Winter Park, FL Real Estate Market Report: Price Trends and Data Analysis

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Active Properties
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
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
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
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
1133 Bella Lago Cove 3 2 1,765 $2,100,000 $1,189 12 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
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
281 Brewer Avenue 5 5 4,029 $1,800,000 $446 7 days
723 Symonds Avenue 4 4 3,065 $1,800,000 $587 60 days
4469 Old Bear Run 5 5 4,288 $1,799,999 $419 168 days
621 Huntington Avenue 3 4 2,399 $1,795,000 $748 118 days
1750 Carollee Lane 4 4 3,249 $1,780,000 $547 129 days
Average: 3.8 3.3 2,546 $1,408,058 $486 84 days
Viewing 1 - 50 of 198
Viewing 1 - 50 of 198
Properties Under Contract
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
1434 Via Sangro Pl 4 3 3,063 $1,300,000 $424 0 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
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
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
2222 Marsh Sedge Lane 4 3 2,192 $739,000 $337 323 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
1908 Cyril Court 4 3 2,471 $639,000 $258 16 days
2504 Forfarshire Drive 3 2 1,915 $630,000 $328 5 days
2087 Laurelwood Way 4 2 1,920 $625,000 $325 14 days
2652 Abbey Road 5 2 1,938 $625,000 $322 7 days
1830 Edwin Boulevard 3 2 1,287 $625,000 $485 84 days
216 Blossom Lane 4 2 1,933 $624,900 $323 3 days
Average: 3.7 3.0 2,378 $1,201,625 $445 59 days
Viewing 1 - 50 of 84
Viewing 1 - 50 of 84
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
1308 Green Cove 4 6 6,981 $6,300,000 $6,300,000 $902 0 days 11/4/25
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
1400 Alabama Drive 5 9 7,916 $5,895,000 $5,400,000 $682 340 days 2/27/26
1155 Woodmere Drive 5 6 5,051 $5,295,000 $5,250,000 $1,039 0 days 10/6/25
1333 Alberta Drive 3 4 3,738 $5,750,000 $5,225,000 $1,397 6 days 8/15/25
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
641 Bonita Drive 5 6 6,699 $5,000,000 $4,800,000 $716 0 days 1/2/26
765 Via Lugano 4 5 4,319 $4,795,000 $4,772,500 $1,105 1 day 9/18/25
1302 Raintree Place 5 6 4,738 $4,995,000 $4,720,000 $996 182 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 $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
2161 Sharon Road 5 7 6,338 $4,650,000 $4,430,000 $698 247 days 10/9/25
1760 Via Venetia 4 7 6,242 $4,650,000 $4,300,000 $688 19 days 5/29/26
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
421 Lakewood Drive 5 9 5,847 $4,500,000 $4,087,500 $699 610 days 8/20/25
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
1117 Kenwood Avenue 4 5 4,353 $3,978,900 $3,755,000 $862 42 days 6/17/26
1820 Glencoe Road 5 7 4,055 $3,825,000 $3,600,000 $887 209 days 2/17/26
2171 Forrest Road 5 6 4,565 $3,595,000 $3,485,000 $763 134 days 10/17/25
641 Virginia Drive 4 3 3,223 $3,250,000 $3,350,000 $1,039 1 day 8/20/25
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
1610 Oakhurst Avenue 5 7 4,255 $3,275,000 $3,200,000 $752 3 days 10/20/25
141 S Phelps Avenue 6 6 5,878 $3,595,000 $3,200,000 $544 63 days 7/31/25
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
1820 Englewood Road 5 6 4,263 $3,190,000 $3,020,000 $708 70 days 10/2/25
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
1730 Winchester Drive 5 6 4,080 $3,150,000 $3,000,000 $735 313 days 8/18/25
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
1891 Lake Spier Drive 5 4 3,932 $2,999,000 $2,800,000 $712 57 days 8/14/25
1074 Mckean Circle 4 3 3,258 $2,895,000 $2,798,000 $858 7 days 9/19/25
670 Williams Drive 5 5 4,091 $2,895,000 $2,755,000 $673 18 days 6/25/26
151 Oakwood Way 4 5 4,129 $2,850,000 $2,750,000 $666 113 days 6/18/26
1445 Holts Grove 5 5 4,489 $2,650,000 $2,700,000 $601 2 days 10/2/25
Average: 3.6 2.9 2,336 $1,068,367 $1,032,710 $391 57 days
Viewing 1 - 50 of 699
Viewing 1 - 50 of 699