 | $95,000 | $129 | $104,990 | 735 | Condominium | 1/1 | 112 |
| 09-17-2021 | 1000 GENIUS DRIVE | $10,650,000 | $768 | $12,495,000 | 13,855 | Single Family Residence | 10/12 | 117 |
| 09-17-2021 | 689 SAINT JOHNS COURT, WINTER PARK FL 32792 | $160,750 | $143 | $157,000 | 1,120 | Condominium | 2/2 | 44 |
| 09-17-2021 | 2421 PASSAMONTE DRIVE # 1F, WINTER PARK FL 32792 | $252,500 | $141 | $240,000 | 1,790 | Condominium | 3/3 | 66 |
| 09-17-2021 | 172 OAK GROVE ROAD, WINTER PARK FL 32789 | $230,000 | $181 | $249,500 | 1,268 | Single Family Residence | 3/3 | 82 |
| 09-17-2021 | 611 ELLEN DRIVE | $260,000 | $260,000 | / | 515 | |||
| 09-17-2021 | 240 ORANGE TERRACE DRIVE, WINTER PARK FL 32789 | $428,565 | $249 | $425,000 | 1,718 | Single Family Residence | 4/2 | 77 |
| 09-17-2021 | 535 N INTERLACHEN AVENUE # 102, WINTER PARK FL 327 | $432,000 | $421 | $429,900 | 1,025 | Condominium | 2/2 | 100 |
| 09-17-2021 | 241 E FAWSETT ROAD, WINTER PARK FL 32789 | $635,000 | $302 | $597,000 | 2,100 | Single Family Residence | 3/2 | 47 |
| 09-17-2021 | 241 E FAWSETT ROAD, WINTER PARK FL 32789 | $635,000 | $597,000 | / | 47 | |||
| 09-16-2021 | 1794 MONDRIAN CIRCLE UNIT 19 | $813,000 | $351 | $808,000 | 2,310 | Townhouse | 3/4 | 105 |
| 09-15-2021 | 237 SCOTTSDALE SQUARE # 237, WINTER PARK FL 32792 | $124,000 | $121 | $124,000 | 1,020 | Condominium | 2/2 | 41 |
| 09-15-2021 | 350 CAROLINA AVENUE # 306, WINTER PARK FL 32789 | $459,000 | $297 | $459,000 | 1,544 | Condominium | 2/2 | 139 |
| 09-15-2021 | 1563 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $500,000 | $261 | $489,900 | 1,915 | Single Family Residence | 3/2 | 41 |
| 09-15-2021 | 1631 HILLCREST AVENUE, WINTER PARK FL 32789 | $698,000 | $365 | $698,000 | 1,912 | Single Family Residence | 3/2 | 49 |
| 09-15-2021 | 1445 BONNIE BURN CIRCLE, WINTER PARK FL 32789 | $680,000 | $323 | $725,000 | 2,104 | Single Family Residence | 3/3 | 87 |
| 09-15-2021 | 1445 BONNIE BURN CIRCLE, WINTER PARK FL 32789 | $680,000 | $725,000 | / | 87 | |||
| 09-14-2021 | 1695 LEE RD # D214, WINTER PARK FL 32789 | $122,000 | $138 | $139,900 | 881 | Condominium | 2/1 | 30 |
| 09-14-2021 | 200 SAINT ANDREWS BOULEVARD # 2402, WINTER PARK FL | $214,000 | $183 | $214,000 | 1,165 | Condominium | 3/2 | 40 |
| 09-14-2021 | 1506 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $241,000 | $145 | $244,000 | 1,652 | Townhouse | 3/3 | 54 |
| 09-14-2021 | 1020 MINNESOTA AVENUE # 7, WINTER PARK FL 32789 | $387,500 | $193 | $399,000 | 2,000 | Townhouse | 3/4 | 29 |
| 09-14-2021 | 674 OSCEOLA AVENUE UNIT 674 | $532,000 | $409 | $524,950 | 1,300 | Townhouse | 2/3 | 20 |
| 09-14-2021 | 311 SCOTTSDALE SQUARE # 311, WINTER PARK FL 32792 | $79,000 | $100 | $82,000 | 785 | Condominium | 1/1 | 41 |
| 09-14-2021 | 1798 MONDRIAN CIRCLE UNIT 21 | $820,000 | $350 | $820,000 | 2,341 | Townhouse | 3/4 | 103 |
| 09-13-2021 | 2550 TEMPLE DRIVE, WINTER PARK FL 32789 | $1,240,000 | $384 | $1,240,000 | 3,227 | Single Family Residence | 4/3 | 140 |
| 09-13-2021 | 2344 WOODCREST DRIVE, WINTER PARK FL 32792 | $408,000 | $231 | $425,000 | 1,764 | Single Family Residence | 3/2 | 48 |
| 09-13-2021 | 1670 PALM AVENUE, WINTER PARK FL 32789 | $550,000 | $263 | $599,990 | 2,087 | Single Family Residence | 4/3 | 50 |
| 09-11-2021 | 130 BURKS CIRCLE, WINTER PARK FL 32789 | $457,500 | $306 | $519,000 | 1,492 | Single Family Residence | 3/3 | 24 |
| 09-10-2021 | 200 SAINT ANDREWS BOULEVARD # 3001, WINTER PARK FL | $180,000 | $142 | $190,000 | 1,266 | Condominium | 2/2 | 18 |
| 09-10-2021 | 2320 INAGUA WAY, WINTER PARK FL 32792 | $259,000 | $177 | $259,000 | 1,456 | Townhouse | 3/2 | 37 |
| 09-10-2021 | 3221 CROWN JEWEL COURT, WINTER PARK FL 32792 | $285,000 | $197 | $290,000 | 1,442 | Townhouse | 3/3 | 100 |
| 09-10-2021 | 2435 CHANTILLY AVENUE, WINTER PARK FL 32789 | $325,000 | $344 | $299,000 | 943 | Single Family Residence | 2/1 | 31 |
| 09-10-2021 | 2435 CHANTILLY AVENUE, WINTER PARK FL 32789 | $325,000 | $299,000 | / | 31 | |||
| 09-10-2021 | 2924 SCARLET ROAD, WINTER PARK FL 32792 | $425,000 | $171 | $425,000 | 2,475 | Single Family Residence | 4/3 | 44 |
| 09-10-2021 | 4044 TENITA DRIVE, WINTER PARK FL 32792 | $500,000 | $254 | $459,000 | 1,964 | Single Family Residence | 3/2 | 50 |
| 09-09-2021 | 1346 CHAPMAN CIRCLE, WINTER PARK FL 32789 | $1,200,000 | $358 | $1,250,000 | 3,349 | Single Family Residence | 4/5 | 57 |
| 09-09-2021 | 1508 CHESTNUT AVENUE, WINTER PARK FL 32789 | $415,000 | $280 | $425,000 | 1,482 | Single Family Residence | 3/2 | 10 |
| 09-08-2021 | 1217 PARK GREEN PLACE, WINTER PARK FL 32789 | $256,500 | $158 | $240,000 | 1,617 | Townhouse | 3/2 | 27 |
| 09-08-2021 | 603 HERITAGE BOULEVARD, WINTER PARK FL 32792 | $350,000 | $200 | $365,000 | 1,749 | Single Family Residence | 4/2 | 47 |
| 09-08-2021 | 2266 HOWARD DRIVE, WINTER PARK FL 32789 | $410,000 | $317 | $429,000 | 1,290 | Single Family Residence | 3/1 | 91 |
| 09-08-2021 | 1772 CHESTNUT AVENUE, WINTER PARK FL 32789 | $525,000 | $262 | $525,000 | 2,000 | Single Family Residence | 3/3 | 78 |
| 09-08-2021 | 1772 CHESTNUT AVENUE, WINTER PARK FL 32789 | $525,000 | $525,000 | / | 78 | |||
| 09-08-2021 | 212 RIPPLING LANE, WINTER PARK FL 32789 | $715,595 | $306 | $700,000 | 2,336 | Single Family Residence | 3/3 | 50 |
| 09-07-2021 | 1745 SPRUCE AVENUE, WINTER PARK FL 32789 | $1,155,000 | $308 | $1,235,000 | 3,748 | Single Family Residence | 4/4 | 55 |
| 09-07-2021 | 603 ELLEN DRIVE, WINTER PARK FL 32789 | $215,000 | $215,000 | / | 514 | |||
| 09-07-2021 | 8401 ADMIRAL POINT, WINTER PARK FL 32792 | $368,500 | $230 | $370,000 | 1,600 | Single Family Residence | 4/2 | 35 |
| 09-03-2021 | 1527 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $200,000 | $121 | $185,000 | 1,652 | Townhouse | 2/3 | 161 |
| 09-03-2021 | 1920 WOODCREST DRIVE # 5, WINTER PARK FL 32792 | $214,000 | $173 | $224,900 | 1,236 | Condominium | 2/2 | 148 |
| 09-03-2021 | 674 DOUGLAS AVENUE, WINTER PARK FL 32789 | $315,000 | $250 | $300,000 | 1,260 | Single Family Residence | 2/2 | 158 |
| 09-03-2021 | 640 N PARK AVENUE # 35, WINTER PARK FL 32789 | $320,000 | $475 | $329,000 | 673 | Condominium | 1/1 | 216 |
| 09-03-2021 | 7525 HULL ST, WINTER PARK FL 32792 | $355,000 | $238 | $345,000 | 1,489 | Single Family Residence | 4/2 | 43 |
| 09-03-2021 | 1521 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $455,000 | $163 | $429,900 | 2,791 | Single Family Residence | 4/4 | 68 |
| 09-03-2021 | 4413 GLENMOOR COURT, WINTER PARK FL 32792 | $509,400 | $259 | $509,400 | 1,966 | 4/3 | 8 | |
| 09-03-2021 | 352 CAMBRIDGE BOULEVARD, WINTER PARK FL 32789 | $525,000 | $273 | $525,000 | 1,917 | 5/3 | 4 | |
| 09-03-2021 | 1786 MONDRIAN CIRCLE # 15, WINTER PARK FL 32789 | $835,000 | $361 | $835,000 | 2,310 | Townhouse | 3/4 | 178 |
| 09-03-2021 | 1651 SUMMERLAND AVENUE, WINTER PARK FL 32789 | $865,000 | $286 | $899,000 | 3,023 | Single Family Residence | 4/3 | 145 |
| 09-02-2021 | 2650 EUSTON ROAD, WINTER PARK FL 32789 | $375,600 | $195 | $390,000 | 1,918 | Single Family Residence | 4/2 | 64 |
| 09-01-2021 | 101 S NEW YORK AVENUE # 304, WINTER PARK FL 32789 | $1,375,000 | $440 | $1,449,000 | 3,118 | Condominium | 3/4 | 204 |
| 09-01-2021 | 5338 ORANGE AVENUE, WINTER PARK FL 32792 | $247,000 | $226 | $245,000 | 1,092 | Single Family Residence | 3/2 | 81 |
| 09-01-2021 | 609 ELLEN DRIVE, WINTER PARK FL 32789 | $270,000 | $270,000 | / | 499 | |||
| 09-01-2021 | 1711 VIA TUSCANY, WINTER PARK FL 32789 | $2,713,000 | $583 | $2,799,000 | 4,647 | Single Family Residence | 5/7 | 67 |
| 08-31-2021 | 1044 N KENTUCKY AVENUE, WINTER PARK FL 32789 | $1,400,000 | $476 | $1,350,000 | 2,940 | Single Family Residence | 5/4 | 61 |
| 08-31-2021 | 285 RIPPLING LANE, WINTER PARK FL 32789 | $1,425,000 | $500 | $1,600,000 | 2,849 | Single Family Residence | 2/3 | 75 |
| 08-31-2021 | 780 PINETREE ROAD, WINTER PARK FL 32789 | $1,700,000 | $373 | $1,795,000 | 4,553 | Single Family Residence | 4/5 | 120 |
| 08-31-2021 | 5528 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $330,000 | $209 | $330,000 | 1,573 | Single Family Residence | 3/2 | 37 |
| 08-31-2021 | 1575 N ORANGE AVENUE, WINTER PARK FL 32789 | $510,000 | $276 | $499,000 | 1,844 | Single Family Residence | 3/3 | 68 |
| 08-31-2021 | 1788 MONDRIAN CIRCLE # 16, WINTER PARK FL 32789 | $835,000 | $361 | $835,000 | 2,310 | Townhouse | 3/4 | 90 |
| 08-31-2021 | 274 SYLVAN BOULEVARD, WINTER PARK FL 32789 | $895,000 | $222 | $895,000 | 4,014 | Single Family Residence | 5/4 | 47 |
| 08-31-2021 | 777 HALIFAX AVENUE, WINTER PARK FL 32792 | $926,184 | $293 | $926,184 | 3,161 | Single Family Residence | 4/5 | 173 |
| 08-31-2021 | 811 HAMILTON PLACE COURT, WINTER PARK FL 32789 | $965,000 | $279 | $965,000 | 3,457 | 4/4 | 2 | |
| 08-30-2021 | 1250 S DENNING DRIVE # 109, WINTER PARK FL 32789 | $160,000 | $243 | $160,000 | 658 | Condominium | 1/1 | 39 |
| 08-30-2021 | 2043 LINDEN ROAD, WINTER PARK FL 32792 | $282,500 | $275 | $282,500 | 1,025 | Single Family Residence | 3/2 | 60 |
| 08-30-2021 | 125 S INTERLACHEN AVENUE # 6, WINTER PARK FL 32789 | $2,990,000 | $718 | $2,990,000 | 4,160 | Townhouse | 3/5 | 167 |
| 08-30-2021 | 645 BALFOUR DRIVE, WINTER PARK FL 32792 | $345,000 | $239 | $350,000 | 1,443 | Single Family Residence | 3/2 | 75 |
| 08-27-2021 | 5530 S LAKE BURKETT LANE, WINTER PARK FL 32792 | $372,000 | $222 | $369,000 | 1,669 | Single Family Residence | 3/3 | 50 |
| 08-27-2021 | 1397 HEAVENLY COVE, WINTER PARK FL 32792 | $575,000 | $186 | $575,000 | 3,091 | Single Family Residence | 5/4 | 106 |
| 08-27-2021 | 1791 GOODRICH AVENUE, WINTER PARK FL 32789 | $570,000 | $320 | $599,000 | 1,779 | Single Family Residence | 4/3 | 57 |
| 08-27-2021 | 2032 KIMBRACE PLACE, WINTER PARK FL 32792 | $999,500 | $293 | $999,500 | 3,408 | Single Family Residence | 4/4 | 39 |
| 08-26-2021 | 1551 ONECO AVENUE, WINTER PARK FL 32789 | $1,235,000 | $378 | $1,249,000 | 3,265 | Single Family Residence | 4/3 | 63 |
| 08-26-2021 | 200 SAINT ANDREWS BOULEVARD # 1703, WINTER PARK FL | $180,000 | $147 | $199,000 | 1,219 | Condominium | 2/2 | 31 |
| 08-26-2021 | 4078 SCARLET IRIS PLACE, WINTER PARK FL 32792 | $1,200,000 | $133 | $999,948 | 9,011 | Single Family Residence | 4/6 | 62 |
| 08-25-2021 | 1882 KAROLINA AVENUE, WINTER PARK FL 32789 | $300,000 | $268 | $300,000 | 1,116 | Single Family Residence | 2/2 | 2 |
| 08-25-2021 | 2013 CORNELL AVENUE, WINTER PARK FL 32789 | $325,000 | $307 | $328,000 | 1,057 | Single Family Residence | 2/1 | 84 |
| 08-24-2021 | 303 SANDLEWOOD TRAIL # 2, WINTER PARK FL 32789 | $200,000 | $208 | $209,000 | 960 | Condominium | 2/3 | 47 |
| 08-24-2021 | 1759 MICHIGAN AVENUE, WINTER PARK FL 32789 | $385,000 | $332 | $389,000 | 1,158 | Single Family Residence | 3/2 | 59 |
| 08-23-2021 | 200 ST. ANDREWS BOULEVARD # 2206, WINTER PARK FL 3 | $165,000 | $167 | $165,000 | 987 | Condominium | 2/2 | 49 |
| 08-23-2021 | 1503 LAWNDALE CIRCLE, WINTER PARK FL 32792 | $275,000 | $244 | $279,000 | 1,126 | Single Family Residence | 2/2 | 60 |
| 08-23-2021 | 4032 WATERVIEW LOOP, WINTER PARK FL 32792 | $368,000 | $234 | $368,000 | 1,566 | Single Family Residence | 3/2 | 47 |
| 08-23-2021 | 200 CAROLINA AVENUE # 207, WINTER PARK FL 32789 | $400,000 | $347 | $400,000 | 1,151 | Condominium | 2/2 | 19 |
| 08-20-2021 | 1861 HARLAND PARK DRIVE, WINTER PARK FL 32789 | $1,120,000 | $366 | $1,150,000 | 3,052 | Single Family Residence | 4/4 | 59 |
| 08-20-2021 | 294 SCOTTSDALE SQUARE # 294, WINTER PARK FL 32792 | $116,500 | $107 | $119,900 | 1,085 | Condominium | 2/2 | 16 |
| 08-20-2021 | 3651 N GOLDENROD ROAD # C210, WINTER PARK FL 32792 | $135,000 | $160 | $135,000 | 840 | Condominium | 2/2 | 60 |
| 08-20-2021 | 238 LEWFIELD CIRCLE # 238, WINTER PARK FL 32792 | $140,000 | $146 | $144,900 | 953 | Condominium | 2/2 | 15 |
| 08-20-2021 | 2224 VENETIAN WAY, WINTER PARK FL 32789 | $1,450,000 | $394 | $1,499,000 | 3,673 | Single Family Residence | 4/4 | 65 |
| 08-20-2021 | 1550 HIBISCUS AVENUE, WINTER PARK FL 32789 | $1,575,000 | $417 | $1,690,000 | 3,776 | Single Family Residence | 4/5 | 73 |
| 08-20-2021 | 7464 SWALLOW RUN # 40, WINTER PARK FL 32792 | $165,000 | $120 | $175,000 | 1,365 | Condominium | 2/2 | 58 |
| 08-20-2021 | 7460 WOODBURN COURT # 33, WINTER PARK FL 32792 | $179,900 | $161 | $179,900 | 1,117 | Condominium | 3/2 | 23 |
| 08-20-2021 | 2265 LEE ROAD # 101B, WINTER PARK FL 32789 | $195,000 | $199,000 | Office | / | 218 | ||
| 08-20-2021 | 2229 VIA TUSCANY, WINTER PARK FL 32789 | $2,400,000 | $528 | $2,295,000 | 4,538 | Single Family Residence | 5/6 | 37 |
| 08-20-2021 | 700 MELROSE AVENUE # 33, WINTER PARK FL 32789 | $255,000 | $237 | $275,000 | 1,074 | Condominium | 2/2 | 29 |
| 08-20-2021 | 7010 CITRUS POINT COURT, WINTER PARK FL 32792 | $350,000 | $224 | $344,900 | 1,558 | Single Family Residence | 4/2 | 54 |
| 08-20-2021 | 2716 LION HEART ROAD, WINTER PARK FL 32792 | $492,500 | $291 | $475,000 | 1,688 | Single Family Residence | 3/2 | 36 |
| 08-20-2021 | 1592 SUNFLOWER COURT, WINTER PARK FL 32792 | $475,000 | $178 | $490,000 | 2,666 | Single Family Residence | 4/3 | 50 |
| 08-20-2021 | 1525 BONNIE BURN CIRCLE, WINTER PARK FL 32789 | $675,000 | $345 | $699,000 | 1,952 | Single Family Residence | 3/2 | 40 |
| 08-19-2021 | 5229 N WOODCREST DRIVE, WINTER PARK FL 32792 | $291,000 | $234 | $280,000 | 1,242 | Single Family Residence | 3/2 | 28 |
| 08-19-2021 | 3269 COLEUS COURT, WINTER PARK FL 32792 | $346,938 | $217 | $349,900 | 1,596 | Single Family Residence | 4/2 | 37 |
| 08-19-2021 | 1523 INDIANA AVENUE, WINTER PARK FL 32789 | $340,000 | $270 | $349,900 | 1,259 | Single Family Residence | 2/2 | 128 |
| 08-19-2021 | 660 NORTHWOOD CIRCLE, WINTER PARK FL 32789 | $385,000 | $191 | $385,000 | 2,008 | Single Family Residence | 4/2 | 32 |
| 08-18-2021 | 312 SCOTTSDALE SQUARE # 312, WINTER PARK FL 32792 | $110,000 | $101 | $119,900 | 1,085 | Condominium | 2/2 | 65 |
| 08-18-2021 | 2333 ANTILLES DRIVE, WINTER PARK FL 32792 | $225,000 | $175 | $215,000 | 1,284 | Townhouse | 3/2 | 36 |
| 08-18-2021 | 3329 AUSTRALIAN CIRCLE, WINTER PARK FL 32792 | $320,000 | $225 | $325,000 | 1,420 | Single Family Residence | 3/2 | 51 |
| 08-18-2021 | 2393 FIRSTLIGHT WAY, WINTER PARK FL 32792 | $390,000 | $168 | $395,000 | 2,312 | Townhouse | 3/3 | 92 |
| 08-18-2021 | 1737 OAKHURST AVENUE, WINTER PARK FL 32789 | $540,000 | $267 | $520,000 | 2,020 | Single Family Residence | 3/3 | 24 |
| 08-17-2021 | 3026 ANTIQUE OAKS CIRCLE # 142, WINTER PARK FL 327 | $172,000 | $155 | $177,000 | 1,105 | Condominium | 2/2 | 47 |
| 08-17-2021 | 3641 HAWTHORNE LN, WINTER PARK FL 32792 | $355,600 | $219 | $345,000 | 1,622 | Single Family Residence | 3/2 | 46 |
| 08-16-2021 | 470 CLARENDON AVENUE, WINTER PARK FL 32789 | $1,280,000 | $426 | $1,280,000 | 3,000 | 3/5 | 5 | |
| 08-16-2021 | $148,000 | $139 | $140,000 | 1,058 | Condominium | 2/2 | 57 | |
| 08-16-2021 | 741 WARRENTON ROAD, WINTER PARK FL 32792 | $230,000 | $192 | $230,000 | 1,196 | Townhouse | 3/2 | 25 |
| 08-16-2021 | 1583 ORANGE AVENUE, WINTER PARK FL 32789 | $350,000 | $234 | $359,000 | 1,495 | Single Family Residence | 3/2 | 109 |
| 08-16-2021 | 2246 KING HENRYS COURT, WINTER PARK FL 32792 | $449,100 | $172 | $419,000 | 2,609 | Single Family Residence | 4/3 | 68 |
| 08-16-2021 | 631 W SWOOPE AVENUE, WINTER PARK FL 32789 | $700,000 | $313 | $719,000 | 2,232 | Single Family Residence | 4/3 | 96 |
| 08-16-2021 | 1768 ELIZABETHS WALK, WINTER PARK FL 32789 | $1,010,000 | $338 | $989,900 | 2,986 | Single Family Residence | 5/4 | 38 |
| 08-13-2021 | 146 SCOTTSDALE SQUARE # 146, WINTER PARK FL 32792 | $107,500 | $105 | $119,000 | 1,020 | Condominium | 2/2 | 73 |
| 08-13-2021 | 7444 WOODBURN COURT # 29, WINTER PARK FL 32792 | $150,000 | $145 | $155,000 | 1,031 | Condominium | 2/3 | 42 |
| 08-13-2021 | 2020 LEANNE COURT, WINTER PARK FL 32792 | $370,000 | $177 | $365,000 | 2,088 | Single Family Residence | 4/3 | 37 |
| 08-13-2021 | 2213 WINTER WOODS BOULEVARD, WINTER PARK FL 32792 | $415,000 | $185 | $415,000 | 2,238 | Single Family Residence | 4/2 | 70 |
| 08-13-2021 | 1741 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $485,000 | $338 | $499,900 | 1,434 | Single Family Residence | 3/2 | 43 |
| 08-13-2021 | 733 MINNESOTA AVENUE, WINTER PARK FL 32789 | $537,000 | $277 | $544,900 | 1,932 | Townhouse | 3/3 | 72 |
| 08-13-2021 | 331 E KINGS WAY E, WINTER PARK FL 32789 | $1,026,000 | $344 | $999,000 | 2,981 | Single Family Residence | 4/4 | 51 |
| 08-12-2021 | 200 SAINT ANDREWS BOULEVARD # 3206, WINTER PARK FL | $208,900 | $171 | $208,990 | 1,219 | Condominium | 2/2 | 51 |
| 08-12-2021 | 2828 CASA ALOMA WAY # 400, WINTER PARK FL 32792 | $245,000 | $177 | $265,000 | 1,378 | Office | / | 328 |
| 08-12-2021 | 1211 SCHULTZ AVENUE, WINTER PARK FL 32789 | $347,500 | $320 | $349,900 | 1,085 | Single Family Residence | 3/2 | 71 |
| 08-12-2021 | 7059 CITRUS POINT COURT, WINTER PARK FL 32792 | $369,900 | $262 | $369,900 | 1,407 | Single Family Residence | 3/2 | 70 |
| 08-12-2021 | 100 S VIRGINIA AVENUE # 403, WINTER PARK FL 32789 | $930,000 | $357 | $950,000 | 2,599 | Condominium | 3/3 | 44 |
| 08-11-2021 | 1000 S SEMORAN BOULEVARD # 304, WINTER PARK FL 327 | $97,500 | $122 | $104,900 | 796 | Condominium | 1/1 | 43 |
| 08-11-2021 | 2501 WINDWARD WAY, WINTER PARK FL 32792 | $185,000 | $178 | $175,000 | 1,038 | Townhouse | 2/1 | 44 |
| 08-11-2021 | 541 VIRGINIA DRIVE, WINTER PARK FL 32789 | $3,400,000 | $741 | $3,499,000 | 4,586 | Single Family Residence | 4/4 | 55 |
| 08-11-2021 | 2259 S KING JAMES COURT, WINTER PARK FL 32792 | $380,000 | $197 | $394,900 | 1,920 | Single Family Residence | 3/2 | 41 |
| 08-10-2021 | 1457 CHAPMAN CIRCLE, WINTER PARK FL 32789 | $1,399,000 | $392 | $1,399,000 | 3,567 | 4/4 | 29 | |
| 08-10-2021 | 2612 EXUMA WAY, WINTER PARK FL 32792 | $152,000 | $149 | $165,000 | 1,020 | Townhouse | 2/2 | 62 |
| 08-10-2021 | 200 SAINT ANDREWS BOULEVARD # 1606, WINTER PARK FL | $215,000 | $218 | $215,000 | 983 | Condominium | 2/2 | 36 |
| 08-10-2021 | 2510 LEEWARD WAY, WINTER PARK FL 32792 | $255,000 | $185 | $236,000 | 1,375 | Townhouse | 2/2 | 27 |
| 08-10-2021 | 3028 DIKEWOOD COURT, WINTER PARK FL 32792 | $315,000 | $196 | $315,000 | 1,606 | Single Family Residence | 3/2 | 28 |
| 08-10-2021 | 1857 WILLOW LANE, WINTER PARK FL 32792 | $325,000 | $190 | $325,000 | 1,706 | Single Family Residence | 4/2 | 35 |
| 08-10-2021 | 1409 MILLER AVENUE, WINTER PARK FL 32789 | $685,000 | $301 | $749,999 | 2,273 | Single Family Residence | 4/3 | 65 |
| 08-09-2021 | 1750 BLUE RIDGE ROAD, WINTER PARK FL 32789 | $1,710,000 | $396 | $1,710,000 | 4,308 | Single Family Residence | 4/5 | 97 |
| 08-09-2021 | 200 SAINT ANDREWS BOULEVARD # 2006, WINTER PARK FL | $175,000 | $177 | $174,900 | 987 | Condominium | 2/2 | 53 |
| 08-09-2021 | 5515 ALBERT DRIVE, WINTER PARK FL 32792 | $275,000 | $179 | $245,000 | 1,535 | Single Family Residence | 4/2 | 27 |
| 08-09-2021 | 1124 PARK GREEN PLACE, WINTER PARK FL 32789 | $270,500 | $210 | $260,000 | 1,282 | Townhouse | 3/2 | 54 |
| 08-09-2021 | 1020 MINNESOTA AVENUE # 4, WINTER PARK FL 32789 | $390,000 | $195 | $400,000 | 2,000 | Townhouse | 3/4 | 35 |
| 08-09-2021 | 1792 MONDRIAN CIRCLE # 18, WINTER PARK FL 32789 | $854,000 | $364 | $864,000 | 2,341 | Townhouse | 3/4 | 181 |
| 08-09-2021 | 4575 WHIMBREL PLACE, WINTER PARK FL 32792 | $910,000 | $277 | $925,000 | 3,284 | Single Family Residence | 5/3 | 345 |
| 08-09-2021 | 136 LEWFIELD CIR # 136, WINTER PARK FL 32792 | $96,000 | $141 | $99,900 | 678 | Condominium | 1/1 | 130 |
| 08-06-2021 | 5101 ORANGE AVENUE, WINTER PARK FL 32792 | $205,000 | $106 | $205,000 | 1,922 | 3/2 | 5 | |
| 08-06-2021 | 5162 LAZY OAKS DRIVE, WINTER PARK FL 32792 | $240,500 | $194 | $220,000 | 1,236 | Townhouse | 2/3 | 71 |
| 08-06-2021 | 5201 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $365,000 | $243 | $364,900 | 1,496 | Single Family Residence | 3/2 | 56 |
| 08-06-2021 | 505 CORNWALL ROAD, WINTER PARK FL 32792 | $450,000 | $248 | $450,000 | 1,813 | Single Family Residence | 4/2 | 30 |
| 08-06-2021 | 1507 INDIANA AVENUE, WINTER PARK FL 32789 | $486,000 | $270 | $499,900 | 1,800 | Townhouse | 3/3 | 83 |
| 08-06-2021 | 207 LAUREL PARK COURT, WINTER PARK FL 32792 | $729,900 | $234 | $729,900 | 3,119 | Single Family Residence | 4/4 | 51 |
| 08-06-2021 | 1166 OXFORD ROAD, WINTER PARK FL 32789 | $835,400 | $221 | $869,500 | 3,764 | Single Family Residence | 4/3 | 376 |
| 08-05-2021 | 1541 CHESTNUT AVENUE, WINTER PARK FL 32789 | $1,150,000 | $404 | $1,150,000 | 2,840 | Single Family Residence | 4/3 | 51 |
| 08-05-2021 | 435 OLOLU DRIVE, WINTER PARK FL 32789 | $340,000 | $202 | $340,000 | 1,680 | Single Family Residence | 4/2 | 74 |
| 08-04-2021 | 1429 HOLTS GROVE CIRCLE, WINTER PARK FL 32789 | $1,930,000 | $417 | $1,985,000 | 4,621 | Single Family Residence | 4/5 | 99 |
| 08-04-2021 | 5217 SEMINOLE AVENUE, WINTER PARK FL 32792 | $235,000 | $292 | $235,000 | 804 | Single Family Residence | 3/1 | 115 |
| 08-04-2021 | 900 N DENNING DRIVE, WINTER PARK FL 32789 | $293,300 | $178 | $299,000 | 1,642 | Single Family Residence | 4/3 | 49 |
| 08-04-2021 | 1414 BESSMOR ROAD, WINTER PARK FL 32789 | $330,000 | $316 | $340,000 | 1,043 | Single Family Residence | 3/1 | 42 |
| 08-04-2021 | 1820 BISCAYNE DRIVE, WINTER PARK FL 32789 | $721,000 | $289 | $739,000 | 2,494 | Single Family Residence | 4/4 | 61 |
| 08-02-2021 | 2224 KING RICHARDS COURT, WINTER PARK FL 32792 | $407,898 | $276 | $399,900 | 1,475 | Single Family Residence | 3/2 | 27 |
| 08-02-2021 | 1802 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $569,500 | $314 | $565,000 | 1,808 | Single Family Residence | 4/3 | 42 |
| 07-31-2021 | 2652 PASSAMONTE DRIVE # 7A, WINTER PARK FL 32792 | $273,000 | $154 | $284,450 | 1,765 | Condominium | 3/3 | 58 |
| 07-30-2021 | 7111 EASTER STREET, WINTER PARK FL 32792 | $110,000 | $151 | $125,000 | 728 | Manufactured Home | 2/1 | 38 |
| 07-30-2021 | 700 MELROSE AVENUE # 3, WINTER PARK FL 32789 | $160,000 | $272 | $159,900 | 587 | Condominium | /1 | 78 |
| 07-30-2021 | 2935 ANTIQUE OAKS CIRCLE # 60, WINTER PARK FL 3279 | $164,900 | $161 | $164,900 | 1,018 | Condominium | 2/2 | 11 |
| 07-30-2021 | 1670 CHESTNUT AVENUE, WINTER PARK FL 32789 | $1,666,270 | $445 | $1,675,000 | 3,738 | Single Family Residence | 4/5 | 2 |
| 07-30-2021 | 3020 ANTIQUE OAKS CIRCLE # 130, WINTER PARK FL 327 | $162,000 | $159 | $170,000 | 1,018 | Condominium | 2/2 | 24 |
| 07-30-2021 | 1760 SUNSET DRIVE, WINTER PARK FL 32789 | $1,805,000 | $441 | $1,799,000 | 4,084 | Single Family Residence | 5/6 | 78 |
| 07-30-2021 | 4245 BEAR GULLY ROAD, WINTER PARK FL 32792 | $2,100,000 | $379 | $2,150,000 | 5,528 | Single Family Residence | 5/5 | 388 |
| 07-30-2021 | 449 GENIUS DRIVE, WINTER PARK FL 32789 | $2,230,000 | $420 | $2,295,000 | 5,307 | Single Family Residence | 4/5 | 47 |
| 07-30-2021 | 2560 PASSAMONTE DRIVE # 9F, WINTER PARK FL 32792 | $269,900 | $142 | $296,900 | 1,892 | Condominium | 3/3 | 80 |
| 07-30-2021 | 7573 DOCKSIDE STREET, WINTER PARK FL 32792 | $300,000 | $222 | $298,000 | 1,348 | Single Family Residence | 3/2 | 30 |
| 07-30-2021 | 110 KILLARNEY BAY COURT # 1, WINTER PARK FL 32789 | $293,000 | $257 | $299,900 | 1,140 | Condominium | 2/2 | 71 |
| 07-30-2021 | 2512 EASTBROOK BOULEVARD, WINTER PARK FL 32792 | $305,000 | $189 | $305,900 | 1,607 | Single Family Residence | 4/3 | 30 |
| 07-30-2021 | 995 MINNESOTA AVENUE, WINTER PARK FL 32789 | $324,900 | $309 | $324,900 | 1,049 | Single Family Residence | 2/1 | 75 |
| 07-30-2021 | 2000 WHITEHALL DRIVE, WINTER PARK FL 32792 | $381,250 | $235 | $360,000 | 1,620 | Single Family Residence | 3/2 | 43 |
| 07-30-2021 | 2717 BOWER ROAD, WINTER PARK FL 32792 | $420,000 | $227 | $409,900 | 1,843 | Single Family Residence | 4/2 | 36 |
| 07-30-2021 | 310 FITZHUGH ROAD, WINTER PARK FL 32792 | $419,800 | $188 | $419,000 | 2,227 | Single Family Residence | 5/3 | 76 |
| 07-30-2021 | 131 S LAKEMONT AVENUE, WINTER PARK FL 32792 | $425,000 | $235 | $425,000 | 1,808 | Single Family Residence | 3/2 | 29 |
| 07-30-2021 | 7518 UNIVERSITY GARDEN DRIVE, WINTER PARK FL 32792 | $450,000 | $213 | $449,900 | 2,110 | 1/2 Duplex | 6/4 | 47 |
| 07-30-2021 | 640 N PARK AVENUE # 3, WINTER PARK FL 32789 | $435,000 | $484 | $450,000 | 897 | Condominium | 2/1 | 68 |
| 07-30-2021 | 8001 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $465,000 | $205 | $465,000 | 2,267 | Single Family Residence | 4/3 | 70 |
| 07-30-2021 | 1816 MONDRIAN CIRCLE, WINTER PARK FL 32789 | $622,500 | $268 | $639,000 | 2,320 | Townhouse | 3/4 | 134 |
| 07-30-2021 | 2255 CHANTILLY AVENUE, WINTER PARK FL 32789 | $779,000 | $246 | $799,000 | 3,158 | Single Family Residence | 4/4 | 153 |
| 07-30-2021 | 211 SCOTTSDALE SQUARE # 211, WINTER PARK FL 32792 | $107,871 | $105 | $92,500 | 1,020 | Condominium | 2/2 | 44 |
| 07-30-2021 | 45 CYPRESS LANE, WINTER PARK FL 32789 | $954,000 | $256 | $949,000 | 3,718 | Single Family Residence | 4/4 | 77 |
| 07-29-2021 | 1806 LAURELTON HALL LANE, WINTER PARK FL 32789 | $1,280,000 | $379 | $1,380,000 | 3,370 | Single Family Residence | 4/4 | 50 |
| 07-29-2021 | 2427 GALLERY VIEW DRIVE # 7, WINTER PARK FL 32792 | $255,000 | $253 | $255,000 | 1,004 | Condominium | 2/2 | 35 |
| 07-29-2021 | 2724 AMBERGATE ROAD, WINTER PARK FL 32792 | $289,900 | $201 | $289,900 | 1,436 | Single Family Residence | 3/2 | 42 |
| 07-29-2021 | 1653 PERUVIAN LANE, WINTER PARK FL 32792 | $315,000 | $273 | $315,000 | 1,152 | Single Family Residence | 3/2 | 42 |
| 07-29-2021 | 5532 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $325,000 | $248 | $326,900 | 1,310 | Single Family Residence | 3/2 | 36 |
| 07-29-2021 | 1610 ASTER DR, WINTER PARK FL 32792 | $325,000 | $173 | $339,000 | 1,878 | Single Family Residence | 3/2 | 50 |
| 07-29-2021 | $430,000 | $299 | $430,000 | 1,436 | Single Family Residence | 3/2 | 14 | |
| 07-28-2021 | 164 BREWER AVENUE, WINTER PARK FL 32789 | $1,015,000 | $296 | $1,025,000 | 3,420 | Single Family Residence | 5/5 | 84 |
| 07-28-2021 | 1220 VIA DEL MAR, WINTER PARK FL 32789 | $1,200,000 | $300 | $1,195,000 | 3,993 | Single Family Residence | 4/5 | 41 |
| 07-28-2021 | 7637 UNIVERSITY GARDEN DRIVE, WINTER PARK FL 32792 | $305,000 | $145 | $239,900 | 2,090 | Duplex | / | 13 |
| 07-28-2021 | 7532 HULL STREET, WINTER PARK FL 32792 | $313,623 | $259 | $320,000 | 1,210 | Single Family Residence | 3/2 | 69 |
| 07-28-2021 | 2530 FRANKLIN AVENUE, WINTER PARK FL 32789 | $449,900 | $248 | $449,900 | 1,809 | Single Family Residence | 3/2 | 35 |
| 07-28-2021 | 1310 ALOMA AVENUE, WINTER PARK FL 32789 | $730,000 | $278 | $749,085 | 2,623 | Single Family Residence | 4/3 | 63 |
| 07-27-2021 | 3253 COLEUS COURT, WINTER PARK FL 32792 | $320,000 | $179 | $320,000 | 1,782 | Single Family Residence | 3/2 | 30 |
| 07-27-2021 | 411 HOLT AVENUE, WINTER PARK FL 32789 | $650,000 | $526 | $650,000 | 1,234 | Single Family Residence | 3/2 | 48 |
| 07-26-2021 | 125 S INTERLACHEN AVENUE # 2, WINTER PARK FL 32789 | $2,250,000 | $693 | $2,250,000 | 3,244 | Townhouse | 3/5 | 103 |
| 07-26-2021 | 609 ELLENDALE DRIVE, WINTER PARK FL 32792 | $265,000 | $198 | $275,000 | 1,334 | Single Family Residence | 3/2 | 81 |
| 07-26-2021 | 1584 LAWNDALE CIRCLE, WINTER PARK FL 32792 | $355,000 | $268 | $339,000 | 1,322 | Single Family Residence | 3/2 | 46 |
| 07-26-2021 | 219 CORNWALL ROAD, WINTER PARK FL 32792 | $377,000 | $239 | $385,000 | 1,571 | Single Family Residence | 3/2 | 18 |
| 07-23-2021 | 5212 ARDMORE DRIVE, WINTER PARK FL 32792 | $325,000 | $249 | $299,900 | 1,301 | Single Family Residence | 3/2 | 36 |
| 07-23-2021 | 1853 WILLOW LANE, WINTER PARK FL 32792 | $462,500 | $212 | $485,000 | 2,175 | Single Family Residence | 4/3 | 105 |
| 07-23-2021 | 1136 S PENNSYLVANIA AVENUE, WINTER PARK FL 32789 | $765,000 | $314 | $775,000 | 2,434 | Townhouse | 3/3 | 183 |
| 07-23-2021 | 6902 MILLS ROAD, WINTER PARK FL 32792 | $100,000 | $151 | $85,000 | 660 | Single Family Residence | 1/1 | 45 |
| 07-23-2021 | 6904 MILLS ROAD, WINTER PARK FL 32792 | $110,000 | $183 | $85,000 | 598 | Mobile Home | 1/1 | 45 |
| 07-22-2021 | 140 E MORSE BOULEVARD # F, WINTER PARK FL 32789 | $1,525,000 | $665 | $1,599,000 | 2,291 | Condominium | 3/4 | 47 |
| 07-22-2021 | 2500 LEE ROAD # 230, WINTER PARK FL 32789 | $215,000 | $204 | $225,900 | 1,050 | Condominium | 2/2 | 77 |
| 07-22-2021 | 1201 PARK GREEN PLACE, WINTER PARK FL 32789 | $260,000 | $204 | $260,000 | 1,272 | Townhouse | 2/2 | 47 |
| 07-22-2021 | 1408 WESTDALE AVENUE, WINTER PARK FL 32792 | $325,000 | $253 | $320,000 | 1,284 | Single Family Residence | 3/2 | 32 |
| 07-22-2021 | 837 W LYMAN AVENUE, WINTER PARK FL 32789 | $675,000 | $454 | $675,000 | 1,485 | 3/3 | 5 | |
| 07-21-2021 | 3651 N GOLDENROD ROAD # 104, WINTER PARK FL 32792 | $126,000 | $150 | $131,000 | 840 | Condominium | 2/2 | 41 |
| 07-21-2021 | 5524 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $365,000 | $232 | $350,000 | 1,572 | Single Family Residence | 3/2 | 41 |
| 07-21-2021 | 1928 SHADYHILL TERRACE, WINTER PARK FL 32792 | $400,000 | $201 | $399,990 | 1,983 | Single Family Residence | 4/2 | 33 |
| 07-21-2021 | 2886 WILD GINGER COURT, WINTER PARK FL 32792 | $699,900 | $204 | $699,900 | 3,415 | Single Family Residence | 4/4 | 59 |
| 07-20-2021 | 2345 SHADOWLAND LOOP, WINTER PARK FL 32792 | $375,000 | $213 | $369,000 | 1,755 | Townhouse | 3/3 | 50 |
| 07-16-2021 | 200 SAINT ANDREWS BOULEVARD # 806, WINTER PARK FL | $185,500 | $187 | $175,000 | 987 | Condominium | 2/2 | 32 |
| 07-16-2021 | 610 GENIUS DRIVE, WINTER PARK FL 32789 | $2,100,000 | $404 | $2,150,000 | 5,196 | Single Family Residence | 5/6 | 77 |
| 07-16-2021 | 7133 TIMBER DRIVE, WINTER PARK FL 32792 | $201,000 | $179 | $225,000 | 1,121 | Single Family Residence | 2/2 | 53 |
| 07-16-2021 | 797 PINETREE ROAD, WINTER PARK FL 32789 | $2,600,000 | $2,749,000 | / | 354 | |||
| 07-16-2021 | 535 N INTERLACHEN AVENUE # 207, WINTER PARK FL 327 | $360,000 | $347 | $379,000 | 1,036 | Condominium | 1/2 | 44 |
| 07-16-2021 | 535 INTERLACHEN AVE N # 306, WINTER PARK FL 32789 | $375,000 | $386 | $384,900 | 970 | Condominium | 2/2 | 228 |
| 07-16-2021 | 1210 BURNING TREE LANE, WINTER PARK FL 32792 | $529,000 | $283 | $529,000 | 1,868 | Single Family Residence | 3/2 | 65 |
| 07-16-2021 | 1790 MONDRIAN CIRCLE # 17, WINTER PARK FL 32789 | $854,000 | $364 | $864,000 | 2,341 | Townhouse | 3/4 | 43 |
| 07-16-2021 | 307 SCOTTSDALE SQUARE # 307, WINTER PARK FL 32792 | $82,700 | $105 | $97,000 | 785 | Condominium | 1/1 | 32 |
| 07-15-2021 | 315 E NEW ENGLAND AVENUE # 11, WINTER PARK FL 3278 | $1,385,000 | $686 | $1,380,000 | 2,018 | Condominium | 3/2 | 70 |
| 07-15-2021 | 151 N ORLANDO AVENUE # 104, WINTER PARK FL 32789 | $195,000 | $240 | $195,000 | 810 | Condominium | 2/1 | 35 |
| 07-15-2021 | 5439 ALBERT DRIVE, WINTER PARK FL 32792 | $285,000 | $221 | $275,000 | 1,286 | Single Family Residence | 3/2 | 41 |
| 07-15-2021 | 2814 SHERIFF WAY, WINTER PARK FL 32792 | $380,000 | $195 | $350,000 | 1,948 | Single Family Residence | 4/2 | 48 |
| 07-15-2021 | 2827 WOODSIDE AVENUE, WINTER PARK FL 32789 | $377,900 | $372 | $369,900 | 1,015 | Single Family Residence | 2/1 | 64 |
| 07-14-2021 | 7476 CANFORD COURT # 12, WINTER PARK FL 32792 | $168,000 | $123 | $170,000 | 1,365 | Condominium | 2/2 | 52 |
| 07-14-2021 | 7773 COUNTRY PLACE # 8, WINTER PARK FL 32792 | $188,000 | $176 | $180,000 | 1,068 | Condominium | 2/2 | 34 |
| 07-14-2021 | 2411 GALLERY VIEW DRIVE # 201, WINTER PARK FL 3279 | $205,000 | $199 | $205,000 | 1,026 | Condominium | 2/2 | 4 |
| 07-14-2021 | 1546 SUGARWOOD CIRCLE, WINTER PARK FL 32792 | $405,000 | $183 | $399,900 | 2,213 | Single Family Residence | 3/3 | 57 |
| 07-14-2021 | 290 W LYMAN AVENUE, WINTER PARK FL 32789 | $870,000 | $433 | $875,000 | 2,009 | Villa | 3/3 | 56 |
| 07-13-2021 | 1650 PALM AVENUE, WINTER PARK FL 32789 | $1,700,000 | $420 | $1,695,000 | 4,041 | Single Family Residence | 5/5 | 117 |
| 07-13-2021 | 1880 CHILEAN LANE, WINTER PARK FL 32792 | $308,000 | $179 | $315,000 | 1,715 | Single Family Residence | 3/3 | 34 |
| 07-13-2021 | 315 E NEW ENGLAND AVENUE E # 8, WINTER PARK FL 327 | $975,000 | $608 | $985,000 | 1,602 | Condominium | 2/2 | 132 |
| 07-12-2021 | 106 SCOTTSDALE SQUARE # 106, WINTER PARK FL 32792 | $135,000 | $108 | $135,000 | 1,250 | Condominium | 3/2 | 48 |
| 07-12-2021 | 2407 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $1,325,000 | $422 | $1,360,000 | 3,133 | Single Family Residence | 5/5 | 63 |
| 07-12-2021 | 7484 CANFORD COURT # 8, WINTER PARK FL 32792 | $193,000 | $120 | $185,000 | 1,600 | Condominium | 2/3 | 33 |
| 07-12-2021 | 200 SAINT ANDREWS BOULEVARD # 3707, WINTER PARK FL | $225,000 | $184 | $225,000 | 1,219 | Condominium | 2/2 | 39 |
| 07-12-2021 | 225 LAUREL PARK COURT, WINTER PARK FL 32792 | $295,000 | $295,000 | / | 109 | |||
| 07-12-2021 | 2221 SHADOWLAND LOOP, WINTER PARK FL 32792 | $392,000 | $169 | $399,990 | 2,312 | Townhouse | 3/3 | 21 |
| 07-09-2021 | 2700 WRIGHT AVENUE, WINTER PARK FL 32789 | $1,175,000 | $436 | $1,175,000 | 2,692 | Single Family Residence | 4/5 | 183 |
| 07-09-2021 | 7712 COUNTRY PLACE # 5, WINTER PARK FL 32792 | $170,000 | $159 | $158,000 | 1,068 | Condominium | 2/2 | 17 |
| 07-09-2021 | 151 N ORLANDO AVENUE # 204, WINTER PARK FL 32789 | $184,000 | $259 | $198,000 | 710 | Condominium | 2/1 | 210 |
| 07-09-2021 | 7539 DOCKSIDE STREET, WINTER PARK FL 32792 | $293,000 | $210 | $305,000 | 1,394 | Single Family Residence | 3/2 | 69 |
| 07-09-2021 | 1311 SUFFOLK ROAD, WINTER PARK FL 32789 | $360,500 | $307 | $359,900 | 1,172 | Single Family Residence | 2/1 | 50 |
| 07-09-2021 | 333 CAMBRIDGE BOULEVARD, WINTER PARK FL 32789 | $425,000 | $257 | $425,000 | 1,651 | Single Family Residence | 3/2 | 53 |
| 07-08-2021 | 2600 PASSAMONTE DRIVE # 8F, WINTER PARK FL 32792 | $287,000 | $160 | $294,990 | 1,790 | Townhouse | 3/3 | 43 |
| 07-08-2021 | 3333 COLEUS COURT, WINTER PARK FL 32792 | $300,000 | $212 | $295,000 | 1,412 | Single Family Residence | 3/2 | 38 |
| 07-08-2021 | 3233 RAIDERS RUN, WINTER PARK FL 32792 | $350,000 | $200 | $349,900 | 1,749 | Single Family Residence | 4/2 | 35 |
| 07-08-2021 | 5124 TANGERINE AVENUE, WINTER PARK FL 32792 | $370,000 | $207 | $350,000 | 1,784 | Single Family Residence | 4/2 | 22 |
| 07-07-2021 | 327 ELKHORN COURT, WINTER PARK FL 32792 | $327,500 | $135 | $327,500 | 2,409 | Single Family Residence | 4/3 | 23 |
| 07-07-2021 | 3321 BENNINGTON COURT, WINTER PARK FL 32792 | $390,000 | $239 | $399,900 | 1,626 | Single Family Residence | 3/2 | 34 |
| 07-07-2021 | 1441 MIZELL AVENUE, WINTER PARK FL 32789 | $590,000 | $415 | $575,000 | 1,421 | Single Family Residence | 3/3 | 34 |
| 07-06-2021 | 3651 N GOLDENROD ROAD # D206, WINTER PARK FL 32792 | $121,000 | $144 | $121,700 | 840 | Condominium | 2/2 | 114 |
| 07-06-2021 | 7455 GLEN OAKS WAY # 95, WINTER PARK FL 32792 | $132,000 | $128 | $135,000 | 1,031 | Condominium | 2/2 | 35 |
| 07-06-2021 | 851 MILES AVENUE # 5, WINTER PARK FL 32789 | $155,000 | $191 | $149,900 | 808 | Condominium | 2/1 | 28 |
| 07-06-2021 | 200 SAINT ANDREWS BOULEVARD # 1805, WINTER PARK FL | $173,000 | $141 | $173,000 | 1,219 | Condominium | 2/2 | 87 |
| 07-06-2021 | 7627 VILLAGE GREEN DRIVE, WINTER PARK FL 32792 | $345,000 | $209 | $340,000 | 1,647 | Single Family Residence | 3/2 | 25 |
| 07-06-2021 | 102 RANCH ROAD, WINTER PARK FL 32792 | $560,000 | $180 | $539,000 | 3,110 | Single Family Residence | 4/4 | 55 |
| 07-02-2021 | 451 W COMSTOCK AVENUE, WINTER PARK FL 32789 | $1,250,000 | $352 | $1,275,000 | 3,549 | Single Family Residence | 4/5 | 145 |
| 07-02-2021 | 903 BUNGALOW AVENUE, WINTER PARK FL 32789 | $650,000 | $332 | $650,000 | 1,954 | 3/3 | 6 | |
| 07-01-2021 | 1820 ANZLE AVENUE, WINTER PARK FL 32789 | $1,025,000 | $311 | $1,025,000 | 3,289 | Single Family Residence | 4/4 | 122 |
| 07-01-2021 | 1602 ALABAMA DRIVE # 105, WINTER PARK FL 32789 | $1,295,000 | $617 | $1,295,000 | 2,096 | Condominium | 2/3 | 21 |
| 07-01-2021 | 2219 VENETIAN WAY, WINTER PARK FL 32789 | $2,400,000 | $377 | $2,550,000 | 6,362 | Single Family Residence | 6/6 | 148 |
| 07-01-2021 | 653 OLOLU DRIVE, WINTER PARK FL 32789 | $310,100 | $346 | $289,900 | 896 | Duplex | / | 18 |
| 06-30-2021 | 2308 INAGUA WAY, WINTER PARK FL 32792 | $226,000 | $147 | $225,000 | 1,536 | Townhouse | 3/2 | 41 |
| 06-30-2021 | 7432 BLUE JACKET PLACE E, WINTER PARK FL 32792 | $270,000 | $241 | $249,900 | 1,119 | Single Family Residence | 3/2 | 35 |
| 06-30-2021 | 1945 ALBERT LEE PARKWAY, WINTER PARK FL 32789 | $300,000 | $193 | $325,900 | 1,547 | Single Family Residence | 3/2 | 59 |
| 06-30-2021 | 722 CARVELL DRIVE, WINTER PARK FL 32792 | $360,000 | $227 | $355,000 | 1,581 | Single Family Residence | 3/2 | 43 |
| 06-30-2021 | 1118 SCHULTZ AVENUE, WINTER PARK FL 32789 | $410,000 | $246 | $419,000 | 1,661 | Townhouse | 3/3 | 77 |
| 06-30-2021 | 1065 ARAGON AVENUE # 1065, WINTER PARK FL 32789 | $410,000 | $245 | $425,000 | 1,669 | Condominium | 3/3 | 40 |
| 06-30-2021 | 2540 EUSTON ROAD, WINTER PARK FL 32789 | $451,000 | $240 | $449,900 | 1,877 | Single Family Residence | 3/2 | 42 |
| 06-30-2021 | 221 OAKWOOD WAY, WINTER PARK FL 32789 | $650,000 | $245 | $650,000 | 2,648 | Single Family Residence | 4/3 | 3 |
| 06-29-2021 | 5157 LAZY OAKS DRIVE, WINTER PARK FL 32792 | $227,000 | $225 | $220,000 | 1,008 | Condominium | 2/2 | 27 |
| 06-29-2021 | 1710 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $235,000 | $158 | $225,000 | 1,481 | Townhouse | 3/2 | 47 |
| 06-29-2021 | 653 OLOLU DRIVE, WINTER PARK FL 32789 | $301,100 | $336 | $289,900 | 896 | Single Family Residence | 2/2 | 22 |
| 06-29-2021 | 1304 VIBURNUM LANE, WINTER PARK FL 32792 | $319,500 | $201 | $319,500 | 1,584 | Single Family Residence | 3/2 | 41 |
| 06-29-2021 | 342 CORNWALL ROAD, WINTER PARK FL 32792 | $385,000 | $225 | $395,000 | 1,704 | Single Family Residence | 3/2 | 40 |
| 06-28-2021 | 7138 TIMBER DRIVE, WINTER PARK FL 32792 | $310,000 | $235 | $285,000 | 1,317 | Single Family Residence | 3/2 | 42 |
| 06-28-2021 | 1751 GOODRICH AVENUE, WINTER PARK FL 32789 | $825,000 | $380 | $829,000 | 2,170 | Single Family Residence | 4/4 | 127 |
| 06-25-2021 | 212 SCOTTSDALE SQUARE # 212, WINTER PARK FL 32792 | $100,000 | $98 | $100,000 | 1,020 | Condominium | 2/2 | 66 |
| 06-25-2021 | 1180 TOM GURNEY DRIVE, WINTER PARK FL 32789 | $2,625,000 | $609 | $2,750,000 | 4,309 | Single Family Residence | 4/5 | 57 |
| 06-25-2021 | 3130 HEARTWOOD AVENUE, WINTER PARK FL 32792 | $330,000 | $202 | $330,000 | 1,627 | Single Family Residence | 3/2 | 53 |
| 06-25-2021 | 334 CORNWALL ROAD, WINTER PARK FL 32792 | $359,000 | $245 | $359,000 | 1,465 | Single Family Residence | 3/2 | 41 |
| 06-25-2021 | 656 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $791,000 | $266 | $799,000 | 2,970 | Single Family Residence | 4/4 | 50 |
| 06-24-2021 | 200 SAINT ANDREWS BOULEVARD # 601, WINTER PARK FL | $135,000 | $185 | $135,000 | 727 | Condominium | 1/1 | 58 |
| 06-24-2021 | 5164 LAZY OAKS DRIVE, WINTER PARK FL 32792 | $230,000 | $186 | $225,000 | 1,236 | Townhouse | 2/3 | 49 |
| 06-24-2021 | 1908 CARRIGAN AVENUE, WINTER PARK FL 32792 | $272,500 | $242 | $274,987 | 1,122 | Single Family Residence | 3/1 | 99 |
| 06-24-2021 | 957 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $590,000 | $250 | $589,000 | 2,356 | Single Family Residence | 4/3 | 36 |
| 06-24-2021 | 1861 SHILOH LANE, WINTER PARK FL 32789 | $625,000 | $255 | $625,000 | 2,449 | Single Family Residence | 4/3 | 29 |
| 06-22-2021 | 1008 TUSCANY PLACE, WINTER PARK FL 32789 | $1,300,000 | $433 | $1,125,000 | 2,998 | Single Family Residence | 4/3 | 40 |
| 06-22-2021 | 551 GILBERT ROAD, WINTER PARK FL 32792 | $395,000 | $207 | $375,000 | 1,900 | Single Family Residence | 3/2 | 42 |
| 06-22-2021 | 7604 WAUNAQUA DRIVE, WINTER PARK FL 32792 | $430,000 | $206 | $429,000 | 2,080 | Single Family Residence | 4/3 | 111 |
| 06-22-2021 | 1433 CHAPMAN CIRCLE, WINTER PARK FL 32789 | $865,000 | $272 | $875,000 | 3,170 | Single Family Residence | 3/4 | 145 |
| 06-21-2021 | 5474 PEACO PLACE, WINTER PARK FL 32792 | $240,000 | $218 | $220,000 | 1,100 | 1/2 Duplex | 3/2 | 33 |
| 06-21-2021 | 1627 LOOKOUT LANDING, WINTER PARK FL 32789 | $2,650,000 | $431 | $2,650,000 | 6,136 | Single Family Residence | 5/6 | 1 |
| 06-21-2021 | 1560 LAWNDALE CIRCLE, WINTER PARK FL 32792 | $325,000 | $229 | $315,000 | 1,415 | Single Family Residence | 3/2 | 46 |
| 06-21-2021 | 2032 HOUNDSLAKE DRIVE, WINTER PARK FL 32792 | $342,000 | $222 | $319,500 | 1,540 | Single Family Residence | 3/2 | 32 |
| 06-18-2021 | 1960 STAUNTON AVENUE, WINTER PARK FL 32789 | $245,000 | $185 | $249,900 | 1,323 | Duplex | / | 39 |
| 06-18-2021 | 2136 CONIFER AVENUE, WINTER PARK FL 32792 | $317,500 | $195 | $315,000 | 1,623 | Single Family Residence | 4/2 | 35 |
| 06-18-2021 | 2016 SYCAMORE DRIVE, WINTER PARK FL 32789 | $325,000 | $251 | $324,900 | 1,290 | Single Family Residence | 2/1 | 29 |
| 06-18-2021 | 5350 N LAKE BURKETT LANE, WINTER PARK FL 32792 | $330,000 | $200 | $330,000 | 1,647 | Single Family Residence | 3/3 | 58 |
| 06-18-2021 | 2013 NOTTINGHAM DRIVE, WINTER PARK FL 32792 | $350,000 | $243 | $330,000 | 1,438 | Single Family Residence | 3/2 | 37 |
| 06-18-2021 | 801 ELLENDALE DRIVE, WINTER PARK FL 32792 | $350,500 | $231 | $349,500 | 1,516 | Single Family Residence | 3/2 | 25 |
| 06-18-2021 | 689 BRECHIN DRIVE, WINTER PARK FL 32792 | $425,000 | $239 | $424,000 | 1,772 | Single Family Residence | 3/2 | 36 |
| 06-18-2021 | 1411 HARMON AVENUE, WINTER PARK FL 32789 | $510,000 | $266 | $479,900 | 1,913 | Townhouse | 3/3 | 36 |
| 06-17-2021 | 7757 FERNBROOK WAY, WINTER PARK FL 32792 | $240,000 | $180 | $235,000 | 1,332 | Townhouse | 3/3 | 112 |
| 06-17-2021 | 423 WARRENTON ROAD # 423, WINTER PARK FL 32792 | $220,000 | $189 | $239,000 | 1,163 | Condominium | 2/2 | 42 |
| 06-17-2021 | 2032 HARMON AVENUE, WINTER PARK FL 32789 | $330,000 | $241 | $339,900 | 1,366 | Single Family Residence | 2/3 | 36 |
| 06-17-2021 | 1503 MICHIGAN AVENUE, WINTER PARK FL 32789 | $373,000 | $250 | $399,000 | 1,488 | Duplex | / | 44 |
| 06-17-2021 | 1385 SAWGRASS COURT, WINTER PARK FL 32792 | $475,000 | $236 | $495,000 | 2,011 | Single Family Residence | 3/2 | 94 |
| 06-17-2021 | 1610 PALM AVENUE, WINTER PARK FL 32789 | $660,000 | $280 | $695,000 | 2,352 | Single Family Residence | 3/3 | 66 |
| 06-17-2021 | 141 SCOTTSDALE SQUARE # 141, WINTER PARK FL 32792 | $75,000 | $125 | $75,000 | 600 | Condominium | /1 | 32 |
| 06-16-2021 | 1821 BLUE RIDGE ROAD, WINTER PARK FL 32789 | $1,800,000 | $497 | $1,800,000 | 3,619 | Single Family Residence | 5/5 | 29 |
| 06-16-2021 | 5237 N ORANGE AVENUE, WINTER PARK FL 32792 | $250,000 | $151 | $259,000 | 1,652 | Single Family Residence | 3/1 | 70 |
| 06-16-2021 | 625 COUNTRY CLUB DRIVE, WINTER PARK FL 32789 | $285,000 | $295,000 | / | 431 | |||
| 06-16-2021 | 595 HUNTINGTON AVENUE # 4, WINTER PARK FL 32789 | $511,500 | $262 | $525,000 | 1,951 | Townhouse | 3/3 | 73 |
| 06-16-2021 | 2117 WHITEHALL DRIVE, WINTER PARK FL 32792 | $595,000 | $327 | $595,000 | 1,816 | Single Family Residence | 4/3 | 35 |
| 06-15-2021 | 865 W CANTON AVENUE, WINTER PARK FL 32789 | $985,000 | $351 | $1,000,000 | 2,803 | Single Family Residence | 4/3 | 99 |
| 06-15-2021 | 161 CORTLAND AVENUE, WINTER PARK FL 32789 | $1,850,000 | $513 | $1,600,000 | 3,603 | Single Family Residence | 4/5 | 71 |
| 06-15-2021 | 5647 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $275,000 | $209 | $265,000 | 1,310 | Single Family Residence | 3/2 | 32 |
| 06-15-2021 | 609 CARVELL DRIVE, WINTER PARK FL 32792 | $310,000 | $191 | $320,000 | 1,622 | Single Family Residence | 3/2 | 27 |
| 06-15-2021 | 7058 CITRUS POINT COURT, WINTER PARK FL 32792 | $330,000 | $187 | $330,000 | 1,759 | Single Family Residence | 3/2 | 62 |
| 06-15-2021 | 1987 BISCAYNE DRIVE, WINTER PARK FL 32789 | $332,500 | $226 | $330,000 | 1,469 | Single Family Residence | 3/3 | 42 |
| 06-14-2021 | 186 SCOTTSDALE SQUARE # 186, WINTER PARK FL 32792 | $104,995 | $102 | $104,995 | 1,020 | Condominium | 2/2 | 210 |
| 06-14-2021 | 1807 BARKER DRIVE, WINTER PARK FL 32789 | $1,189,000 | $312 | $1,189,000 | 3,804 | Single Family Residence | 5/3 | 168 |
| 06-14-2021 | 244 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $140,000 | $146 | $145,000 | 953 | Condominium | 2/2 | 48 |
| 06-14-2021 | 200 SAINT ANDREWS BOULEVARD # 2212, WINTER PARK FL | $162,500 | $133 | $149,900 | 1,219 | Condominium | 2/2 | 54 |
| 06-14-2021 | $250,000 | $249 | $250,000 | 1,004 | Single Family Residence | 2/1 | 31 | |
| 06-14-2021 | 1712 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $450,000 | $236 | $479,000 | 1,899 | Single Family Residence | 4/2 | 111 |
| 06-14-2021 | 1323 HEAVENLY COVE, WINTER PARK FL 32792 | $655,000 | $246 | $700,000 | 2,654 | Single Family Residence | 4/3 | 46 |
| 06-14-2021 | 7651 UNIVERSITY BOULEVARD, WINTER PARK FL 32792 | $749,000 | $532 | $749,000 | 1,406 | Retail | / | 874 |
| 06-11-2021 | 1236 VIA DEL MAR, WINTER PARK FL 32789 | $1,050,000 | $459 | $1,050,000 | 2,285 | Single Family Residence | 3/3 | 42 |
| 06-11-2021 | 1551 HARRIS CIRCLE, WINTER PARK FL 32789 | $1,235,000 | $374 | $1,275,000 | 3,300 | Single Family Residence | 4/3 | 38 |
| 06-11-2021 | 2393 ANTILLES DRIVE, WINTER PARK FL 32792 | $220,000 | $171 | $225,000 | 1,284 | Townhouse | 3/2 | 60 |
| 06-11-2021 | 125 S INTERLACHEN AVENUE # 5, WINTER PARK FL 32789 | $2,225,000 | $685 | $2,250,000 | 3,244 | Townhouse | 3/5 | 85 |
| 06-11-2021 | 7525 HULL STREET, WINTER PARK FL 32792 | $275,000 | $184 | $275,000 | 1,489 | Single Family Residence | 3/2 | 31 |
| 06-11-2021 | 1063 LUNDY COURT, WINTER PARK FL 32792 | $330,000 | $203 | $325,000 | 1,619 | Single Family Residence | 4/2 | 73 |
| 06-11-2021 | 2724 LION HEART ROAD, WINTER PARK FL 32792 | $390,000 | $245 | $400,000 | 1,587 | Single Family Residence | 4/2 | 37 |
| 06-11-2021 | 2849 NORTHWOOD BOULEVARD, WINTER PARK FL 32789 | $536,000 | $291 | $499,900 | 1,840 | Single Family Residence | 3/2 | 51 |
| 06-11-2021 | 1780 VIA PALERMO, WINTER PARK FL 32789 | $862,500 | $234 | $884,900 | 3,677 | Single Family Residence | 5/5 | 149 |
| 06-10-2021 | 3224 OAK LAWN PLACE # 209, WINTER PARK FL 32792 | $140,000 | $121 | $149,900 | 1,151 | Condominium | 3/3 | 64 |
| 06-10-2021 | 196 SANDLEWOOD TRAIL # 5, WINTER PARK FL 32789 | $175,000 | $154 | $189,900 | 1,133 | Townhouse | 2/3 | 64 |
| 06-10-2021 | 2640 N LAKEMONT AVENUE, WINTER PARK FL 32792 | $375,000 | $183 | $379,000 | 2,048 | Single Family Residence | 3/2 | 84 |
| 06-09-2021 | 1470 PLACE PICARDY, WINTER PARK FL 32789 | $1,525,000 | $360 | $1,600,000 | 4,227 | Single Family Residence | 5/6 | 62 |
| 06-09-2021 | 727 DENSMORE DRIVE, WINTER PARK FL 32792 | $260,000 | $247 | $289,900 | 1,050 | Single Family Residence | 2/2 | 41 |
| 06-09-2021 | 1541 ONECO AVENUE, WINTER PARK FL 32789 | $499,900 | $278 | $499,900 | 1,796 | Single Family Residence | 3/2 | 17 |
| 06-09-2021 | 461 FAIRFAX AVENUE, WINTER PARK FL 32789 | $672,400 | $324 | $675,000 | 2,069 | Townhouse | 2/3 | 192 |
| 06-08-2021 | 3341 COLEUS COURT, WINTER PARK FL 32792 | $306,000 | $187 | $294,900 | 1,630 | Single Family Residence | 3/2 | 36 |
| 06-08-2021 | 1253 INDIANA AVENUE, WINTER PARK FL 32789 | $415,000 | $255 | $425,000 | 1,626 | Townhouse | 3/3 | 55 |
| 06-08-2021 | 1485 WESTCHESTER AVENUE, WINTER PARK FL 32789 | $650,000 | $320 | $634,900 | 2,031 | Single Family Residence | 3/3 | 33 |
| 06-08-2021 | 1441 PLACE VENDOME, WINTER PARK FL 32789 | $750,000 | $226 | $824,900 | 3,305 | Single Family Residence | 4/3 | 70 |
| 06-08-2021 | 1370 SUNSET DRIVE, WINTER PARK FL 32789 | $917,500 | $254 | $935,000 | 3,606 | Single Family Residence | 4/4 | 135 |
| 06-07-2021 | 607 WARRENTON ROAD, WINTER PARK FL 32792 | $235,000 | $172 | $259,000 | 1,365 | Townhouse | 3/2 | 102 |
| 06-07-2021 | 5335 POINSETTA AVENUE, WINTER PARK FL 32792 | $295,000 | $212 | $279,900 | 1,386 | Single Family Residence | 3/2 | 39 |
| 06-07-2021 | 631 DEPUGH STREET, WINTER PARK FL 32789 | $350,000 | $257 | $350,000 | 1,360 | Single Family Residence | 2/1 | 48 |
| 06-07-2021 | 608 WORTHINGTON DRIVE, WINTER PARK FL 32789 | $497,500 | $281 | $449,900 | 1,770 | Single Family Residence | 3/2 | 27 |
| 06-07-2021 | 940 MOSS LANE, WINTER PARK FL 32789 | $845,000 | $261 | $849,000 | 3,233 | Single Family Residence | 4/3 | 76 |
| 06-05-2021 | 1510 GLENCOE ROAD, WINTER PARK FL 32789 | $825,000 | $315 | $825,000 | 2,613 | Single Family Residence | 4/4 | 6 |
| 06-04-2021 | 228 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $141,000 | $147 | $141,000 | 953 | 2/2 | 5 | |
| 06-04-2021 | 215 SANDLEWOOD TRAIL # 7, WINTER PARK FL 32789 | $200,000 | $208 | $205,000 | 960 | Townhouse | 2/3 | 106 |
| 06-04-2021 | 1602 ALABAMA DRIVE, WINTER PARK FL 32789 | $2,050,000 | $756 | $2,100,000 | 2,709 | Condominium | 3/4 | 106 |
| 06-04-2021 | 3628 DATURA COURT, WINTER PARK FL 32792 | $215,000 | $114 | $233,000 | 1,872 | Single Family Residence | 4/2 | 116 |
| 06-04-2021 | 1780 WALNUT AVENUE, WINTER PARK FL 32789 | $642,500 | $312 | $624,900 | 2,054 | Single Family Residence | 3/3 | 38 |
| 06-04-2021 | 393 SYLVAN DRIVE, WINTER PARK FL 32789 | $632,000 | $355 | $629,000 | 1,776 | Single Family Residence | 3/3 | 31 |
| 06-04-2021 | 1413.5 MILLER AVENUE, WINTER PARK FL 32789 | $640,000 | $412 | $649,000 | 1,551 | Single Family Residence | 3/3 | 36 |
| 06-04-2021 | 2600 VENETIAN WAY, WINTER PARK FL 32789 | $669,000 | $489 | $699,000 | 1,368 | Single Family Residence | 3/2 | 93 |
| 06-03-2021 | 3236 OAK LAWN PLACE # 206, WINTER PARK FL 32792 | $152,500 | $147 | $165,000 | 1,031 | Condominium | 2/3 | 40 |
| 06-03-2021 | 2501 SALISBURY BOULEVARD, WINTER PARK FL 32789 | $325,000 | $257 | $329,000 | 1,262 | Single Family Residence | 3/2 | 60 |
| 06-03-2021 | 1914 ASTER DRIVE, WINTER PARK FL 32792 | $345,000 | $209 | $339,900 | 1,645 | Single Family Residence | 3/2 | 71 |
| 06-03-2021 | 1051 N KENTUCKY AVENUE, WINTER PARK FL 32789 | $685,000 | $414 | $695,000 | 1,652 | Townhouse | 3/3 | 36 |
| 06-02-2021 | 1048 LUNDY COURT, WINTER PARK FL 32792 | $400,000 | $144 | $400,000 | 2,762 | Single Family Residence | 4/3 | 85 |
| 06-02-2021 | 624 SELKIRK DRIVE, WINTER PARK FL 32792 | $600,000 | $290 | $549,900 | 2,062 | Single Family Residence | 4/3 | 42 |
| 06-01-2021 | 7344 SWALLOW RUN # 7344, WINTER PARK FL 32792 | $107,000 | $133 | $112,500 | 802 | Condominium | 2/2 | 86 |
| 06-01-2021 | 1762 ELIZABETHS WALK, WINTER PARK FL 32789 | $1,200,000 | $317 | $1,250,000 | 3,775 | Single Family Residence | 4/4 | 105 |
| 06-01-2021 | 3651 N GOLDENROD ROAD # C110, WINTER PARK FL 32792 | $127,000 | $151 | $129,900 | 840 | Condominium | 2/2 | 35 |
| 06-01-2021 | 1713 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $235,000 | $160 | $235,000 | 1,460 | Townhouse | 3/2 | 54 |
| 06-01-2021 | 410 KILLARNEY BAY COURT # 1, WINTER PARK FL 32789 | $310,000 | $267 | $294,900 | 1,160 | Condominium | 2/2 | 65 |
| 06-01-2021 | 1814 MONDRIAN CIRCLE, WINTER PARK FL 32789 | $675,000 | $280 | $675,000 | 2,407 | Townhouse | 3/4 | 107 |
| 05-28-2021 | 3051 AARON BURR AVENUE # 8, WINTER PARK FL 32792 | $114,000 | $110 | $114,900 | 1,035 | Condominium | 2/2 | 79 |
| 05-28-2021 | 130 SCOTTSDALE SQUARE # 130, WINTER PARK FL 32792 | $100,000 | $98 | $115,000 | 1,020 | Condominium | 2/2 | 77 |
| 05-28-2021 | 1813 HARLAND PARK DRIVE, WINTER PARK FL 32789 | $1,160,000 | $326 | $1,160,000 | 3,551 | Single Family Residence | 4/4 | 89 |
| 05-28-2021 | 1730 GREENWICH AVENUE, WINTER PARK FL 32789 | $1,600,000 | $346 | $1,625,000 | 4,611 | Single Family Residence | 4/5 | 268 |
| 05-28-2021 | 7028 BETTY STREET, WINTER PARK FL 32792 | $338,000 | $183 | $349,900 | 1,844 | Single Family Residence | 3/2 | 59 |
| 05-28-2021 | 2217 SUSSEX ROAD, WINTER PARK FL 32792 | $415,000 | $231 | $415,000 | 1,792 | Single Family Residence | 4/2 | 30 |
| 05-28-2021 | 250 CAROLINA AVENUE # 403, WINTER PARK FL 32789 | $439,000 | $336 | $439,000 | 1,304 | Condominium | 2/2 | 36 |
| 05-28-2021 | 4985 N HIBISCUS AVENUE, WINTER PARK FL 32792 | $550,000 | $192 | $550,000 | 2,862 | Mixed Use | / | 37 |
| 05-28-2021 | 1500 CAVENDISH ROAD, WINTER PARK FL 32789 | $730,000 | $296 | $749,000 | 2,463 | Single Family Residence | 4/3 | 59 |
| 05-27-2021 | 2708 WRIGHT AVENUE, WINTER PARK FL 32789 | $1,049,000 | $325 | $1,049,000 | 3,226 | Single Family Residence | 4/4 | 106 |
| 05-27-2021 | 2629 ALOMA AVENUE, WINTER PARK FL 32792 | $182,000 | $176 | $182,000 | 1,032 | 3/2 | 9 | |
| 05-27-2021 | 7760 FERNBROOK WAY, WINTER PARK FL 32792 | $245,000 | $183 | $249,900 | 1,332 | Townhouse | 3/2 | 58 |
| 05-27-2021 | 5067 TANGERINE AVENUE, WINTER PARK FL 32792 | $289,500 | $188 | $289,500 | 1,534 | 3/2 | 1 | |
| 05-27-2021 | 2773 CADY WAY, WINTER PARK FL 32792 | $400,000 | $270 | $394,900 | 1,478 | Single Family Residence | 3/2 | 24 |
| 05-27-2021 | 1051 ARAGON AVENUE, WINTER PARK FL 32789 | $397,000 | $237 | $399,000 | 1,669 | Condominium | 3/3 | 1 |
| 05-26-2021 | 200 SAINT ANDREWS BOULEVARD # 310, WINTER PARK FL | $157,000 | $184 | $150,000 | 850 | Condominium | 1/1 | 21 |
| 05-26-2021 | 2891 WILD GINGER COURT, WINTER PARK FL 32792 | $660,000 | $173 | $699,500 | 3,815 | Single Family Residence | 4/5 | 43 |
| 05-26-2021 | 1820 SHILOH LANE, WINTER PARK FL 32789 | $775,000 | $375 | $788,000 | 2,064 | Single Family Residence | 4/2 | 50 |
| 05-26-2021 | 2180 FORREST ROAD, WINTER PARK FL 32789 | $825,000 | $316 | $799,000 | 2,605 | Single Family Residence | 4/3 | 38 |
| 05-25-2021 | 3651 N GOLDENROD ROAD # B210, WINTER PARK FL 32792 | $125,000 | $148 | $125,000 | 840 | Condominium | 2/2 | 65 |
| 05-25-2021 | 1250 S DENNING DRIVE # 214, WINTER PARK FL 32789 | $165,000 | $181 | $165,000 | 908 | Condominium | 2/2 | 16 |
| 05-25-2021 | 1250 S DENNING DRIVE # 112, WINTER PARK FL 32789 | $195,000 | $214 | $195,000 | 908 | Condominium | 2/2 | 36 |
| 05-25-2021 | 541 COUNTRY CLUB DRIVE, WINTER PARK FL 32789 | $215,000 | $225,000 | / | 400 | |||
| 05-25-2021 | 507 S LAKEMONT AVENUE, WINTER PARK FL 32792 | $575,000 | $271 | $589,000 | 2,121 | Single Family Residence | 4/2 | 76 |
| 05-24-2021 | 3217 DWARF PINE AVENUE, WINTER PARK FL 32792 | $254,000 | $181 | $248,900 | 1,402 | Single Family Residence | 3/2 | 41 |
| 05-24-2021 | 5427 PEACO PLACE, WINTER PARK FL 32792 | $349,900 | $177 | $349,000 | 1,974 | Duplex | / | 30 |
| 05-24-2021 | 7305 HOUSTON AVENUE W, WINTER PARK FL 32792 | $357,400 | $155 | $359,900 | 2,300 | Single Family Residence | 4/3 | 41 |
| 05-24-2021 | 5319 PINE LILY CIRCLE, WINTER PARK FL 32792 | $500,000 | $220 | $489,000 | 2,265 | Single Family Residence | 4/2 | 33 |
| 05-24-2021 | 1560 GROVE TERRACE, WINTER PARK FL 32789 | $657,000 | $401 | $659,000 | 1,638 | Single Family Residence | 3/2 | 81 |
| 05-21-2021 | 1671 CHESTNUT AVENUE, WINTER PARK FL 32789 | $1,000,000 | $314 | $1,019,000 | 3,178 | Single Family Residence | 5/5 | 120 |
| 05-21-2021 | 1780 OAKHURST AVENUE, WINTER PARK FL 32789 | $1,060,000 | $362 | $1,150,000 | 2,925 | Single Family Residence | 4/4 | 64 |
| 05-21-2021 | 200 ST ANDREWS BOULEVARD # 702, WINTER PARK FL 327 | $128,000 | $176 | $129,900 | 727 | Condominium | 1/1 | 244 |
| 05-21-2021 | 200 SAINT ANDREWS BOULEVARD # 3202, WINTER PARK FL | $158,000 | $129 | $169,900 | 1,219 | Condominium | 2/2 | 24 |
| 05-21-2021 | 1508 WINTER GREEN BOULEVARD, WINTER PARK FL 32792 | $220,000 | $133 | $229,900 | 1,652 | Townhouse | 3/3 | 78 |
| 05-21-2021 | 1554 MINNESOTA AVENUE, WINTER PARK FL 32789 | $213,000 | $282 | $247,850 | 754 | Single Family Residence | 2/1 | 49 |
| 05-21-2021 | 7021 CITRUS POINT COURT, WINTER PARK FL 32792 | $295,000 | $195 | $289,900 | 1,509 | Single Family Residence | 3/2 | 29 |
| 05-21-2021 | 2212 MAPLETON COURT, WINTER PARK FL 32792 | $298,000 | $226 | $289,990 | 1,318 | Single Family Residence | 3/2 | 30 |
| 05-21-2021 | 180 S KNOWLES AVENUE # 8, WINTER PARK FL 32789 | $380,000 | $408 | $350,000 | 930 | Office | / | 58 |
| 05-20-2021 | 7309 FOREST HILL COURT # 227, WINTER PARK FL 32792 | $160,000 | $155 | $160,000 | 1,031 | Condominium | 2/3 | 18 |
| 05-20-2021 | 2400 VENETIAN WAY, WINTER PARK FL 32789 | $1,950,000 | $454 | $2,150,000 | 4,293 | Single Family Residence | 5/5 | 316 |
| 05-20-2021 | 3250 CROWN JEWEL, WINTER PARK FL 32792 | $280,000 | $194 | $279,900 | 1,442 | Townhouse | 3/3 | 45 |
| 05-20-2021 | 5119 ORANGE AVENUE, WINTER PARK FL 32792 | $300,000 | $204 | $295,000 | 1,465 | Single Family Residence | 3/2 | 61 |
| 05-20-2021 | 1759 MICHIGAN AVENUE, WINTER PARK FL 32789 | $299,900 | $258 | $299,900 | 1,158 | Single Family Residence | 3/2 | 35 |
| 05-20-2021 | 3231 LOWNDES DRIVE, WINTER PARK FL 32792 | $320,000 | $182 | $349,000 | 1,749 | Single Family Residence | 4/2 | 154 |
| 05-20-2021 | 1503 INDIANA AVENUE, WINTER PARK FL 32789 | $507,000 | $275 | $512,000 | 1,843 | Townhouse | 3/3 | 65 |
| 05-20-2021 | 1441 NORFOLK AVENUE, WINTER PARK FL 32789 | $595,000 | $302 | $580,000 | 1,967 | Single Family Residence | 3/2 | 22 |
| 05-20-2021 | 2383 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $850,000 | $225 | $850,000 | 3,768 | Single Family Residence | 4/4 | 43 |
| 05-19-2021 | 270 SCOTTSDALE SQUARE # 270, WINTER PARK FL 32792 | $115,000 | $88 | $129,995 | 1,300 | Condominium | 3/2 | 674 |
| 05-19-2021 | 200 SAINT ANDREWS BOULEVARD # 3105, WINTER PARK FL | $160,000 | $131 | $170,000 | 1,219 | Condominium | 2/2 | 37 |
| 05-19-2021 | 2500 LEE ROAD # 220, WINTER PARK FL 32789 | $174,000 | $204 | $175,000 | 851 | Condominium | 2/1 | 17 |
| 05-19-2021 | 1925 HOUNDSLAKE DR, WINTER PARK FL 32792 | $330,000 | $197 | $330,000 | 1,671 | Single Family Residence | 3/2 | 35 |
| 05-19-2021 | 1420 MILLER AVENUE, WINTER PARK FL 32789 | $550,000 | $293 | $550,000 | 1,874 | Single Family Residence | 3/3 | 233 |
| 05-18-2021 | 453 FLETCHER PLACE, WINTER PARK FL 32789 | $1,030,000 | $275 | $1,050,000 | 3,737 | Single Family Residence | 5/4 | 178 |
| 05-18-2021 | 1602 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $1,077,000 | $384 | $1,099,000 | 2,804 | Single Family Residence | 4/4 | 78 |
| 05-18-2021 | 2917 ANTIQUE OAKS CIRCLE # 19, WINTER PARK FL 3279 | $169,900 | $166 | $169,900 | 1,018 | Condominium | 2/2 | 61 |
| 05-18-2021 | 900 N DENNING DRIVE, WINTER PARK FL 32789 | $204,310 | $124 | $204,310 | 1,642 | Single Family Residence | 4/3 | 1 |
| 05-18-2021 | 5061 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $355,000 | $286 | $349,500 | 1,240 | Single Family Residence | 3/2 | 48 |
| 05-18-2021 | 2767 BOWER ROAD, WINTER PARK FL 32792 | $470,000 | $277 | $459,900 | 1,692 | Single Family Residence | 3/2 | 68 |
| 05-18-2021 | 931 BUNGALOW AVENUE, WINTER PARK FL 32789 | $850,000 | $343 | $859,000 | 2,472 | Single Family Residence | 4/4 | 70 |
| 05-17-2021 | 181 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $103,000 | $151 | $107,000 | 678 | Condominium | 1/1 | 41 |
| 05-17-2021 | 209 LEWFIELD CIRCLE # 209, WINTER PARK FL 32792 | $114,500 | $123 | $109,900 | 927 | Condominium | 2/2 | 85 |
| 05-17-2021 | 3137 THISTLEHILL DRIVE, WINTER PARK FL 32792 | $265,000 | $220 | $280,000 | 1,200 | Single Family Residence | 3/2 | 18 |
| 05-17-2021 | 2957 ROUEN AVENUE, WINTER PARK FL 32789 | $285,000 | $269 | $295,000 | 1,056 | Single Family Residence | 3/2 | 254 |
| 05-17-2021 | 5619 GARDEN GROVE CIRCLE, WINTER PARK FL 32792 | $325,000 | $181 | $315,000 | 1,786 | Single Family Residence | 4/2 | 26 |
| 05-17-2021 | 2265 KING JOHNS COURT, WINTER PARK FL 32792 | $415,000 | $207 | $399,000 | 2,002 | Single Family Residence | 3/2 | 40 |
| 05-17-2021 | 5111 LAKE HOWELL ROAD, WINTER PARK FL 32792 | $407,000 | $251 | $399,900 | 1,620 | Single Family Residence | 4/3 | 36 |
| 05-17-2021 | 633 DUNRAVEN DRIVE, WINTER PARK FL 32792 | $407,500 | $214 | $425,000 | 1,896 | Single Family Residence | 3/2 | 39 |
| 05-17-2021 | 1365 GROVE TERRACE, WINTER PARK FL 32789 | $986,000 | $312 | $985,000 | 3,159 | Single Family Residence | 4/3 | 81 |
| 05-14-2021 | 315 E NEW ENGLAND AVENUE # 17, WINTER PARK FL 3278 | $1,025,000 | $677 | $1,025,000 | 1,514 | Condominium | 2/2 | 43 |
| 05-14-2021 | 2388 WINTER PARK ROAD, WINTER PARK FL 32789 | $1,250,000 | $411 | $1,250,000 | 3,034 | Single Family Residence | 4/6 | 1 |
| 05-14-2021 | 3651 N GOLDENROD ROAD # 101, WINTER PARK FL 32792 | $125,000 | $132 | $129,900 | 940 | Condominium | 2/2 | 53 |
| 05-14-2021 | 7465 CANFORD COURT # 16, WINTER PARK FL 32792 | $175,000 | $110 | $170,000 | 1,578 | Condominium | 2/3 | 24 |
| 05-14-2021 | 2808 WHISPERING WAY, WINTER PARK FL 32792 | $290,000 | $228 | $279,900 | 1,271 | Single Family Residence | 3/2 | 40 |
| 05-14-2021 | 2685 BONGART ROAD, WINTER PARK FL 32792 | $300,000 | $250 | $299,999 | 1,198 | Single Family Residence | 3/2 | 70 |
| 05-14-2021 | 479 HOLT AVENUE, WINTER PARK FL 32789 | $525,000 | $366 | $525,000 | 1,432 | Single Family Residence | 3/2 | 33 |
| 05-14-2021 | 1815 BARKER DRIVE, WINTER PARK FL 32789 | $525,000 | $328 | $525,000 | 1,600 | Single Family Residence | 4/2 | 1 |
| 05-14-2021 | 791 DOUGLAS AVENUE, WINTER PARK FL 32789 | $639,683 | $382 | $595,900 | 1,672 | Single Family Residence | 3/3 | 898 |
| 05-14-2021 | 1420 CHAPMAN CIRCLE, WINTER PARK FL 32789 | $860,000 | $259 | $875,000 | 3,313 | Single Family Residence | 4/4 | 131 |
| 05-14-2021 | 1784 MONDRIAN CIRCLE # 14, WINTER PARK FL 32789 | $850,000 | $363 | $875,000 | 2,341 | Townhouse | 3/4 | 76 |
| 05-13-2021 | 1711 ONECO AVENUE, WINTER PARK FL 32789 | $1,120,000 | $346 | $1,100,000 | 3,233 | Single Family Residence | 5/4 | 49 |
| 05-13-2021 | 275 STIRLING AVENUE, WINTER PARK FL 32789 | $2,080,000 | $682 | $2,300,000 | 3,046 | Single Family Residence | 3/3 | 27 |
| 05-13-2021 | 3354 COLEUS COURT, WINTER PARK FL 32792 | $325,000 | $157 | $325,000 | 2,068 | Single Family Residence | 4/3 | 77 |
| 05-13-2021 | 1840 MAYWOOD ROAD, WINTER PARK FL 32792 | $336,900 | $214 | $330,000 | 1,570 | Single Family Residence | 4/2 | 36 |
| 05-13-2021 | 7588 GLENMOOR LANE, WINTER PARK FL 32792 | $355,000 | $177 | $370,000 | 1,998 | Single Family Residence | 4/2 | 35 |
| 05-13-2021 | 667 DUNBLANE DRIVE, WINTER PARK FL 32792 | $550,000 | $272 | $545,000 | 2,017 | Single Family Residence | 3/2 | 33 |
| 05-13-2021 | 1805 HARLAND PARK DRIVE, WINTER PARK FL 32789 | $985,000 | $322 | $975,000 | 3,052 | Single Family Residence | 4/4 | 42 |
| 05-13-2021 | 292 SCOTTSDALE SQUARE, WINTER PARK FL 32792 | $98,000 | $90 | $98,000 | 1,085 | Condominium | 2/2 | 22 |
| 05-13-2021 | 166 LEWFIELD CIR # 166, WINTER PARK FL 32792 | $96,000 | $141 | $99,900 | 678 | Condominium | 1/1 | 42 |
| 05-12-2021 | 315 E NEW ENGLAND AVENUE # 15, WINTER PARK FL 3278 | $1,300,000 | $463 | $1,399,000 | 2,806 | Condominium | 3/4 | 181 |
| 05-12-2021 | 2511 WINDWARD WAY, WINTER PARK FL 32792 | $175,000 | $194 | $172,500 | 898 | Townhouse | 2/1 | 34 |
| 05-12-2021 | 1001 VIA TUSCANY OAKS WAY, WINTER PARK FL 32789 | $2,195,000 | $406 | $2,195,000 | 5,395 | Single Family Residence | 4/6 | 44 |
| 05-12-2021 | 315 E NEW ENGLAND AVENUE # 31, WINTER PARK FL 3278 | $2,375,000 | $659 | $2,450,000 | 3,603 | Condominium | 4/5 | 98 |
| 05-12-2021 | 1500 BROAD WING LANE, WINTER PARK FL 32792 | $359,620 | $151 | $359,620 | 2,376 | 3/3 | 7 | |
| 05-12-2021 | 2218 FOSGATE DRIVE, WINTER PARK FL 32789 | $570,000 | $162 | $625,000 | 3,502 | Single Family Residence | 4/4 | 62 |
| 05-12-2021 | 7809 GEORGEANN STREET, WINTER PARK FL 32792 | $660,000 | $308 | $679,000 | 2,138 | Single Family Residence | 3/2 | 41 |
| 05-12-2021 | 126 LEWFIELD CIRCLE # 126, WINTER PARK FL 32792 | $99,900 | $147 | $99,900 | 678 | Condominium | 1/1 | 50 |
| 05-11-2021 | 2813 NORTHWOOD BOULEVARD, WINTER PARK FL 32789 | $1,045,000 | $303 | $1,099,999 | 3,443 | Single Family Residence | 4/4 | 251 |
| 05-11-2021 | $272,000 | $170 | $295,000 | 1,596 | Single Family Residence | 4/2 | 70 | |
| 05-11-2021 | 1735 CHESTNUT AVENUE, WINTER PARK FL 32789 | $500,000 | $355 | $499,000 | 1,405 | Single Family Residence | 3/2 | 38 |
| 05-10-2021 | 1637 MAGNOLIA AVENUE, WINTER PARK FL 32789 | $1,425,000 | $394 | $1,399,000 | 3,616 | Single Family Residence | 4/5 | 110 |
| 05-10-2021 | 7708 COUNTRY PLACE # 7, WINTER PARK FL 32792 | $160,000 | $130 | $160,000 | 1,230 | Condominium | 3/2 | 193 |
| 05-10-2021 | 2825 ROXBURY ROAD, WINTER PARK FL 32789 | $265,000 | $210 | $269,000 | 1,261 | Single Family Residence | 2/2 | 110 |
| 05-10-2021 | 102 S INTERLACHEN AVE AVENUE # 207, WINTER PARK FL | $347,000 | $385 | $374,900 | 901 | Condominium | 2/1 | 160 |
| 05-10-2021 | 1861 TAYLOR AVENUE, WINTER PARK FL 32789 | $410,000 | $328 | $425,000 | 1,249 | Single Family Residence | 2/2 | 48 |
| 05-10-2021 | 151 OAKWOOD WAY, WINTER PARK FL 32789 | $650,000 | $409 | $650,000 | 1,586 | Single Family Residence | 3/2 | 6 |
| 05-10-2021 | 1435 INDIANA AVENUE, WINTER PARK FL 32789 | $925,000 | $355 | $949,000 | 2,602 | Single Family Residence | 3/5 | 35 |
| 05-07-2021 | 851 MILES AVENUE # 16, WINTER PARK FL 32789 | $128,000 | $158 | $135,000 | 808 | Condominium | 2/1 | 23 |
| 05-07-2021 | 1850 VIA TUSCANY, WINTER PARK FL 32789 | $1,500,000 | $462 | $1,500,000 | 3,242 | Single Family Residence | 4/5 | 31 |
| 05-07-2021 | 2265 LEE ROAD # 203B, WINTER PARK FL 32789 | $150,000 | $140 | $180,000 | 1,070 | Office | / | 194 |
| 05-07-2021 | 151 N ORLANDO AVENUE # 247, WINTER PARK FL 32789 | $189,000 | $246 | $189,000 | 768 | Condominium | 2/1 | 84 |
| 05-07-2021 | 1811 VIA TUSCANY, WINTER PARK FL 32789 | $2,625,000 | $628 | $2,495,000 | 4,176 | Single Family Residence | 4/5 | 68 |
| 05-07-2021 | 875 W LYMAN AVENUE, WINTER PARK FL 32789 | $295,000 | $415 | $295,000 | 710 | Single Family Residence | 2/2 | 50 |
| 05-07-2021 | 7674 GLENMOOR LANE, WINTER PARK FL 32792 | $299,300 | $228 | $300,000 | 1,309 | Single Family Residence | 2/2 | 23 |
| 05-07-2021 | 3873 WATERVIEW LOOP, WINTER PARK FL 32792 | $297,500 | $187 | $313,500 | 1,588 | Single Family Residence | 3/3 | 48 |
| 05-07-2021 | 729 ELLENDALE DRIVE, WINTER PARK FL 32792 | $367,500 | $226 | $359,900 | 1,620 | Single Family Residence | 4/3 | 43 |
| 05-07-2021 | 4053 COOL WATER COURT, WINTER PARK FL 32792 | $415,000 | $215 | $389,900 | 1,930 | Single Family Residence | 3/2 | 31 |
| 05-07-2021 | 8113 LAZY BEAR LANE, WINTER PARK FL 32792 | $435,000 | $191 | $440,000 | 2,267 | Single Family Residence | 4/3 | 120 |
| 05-07-2021 | 1267 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $555,000 | $242 | $534,000 | 2,293 | Single Family Residence | 4/3 | 38 |
| 05-06-2021 | 3392 HAMLET LOOP, WINTER PARK FL 32792 | $281,000 | $201 | $268,900 | 1,397 | Single Family Residence | 3/3 | 24 |
| 05-06-2021 | 8037 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $457,900 | $178 | $479,000 | 2,572 | Single Family Residence | 4/3 | 120 |
| 05-06-2021 | 1617 GOLFSIDE DRIVE, WINTER PARK FL 32792 | $655,000 | $230 | $650,000 | 2,842 | Single Family Residence | 4/4 | 44 |
| 05-05-2021 | 110 LEWFIELD CIRCLE # 110, WINTER PARK FL 32792 | $140,500 | $147 | $140,000 | 953 | Condominium | 2/2 | 36 |
| 05-05-2021 | 2924 ANTIQUE OAKS CIRCLE # 47, WINTER PARK FL 3279 | $140,000 | $126 | $147,500 | 1,105 | Condominium | 2/2 | 23 |
| 05-05-2021 | 2023 VENETIAN WAY, WINTER PARK FL 32789 | $1,625,000 | $488 | $1,700,000 | 3,326 | Single Family Residence | 4/4 | 202 |
| 05-05-2021 | 5138 OAK HILL DRIVE, WINTER PARK FL 32792 | $251,000 | $255 | $250,000 | 981 | Single Family Residence | 3/2 | 35 |
| 05-05-2021 | 1813 IVY LANE, WINTER PARK FL 32792 | $290,000 | $216 | $295,000 | 1,341 | Single Family Residence | 3/2 | 114 |
| 05-04-2021 | 511 FAIRFAX AVENUE, WINTER PARK FL 32789 | $1,150,000 | $332 | $1,225,000 | 3,463 | Single Family Residence | 4/3 | 47 |
| 05-04-2021 | 1840 VIA GENOA, WINTER PARK FL 32789 | $1,860,000 | $451 | $1,749,000 | 4,120 | Single Family Residence | 4/5 | 33 |
| 05-04-2021 | 2500 BARBADOS DRIVE, WINTER PARK FL 32792 | $233,600 | $181 | $219,900 | 1,284 | Townhouse | 3/2 | 26 |
| 05-04-2021 | 21 KILLARNEY DRIVE, WINTER PARK FL 32789 | $2,235,000 | $440 | $2,495,000 | 5,077 | Single Family Residence | 5/5 | 77 |
| 05-04-2021 | 2894 WILD GINGER COURT, WINTER PARK FL 32792 | $735,000 | $181 | $779,500 | 4,042 | Single Family Residence | 4/4 | 126 |
| 05-03-2021 | 607 GRENADINE COURT # 607, WINTER PARK FL 32792 | $150,000 | $144 | $150,000 | 1,037 | Condominium | 2/2 | 50 |
| 05-03-2021 | 1520 HIGHLAND ROAD, WINTER PARK FL 32789 | $1,900,000 | $402 | $1,995,000 | 4,720 | Single Family Residence | 5/7 | 88 |
| 05-03-2021 | 2645 EXUMA WAY, WINTER PARK FL 32792 | $192,500 | $188 | $205,000 | 1,020 | Townhouse | 2/2 | 87 |
| 05-03-2021 | 7896 PLEASANT PINE CIRCLE, WINTER PARK FL 32792 | $415,000 | $225 | $395,000 | 1,843 | Single Family Residence | 4/2 | 55 |
| 04-30-2021 | 1970 LAUREL ROAD, WINTER PARK FL 32789 | $1,210,000 | $351 | $1,245,000 | 3,440 | Single Family Residence | 4/4 | 225 |
| 04-30-2021 | 2500 LEE ROAD # 135, WINTER PARK FL 32789 | $128,000 | $150 | $131,500 | 851 | Condominium | 2/1 | 62 |
| 04-30-2021 | 700 MELROSE AVENUE # 22, WINTER PARK FL 32789 | $170,000 | $158 | $190,000 | 1,074 | Condominium | 2/2 | 255 |
| 04-30-2021 | 6900 ALOMA AVENUE # 6900, WINTER PARK FL 32792 | $310,000 | $145 | $335,000 | 2,128 | Office | / | 197 |
| 04-30-2021 | 2107 BROOKVIEW DRIVE, WINTER PARK FL 32792 | $353,000 | $253 | $353,000 | 1,392 | Single Family Residence | 3/2 | 1 |
| 04-30-2021 | 8420 ADMIRAL POINT, WINTER PARK FL 32792 | $340,000 | $240 | $360,000 | 1,414 | Single Family Residence | 3/2 | 44 |
| 04-30-2021 | 707 HALIFAX AVENUE, WINTER PARK FL 32792 | $375,000 | $240 | $365,000 | 1,562 | Single Family Residence | 3/2 | 43 |
| 04-30-2021 | 2041 SUSSEX ROAD, WINTER PARK FL 32792 | $407,000 | $203 | $397,000 | 2,000 | Single Family Residence | 4/2 | 29 |
| 04-30-2021 | 350 CAROLINA AVENUE # 202, WINTER PARK FL 32789 | $459,000 | $301 | $459,000 | 1,523 | Condominium | 2/2 | 36 |
| 04-30-2021 | 1562 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $547,500 | $311 | $534,500 | 1,760 | Single Family Residence | 4/3 | 29 |
| 04-30-2021 | 972 BUNGALOW AVENUE, WINTER PARK FL 32789 | $580,000 | $329 | $574,900 | 1,759 | Single Family Residence | 3/2 | 39 |
| 04-30-2021 | 1469 MILLER AVENUE, WINTER PARK FL 32789 | $792,500 | $259 | $824,900 | 3,050 | Single Family Residence | 4/4 | 267 |
| 04-30-2021 | 311 E MORSE BOULEVARD # 1, WINTER PARK FL 32789 | $910,000 | $463 | $939,900 | 1,964 | Condominium | 2/2 | 282 |
| 04-29-2021 | 870 MAYFIELD AVENUE, WINTER PARK FL 32789 | $2,275,000 | $392 | $2,295,000 | 5,797 | Single Family Residence | 6/6 | 64 |
| 04-29-2021 | 1444 AUBURN GREEN LOOP, WINTER PARK FL 32792 | $315,000 | $222 | $315,000 | 1,415 | Single Family Residence | 3/2 | 35 |
| 04-29-2021 | 1909 NATALEN ROAD, WINTER PARK FL 32792 | $439,000 | $236 | $439,000 | 1,855 | Single Family Residence | 4/3 | 66 |
| 04-29-2021 | 345 MERRIE OAKS ROAD, WINTER PARK FL 32792 | $465,000 | $248 | $465,000 | 1,874 | 4/3 | 5 | |
| 04-29-2021 | 1796 MONDRIAN CIRCLE # 20, WINTER PARK FL 32789 | $770,000 | $333 | $775,000 | 2,310 | Townhouse | 3/4 | 22 |
| 04-29-2021 | 972 MAYFIELD AVENUE, WINTER PARK FL 32789 | $950,000 | $329 | $869,000 | 2,882 | Single Family Residence | 4/4 | 43 |
| 04-28-2021 | 1756 CLEMATIS LANE, WINTER PARK FL 32792 | $315,000 | $158 | $315,000 | 1,983 | Single Family Residence | 4/3 | 56 |
| 04-28-2021 | 1635 BERKSHIRE AVENUE, WINTER PARK FL 32789 | $405,000 | $296 | $389,900 | 1,367 | Single Family Residence | 3/3 | 49 |
| 04-28-2021 | 157 SCOTTSDALE SQUARE # 157, WINTER PARK FL 32792 | $59,000 | $57 | $63,500 | 1,020 | Condominium | 2/2 | 27 |
| 04-27-2021 | 3651 N GOLDENROD ROAD # 106, WINTER PARK FL 32792 | $110,000 | $130 | $115,000 | 840 | Condominium | 2/2 | 30 |
| 04-27-2021 | 2006 BENTWOOD DRIVE, WINTER PARK FL 32792 | $345,000 | $191 | $330,000 | 1,798 | Single Family Residence | 3/2 | 54 |
| 04-27-2021 | 767 MCINTYRE AVENUE, WINTER PARK FL 32789 | $500,000 | $551 | $499,000 | 906 | Single Family Residence | 2/1 | 40 |
Listing information has been provided by My Florida Regional MLS DBA Stellar MLS.
IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by My Florida Regional MLS DBA Stellar MLS.
IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by My Florida Regional MLS DBA Stellar MLS.
contact
- Virginia Bellhorn ,
- Watson Realty Corp
- 2100 Alafaya Trl Suite # 100 Oviedo, FL 32765-9488
- vbellhorn@gmail.com
