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Winter Park, FL Real Estate Market Report: Price Trends and Data Analysis
| Active Properties | ||||||
|---|---|---|---|---|---|---|
| Address | Beds | Baths | Living ft2 | List Price | Cost per ft2 | DOM |
| 901 Golfview Terrace | 5 | 6 | 5,479 | $6,995,000 | $1,276 | 38 days |
| 1260 Alabama Drive | 6 | 7 | 6,396 | $6,900,000 | $1,078 | 237 days |
| 698 N New York Avenue | 5 | 6 | 5,096 | $6,195,000 | $1,215 | 32 days |
| 1011 Mckean Circle | 5 | 7 | 4,806 | $6,000,000 | $1,248 | 10 days |
| 1571 Woodland Avenue | 5 | 8 | 7,397 | $6,000,000 | $811 | 150 days |
| 2228 Azalea Place | 5 | 6 | 5,152 | $5,600,000 | $1,086 | 121 days |
| 1166 Palmer Avenue | 5 | 7 | 5,181 | $5,500,000 | $1,061 | 39 days |
| 2661 Via Tuscany | 4 | 5 | 3,880 | $5,500,000 | $1,417 | 47 days |
| 825 Palmer Avenue | 5 | 7 | 5,122 | $5,195,900 | $1,014 | 45 days |
| 231 Chelton Circle | 4 | 7 | 5,550 | $4,700,000 | $846 | 138 days |
| 617 N Interlachen Avenue | 11 | 8 | 3,615 | $4,695,000 | $1,298 | 7 days |
| 1631 Hillcrest Avenue | 5 | 6 | 4,754 | $4,500,000 | $946 | 4 days |
| 857 Brock Street | 5 | 6 | 4,827 | $4,350,000 | $901 | 77 days |
| 702 Via Bella | 4 | 6 | 3,720 | $4,250,000 | $1,142 | 41 days |
| 540 N Pennsylvania Avenue | 4 | 2 | 1,652 | $3,950,000 | $2,391 | 42 days |
| 620 Virginia Drive | 6 | 5 | 4,677 | $3,890,000 | $831 | 74 days |
| 2622 Lake Howell Lane | 4 | 3 | 3,377 | $3,750,000 | $1,110 | 74 days |
| 276 Detmar Drive | 4 | 5 | 4,202 | $3,600,000 | $856 | 62 days |
| 1441 Cardinal Court | 4 | 6 | 4,066 | $3,600,000 | $885 | 194 days |
| 1742 Temple Drive | 4 | 5 | 3,658 | $3,545,995 | $969 | 36 days |
| 2240 Venetian Way | 4 | 4 | 4,036 | $3,500,000 | $867 | 143 days |
| 1600 Legion Drive | 5 | 6 | 4,483 | $3,495,000 | $779 | 7 days |
| 662 Granville Drive | 5 | 6 | 4,478 | $3,495,000 | $780 | 38 days |
| 1751 Glencoe Road | 5 | 7 | 4,520 | $3,390,000 | $750 | 12 days |
| 1761 Legion Drive | 5 | 6 | 4,949 | $3,265,000 | $659 | 61 days |
| 2823 Parkland Circle | 5 | 6 | 4,459 | $3,250,000 | $728 | 18 days |
| 1825 Whitehall Drive | 4 | 6 | 4,311 | $3,195,000 | $741 | 5 days |
| 2119 Howard Drive | 5 | 6 | 4,139 | $3,195,000 | $771 | 25 days |
| 1836 Whitehall Drive | 5 | 7 | 4,168 | $2,995,000 | $718 | 134 days |
| 532 Langholm Drive | 5 | 5 | 4,050 | $2,990,000 | $738 | 33 days |
| 1821 Englewood Road | 5 | 6 | 3,863 | $2,950,000 | $763 | 402 days |
| 1773 Walnut Avenue | 5 | 5 | 3,784 | $2,725,000 | $720 | 45 days |
| 648 Worthington Drive | 5 | 5 | 3,588 | $2,700,000 | $752 | 73 days |
| 1681 Woodland Avenue | 5 | 5 | 3,682 | $2,629,000 | $714 | 7 days |
| 1823 Sunset Drive | 5 | 5 | 3,479 | $2,549,000 | $732 | 111 days |
| 1760 Oakhurst Avenue | 5 | 5 | 3,700 | $2,500,000 | $675 | 14 days |
| 450 Lakewood Drive | 5 | 6 | 4,572 | $2,500,000 | $546 | 178 days |
| 938 Enclave Place | 5 | 5 | 3,865 | $2,300,000 | $595 | 159 days |
| 1840 Laurel Road | 5 | 5 | 2,868 | $2,299,000 | $801 | 90 days |
| 930 Enclave Place | 5 | 5 | 3,813 | $2,275,000 | $596 | 165 days |
| 1803 Barker Drive | 4 | 3 | 3,463 | $2,190,000 | $632 | 41 days |
| 918 Enclave Place | 5 | 5 | 3,713 | $2,125,000 | $572 | 24 days |
| 1271 Palmer Avenue | 4 | 5 | 2,850 | $2,125,000 | $745 | 40 days |
| 555 E Lake Sue Avenue | 4 | 4 | 3,776 | $2,095,000 | $554 | 32 days |
| 1951 Winter Park Road | 4 | 4 | 3,479 | $2,089,000 | $600 | 33 days |
| 914 Enclave Place | 5 | 5 | 3,617 | $2,070,000 | $572 | 220 days |
| 1133 Bella Lago Cove | 3 | 2 | 1,765 | $1,999,900 | $1,133 | 103 days |
| 240 N Phelps Avenue | 5 | 5 | 2,889 | $1,999,900 | $692 | 137 days |
| 2007 Edwin Boulevard | 4 | 4 | 3,314 | $1,995,000 | $601 | 28 days |
| 513 Dunraven Drive | 5 | 5 | 3,560 | $1,950,000 | $547 | 28 days |
| Average: | 3.9 | 3.4 | 2,585 | $1,462,034 | $499 | 89 days |
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| Properties Under Contract | ||||||
|---|---|---|---|---|---|---|
| Address | Beds | Baths | Living ft2 | List Price | Cost per ft2 | DOM |
| 1525 Granville Drive | 5 | 6 | 5,211 | $4,595,000 | $881 | 63 days |
| 160 W Rockwood Way | 5 | 6 | 4,015 | $3,395,000 | $845 | 41 days |
| 609 S Phelps Avenue | 5 | 5 | 4,018 | $2,800,000 | $696 | 151 days |
| 1754 Taylor Avenue | 5 | 5 | 3,670 | $2,569,999 | $700 | 82 days |
| 2812 Mulford Avenue | 5 | 6 | 3,656 | $2,495,000 | $682 | 0 days |
| 541 W Canton Avenue | 4 | 4 | 3,553 | $2,495,000 | $702 | 198 days |
| 2228 Howard Drive | 4 | 4 | 3,294 | $2,460,000 | $746 | 120 days |
| 2412 Chantilly Avenue | 5 | 7 | 4,506 | $2,394,500 | $531 | 104 days |
| 645 Pansy Avenue | 4 | 5 | 3,661 | $2,390,000 | $652 | 27 days |
| 304 Santiago Drive | 5 | 5 | 4,213 | $2,195,000 | $521 | 2 days |
| 1885 Temple Drive | 5 | 4 | 3,691 | $2,195,000 | $594 | 316 days |
| 525 S Lakemont Avenue | 4 | 4 | 3,330 | $1,999,990 | $600 | 61 days |
| 1702 Arbor Park Drive | 4 | 4 | 2,950 | $1,900,000 | $644 | 24 days |
| 2501 Lafayette Avenue | 4 | 4 | 2,819 | $1,795,000 | $636 | 75 days |
| 1225 Sharon Place | 5 | 4 | 3,097 | $1,749,000 | $564 | 5 days |
| 1420 Magnolia Avenue | 4 | 4 | 3,174 | $1,690,000 | $532 | 102 days |
| 341 E Reading Way | 4 | 4 | 3,723 | $1,525,000 | $409 | 99 days |
| 1581 Magnolia Ave | 4 | 4 | 2,642 | $1,425,000 | $539 | 134 days |
| 952 Moss Lane | 4 | 5 | 3,474 | $1,319,950 | $379 | 17 days |
| 1600 S Pennsylvania Avenue | 3 | 2 | 2,158 | $1,150,000 | $532 | 143 days |
| 2667 Cochise Trail | 4 | 3 | 2,868 | $985,000 | $343 | 76 days |
| 870 N Phelps Avenue | 4 | 3 | 2,301 | $850,000 | $369 | 10 days |
| 2286 Marsh Sedge Lane | 4 | 3 | 2,192 | $770,000 | $351 | 52 days |
| 1592 Arbor Park Drive | 4 | 3 | 2,016 | $700,000 | $347 | 12 days |
| 2157 Lake Drive | 3 | 3 | 2,124 | $689,000 | $324 | 111 days |
| 433 Gilbert Road | 3 | 2 | 1,800 | $669,900 | $372 | 78 days |
| 2833 Prince John Road | 4 | 2 | 1,605 | $669,000 | $416 | 51 days |
| 943 Fairway Drive | 4 | 3 | 2,067 | $650,000 | $314 | 62 days |
| 1409 Sunset Drive | 2 | 2 | 1,107 | $649,000 | $586 | 30 days |
| 2825 Mulford Avenue | 2 | 2 | 1,249 | $629,000 | $503 | 5 days |
| 1416 Border Drive | 3 | 1 | 1,243 | $620,000 | $498 | 53 days |
| 1409 Aster Court | 4 | 2 | 2,050 | $589,900 | $287 | 5 days |
| 8113 Lazy Bear Lane | 4 | 3 | 2,267 | $585,000 | $258 | 3 days |
| 346 Elkhorn Court | 4 | 2 | 1,891 | $575,000 | $304 | 4 days |
| 1931 Aster Drive | 3 | 3 | 2,031 | $575,000 | $283 | 4 days |
| 5233 Lake Howell Road | 4 | 3 | 1,778 | $562,000 | $316 | 53 days |
| 333 Cornwall Road | 4 | 2 | 1,660 | $549,900 | $331 | 151 days |
| 510 Fitzwalter Drive | 3 | 2 | 1,385 | $530,000 | $382 | 5 days |
| 2174 Shadyhill Terrace | 4 | 2 | 1,983 | $529,900 | $267 | 3 days |
| 2211 King Richards Court | 4 | 2 | 1,845 | $529,000 | $286 | 50 days |
| 525 Ololu Drive | 3 | 3 | 1,786 | $490,900 | $274 | 171 days |
| 5334 Lanyard Court | 3 | 2 | 1,561 | $479,900 | $307 | 6 days |
| 1211 Schultz Avenue | 3 | 2 | 1,085 | $475,000 | $437 | 12 days |
| 2824 Prince John Road | 2 | 2 | 1,438 | $475,000 | $330 | 39 days |
| 3641 Hawthorne Lane | 3 | 2 | 1,622 | $449,990 | $277 | 81 days |
| 1320 Buckingham Road | 3 | 2 | 1,388 | $449,000 | $323 | 6 days |
| 3150 Shady Pine Avenue | 4 | 2 | 1,624 | $439,900 | $270 | 5 days |
| 1818 Dover Road | 3 | 2 | 1,873 | $439,900 | $234 | 3 days |
| 7640 Village Green Dr | 3 | 2 | 1,631 | $439,000 | $269 | 13 days |
| 259 Orange Terrace Drive | 3 | 2 | 1,248 | $439,000 | $351 | 112 days |
| Average: | 3.7 | 3.1 | 2,330 | $1,135,044 | $433 | 62 days |
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| Sold Properties | ||||||||
|---|---|---|---|---|---|---|---|---|
| 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 | $13,000,000 | $1,066 | 4 days | 2/24/26 |
| 1821 Pinetree Road | 5 | 7 | 5,006 | $6,997,000 | $7,164,000 | $1,431 | 5 days | 5/15/26 |
| 1120 Preserve Point Drive | 7 | 11 | 11,255 | $8,950,000 | $7,000,000 | $621 | 309 days | 8/28/26 |
| 405 Lakewood Drive | 4 | 3 | 4,208 | $6,700,000 | $6,500,000 | $1,544 | 0 days | 7/31/26 |
| 1308 Green Cove | 4 | 6 | 6,981 | $6,300,000 | $6,300,000 | $902 | 0 days | 11/4/25 |
| 550 Palmer Avenue | 5 | 7 | 5,939 | $6,495,000 | $6,200,000 | $1,043 | 285 days | 8/21/26 |
| 1860 Summerland Avenue | 5 | 6 | 5,022 | $5,675,000 | $6,111,000 | $1,216 | 8 days | 12/5/25 |
| 374 Henkel Circle | 5 | 6 | 4,735 | $5,700,000 | $5,700,000 | $1,203 | 0 days | 10/30/25 |
| 1530 Alabama Drive | 5 | 4 | 3,680 | $5,900,000 | $5,600,000 | $1,521 | 0 days | 10/2/26 |
| 2025 Summerland Avenue | 5 | 5 | 4,432 | $5,295,000 | $5,410,000 | $1,220 | 0 days | 9/2/26 |
| 1400 Alabama Drive | 5 | 9 | 7,916 | $5,895,000 | $5,400,000 | $682 | 340 days | 2/27/26 |
| 1221 Richmond Road | 5 | 6 | 5,164 | $4,995,000 | $5,125,000 | $992 | 3 days | 6/24/26 |
| 1240 Harding Street | 5 | 6 | 6,708 | $5,999,000 | $5,125,000 | $764 | 17 days | 11/7/25 |
| 1660 Palmer Avenue | 5 | 7 | 5,636 | $4,950,000 | $4,950,000 | $878 | 520 days | 7/30/26 |
| 641 Bonita Drive | 5 | 6 | 6,699 | $5,000,000 | $4,800,000 | $716 | 0 days | 1/2/26 |
| 1302 Raintree Place | 5 | 6 | 4,738 | $4,995,000 | $4,720,000 | $996 | 182 days | 5/15/26 |
| 2525 Temple Drive | 5 | 5 | 4,542 | $4,750,000 | $4,650,000 | $1,023 | 9 days | 10/5/26 |
| 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 | $4,500,000 | $781 | 222 days | 4/30/26 |
| 1812 Stonehurst Road | 5 | 7 | 5,160 | $4,450,000 | $4,450,000 | $862 | 0 days | 12/23/25 |
| 1760 Via Venetia | 4 | 7 | 6,242 | $4,650,000 | $4,300,000 | $688 | 19 days | 5/29/26 |
| 650 Dixie Parkway | 6 | 7 | 6,007 | $4,250,000 | $4,250,000 | $707 | 3 days | 7/24/26 |
| 1336 College Point | 4 | 5 | 3,181 | $4,595,000 | $4,250,000 | $1,336 | 109 days | 6/1/26 |
| 702 Via Bella | 4 | 6 | 3,720 | $4,250,000 | $4,150,000 | $1,115 | 149 days | 2/18/26 |
| 229 Alexander Place | 4 | 6 | 4,431 | $4,250,000 | $4,000,000 | $902 | 64 days | 10/7/26 |
| 1180 Via Lugano | 5 | 6 | 4,961 | $4,900,000 | $4,000,000 | $806 | 47 days | 9/14/26 |
| 2020 Via Tuscany | 4 | 5 | 4,665 | $4,195,000 | $3,978,550 | $852 | 4 days | 5/18/26 |
| 1161 Valencia Avenue | 4 | 5 | 4,181 | $3,995,000 | $3,965,000 | $948 | 311 days | 7/17/26 |
| 1417 Williams Drive | 5 | 6 | 4,891 | $3,999,000 | $3,925,000 | $802 | 6 days | 9/25/26 |
| 1117 Kenwood Avenue | 4 | 5 | 4,353 | $3,978,900 | $3,755,000 | $862 | 42 days | 6/17/26 |
| 150 Dana Way | 5 | 5 | 4,451 | $3,799,000 | $3,675,000 | $825 | 35 days | 7/30/26 |
| 1820 Glencoe Road | 5 | 7 | 4,055 | $3,825,000 | $3,600,000 | $887 | 209 days | 2/17/26 |
| 1150 Via Salerno | 4 | 6 | 3,826 | $3,750,000 | $3,550,000 | $927 | 427 days | 10/14/26 |
| 1782 Pine Avenue | 5 | 7 | 4,782 | $3,697,000 | $3,500,000 | $731 | 122 days | 7/30/26 |
| 2905 Parkland Drive | 6 | 8 | 4,850 | $3,395,000 | $3,443,500 | $710 | 5 days | 8/17/26 |
| 1391 Richmond Road | 4 | 6 | 4,635 | $3,325,000 | $3,325,000 | $717 | 375 days | 12/5/25 |
| 700 Pinetree Road | 4 | 5 | 3,897 | $3,295,000 | $3,278,530 | $841 | 1 day | 5/20/26 |
| 1811 Oneco Avenue | 5 | 6 | 4,508 | $3,275,000 | $3,275,000 | $726 | 0 days | 7/23/26 |
| 1900 W Fawsett Road | 4 | 5 | 4,600 | $3,350,000 | $3,200,000 | $695 | 6 days | 11/4/25 |
| 1910 Glencoe Road | 4 | 6 | 3,788 | $3,290,000 | $3,150,000 | $831 | 15 days | 6/29/26 |
| 611 Williams Drive | 5 | 5 | 4,686 | $2,995,000 | $3,100,001 | $661 | 6 days | 4/13/26 |
| 141 Glenridge Way | 5 | 5 | 5,243 | $3,250,000 | $3,100,000 | $591 | 49 days | 7/6/26 |
| 1351 Magnolia Avenue | 5 | 5 | 3,460 | $3,100,000 | $3,000,000 | $867 | 0 days | 7/22/26 |
| 2040 Randall Circle | 5 | 6 | 4,636 | $3,350,000 | $3,000,000 | $647 | 74 days | 6/29/26 |
| 473 Fletcher Place | 5 | 6 | 4,296 | $3,250,000 | $3,000,000 | $698 | 91 days | 5/15/26 |
| 1597 Oakhurst Avenue | 5 | 5 | 4,410 | $2,699,000 | $2,925,000 | $663 | 2 days | 9/16/26 |
| 516 Henkel Circle | 5 | 6 | 4,143 | $3,350,000 | $2,925,000 | $706 | 125 days | 3/24/26 |
| 1724 Pine Avenue | 3 | 5 | 4,425 | $3,095,000 | $2,875,000 | $649 | 6 days | 7/15/26 |
| 255 Stirling Avenue | 4 | 4 | 3,635 | $3,100,000 | $2,835,000 | $779 | 25 days | 11/24/25 |
| Average: | 3.6 | 2.9 | 2,335 | $1,106,265 | $1,066,826 | $399 | 56 days | |
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