Below is a list of properties that are active, under contract or have sold in Winter Park in the last 90 days. This will give you a general idea where the Winter Park housing market trends are headed. Sign up for the monthly reports to stay updated or create your own custom market report for the area you are interested in.
| Address | Beds | Baths | Living ft2 | List Price | Cost per ft2 | DOM |
|---|---|---|---|---|---|---|
| 1120 Preserve Point Drive | 7 | 11 | 11,255 | $8,950,000 | $795 | 294 days |
| 40 Palmer Avenue | 5 | 6 | 5,905 | $7,250,000 | $1,227 | 168 days |
| 1260 Alabama Drive | 6 | 7 | 6,396 | $6,900,000 | $1,078 | 146 days |
| 550 Palmer Avenue | 5 | 7 | 5,939 | $6,495,000 | $1,093 | 278 days |
| 1571 Woodland Avenue | 5 | 8 | 7,397 | $6,000,000 | $811 | 59 days |
| 2228 Azalea Place | 5 | 6 | 5,152 | $5,600,000 | $1,086 | 30 days |
| 313 Sylvan Drive | 4 | 5 | 4,775 | $5,500,000 | $1,151 | 42 days |
| 231 Chelton Circle | 4 | 7 | 5,550 | $4,950,000 | $891 | 47 days |
| 1180 Via Lugano | 5 | 6 | 4,961 | $4,900,000 | $987 | 20 days |
| 1441 Cardinal Court | 4 | 6 | 4,066 | $4,285,000 | $1,053 | 103 days |
| 229 Alexander Place | 4 | 6 | 4,431 | $4,250,000 | $959 | 14 days |
| 1150 Via Salerno | 4 | 6 | 3,850 | $4,195,000 | $1,089 | 394 days |
| 1600 Legion Drive | 5 | 6 | 4,483 | $3,795,000 | $846 | 42 days |
| 207 E Kings Way | 5 | 5 | 3,719 | $3,650,000 | $981 | 307 days |
| 1836 Whitehall Drive | 5 | 7 | 4,168 | $3,500,000 | $839 | 43 days |
| 2240 Venetian Way | 4 | 4 | 4,036 | $3,500,000 | $867 | 52 days |
| 649 N Park Avenue | 3 | 5 | 3,180 | $3,500,000 | $1,100 | 55 days |
| 1751 Glencoe Road | 5 | 7 | 4,520 | $3,390,000 | $750 | 265 days |
| 1627 Mizell Avenue | 5 | 6 | 3,421 | $3,300,000 | $964 | 71 days |
| 1581 Forest Avenue | 4 | 6 | 4,683 | $3,275,000 | $699 | 137 days |
| 1821 Englewood Road | 5 | 6 | 3,863 | $3,235,000 | $837 | 311 days |
| 660 W Morse Boulevard | 3 | 4 | 3,286 | $2,800,000 | $852 | 32 days |
| 413 W Morse Boulevard | 3 | 4 | 3,048 | $2,695,000 | $884 | 51 days |
| 541 W Canton Avenue | 4 | 4 | 3,553 | $2,650,000 | $745 | 128 days |
| 1754 Taylor Avenue | 5 | 5 | 3,670 | $2,569,999 | $700 | 19 days |
| 1823 Sunset Drive | 5 | 5 | 3,479 | $2,549,000 | $732 | 20 days |
| 450 Lakewood Drive | 5 | 6 | 4,572 | $2,500,000 | $546 | 87 days |
| 2228 Howard Drive | 4 | 4 | 3,294 | $2,460,000 | $746 | 75 days |
| 2838 Wright Avenue | 5 | 5 | 3,479 | $2,399,000 | $689 | 96 days |
| 140 E Morse Boulevard Unit J | 3 | 3 | 2,143 | $2,350,000 | $1,096 | 40 days |
| 1271 Palmer Avenue | 4 | 5 | 2,835 | $2,275,000 | $802 | 4 days |
| 240 N Phelps Avenue | 5 | 5 | 2,889 | $2,250,000 | $778 | 46 days |
| 926 Enclave Place | 5 | 5 | 4,150 | $2,235,000 | $538 | 68 days |
| 1750 Walnut Avenue | 4 | 5 | 3,691 | $2,195,000 | $594 | 17 days |
| 942 Enclave Place | 5 | 5 | 3,831 | $2,195,000 | $572 | 60 days |
| 1885 Temple Drive | 5 | 4 | 3,691 | $2,195,000 | $594 | 257 days |
| 946 Enclave Place | 5 | 5 | 3,989 | $2,175,000 | $545 | 60 days |
| 950 Enclave Place | 5 | 5 | 3,797 | $2,125,000 | $559 | 60 days |
| 147 S Interlachen Avenue Unit 202 | 3 | 5 | 3,272 | $2,100,000 | $641 | 177 days |
| 525 S Lakemont Avenue | 4 | 4 | 3,330 | $2,099,990 | $630 | 49 days |
| 938 Enclave Place | 5 | 5 | 3,865 | $2,099,000 | $543 | 68 days |
| 1398 Grove Terrace | 4 | 4 | 3,450 | $2,095,000 | $607 | 102 days |
| 930 Enclave Place | 5 | 5 | 3,813 | $2,050,000 | $537 | 74 days |
| 922 N Pennsylvania Avenue | 4 | 4 | 3,440 | $1,995,000 | $579 | 13 days |
| 910 Enclave Place | 5 | 5 | 3,620 | $1,899,000 | $524 | 74 days |
| 622 Penn Place | 3 | 4 | 2,767 | $1,895,000 | $684 | 67 days |
| 311 E Morse Boulevard Unit 1-3 | 2 | 2 | 2,304 | $1,895,000 | $822 | 80 days |
| 914 Enclave Place | 5 | 5 | 3,617 | $1,895,000 | $523 | 129 days |
| 2032 Kimbrace Place | 5 | 4 | 3,382 | $1,888,888 | $558 | 48 days |
| 721 Pansy Avenue | 4 | 4 | 2,653 | $1,850,000 | $697 | 130 days |
| Average: | 3.3 | 3.1 | 2,256 | $1,281,382 | $469 | 94 days |
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| Address | Beds | Baths | Living ft2 | List Price | Cost per ft2 | DOM |
|---|---|---|---|---|---|---|
| 405 Lakewood Drive | 4 | 3 | 4,208 | $6,700,000 | $1,592 | 0 days |
| 1660 Palmer Avenue | 5 | 7 | 6,406 | $4,950,000 | $772 | 438 days |
| 650 Dixie Parkway | 6 | 7 | 6,007 | $4,250,000 | $707 | 3 days |
| 150 Dana Way | 5 | 5 | 4,451 | $3,799,000 | $853 | 35 days |
| 1782 Pine Avenue | 5 | 7 | 4,782 | $3,697,000 | $773 | 122 days |
| 2905 Parkland Drive | 6 | 8 | 4,850 | $3,395,000 | $700 | 5 days |
| 1630 Lasbury Avenue | 5 | 5 | 4,917 | $2,750,000 | $559 | 49 days |
| 1529 Holts Grove Circle | 4 | 6 | 4,356 | $2,699,000 | $619 | 75 days |
| 426 Worthington Drive | 5 | 5 | 3,520 | $2,499,000 | $709 | 13 days |
| 1300 Mayfield Avenue | 5 | 6 | 4,389 | $2,490,000 | $567 | 88 days |
| 2412 Chantilly Avenue | 5 | 7 | 4,506 | $2,394,500 | $531 | 104 days |
| 1630 Elm Avenue | 5 | 5 | 3,408 | $2,385,000 | $699 | 16 days |
| 2361 Mulbry Drive | 4 | 4 | 3,130 | $2,249,000 | $718 | 77 days |
| 1130 Park North Place | 5 | 4 | 4,011 | $2,200,000 | $548 | 120 days |
| 2299 Via Tuscany | 4 | 4 | 3,986 | $2,150,000 | $539 | 230 days |
| 2261 Mulbry Drive | 4 | 3 | 3,696 | $1,995,000 | $539 | 28 days |
| 785 N Phelps Avenue | 5 | 4 | 2,964 | $1,900,000 | $641 | 98 days |
| 2625 Park Place Drive | 4 | 5 | 3,460 | $1,799,000 | $519 | 25 days |
| 2501 Lafayette Avenue | 4 | 4 | 2,819 | $1,795,000 | $636 | 14 days |
| 1113 Via Del Mar | 3 | 2 | 2,012 | $1,595,000 | $792 | 164 days |
| 1660 Walnut Avenue | 4 | 4 | 2,249 | $1,569,000 | $697 | 43 days |
| 1565 Forest Avenue | 4 | 2 | 2,163 | $1,495,000 | $691 | 79 days |
| 321 Sylvan Boulevard | 3 | 3 | 2,821 | $1,395,000 | $494 | 0 days |
| 1347 Chapman Circle | 4 | 4 | 2,922 | $1,395,000 | $477 | 5 days |
| 501 Lakeview Avenue | 4 | 5 | 3,253 | $1,390,000 | $427 | 367 days |
| 1298 Beachview Avenue | 1 | 1 | 1,665 | $1,375,000 | $825 | 0 days |
| 266 W Lyman Avenue | 3 | 3 | 2,000 | $1,375,000 | $687 | 4 days |
| 1778 Mondrian Circle | 3 | 4 | 2,377 | $1,339,000 | $563 | 4 days |
| 1600 Alabama Drive Unit 402 | 2 | 2 | 1,574 | $1,250,000 | $794 | 44 days |
| 1600 S Pennsylvania Avenue | 3 | 2 | 2,158 | $1,200,000 | $556 | 51 days |
| 1981 Blue Ridge Road | 4 | 2 | 2,750 | $1,150,000 | $418 | 73 days |
| 1768 Mondrian Circle | 3 | 4 | 2,193 | $1,099,000 | $501 | 101 days |
| 632 Country Club Drive | 3 | 2 | 2,342 | $1,050,000 | $448 | 338 days |
| 1725 Carollee Lane | 3 | 2 | 2,335 | $1,005,000 | $430 | 25 days |
| 1836 Grinnell Terrace | 3 | 2 | 1,907 | $999,000 | $523 | 146 days |
| 2823 Wright Avenue | 3 | 2 | 1,536 | $899,900 | $585 | 82 days |
| 1405 Miller Avenue | 3 | 3 | 1,884 | $899,000 | $477 | 67 days |
| 439 N Capen Avenue | 3 | 3 | 1,861 | $849,000 | $456 | 3 days |
| 938 Golfside Drive | 4 | 3 | 2,366 | $820,000 | $346 | 5 days |
| 729 Monmouth Way | 4 | 3 | 2,332 | $799,000 | $342 | 4 days |
| 1900 Winter Park Road | 4 | 2 | 1,511 | $799,000 | $528 | 77 days |
| 1871 Barker Drive | 3 | 3 | 2,231 | $779,000 | $349 | 8 days |
| 1826 Banchory Road | 4 | 3 | 2,391 | $779,000 | $325 | 0 days |
| 300 Carolina Avenue Unit 301 | 2 | 2 | 1,305 | $739,000 | $566 | 9 days |
| 770 W Webster Avenue | 4 | 2 | 1,008 | $725,000 | $719 | 281 days |
| 1622 Arbor Park Drive | 3 | 2 | 1,351 | $695,000 | $514 | 14 days |
| 2157 Lake Drive | 3 | 3 | 2,124 | $689,000 | $324 | 34 days |
| 1037 N Virginia Avenue | 3 | 1 | 1,101 | $649,000 | $589 | 28 days |
| 2504 Forfarshire Drive | 3 | 2 | 1,915 | $630,000 | $328 | 5 days |
| 2652 Abbey Road | 5 | 2 | 1,938 | $625,000 | $322 | 7 days |
| Average: | 3.3 | 2.9 | 2,239 | $1,179,321 | $450 | 69 days |
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| Address | Beds | Baths | Living ft2 | List Price | Sold Price | Cost per ft2 | DOM | Sold Date |
|---|---|---|---|---|---|---|---|---|
| 2203 Via Tuscany | 6 | 9 | 12,190 | $12,900,000 | $12,900,000 | $1,058 | 4 days | 2/24/26 |
| 1821 Pinetree Road | 5 | 7 | 5,006 | $6,997,000 | $6,997,000 | $1,397 | 5 days | 5/15/26 |
| 1400 Alabama Drive | 5 | 9 | 7,916 | $5,895,000 | $5,895,000 | $744 | 340 days | 2/27/26 |
| 1221 Richmond Road | 5 | 6 | 5,164 | $4,995,000 | $4,995,000 | $967 | 3 days | 6/24/26 |
| 1302 Raintree Place | 5 | 6 | 4,738 | $4,995,000 | $4,995,000 | $1,054 | 182 days | 5/15/26 |
| 1701 Summerland Avenue | 5 | 6 | 5,253 | $4,550,000 | $4,550,000 | $866 | 0 days | 6/5/26 |
| 1521 Harris Circle | 4 | 5 | 3,922 | $4,500,000 | $4,500,000 | $1,147 | 0 days | 5/29/26 |
| 887 Georgia Avenue | 6 | 6 | 5,759 | $5,000,000 | $5,000,000 | $868 | 222 days | 4/30/26 |
| 1760 Via Venetia | 4 | 7 | 6,242 | $4,650,000 | $4,650,000 | $744 | 19 days | 5/29/26 |
| 1336 College Point | 4 | 5 | 3,181 | $4,595,000 | $4,595,000 | $1,444 | 109 days | 6/1/26 |
| 702 Via Bella | 4 | 6 | 3,720 | $4,250,000 | $4,250,000 | $1,142 | 149 days | 2/18/26 |
| 2020 Via Tuscany | 4 | 5 | 4,665 | $4,195,000 | $4,195,000 | $899 | 4 days | 5/18/26 |
| 1161 Valencia Avenue | 4 | 5 | 4,181 | $3,995,000 | $3,995,000 | $955 | 311 days | 7/17/26 |
| 637 N Park Avenue | 3 | 5 | 4,237 | $3,895,000 | $3,895,000 | $919 | 24 days | 2/24/26 |
| 1117 Kenwood Avenue | 4 | 5 | 4,353 | $3,978,900 | $3,978,900 | $914 | 42 days | 6/17/26 |
| 1820 Glencoe Road | 5 | 7 | 4,055 | $3,825,000 | $3,825,000 | $943 | 209 days | 2/17/26 |
| 700 Pinetree Road | 4 | 5 | 3,897 | $3,295,000 | $3,295,000 | $845 | 1 day | 5/20/26 |
| 1811 Oneco Avenue | 5 | 6 | 4,508 | $3,275,000 | $3,275,000 | $726 | 0 days | 7/23/26 |
| 1910 Glencoe Road | 4 | 6 | 3,788 | $3,290,000 | $3,290,000 | $868 | 15 days | 6/29/26 |
| 611 Williams Drive | 5 | 5 | 4,686 | $2,995,000 | $2,995,000 | $639 | 6 days | 4/13/26 |
| 141 Glenridge Way | 5 | 5 | 5,243 | $3,250,000 | $3,250,000 | $619 | 49 days | 7/6/26 |
| 1351 Magnolia Avenue | 5 | 5 | 3,460 | $3,100,000 | $3,100,000 | $895 | 0 days | 7/22/26 |
| 2040 Randall Circle | 5 | 6 | 4,636 | $3,350,000 | $3,350,000 | $722 | 74 days | 6/29/26 |
| 473 Fletcher Place | 5 | 6 | 4,296 | $3,250,000 | $3,250,000 | $756 | 91 days | 5/15/26 |
| 516 Henkel Circle | 5 | 6 | 4,143 | $3,350,000 | $3,350,000 | $808 | 125 days | 3/24/26 |
| 1724 Pine Avenue | 3 | 5 | 4,425 | $3,095,000 | $3,095,000 | $699 | 6 days | 7/15/26 |
| 670 Williams Drive | 5 | 5 | 4,091 | $2,895,000 | $2,895,000 | $707 | 18 days | 6/25/26 |
| 151 Oakwood Way | 4 | 5 | 4,129 | $2,850,000 | $2,850,000 | $690 | 113 days | 6/18/26 |
| 135 W Swoope Avenue | 3 | 3 | 2,667 | $2,540,000 | $2,540,000 | $952 | 7 days | 5/12/26 |
| 1401 Green Cove Road | 3 | 7 | 5,483 | $2,900,000 | $2,900,000 | $528 | 99 days | 3/31/26 |
| 185 Sylvan Boulevard | 4 | 5 | 3,138 | $2,590,000 | $2,590,000 | $825 | 105 days | 3/6/26 |
| 2015 N Park Avenue | 5 | 5 | 3,963 | $2,295,000 | $2,295,000 | $579 | 74 days | 6/2/26 |
| 660 Osceola Avenue Unit 101 | 3 | 4 | 2,714 | $2,195,000 | $2,195,000 | $808 | 145 days | 4/17/26 |
| 2550 Venetian Way | 4 | 5 | 5,051 | $2,399,000 | $2,399,000 | $474 | 63 days | 6/16/26 |
| 2722 Eastern Parkway | 5 | 5 | 3,334 | $2,289,000 | $2,289,000 | $686 | 105 days | 5/21/26 |
| 230 E Rockwood Way | 5 | 4 | 3,374 | $2,189,000 | $2,189,000 | $648 | 5 days | 7/20/26 |
| 800 Juanita Rael | 5 | 4 | 4,021 | $2,300,000 | $2,300,000 | $571 | 56 days | 7/14/26 |
| 2503 Versailles Avenue | 5 | 4 | 4,026 | $2,184,000 | $2,184,000 | $542 | 138 days | 6/11/26 |
| 2423 Via Sienna | 4 | 4 | 3,472 | $2,200,000 | $2,200,000 | $633 | 35 days | 6/26/26 |
| 1636 Elizabeths Walk | 4 | 5 | 3,412 | $2,195,000 | $2,195,000 | $643 | 29 days | 6/18/26 |
| 872 Granville Drive | 4 | 4 | 3,195 | $2,200,000 | $2,200,000 | $688 | 5 days | 5/28/26 |
| 1711 Barcelona Way | 5 | 3 | 3,669 | $2,100,000 | $2,100,000 | $572 | 92 days | 6/15/26 |
| 1624 Barcelona Way | 3 | 3 | 3,818 | $2,235,000 | $2,235,000 | $585 | 211 days | 7/24/26 |
| 311 E Morse Boulevard Unit 2 - 5 | 2 | 2 | 1,900 | $2,100,000 | $2,100,000 | $1,105 | 101 days | 5/21/26 |
| 501 Henkel Circle | 5 | 5 | 3,746 | $1,825,000 | $1,825,000 | $487 | 4 days | 4/10/26 |
| 1760 Alabama Drive | 4 | 3 | 2,841 | $2,198,000 | $2,198,000 | $773 | 75 days | 6/3/26 |
| 319 Santiago Drive | 4 | 5 | 3,515 | $1,990,000 | $1,990,000 | $566 | 104 days | 2/20/26 |
| 543 E Lake Sue Avenue | 4 | 5 | 3,657 | $1,875,000 | $1,875,000 | $512 | 3 days | 6/5/26 |
| 1540 Palm Avenue | 5 | 4 | 3,423 | $1,999,000 | $1,999,000 | $583 | 158 days | 3/26/26 |
| 1713 Elizabeths Walk | 4 | 4 | 3,670 | $1,850,000 | $1,850,000 | $504 | 0 days | 4/15/26 |
| Average: | 3.2 | 2.8 | 2,089 | $1,050,881 | $1,012,553 | $405 | 60 days | |
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