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
40 Palmer Avenue 5 6 5,905 $7,250,000 $1,227 213 days
1260 Alabama Drive 6 7 6,396 $6,900,000 $1,078 191 days
1571 Woodland Avenue 5 8 7,397 $6,000,000 $811 104 days
2661 Via Tuscany 4 5 3,880 $5,999,990 $1,546 1 day
2228 Azalea Place 5 6 5,152 $5,600,000 $1,086 75 days
313 Sylvan Drive 4 5 4,775 $5,500,000 $1,151 87 days
231 Chelton Circle 4 7 5,550 $4,950,000 $891 92 days
857 Brock Street 5 6 4,827 $4,650,000 $963 31 days
1525 Granville Drive 5 6 5,211 $4,595,000 $881 41 days
229 Alexander Place 4 6 4,431 $4,250,000 $959 59 days
1441 Cardinal Court 4 6 4,066 $3,995,000 $982 148 days
620 Virginia Drive 6 5 4,677 $3,890,000 $831 28 days
207 E Kings Way 5 5 3,719 $3,650,000 $981 352 days
276 Detmar Drive 4 5 4,202 $3,600,000 $856 16 days
2240 Venetian Way 4 4 4,036 $3,500,000 $867 97 days
160 W Rockwood Way 5 6 4,015 $3,395,000 $845 0 days
1627 Mizell Avenue 5 6 3,421 $3,300,000 $964 116 days
1581 Forest Avenue 4 6 4,683 $3,275,000 $699 182 days
1761 Legion Drive 5 6 4,924 $3,265,000 $663 15 days
361 E Kings Way 4 5 3,737 $3,199,000 $856 38 days
1821 Englewood Road 5 6 3,863 $3,075,000 $796 356 days
1836 Whitehall Drive 5 7 4,168 $2,995,000 $718 88 days
648 Worthington Drive 5 5 3,588 $2,700,000 $752 27 days
541 W Canton Avenue 4 4 3,553 $2,650,000 $745 173 days
1754 Taylor Avenue 5 5 3,670 $2,569,999 $700 64 days
1823 Sunset Drive 5 5 3,479 $2,549,000 $732 65 days
450 Lakewood Drive 5 6 4,572 $2,500,000 $546 132 days
926 Enclave Place 5 5 4,150 $2,475,000 $596 113 days
2228 Howard Drive 4 4 3,294 $2,460,000 $746 120 days
946 Enclave Place 5 5 3,989 $2,375,000 $595 105 days
938 Enclave Place 5 5 3,865 $2,300,000 $595 113 days
1840 Laurel Road 5 5 2,868 $2,299,000 $801 44 days
930 Enclave Place 5 5 3,813 $2,275,000 $596 119 days
1885 Temple Drive 5 4 3,691 $2,195,000 $594 302 days
1133 Bella Lago Cove 3 2 1,765 $2,100,000 $1,189 57 days
914 Enclave Place 5 5 3,617 $2,070,000 $572 174 days
240 N Phelps Avenue 5 5 2,889 $2,050,000 $709 91 days
525 S Lakemont Avenue 4 4 3,330 $1,999,990 $600 42 days
922 N Pennsylvania Avenue 4 4 3,440 $1,995,000 $579 58 days
751 Pansy Avenue 3 4 2,703 $1,950,000 $721 15 days
1420 Aloma Avenue 3 4 2,422 $1,949,500 $804 34 days
1702 Arbor Park Drive 4 4 2,950 $1,900,000 $644 9 days
2343 Versailles Avenue 4 4 3,307 $1,865,000 $563 28 days
1550 Palm Avenue 4 4 2,706 $1,829,000 $675 16 days
281 Brewer Avenue 5 5 4,029 $1,800,000 $446 52 days
2032 Kimbrace Place 5 4 3,382 $1,800,000 $532 93 days
1750 Carollee Lane 4 4 3,249 $1,780,000 $547 174 days
621 Huntington Avenue 3 4 2,399 $1,770,000 $737 163 days
1840 Anzle Avenue 4 3 2,350 $1,750,000 $744 237 days
2525 Lafayette Avenue 4 4 2,715 $1,749,000 $644 44 days
Average: 3.8 3.3 2,485 $1,358,263 $491 89 days
Viewing 1 - 50 of 219
Viewing 1 - 50 of 219
Properties Under Contract
Address Beds Baths Living ft2 List Price Cost per ft2 DOM
1180 Via Lugano 5 6 4,961 $4,900,000 $987 47 days
2525 Temple Drive 5 5 4,542 $4,750,000 $1,045 9 days
1417 Williams Drive 5 6 4,891 $3,999,000 $817 6 days
1150 Via Salerno 4 6 3,826 $3,750,000 $980 427 days
609 S Phelps Avenue 5 5 4,018 $2,800,000 $696 151 days
948 Poinciana Lane 4 5 3,676 $2,750,000 $748 6 days
1597 Oakhurst Avenue 5 5 4,410 $2,699,000 $612 2 days
2812 Mulford Avenue 5 6 3,656 $2,495,000 $682 0 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
1630 Elm Avenue 5 5 3,408 $2,385,000 $699 16 days
1661 Laurel Road 3 3 3,127 $1,875,000 $599 7 days
631 Williams Drive 4 4 2,972 $1,824,000 $613 1 day
4469 Old Bear Run 5 5 4,288 $1,799,999 $419 170 days
1230 Sunset Drive 4 4 3,250 $1,795,000 $552 4 days
2501 Lafayette Avenue 4 4 2,819 $1,795,000 $636 75 days
890 N Phelps Avenue 4 5 3,630 $1,775,000 $488 8 days
2501 Winter Park Road 5 4 3,304 $1,649,000 $499 181 days
607 Ellen Drive 4 5 2,812 $1,389,500 $494 294 days
1434 Via Sangro Pl 4 3 3,063 $1,300,000 $424 0 days
802 Hamilton Place Court 4 4 2,843 $1,295,000 $455 124 days
1870 Walker Avenue 3 3 2,046 $1,199,000 $586 161 days
632 Country Club Drive 3 2 2,342 $1,050,000 $448 338 days
1800 Magnolia Avenue 4 3 2,431 $950,000 $390 160 days
1492 Via Sangro Pl 4 3 3,063 $920,000 $300 28 days
1246 Verdant Glade Place 4 4 2,137 $765,000 $357 3 days
770 W Webster Avenue 4 2 1,008 $725,000 $719 281 days
2157 Lake Drive 3 3 2,124 $689,000 $324 34 days
3114 Heartleaf Place 4 3 2,702 $685,000 $253 146 days
433 Gilbert Road 3 2 1,770 $669,900 $378 38 days
1009 Lake Bell Drive 3 2 1,467 $650,000 $443 95 days
840 W Canton Avenue 3 2 1,370 $649,900 $474 66 days
1037 N Virginia Avenue 3 1 1,101 $649,000 $589 46 days
531 W Swoope Avenue 2 2 1,188 $635,000 $534 7 days
744 Cornwall Road 4 2 1,968 $630,000 $320 378 days
2361 Roxbury Road 3 2 1,723 $599,000 $347 30 days
1946 Strathaven Road 4 3 2,102 $599,000 $284 86 days
1313 S Denning Drive 3 2 1,700 $589,900 $347 10 days
4033 Tenita Drive 4 2 2,022 $569,000 $281 4 days
5233 Lake Howell Road 4 3 1,778 $562,000 $316 53 days
1905 Bonanza Ct 4 2 1,774 $520,000 $293 3 days
2781 Abbey Road 3 2 1,596 $520,000 $325 3 days
410 Saint Dunstan Way 3 2 1,512 $500,000 $330 73 days
512 N Lakemont Avenue 3 2 1,413 $500,000 $353 167 days
351 Starling Road 3 2 1,979 $499,900 $252 11 days
5334 Lanyard Court 3 2 1,561 $479,900 $307 6 days
2803 Banchory Road 4 2 1,596 $474,000 $296 88 days
2826 Ambergate Road 3 2 1,521 $460,000 $302 3 days
1011 Manchester Circle 4 2 1,699 $450,000 $264 9 days
1456 E Brookshire Court 3 2 1,673 $449,000 $268 5 days
Average: 3.6 3.0 2,268 $1,136,883 $436 72 days
Viewing 1 - 50 of 68
Viewing 1 - 50 of 68
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
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
1155 Woodmere Drive 5 6 5,051 $5,295,000 $5,250,000 $1,039 0 days 10/6/25
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
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
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
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
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
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
1782 Pine Avenue 5 7 4,782 $3,697,000 $3,500,000 $731 122 days 7/30/26
2171 Forrest Road 5 6 4,565 $3,595,000 $3,485,000 $763 134 days 10/17/25
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
1610 Oakhurst Avenue 5 7 4,255 $3,275,000 $3,200,000 $752 3 days 10/20/25
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
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
1506 Williams Drive 4 5 6,387 $2,800,000 $2,800,000 $438 0 days 8/7/26
Average: 3.6 3.0 2,359 $1,106,937 $1,069,086 $396 55 days
Viewing 1 - 50 of 706
Viewing 1 - 50 of 706