Winter Park Properties for Sale in Winter Park, FL
67 Matching Listings
Order By: 
$100,000
Winter Park
-13.04% ($15,000) 1 Price Change : Last Change 2 Days Ago
195 Scottsdale Square Unit 195, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 35
$117,786
Winter Park
-5.61% ($7,000) 7 Price Changes : Last Change 6 Days Ago
205 Scottsdale Square Unit 205, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 865
$119,786
Winter Park
-9.79% ($13,000) 2 Price Changes : Last Change 64 Days Ago
171 Scottsdale Square Unit 171, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 1204
$119,786
Winter Park
-9.79% ($13,000) 1 Price Change : Last Change 29 Days Ago
249 Scottsdale Square Unit 249, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 861
$119,900
Winter Park
-7.70% ($10,000) 1 Price Change : Last Change 2 Days Ago
133 Scottsdale Square Unit 133, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 40
$119,999
Winter Park
-14.29% ($20,001) 2 Price Changes : Last Change 2 Days Ago
125 Scottsdale Square Unit 125, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 96
$137,786
Winter Park
-27.40% ($52,000) 5 Price Changes : Last Change 6 Days Ago
172 Scottsdale Square Unit 172, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 861
$142,000
Winter Park
214 Scottsdale Square Unit 214, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 51
$144,900
Winter Park
130 Scottsdale Square Unit 130, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 7
$145,000
Winter Park
178 Scottsdale Square Unit 178, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 102
$149,999
Winter Park
-9.09% ($15,000) 1 Price Change : Last Change 10 Days Ago
238 Scottsdale Square Unit 238, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 102
$152,000
Winter Park
-10.59% ($18,000) 3 Price Changes : Last Change 19 Days Ago
280 Scottsdale Square Unit 280, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 139
$155,786
Winter Park
-6.60% ($11,000) 2 Price Changes : Last Change 29 Days Ago
292 Scottsdale Square Unit 292, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 92
$159,900
Winter Park
204 Scottsdale Square Unit 204, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 131
$162,000
Winter Park
268 Scottsdale Square Unit 268, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 71
$169,000
Winter Park
-5.59% ($10,000) 5 Price Changes : Last Change 2 Days Ago
161 Lewfield Circle Unit 161, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 117
$179,000
Winter Park
$179,900
Winter Park
-4.30% ($8,090) 1 Price Change : Last Change 39 Days Ago
146 Lewfield Circle Unit 146, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 83
$182,500
Winter Park
141 Lewfield Circle Unit 141, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 23
$185,900
Winter Park
-2.11% ($4,000) 1 Price Change : Last Change 2 Days Ago
$197,900
Winter Park
700 Melrose Avenue Unit G, Winter Park, FL 32789
Condominium -
Waterfront Yes
Days Listed: 7
$200,000
Winter Park
229 Lewfield Circle Unit 229, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 20
$209,000
Winter Park
110 Lewfield Circle Unit 110, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 1
$211,900
Winter Park
-5.40% ($12,100) 1 Price Change : Last Change 10 Days Ago
$213,000
Winter Park
-3.18% ($7,000) 1 Price Change : Last Change 2 Days Ago
$215,000
Winter Park
107 Lewfield Circle Unit 107, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 13
$217,000
Winter Park
-4.82% ($11,000) 4 Price Changes : Last Change 2 Days Ago
208 Lewfield Circle Unit 208, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 125
$239,000
Winter Park
-2.81% ($6,900) 1 Price Change : Last Change 41 Days Ago
668 Saint Johns Court Unit S, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 173
$239,900
Winter Park
608 Montego Bay Court Unit S, Winter Park, FL 32792
Condominium -
Waterfront No
Days Listed: 16
$245,000
Winter Park
700 Melrose Avenue Unit K4, Winter Park, FL 32789
Condominium -
Waterfront No
Days Listed: 21
Data feed last updated 04-24-2024 at 6:00 AM
Most Recent Sales - (559) - WINTER PARK PINES as of 2024-04-24
| Sale Date | Address | Sale Price | $/SF | List Price | Sq. Ft. | Type | Bd/Ba | Days Listed |
| 04-22-2024 | 266 N RANGER BOULEVARD | $465,000 | $293 | $485,000 | 1,582 | Single Family Residence | 3/2 | 41 |
| 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 |
| 04-17-2024 | 195 SCOTTSDALE SQUARE UNIT 195 | $92,000 | $153 | $100,000 | 600 | Condominium | 1/1 | 29 |
| 04-17-2024 | 404 BARCLAY DRIVE | $420,000 | $251 | $437,000 | 1,672 | Single Family Residence | 4/2 | 169 |
| 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 |
| 04-10-2024 | 700 MELROSE AVENUE UNIT E 26 | $239,000 | $327 | $239,000 | 730 | Condominium | 1/1 | 55 |
| 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 | |||
| 04-04-2024 | 190 BALFOUR DRIVE UNIT 1 | $345,000 | $281 | $348,000 | 1,225 | Condominium | 2/2 | 84 |
| 03-28-2024 | 2639 CARVELL COURT | $411,000 | $314 | $409,900 | 1,308 | Single Family Residence | 3/2 | 37 |
| 03-28-2024 | 674 DOUGLAS AVENUE | $452,500 | $359 | $465,000 | 1,260 | Single Family Residence | 2/2 | 42 |
| 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 |
| 03-25-2024 | 100 S VIRGINIA AVENUE UNIT 402 | $1,242,802 | $478 | $1,250,000 | 2,599 | Condominium | 3/3 | 55 |
| 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 | 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 |
| 03-13-2024 | 168 SCOTTSDALE SQUARE UNIT 168 | $153,000 | $122 | $172,000 | 1,250 | Condominium | 3/2 | 69 |
| 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 |
| 03-06-2024 | 237 SCOTTSDALE SQ UNIT 237 | $115,000 | $112 | $130,000 | 1,020 | Condominium | 2/2 | 107 |
| 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 |
| 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 |
| 02-28-2024 | 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 |
| 02-27-2024 | 200 S INTERLACHEN AVENUE UNIT 450 | $2,200,000 | $707 | $2,399,000 | 3,110 | Condominium | 3/4 | 118 |
| 02-23-2024 | 341 BECKETT COURT | $485,000 | $313 | $475,000 | 1,548 | Single Family Residence | 3/2 | 51 |
| 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 |
| 02-15-2024 | 700 MELROSE AVENUE UNIT K3 | $265,000 | $246 | $279,999 | 1,074 | Condominium | 2/2 | 98 |
| 02-09-2024 | 220 LEWFIELD CIRCLE | $249,900 | $192 | $249,900 | 1,300 | Condominium | 2/3 | 146 |
| 02-08-2024 | 2906 BANCHORY ROAD | $660,000 | $304 | $674,900 | 2,171 | Single Family Residence | 4/2 | 35 |
| 01-31-2024 | 1695 LEE ROAD UNIT D109 | $140,000 | $219 | $140,000 | 638 | Condominium | 1/1 | 79 |
| 01-31-2024 | 720 W NEW ENGLAND AVENUE | $351,300 | $322 | $399,900 | 1,089 | Single Family Residence | 2/1 | 78 |
| 01-31-2024 | 819 APPALACHEE AVENUE | $412,500 | $237 | $425,000 | 1,738 | Single Family Residence | 4/2 | 43 |
| 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 |
| 01-19-2024 | 722 WARRENTON ROAD | $291,000 | $213 | $290,000 | 1,362 | 1/2 Duplex | 2/2 | 36 |
| 01-19-2024 | 1720 PALM AVENUE | $950,000 | $572 | $949,000 | 1,658 | Single Family Residence | 4/2 | 25 |
| 01-16-2024 | 314 SCOTTSDALE SQUARE UNIT 314 | $118,000 | $108 | $130,000 | 1,085 | Condominium | 2/2 | 40 |
| 01-12-2024 | 1640 ONECO AVENUE | $2,400,000 | $600 | $2,350,000 | 4,000 | Single Family Residence | 5/6 | 57 |
| 01-05-2024 | 344 SCOTTSDALE SQUARE UNIT 344 | $136,000 | $133 | $136,000 | 1,020 | Condominium | 2/2 | 71 |
| 12-19-2023 | 808 DENSMORE DR | $450,000 | $308 | $460,000 | 1,460 | Single Family Residence | 3/2 | 111 |
| 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 |
| 12-15-2023 | 617 MONTEGO BAY CT #617 | $223,000 | $215 | $230,000 | 1,037 | Condominium | 2/2 | 52 |
| 12-15-2023 | 140 E MORSE BLVD #I | $2,200,000 | $960 | $2,399,000 | 2,291 | Condominium | 3/2 | 88 |
| 12-13-2023 | 178 LEWFIELD CIRCLE # 178, WINTER PARK FL 32792 | $169,000 | $249 | $185,000 | 678 | Condominium | 1/1 | 78 |
| 12-11-2023 | 324 SCOTTSDALE SQUARE # 324, WINTER PARK FL 32792 | $130,000 | $127 | $135,000 | 1,020 | Condominium | 2/2 | 42 |
| 11-27-2023 | 620 MONTEGO BAY COURT # 620, WINTER PARK FL 32792 | $255,000 | $227 | $269,000 | 1,120 | Condominium | 2/2 | 53 |
| 11-21-2023 | 100 S VIRGINIA AVENUE UNIT 201 | $1,000,000 | $362 | $1,100,000 | 2,756 | Condominium | 3/3 | 79 |
| 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 |
| 11-15-2023 | 1414 BESSMOR ROAD, WINTER PARK FL 32789 | $430,000 | $412 | $430,000 | 1,043 | Single Family Residence | 3/1 | 27 |
| 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 | 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 | 2734 AMSDEN ROAD, WINTER PARK FL 32792 | $391,000 | $286 | $389,900 | 1,364 | Single Family Residence | 3/2 | 37 |
| 11-10-2023 | 418 GILBERT ROAD, WINTER PARK FL 32792 | $690,000 | $410 | $699,000 | 1,680 | Single Family Residence | 3/3 | 61 |
| 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 |
| 11-01-2023 | 3651 N GOLDENROD ROAD # E101, WINTER PARK FL 32792 | $200,000 | $238 | $204,999 | 840 | Condominium | 2/2 | 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 |
| 10-30-2023 | 673 GRENADINE COURT S # 673, WINTER PARK FL 32792 | $259,900 | $250 | $259,900 | 1,037 | Condominium | 2/2 | 34 |
| 10-30-2023 | 2732 LION HEART ROAD, WINTER PARK FL 32792 | $624,000 | $315 | $632,000 | 1,975 | Single Family Residence | 3/2 | 47 |
| 10-26-2023 | 614 GRENADINE COURT # 614, WINTER PARK FL 32792 | $155,500 | $204 | $159,900 | 759 | Condominium | 1/1 | 30 |
| 10-24-2023 | 2680 FITZHUGH ROAD, WINTER PARK FL 32792 | $630,000 | $305 | $630,000 | 2,064 | Single Family Residence | 4/3 | 37 |
| 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 |
| 10-17-2023 | 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 | 2779 WILL O TH GREEN, WINTER PARK FL 32792 | $510,000 | $314 | $490,000 | 1,620 | Single Family Residence | 3/2 | 35 |
| 10-13-2023 | 292 SCOTTSDALE SQUARE # 292, WINTER PARK FL 32792 | $135,000 | $124 | $150,000 | 1,085 | Condominium | 2/2 | 95 |
| 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 |
| 10-06-2023 | 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 |
| 10-04-2023 | 173 SCOTTSDALE SQUARE # 173, WINTER PARK FL 32792 | $95,333 | $121 | $89,900 | 785 | Condominium | 1/1 | 21 |
| 09-29-2023 | 712 BONGART ROAD, WINTER PARK FL 32792 | $380,500 | $195 | $399,900 | 1,950 | Single Family Residence | 5/2 | 37 |
| 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 |
| 09-25-2023 | 423 LONDON ROAD, WINTER PARK FL 32792 | $778,000 | $253 | $799,900 | 3,072 | Single Family Residence | 4/3 | 40 |
| 09-21-2023 | 2708 BONGART ROAD, WINTER PARK FL 32792 | $425,000 | $286 | $425,000 | 1,486 | Single Family Residence | 4/2 | 72 |
| 09-08-2023 | 536 CORNWALL ROAD, WINTER PARK FL 32792 | $510,000 | $362 | $480,000 | 1,405 | Single Family Residence | 4/2 | 29 |
| 08-30-2023 | 902 ELLENDALE DRIVE, WINTER PARK FL 32792 | $515,000 | $266 | $515,000 | 1,936 | Single Family Residence | 4/2 | 34 |
| 08-28-2023 | 700 MELROSE AVENUE # 33, WINTER PARK FL 32789 | $220,000 | $239 | $229,000 | 917 | Condominium | 1/1 | 116 |
| 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 |
| 08-23-2023 | 241 SCOTTSDALE SQUARE # 241, WINTER PARK FL 32792 | $120,000 | $158 | $125,000 | 756 | Condominium | 1/1 | 60 |
| 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 | 161 SCOTTSDALE SQUARE # 161, WINTER PARK FL 32792 | $125,000 | $165 | $135,000 | 756 | Condominium | 1/1 | 84 |
| 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 |
| 08-07-2023 | 627 GILBERT ROAD, WINTER PARK FL 32792 | $584,999 | $272 | $589,999 | 2,148 | Single Family Residence | 4/2 | 77 |
| 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 | 140 E MORSE BOULEVARD # G, WINTER PARK FL 32789 | $3,200,000 | $950 | $3,400,000 | 3,367 | Condominium | 3/4 | 29 |
| 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 | 626 CARVELL DRIVE, WINTER PARK FL 32792 | $389,000 | $272 | $389,000 | 1,428 | Single Family Residence | 4/2 | 24 |
| 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 | 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 |
| 07-24-2023 | 290 SCOTTSDALE SQUARE # 290, WINTER PARK FL 32792 | $152,000 | $116 | $169,000 | 1,300 | Condominium | 3/2 | 18 |
| 07-21-2023 | 273 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $180,000 | $265 | $174,900 | 678 | Condominium | 1/1 | 23 |
| 07-19-2023 | 722 WARRENTON ROAD, WINTER PARK FL 32792 | $217,000 | $159 | $217,000 | 1,362 | 1/2 Duplex | 2/2 | 1 |
| 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 |
| 07-17-2023 | 154 SCOTTSDALE SQUARE # 154, WINTER PARK FL 32792 | $128,000 | $117 | $140,000 | 1,085 | Condominium | 2/2 | 225 |
| 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 |
| 07-10-2023 | 321 ELKHORN COURT, WINTER PARK FL 32792 | $585,000 | $304 | $589,500 | 1,921 | Single Family Residence | 4/3 | 46 |
| 07-07-2023 | 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 |
| 07-06-2023 | 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 |
| 07-03-2023 | 543 WARRENTON ROAD # 543, WINTER PARK FL 32792 | $284,000 | $206 | $275,000 | 1,374 | Condominium | 3/3 | 21 |
| 06-30-2023 | 700 MELROSE AVENUE # 4, WINTER PARK FL 32789 | $170,000 | $232 | $175,000 | 730 | Condominium | 1/1 | 38 |
| 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 | 528 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $520,000 | $314 | $514,900 | 1,656 | Single Family Residence | 3/2 | 78 |
| 06-29-2023 | 152 LEWFIELD CIRCLE # 152, WINTER PARK FL 32792 | $165,000 | $243 | $165,000 | 678 | Condominium | 1/1 | 57 |
| 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 | 643 GILBERT ROAD, WINTER PARK FL 32792 | $483,500 | $221 | $544,000 | 2,185 | Single Family Residence | 4/2 | 81 |
| 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 | 1640 PALM AVENUE, WINTER PARK FL 32789 | $899,000 | $461 | $899,000 | 1,946 | Single Family Residence | 4/3 | 29 |
| 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 |
| 06-12-2023 | 2619 LAFAYETTE AVE, WINTER PARK FL 32789 | $405,000 | $290 | $425,000 | 1,393 | Single Family Residence | 4/2 | 20 |
| 06-09-2023 | 669 GRENADINE COURT # 669, WINTER PARK FL 32792 | $235,000 | $226 | $239,900 | 1,037 | Condominium | 2/2 | 118 |
| 06-07-2023 | 2808 AMSDEN ROAD, WINTER PARK FL 32792 | $515,000 | $254 | $515,000 | 2,020 | Single Family Residence | 3/4 | 55 |
| 06-05-2023 | 149 LEWFIELD CIRCLE # 149, WINTER PARK FL 32792 | $170,000 | $250 | $170,000 | 678 | Condominium | 1/1 | 43 |
| 06-05-2023 | 2613 LAFAYETTE AVENUE, WINTER PARK FL 32789 | $399,000 | $361 | $399,000 | 1,104 | Single Family Residence | 2/1 | 28 |
| 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 | |||
| 06-01-2023 | 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 | 1691 PALM AVENUE, WINTER PARK FL 32789 | $1,825,000 | $593 | $1,800,000 | 3,075 | Single Family Residence | 4/4 | 50 |
| 05-31-2023 | 654 FRIAR ROAD, WINTER PARK FL 32792 | $550,000 | $310 | $550,000 | 1,772 | Single Family Residence | 3/2 | 10 |
| 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 | 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 | 2755 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $486,000 | $304 | $475,000 | 1,595 | Single Family Residence | 4/2 | 37 |
| 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 |
| 05-24-2023 | 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 | 192 LEWFIELD CIRCLE # 192, WINTER PARK FL 32792 | $163,000 | $240 | $169,000 | 678 | Condominium | 1/1 | 35 |
| 05-17-2023 | 621 TRINIDAD COURT # 621, WINTER PARK FL 32792 | $239,900 | $231 | $239,900 | 1,037 | Condominium | 2/2 | 37 |
| 05-12-2023 | 735 WARRENTON ROAD, WINTER PARK FL 32792 | $285,000 | $238 | $250,000 | 1,196 | 1/2 Duplex | 3/2 | 22 |
| 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 |
| 05-08-2023 | 723 MONMOUTH WAY, WINTER PARK FL 32792 | $725,000 | $299 | $725,000 | 2,423 | Single Family Residence | 5/3 | 40 |
| 05-04-2023 | 700 MELROSE AVENUE # 1, WINTER PARK FL 32789 | $239,000 | $303 | $239,000 | 787 | Condominium | 1/1 | 1 |
| 05-02-2023 | 640 DOUGLAS AVENUE, WINTER PARK FL 32789 | $467,000 | $364 | $419,000 | 1,280 | Single Family Residence | 3/2 | 34 |
| 05-01-2023 | 2747 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $520,000 | $323 | $535,000 | 1,608 | Single Family Residence | 3/2 | 77 |
| 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 |
| 04-27-2023 | 204 LEWFIELD CIRCLE # 204, WINTER PARK FL 32792 | $209,000 | $225 | $200,000 | 927 | Condominium | 2/2 | 41 |
| 04-24-2023 | 206 BALFOUR DRIVE # 6, WINTER PARK FL 32792 | $370,000 | $302 | $370,000 | 1,225 | Condominium | 2/2 | 42 |
| 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 | 418 GILBERT ROAD, WINTER PARK FL 32792 | $400,000 | $212 | $450,000 | 1,880 | Single Family Residence | 4/3 | 65 |
| 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 |
| 04-15-2023 | 280 SCOTTSDALE SQUARE # 280, WINTER PARK FL 32792 | $130,000 | $119 | $144,900 | 1,085 | Condominium | 2/2 | 64 |
| 04-10-2023 | 2430 CHANTILLY AVENUE, WINTER PARK FL 32789 | $367,000 | $423 | $345,000 | 867 | Single Family Residence | 2/1 | 25 |
| 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 |
| 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 | 239 LEWFIELD CIR # 239, WINTER PARK FL 32792 | $198,000 | $207 | $200,000 | 953 | Condominium | 2/2 | 70 |
| 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 |
| 03-28-2023 | 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 | |||
| 03-27-2023 | 191 SCOTTSDALE SQUARE # 191, WINTER PARK FL 32792 | $118,000 | $150 | $125,000 | 785 | Condominium | 1/1 | 19 |
| 03-27-2023 | 356 FLEET ROAD, WINTER PARK FL 32792 | $546,000 | $294 | $569,000 | 1,853 | Single Family Residence | 3/3 | 35 |
| 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 |
| 03-20-2023 | 367 FITZHUGH ROAD, WINTER PARK FL 32792 | $830,000 | $371 | $885,000 | 2,234 | Single Family Residence | 4/3 | 195 |
| 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 | 252 LEWFIELD CIRCLE # 252, WINTER PARK FL 32792 | $192,500 | $207 | $195,000 | 927 | Condominium | 2/2 | 57 |
| 03-15-2023 | 2817 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $617,000 | $282 | $620,000 | 2,183 | Single Family Residence | 4/4 | 47 |
| 03-10-2023 | 2601 AMSDEN ROAD, WINTER PARK FL 32792 | $365,000 | $309 | $375,000 | 1,181 | Single Family Residence | 3/2 | 149 |
| 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 | 2825 FITZOOTH DRIVE # 6, WINTER PARK FL 32792 | $625,000 | $265 | $610,000 | 2,356 | Single Family Residence | 4/3 | 40 |
| 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 | 453 WARRENTON ROAD # 453, WINTER PARK FL 32792 | $275,000 | $263 | $279,900 | 1,043 | Condominium | 2/2 | 47 |
| 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 | 564 S RANGER BOULEVARD, WINTER PARK FL 32792 | $725,000 | $301 | $725,000 | 2,407 | Single Family Residence | 4/3 | 57 |
| 02-28-2023 | $7,000,000 | $1,301 | $7,200,000 | 5,377 | Single Family Residence | 4/5 | 5 | |
| 02-24-2023 | 1114 WASHINGTON AVENUE # 3, WINTER PARK FL 32789 | $440,000 | $299 | $450,000 | 1,468 | Condominium | 2/3 | 38 |
| 02-23-2023 | 2840 CADY WAY, WINTER PARK FL 32792 | $375,000 | $266 | $395,000 | 1,407 | Single Family Residence | 3/2 | 35 |
| 02-21-2023 | 103 SCOTTSDALE SQUARE # 103, WINTER PARK FL 32792 | $128,000 | $125 | $134,900 | 1,020 | Condominium | 2/2 | 46 |
| 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 | 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 | 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 |
| 01-25-2023 | 1695 LEE ROAD # B109, WINTER PARK FL 32789 | $127,000 | $199 | $134,900 | 638 | Condominium | 1/1 | 58 |
| 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 |
| 01-16-2023 | 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 |
| 01-05-2023 | 326 SCOTTSDALE SQUARE # 326, WINTER PARK FL 32792 | $112,000 | $103 | $145,000 | 1,085 | Condominium | 2/2 | 42 |
| 01-03-2023 | 470 W COMSTOCK AVENUE, WINTER PARK FL 32789 | $450,000 | $450,000 | / | 294 | |||
| 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 |
| 12-27-2022 | 2641 CARVELL COURT, WINTER PARK FL 32792 | $340,000 | $159 | $350,000 | 2,126 | Single Family Residence | 4/2 | 131 |
| 12-27-2022 | 1224 DENTON ROAD, WINTER PARK FL 32792 | $420,000 | $249 | $399,000 | 1,682 | Single Family Residence | 4/2 | 224 |
| 12-20-2022 | 759 S RANGER BOULEVARD, WINTER PARK FL 32792 | $640,000 | $272 | $649,000 | 2,349 | Single Family Residence | 4/3 | 47 |
| 12-16-2022 | 161 SCOTTSDALE SQUARE # 161, WINTER PARK FL 32792 | $100,000 | $132 | $105,000 | 756 | Condominium | 1/1 | 58 |
| 12-15-2022 | 196 BALFOUR DRIVE # 4, WINTER PARK FL 32792 | $325,000 | $252 | $345,000 | 1,287 | Condominium | 2/2 | 42 |
| 12-06-2022 | 668 SAINT JOHNS COURT, WINTER PARK FL 32792 | $210,000 | $202 | $210,000 | 1,037 | Condominium | 2/2 | 28 |
| 12-05-2022 | 811 DOUGLAS AVENUE, WINTER PARK FL 32789 | $335,000 | $314 | $390,000 | 1,066 | Single Family Residence | 3/2 | 218 |
| 12-01-2022 | 700 MELROSE AVENUE # 4, WINTER PARK FL 32789 | $225,000 | $227 | $225,000 | 987 | Condominium | 1/1 | 31 |
| 11-29-2022 | 715 DOUGLAS AVENUE, WINTER PARK FL 32789 | $225,000 | $280,000 | / | 518 | |||
| 11-28-2022 | 700 MELROSE AVENUE # K22, WINTER PARK FL 32789 | $200,000 | $259 | $200,000 | 772 | Condominium | 1/1 | 47 |
| 11-22-2022 | 1128 WASHINGTON AVENUE # 10, WINTER PARK FL 32789 | $430,000 | $253 | $459,900 | 1,693 | Condominium | 3/3 | 109 |
| 11-21-2022 | 1217 CARVELL DRIVE, WINTER PARK FL 32792 | $375,000 | $250 | $375,000 | 1,498 | Single Family Residence | 3/2 | 60 |
| 11-17-2022 | 680 GRENADINE COURT, WINTER PARK FL 32792 | $145,000 | $191 | $150,000 | 759 | Condominium | 1/1 | 45 |
| 11-17-2022 | 2839 LION HEART ROAD, WINTER PARK FL 32792 | $670,000 | $277 | $675,000 | 2,417 | Single Family Residence | 4/3 | 64 |
| 11-14-2022 | 174 LEWFIELD CIRCLE # 174, WINTER PARK FL 32792 | $160,000 | $235 | $165,000 | 678 | Condominium | 1/1 | 32 |
| 11-11-2022 | 1695 LEE ROAD # A111, WINTER PARK FL 32789 | $172,000 | $195 | $185,000 | 881 | Condominium | 2/1 | 41 |
| 11-10-2022 | 2862 KINGS DEER ROAD, WINTER PARK FL 32792 | $485,000 | $275 | $500,000 | 1,763 | Single Family Residence | 3/2 | 42 |
| 11-03-2022 | 2686 BANCHORY ROAD, WINTER PARK FL 32792 | $490,000 | $295 | $469,000 | 1,656 | Single Family Residence | 3/2 | 42 |
| 10-28-2022 | 700 MELROSE AVENUE # M, WINTER PARK FL 32789 | $195,000 | $267 | $219,900 | 730 | Condominium | 1/1 | 75 |
| 10-28-2022 | 664 GRENADINE COURT, WINTER PARK FL 32792 | $230,000 | $170 | $245,000 | 1,350 | Condominium | 3/2 | 113 |
| 10-25-2022 | 330 SCOTTSDALE SQUARE # 330, WINTER PARK FL 32792 | $139,000 | $136 | $144,900 | 1,020 | Condominium | 2/2 | 68 |
| 10-21-2022 | 277 SCOTTSDALE SQUARE # 277, WINTER PARK FL 32792 | $126,000 | $123 | $134,900 | 1,020 | Condominium | 2/2 | 107 |
| 10-14-2022 | 443 WARRENTON ROAD # 443, WINTER PARK FL 32792 | $270,000 | $225 | $280,000 | 1,200 | Condominium | 3/2 | 50 |
| 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 | 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 | 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 | |||
| 10-03-2022 | 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 | |||
| 09-30-2022 | 126 SCOTTSDALE SQUARE # 126, WINTER PARK FL 32792 | $140,000 | $129 | $150,000 | 1,085 | Condominium | 2/2 | 133 |
| 09-28-2022 | 2138 BLOSSOM LANE, WINTER PARK FL 32789 | $485,000 | $297 | $485,000 | 1,629 | Single Family Residence | 3/2 | 42 |
| 09-23-2022 | 760 DOUGLAS AVENUE, WINTER PARK FL 32789 | $400,000 | $299 | $400,000 | 1,334 | Single Family Residence | 3/1 | 41 |
| 09-21-2022 | 1695 LEE ROAD # E115, WINTER PARK FL 32789 | $180,000 | $156 | $180,000 | 1,149 | Condominium | 3/2 | 29 |
| 09-20-2022 | 2723 ALOMA AVENUE, WINTER PARK FL 32792 | $312,000 | $249 | $325,000 | 1,252 | Single Family Residence | 3/2 | 47 |
| 09-16-2022 | 2625 ALOMA AVENUE, WINTER PARK FL 32792 | $450,000 | $284 | $460,000 | 1,584 | Single Family Residence | 3/3 | 39 |
| 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 |
| 09-09-2022 | 2811 WILL O TH GREEN, WINTER PARK FL 32792 | $445,000 | $300 | $450,000 | 1,483 | Single Family Residence | 4/2 | 36 |
| 09-07-2022 | 3651 N GOLDENROD ROAD # B107, WINTER PARK FL 32792 | $185,000 | $196 | $199,000 | 940 | Condominium | 2/2 | 270 |
| 08-26-2022 | 2855 CADY WAY, WINTER PARK FL 32792 | $505,000 | $290 | $525,000 | 1,736 | Single Family Residence | 3/2 | 64 |
| 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 | 301 CORNWALL ROAD, WINTER PARK FL 32792 | $512,000 | $310 | $537,000 | 1,648 | Single Family Residence | 3/2 | 44 |
| 08-18-2022 | 611 SAINT JOHNS COURT # 611, WINTER PARK FL 32792 | $206,600 | $184 | $204,900 | 1,120 | Condominium | 2/2 | 28 |
| 08-17-2022 | 233 LINCOLNSHIRE, WINTER PARK FL 32792 | $495,000 | $221 | $485,000 | 2,236 | Single Family Residence | 4/2 | 114 |
| 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 | 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 | 2812 BANCHORY ROAD, WINTER PARK FL 32792 | $521,000 | $272 | $499,999 | 1,914 | Single Family Residence | 3/2 | 34 |
| 07-29-2022 | 655 TRINIDAD COURT, WINTER PARK FL 32792 | $166,000 | $218 | $155,000 | 759 | Condominium | 1/1 | 22 |
| 07-28-2022 | 2653 EASTHAM ROAD, WINTER PARK FL 32792 | $410,000 | $265 | $410,000 | 1,542 | Single Family Residence | 3/2 | 42 |
| 07-27-2022 | 624 WARRENTON ROAD, WINTER PARK FL 32792 | $280,000 | $205 | $298,000 | 1,365 | Villa | 3/2 | 24 |
| 07-26-2022 | 612 BALFOUR DRIVE, WINTER PARK FL 32792 | $375,000 | $249 | $374,900 | 1,504 | Single Family Residence | 3/2 | 370 |
| 07-25-2022 | 212 LEWFIELD CIRCLE # 212, WINTER PARK FL 32792 | $180,000 | $194 | $175,000 | 927 | Condominium | 2/2 | 15 |
| 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 | 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 |
| 07-21-2022 | 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 |
| 07-20-2022 | 710 WARRENTON ROAD, WINTER PARK FL 32792 | $275,000 | $201 | $260,000 | 1,362 | 1/2 Duplex | 2/2 | 83 |
| 07-18-2022 | 700 MELROSE AVENUE # K, WINTER PARK FL 32789 | $235,000 | $304 | $239,900 | 772 | Condominium | 1/1 | 29 |
| 07-15-2022 | 169 LEWFIELD CIRCLE # 169, WINTER PARK FL 32792 | $145,000 | $213 | $150,000 | 678 | Condominium | 1/1 | 59 |
| 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 | 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 |
| 07-08-2022 | 232 SCOTTSDALE SQUARE # 232, WINTER PARK FL 32792 | $152,000 | $140 | $158,000 | 1,085 | Condominium | 2/2 | 176 |
| 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 | 103 CORNWALL ROAD, WINTER PARK FL 32792 | $621,000 | $272 | $649,900 | 2,280 | Single Family Residence | 4/3 | 30 |
| 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 | 1136 WASHINGTON AVENUE # 14, WINTER PARK FL 32789 | $574,900 | $339 | $574,900 | 1,693 | Townhouse | 3/3 | 35 |
| 06-28-2022 | 181 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $175,000 | $258 | $165,000 | 678 | Condominium | 1/1 | 19 |
| 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 |
| 06-24-2022 | 102 S RANGER BOULEVARD, WINTER PARK FL 32792 | $460,000 | $264 | $450,000 | 1,740 | Single Family Residence | 4/2 | 30 |
| 06-23-2022 | 1695 LEE ROAD # E101, WINTER PARK FL 32789 | $173,000 | $150 | $175,000 | 1,149 | Condominium | 3/2 | 37 |
| 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 |
| 06-21-2022 | 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 |
| 06-17-2022 | 653 BALFOUR DRIVE, WINTER PARK FL 32792 | $369,500 | $294 | $369,500 | 1,255 | Single Family Residence | 3/2 | 84 |
| 06-17-2022 | 2819 BANCHORY ROAD, WINTER PARK FL 32792 | $610,000 | $204 | $599,900 | 2,980 | Single Family Residence | 4/4 | 47 |
| 06-11-2022 | $128,000 | $117 | $135,000 | 1,085 | Condominium | 2/2 | 97 | |
| 06-10-2022 | 2404 GALLERY VIEW DRIVE # 6, WINTER PARK FL 32792 | $245,000 | $271 | $245,000 | 902 | Condominium | 2/2 | 50 |
| 06-06-2022 | 137 CORNWALL ROAD, WINTER PARK FL 32792 | $468,600 | $296 | $450,000 | 1,580 | Single Family Residence | 4/2 | 19 |
| 06-03-2022 | 3651 N GOLDENROD ROAD # D201, WINTER PARK FL 32792 | $177,000 | $210 | $177,500 | 840 | Condominium | 2/2 | 32 |
| 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 | 704 CORNWALL ROAD, WINTER PARK FL 32792 | $481,000 | $277 | $450,000 | 1,735 | Single Family Residence | 4/2 | 27 |
| 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 |
| 05-20-2022 | 716 ROUGHBEARD ROAD, WINTER PARK FL 32792 | $649,000 | $281 | $649,000 | 2,308 | Single Family Residence | 4/3 | 57 |
| 05-16-2022 | 3651 N GOLDENROD ROAD # 102, WINTER PARK FL 32792 | $180,000 | $214 | $149,900 | 840 | Condominium | 2/2 | 18 |
| 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 |
| 05-12-2022 | 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 | 1126 WASHINGTON AVENUE # A, WINTER PARK FL 32789 | $525,000 | $319 | $525,000 | 1,641 | Condominium | 3/3 | 36 |
| 05-09-2022 | 2419 GALLERY VIEW DRIVE UNIT 6 | $257,000 | $255 | $265,000 | 1,004 | Condominium | 2/2 | 47 |
| 05-04-2022 | 191 SCOTTSDALE SQUARE # 191, WINTER PARK FL 32792 | $119,000 | $151 | $119,000 | 785 | Condominium | 1/1 | 48 |
| 05-03-2022 | 353 ELKHORN COURT, WINTER PARK FL 32792 | $540,000 | $301 | $550,000 | 1,793 | Single Family Residence | 4/2 | 47 |
| 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 | 334 SCOTTSDALE SQUARE # 334, WINTER PARK FL 32792 | $140,000 | $112 | $150,000 | 1,250 | Condominium | 3/2 | 29 |
| 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 | 2717 BOWER ROAD, WINTER PARK FL 32792 | $530,000 | $287 | $499,900 | 1,843 | Single Family Residence | 4/2 | 78 |
| 04-28-2022 | 225 SCOTTSDALE SQUARE # 225, WINTER PARK FL 32792 | $133,000 | $130 | $135,000 | 1,020 | Condominium | 2/2 | 57 |
| 04-25-2022 | 733 FRIAR ROAD, WINTER PARK FL 32792 | $488,000 | $265 | $489,900 | 1,838 | Single Family Residence | 3/2 | 33 |
| 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 | 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 |
| 04-18-2022 | 145 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $126,000 | $185 | $110,000 | 678 | Condominium | 1/1 | 31 |
| 04-15-2022 | 168 LEWFIELD CIRCLE # 168, WINTER PARK FL 32792 | $146,000 | $215 | $135,000 | 678 | Condominium | 1/1 | 26 |
| 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 |
| 04-08-2022 | 114 SCOTTSDALE SQUARE # 114, WINTER PARK FL 32792 | $131,500 | $121 | $129,000 | 1,085 | Condominium | 2/2 | 21 |
| 04-07-2022 | 1131 DENTON ROAD, WINTER PARK FL 32792 | $360,000 | $253 | $369,900 | 1,422 | Single Family Residence | 4/2 | 18 |
| 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 |
| 04-04-2022 | 1802 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $751,000 | $415 | $699,000 | 1,808 | Single Family Residence | 3/3 | 39 |
| 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 | 427 ELLENDALE DRIVE, WINTER PARK FL 32792 | $376,900 | $272 | $379,900 | 1,384 | Single Family Residence | 3/2 | 49 |
| 03-30-2022 | 738 S RANGER BOULEVARD, WINTER PARK FL 32792 | $675,000 | $290 | $649,900 | 2,327 | Single Family Residence | 4/3 | 70 |
| 03-25-2022 | 620 MONTEGO BAY COURT # 620, WINTER PARK FL 32792 | $221,000 | $197 | $199,500 | 1,120 | Condominium | 2/2 | 21 |
| 03-23-2022 | 210 SCOTTSDALE SQUARE # 210, WINTER PARK FL 32792 | $130,000 | $119 | $139,900 | 1,085 | Condominium | 2/2 | 98 |
| 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 | 3651 N GOLDENROD ROAD # B102, WINTER PARK FL 32792 | $172,000 | $204 | $169,000 | 840 | Condominium | 2/2 | 25 |
| 03-21-2022 | 2834 CHANTILLY AVE | $384,450 | $330 | $339,000 | 1,165 | Single Family Residence | 3/2 | 25 |
| 03-20-2022 | 214 SCOTTSDALE SQUARE # 214, WINTER PARK FL 32792 | $144,000 | $132 | $149,000 | 1,085 | Condominium | 2/2 | 94 |
| 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 |
| 03-11-2022 | 185 LEWFIELD CIRCLE # 185, WINTER PARK FL 32792 | $125,000 | $184 | $125,000 | 678 | Condominium | 1/1 | 27 |
| 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 |
| 03-08-2022 | 2860 WILL O TH GREEN STREET, WINTER PARK FL 32792 | $440,000 | $335 | $425,000 | 1,312 | Single Family Residence | 3/2 | 20 |
| 03-07-2022 | 600 MONTEGO BAY COURT # 600, WINTER PARK FL 32792 | $175,000 | $168 | $170,000 | 1,037 | Condominium | 2/2 | 19 |
| 03-04-2022 | 700 MELROSE AVENUE # 31, WINTER PARK FL 32789 | $260,000 | $320 | $229,900 | 810 | Condominium | 1/1 | 29 |
| 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 | 769 W LYMAN AVENUE, WINTER PARK FL 32789 | $320,000 | $349,900 | / | 170 | |||
| 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 | 2754 PRINCE JOHN ROAD, WINTER PARK FL 32792 | $400,000 | $227 | $430,000 | 1,760 | Single Family Residence | 3/2 | 77 |
| 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 |
| 02-23-2022 | 624 MONMOUTH WAY, WINTER PARK FL 32792 | $617,000 | $195 | $685,000 | 3,155 | Single Family Residence | 5/4 | 29 |
| 02-22-2022 | 668 SAINT JOHNS COURT, WINTER PARK FL 32792 | $172,000 | $165 | $172,000 | 1,037 | 2/2 | 2 | |
| 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 |
| 02-18-2022 | 128 OAK GROVE ROAD, WINTER PARK FL 32789 | $293,000 | $253 | $289,900 | 1,156 | Single Family Residence | 3/2 | 23 |
| 02-15-2022 | 1695 LEE ROAD # D113, WINTER PARK FL 32789 | $130,000 | $147 | $129,999 | 881 | Condominium | 2/1 | 30 |
| 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 | 327 ELKHORN COURT, WINTER PARK FL 32792 | $589,900 | $299 | $589,900 | 1,968 | Single Family Residence | 4/3 | 34 |
| 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 | 1122 DENTON ROAD, WINTER PARK FL 32792 | $449,000 | $275 | $429,000 | 1,628 | Single Family Residence | 4/2 | 24 |
| 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 | 198 LEWFIELD CIRCLE # 198, WINTER PARK FL 32792 | $189,000 | $149 | $189,000 | 1,268 | Condominium | 3/2 | 55 |
| 02-03-2022 | 1123 DENTON ROAD, WINTER PARK FL 32792 | $367,500 | $180 | $387,500 | 2,040 | Single Family Residence | 4/3 | 122 |
| 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 | 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 | |||
| 01-28-2022 | 741 SAINT DUNSTAN WAY, WINTER PARK FL 32792 | $435,000 | $206 | $400,000 | 2,104 | Single Family Residence | 4/2 | 292 |
| 01-28-2022 | 660 NORTHWOOD CIRCLE, WINTER PARK FL 32789 | $620,000 | $308 | $687,500 | 2,008 | Single Family Residence | 5/3 | 51 |
| 01-21-2022 | 234 SCOTTSDALE SQUARE # 234, WINTER PARK FL 32792 | $127,000 | $117 | $125,990 | 1,085 | Condominium | 2/2 | 20 |
| 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 | 2902 BANCHORY ROAD, WINTER PARK FL 32792 | $685,000 | $262 | $674,990 | 2,612 | Single Family Residence | 4/3 | 17 |
| 01-14-2022 | 3651 N GOLDENROD ROAD # B102, WINTER PARK FL 32792 | $128,000 | $152 | $159,000 | 840 | Condominium | 2/2 | 122 |
| 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 |
| 01-07-2022 | 157 SCOTTSDALE SQUARE # 157, WINTER PARK FL 32792 | $137,000 | $134 | $139,900 | 1,020 | Condominium | 2/2 | 63 |
| 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 | 190 BALFOUR DRIVE # 1, WINTER PARK FL 32792 | $238,000 | $194 | $250,000 | 1,225 | Condominium | 2/2 | 82 |
| 12-31-2021 | 700 MELROSE AVENUE # 23, WINTER PARK FL 32789 | $240,000 | $223 | $240,000 | 1,074 | 2/2 | 5 | |
| 12-30-2021 | 133 SCOTTSDALE SQUARE # 133, WINTER PARK FL 32792 | $77,000 | $98 | $79,000 | 785 | Condominium | 1/1 | 106 |
| 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 | 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 |
| 12-22-2021 | 741 FRIAR ROAD, WINTER PARK FL 32792 | $500,000 | $253 | $450,000 | 1,970 | Single Family Residence | 4/3 | 21 |
| 12-17-2021 | 127 LEWFIELD CIRCLE # 127, WINTER PARK FL 32792 | $113,000 | $166 | $115,000 | 678 | Condominium | 1/1 | 100 |
| 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 | 128 OAK GROVE ROAD, WINTER PARK FL 32789 | $250,000 | $216 | $275,000 | 1,156 | Single Family Residence | 3/2 | 34 |
| 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 |
| 12-09-2021 | 248 SCOTTSDALE SQUARE # 248, WINTER PARK FL 32792 | $157,000 | $125 | $159,900 | 1,250 | Condominium | 3/2 | 35 |
| 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 | 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 |
| 12-06-2021 | 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 | 234 LEWFIELD CIRCLE # 234, WINTER PARK FL 32792 | $168,500 | $176 | $168,500 | 953 | Condominium | 2/2 | 52 |
| 12-03-2021 | 521 CAROLINA AVENUE, WINTER PARK FL 32789 | $450,000 | $280 | $475,000 | 1,602 | Single Family Residence | 4/2 | 191 |
| 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 |
| 12-01-2021 | 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 | 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 |
| 11-18-2021 | 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 |
| 11-15-2021 | 609 CARVELL DRIVE, WINTER PARK FL 32792 | $390,000 | $240 | $414,900 | 1,622 | Single Family Residence | 4/2 | 88 |
| 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 |
| 11-05-2021 | 3318 YOUNG STREET, WINTER PARK FL 32792 | $350,000 | $164 | $350,000 | 2,127 | Single Family Residence | 4/2 | 43 |
| 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 |
| 11-03-2021 | 640 OSCEOLA AVENUE | $1,080,000 | $400 | $1,120,000 | 2,696 | Condominium | 3/3 | 104 |
| 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 | 247 W LYMAN AVENUE, WINTER PARK FL 32789 | $880,000 | $540 | $850,000 | 1,628 | Single Family Residence | 4/3 | 29 |
| 10-29-2021 | 728 ROUGHBEARD ROAD, WINTER PARK FL 32792 | $480,000 | $248 | $480,000 | 1,931 | Single Family Residence | 4/3 | 121 |
| 10-28-2021 | 739 ROUGHBEARD ROAD, WINTER PARK FL 32792 | $495,000 | $225 | $475,000 | 2,194 | Single Family Residence | 5/3 | 57 |
| 10-27-2021 | 171 OAK GROVE ROAD, WINTER PARK FL 32789 | $285,000 | $243 | $279,900 | 1,170 | Single Family Residence | 3/2 | 35 |
| 10-25-2021 | 302 LEWFIELD CIRCLE # 302, WINTER PARK FL 32792 | $112,000 | $165 | $119,990 | 678 | Condominium | 1/1 | 18 |
| 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 | 417 CARVELL DRIVE, WINTER PARK FL 32792 | $399,500 | $219 | $398,000 | 1,823 | Single Family Residence | 4/3 | 77 |
| 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 |
| 10-11-2021 | 641 NORTHWOOD CIRCLE, WINTER PARK FL 32789 | $250,000 | $319,900 | / | 301 | |||
| 10-08-2021 | 216 BALFOUR DRIVE # 11, WINTER PARK FL 32792 | $281,500 | $185 | $279,000 | 1,520 | Condominium | 3/2 | 22 |
| 10-06-2021 | 2619 AMBERGATE ROAD, WINTER PARK FL 32792 | $330,000 | $268 | $339,000 | 1,227 | Single Family Residence | 3/2 | 49 |
| 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 | 460 W LYMAN AVENUE, WINTER PARK FL 32789 | $670,000 | $699,000 | / | 193 | |||
| 10-01-2021 | 2870 CHANTILLY AVENUE, WINTER PARK FL 32789 | $286,000 | $234 | $290,000 | 1,220 | Single Family Residence | 3/2 | 57 |
| 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 | 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 | 117 SCOTTSDALE SQUARE # 117, WINTER PARK FL 32792 | $80,000 | $101 | $75,000 | 785 | Condominium | 1/1 | 43 |
| 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 |
| 09-27-2021 | 340 FLEET ROAD, WINTER PARK FL 32792 | $344,900 | $249 | $344,900 | 1,381 | Single Family Residence | 2/2 | 38 |
| 09-27-2021 | 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 |
| 09-24-2021 | 2830 LION HEART ROAD, WINTER PARK FL 32792 | $440,000 | $244 | $425,000 | 1,802 | Single Family Residence | 3/2 | 37 |
| 09-22-2021 | 632 MONTEGO BAY COURT # 632, WINTER PARK FL 32792 | $181,000 | $174 | $172,500 | 1,037 | Condominium | 2/2 | 50 |
| 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 | 172 OAK GROVE ROAD, WINTER PARK FL 32789 | $230,000 | $181 | $249,500 | 1,268 | Single Family Residence | 3/3 | 82 |
| 09-15-2021 | 237 SCOTTSDALE SQUARE # 237, WINTER PARK FL 32792 | $124,000 | $121 | $124,000 | 1,020 | Condominium | 2/2 | 41 |
| 09-14-2021 | 1695 LEE RD # D214, WINTER PARK FL 32789 | $122,000 | $138 | $139,900 | 881 | Condominium | 2/1 | 30 |
| 09-14-2021 | 311 SCOTTSDALE SQUARE # 311, WINTER PARK FL 32792 | $79,000 | $100 | $82,000 | 785 | Condominium | 1/1 | 41 |
| 09-13-2021 | 1670 PALM AVENUE, WINTER PARK FL 32789 | $550,000 | $263 | $599,990 | 2,087 | Single Family Residence | 4/3 | 50 |
| 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 |
| 09-03-2021 | 674 DOUGLAS AVENUE, WINTER PARK FL 32789 | $315,000 | $250 | $300,000 | 1,260 | Single Family Residence | 2/2 | 158 |
| 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 |
| 08-30-2021 | 645 BALFOUR DRIVE, WINTER PARK FL 32792 | $345,000 | $239 | $350,000 | 1,443 | Single Family Residence | 3/2 | 75 |
| 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 | 700 MELROSE AVENUE # 33, WINTER PARK FL 32789 | $255,000 | $237 | $275,000 | 1,074 | Condominium | 2/2 | 29 |
| 08-20-2021 | 2716 LION HEART ROAD, WINTER PARK FL 32792 | $492,500 | $291 | $475,000 | 1,688 | Single Family Residence | 3/2 | 36 |
| 08-19-2021 | 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 |
| 08-16-2021 | 741 WARRENTON ROAD, WINTER PARK FL 32792 | $230,000 | $192 | $230,000 | 1,196 | Townhouse | 3/2 | 25 |
| 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 | 733 MINNESOTA AVENUE, WINTER PARK FL 32789 | $537,000 | $277 | $544,900 | 1,932 | Townhouse | 3/3 | 72 |
| 08-12-2021 | 100 S VIRGINIA AVENUE # 403, WINTER PARK FL 32789 | $930,000 | $357 | $950,000 | 2,599 | Condominium | 3/3 | 44 |
| 08-09-2021 | 136 LEWFIELD CIR # 136, WINTER PARK FL 32792 | $96,000 | $141 | $99,900 | 678 | Condominium | 1/1 | 130 |
| 08-06-2021 | 505 CORNWALL ROAD, WINTER PARK FL 32792 | $450,000 | $248 | $450,000 | 1,813 | Single Family Residence | 4/2 | 30 |
| 08-04-2021 | 1414 BESSMOR ROAD, WINTER PARK FL 32789 | $330,000 | $316 | $340,000 | 1,043 | Single Family Residence | 3/1 | 42 |
| 08-02-2021 | 1802 ARBOR PARK DRIVE, WINTER PARK FL 32789 | $569,500 | $314 | $565,000 | 1,808 | Single Family Residence | 4/3 | 42 |
| 07-30-2021 | 700 MELROSE AVENUE # 3, WINTER PARK FL 32789 | $160,000 | $272 | $159,900 | 587 | Condominium | /1 | 78 |
| 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 | 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 | 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 |
| 07-26-2021 | 609 ELLENDALE DRIVE, WINTER PARK FL 32792 | $265,000 | $198 | $275,000 | 1,334 | Single Family Residence | 3/2 | 81 |
| 07-26-2021 | 219 CORNWALL ROAD, WINTER PARK FL 32792 | $377,000 | $239 | $385,000 | 1,571 | Single Family Residence | 3/2 | 18 |
| 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 | 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 |
| 07-16-2021 | 307 SCOTTSDALE SQUARE # 307, WINTER PARK FL 32792 | $82,700 | $105 | $97,000 | 785 | Condominium | 1/1 | 32 |
| 07-15-2021 | 2814 SHERIFF WAY, WINTER PARK FL 32792 | $380,000 | $195 | $350,000 | 1,948 | Single Family Residence | 4/2 | 48 |
| 07-14-2021 | 2411 GALLERY VIEW DRIVE # 201, WINTER PARK FL 3279 | $205,000 | $199 | $205,000 | 1,026 | Condominium | 2/2 | 4 |
| 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 |
| 07-12-2021 | 106 SCOTTSDALE SQUARE # 106, WINTER PARK FL 32792 | $135,000 | $108 | $135,000 | 1,250 | Condominium | 3/2 | 48 |
| 07-07-2021 | 327 ELKHORN COURT, WINTER PARK FL 32792 | $327,500 | $135 | $327,500 | 2,409 | Single Family Residence | 4/3 | 23 |
| 07-06-2021 | 3651 N GOLDENROD ROAD # D206, WINTER PARK FL 32792 | $121,000 | $144 | $121,700 | 840 | Condominium | 2/2 | 114 |
| 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 |
| 06-30-2021 | 722 CARVELL DRIVE, WINTER PARK FL 32792 | $360,000 | $227 | $355,000 | 1,581 | Single Family Residence | 3/2 | 43 |
| 06-29-2021 | 342 CORNWALL ROAD, WINTER PARK FL 32792 | $385,000 | $225 | $395,000 | 1,704 | Single Family Residence | 3/2 | 40 |
| 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 | 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 |
| 06-22-2021 | 551 GILBERT ROAD, WINTER PARK FL 32792 | $395,000 | $207 | $375,000 | 1,900 | Single Family Residence | 3/2 | 42 |
| 06-18-2021 | 801 ELLENDALE DRIVE, WINTER PARK FL 32792 | $350,500 | $231 | $349,500 | 1,516 | Single Family Residence | 3/2 | 25 |
| 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 | 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 |
| 06-15-2021 | 609 CARVELL DRIVE, WINTER PARK FL 32792 | $310,000 | $191 | $320,000 | 1,622 | Single Family Residence | 3/2 | 27 |
| 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 | 244 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $140,000 | $146 | $145,000 | 953 | Condominium | 2/2 | 48 |
| 06-11-2021 | 2724 LION HEART ROAD, WINTER PARK FL 32792 | $390,000 | $245 | $400,000 | 1,587 | Single Family Residence | 4/2 | 37 |
| 06-09-2021 | 727 DENSMORE DRIVE, WINTER PARK FL 32792 | $260,000 | $247 | $289,900 | 1,050 | Single Family Residence | 2/2 | 41 |
| 06-07-2021 | 607 WARRENTON ROAD, WINTER PARK FL 32792 | $235,000 | $172 | $259,000 | 1,365 | Townhouse | 3/2 | 102 |
| 06-04-2021 | 228 LEWFIELD CIRCLE, WINTER PARK FL 32792 | $141,000 | $147 | $141,000 | 953 | 2/2 | 5 | |
| 06-01-2021 | 3651 N GOLDENROD ROAD # C110, WINTER PARK FL 32792 | $127,000 | $151 | $129,900 | 840 | Condominium | 2/2 | 35 |
| 05-28-2021 | 130 SCOTTSDALE SQUARE # 130, WINTER PARK FL 32792 | $100,000 | $98 | $115,000 | 1,020 | Condominium | 2/2 | 77 |
| 05-27-2021 | 2629 ALOMA AVENUE, WINTER PARK FL 32792 | $182,000 | $176 | $182,000 | 1,032 | 3/2 | 9 | |
| 05-27-2021 | 2773 CADY WAY, WINTER PARK FL 32792 | $400,000 | $270 | $394,900 | 1,478 | Single Family Residence | 3/2 | 24 |
| 05-25-2021 | 3651 N GOLDENROD ROAD # B210, WINTER PARK FL 32792 | $125,000 | $148 | $125,000 | 840 | Condominium | 2/2 | 65 |
| 05-19-2021 | 270 SCOTTSDALE SQUARE # 270, WINTER PARK FL 32792 | $115,000 | $88 | $129,995 | 1,300 | Condominium | 3/2 | 674 |
| 05-18-2021 | 2767 BOWER ROAD, WINTER PARK FL 32792 | $470,000 | $277 | $459,900 | 1,692 | Single Family Residence | 3/2 | 68 |
| 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 | 2957 ROUEN AVENUE, WINTER PARK FL 32789 | $285,000 | $269 | $295,000 | 1,056 | Single Family Residence | 3/2 | 254 |
| 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 | 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 | 791 DOUGLAS AVENUE, WINTER PARK FL 32789 | $639,683 | $382 | $595,900 | 1,672 | Single Family Residence | 3/3 | 898 |
| 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 | 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 | 126 LEWFIELD CIRCLE # 126, WINTER PARK FL 32792 | $99,900 | $147 | $99,900 | 678 | Condominium | 1/1 | 50 |
| 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 | 729 ELLENDALE DRIVE, WINTER PARK FL 32792 | $367,500 | $226 | $359,900 | 1,620 | Single Family Residence | 4/3 | 43 |
| 05-05-2021 | 110 LEWFIELD CIRCLE # 110, WINTER PARK FL 32792 | $140,500 | $147 | $140,000 | 953 | Condominium | 2/2 | 36 |
| 05-03-2021 | 607 GRENADINE COURT # 607, WINTER PARK FL 32792 | $150,000 | $144 | $150,000 | 1,037 | Condominium | 2/2 | 50 |
| 04-30-2021 | 700 MELROSE AVENUE # 22, WINTER PARK FL 32789 | $170,000 | $158 | $190,000 | 1,074 | Condominium | 2/2 | 255 |
| 04-29-2021 | 345 MERRIE OAKS ROAD, WINTER PARK FL 32792 | $465,000 | $248 | $465,000 | 1,874 | 4/3 | 5 | |
| 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 | 767 MCINTYRE AVENUE, WINTER PARK FL 32789 | $500,000 | $551 | $499,000 | 906 | Single Family Residence | 2/1 | 40 |
| 04-26-2021 | 870 GEORGIA AVENUE, WINTER PARK FL 32789 | $1,550,000 | $572 | $1,595,000 | 2,709 | Single Family Residence | 3/3 | 36 |
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
