Downtown Winter Park Market Report

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Rob Sassos

Rob@SimplicityRE.com

866.642.2052

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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
503 N Interlachen Avenue N/A N/A N/A $4,500,000 Unknown 360 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
620 Pinetree Road N/A N/A N/A $2,690,000 Unknown 109 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
1477 W Fairbanks Avenue N/A N/A 6,049 $2,500,000 $413 18 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
1415 Grove Terrace N/A N/A N/A $2,200,000 Unknown 17 days
1750 Walnut Avenue 4 5 3,691 $2,195,000 $594 17 days
1885 Temple Drive 5 4 3,691 $2,195,000 $594 257 days
147 S Interlachen Avenue Unit 202 3 5 3,272 $2,100,000 $641 177 days
1398 Grove Terrace 4 4 3,450 $2,095,000 $607 102 days
922 N Pennsylvania Avenue 4 4 3,440 $1,995,000 $579 13 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
721 Pansy Avenue 4 4 2,653 $1,850,000 $697 130 days
101 S New York Avenue Unit 311 3 4 3,112 $1,849,900 $594 40 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
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
313L Sylvan Drive N/A N/A N/A $1,750,000 Unknown 17 days
Average: 3.4 3.4 2,465 $1,544,899 $542 96 days
Viewing 1 - 50 of 173
Viewing 1 - 50 of 173
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 N/A N/A N/A $1,595,000 Unknown 39 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 N/A N/A N/A $999,000 Unknown 93 days
1836 Grinnell Terrace 3 2 1,907 $999,000 $523 146 days
2823 Wright Avenue N/A N/A N/A $899,900 Unknown 53 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
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
2324 Lee Road N/A N/A 2,124 $750,000 $353 28 days
300 Carolina Avenue Unit 301 2 2 1,305 $739,000 $566 9 days
770 W Webster Avenue Unit REAR LOT N/A N/A N/A $725,000 Unknown 281 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
1622 Arbor Park Drive N/A N/A N/A $695,000 Unknown 14 days
Average: 3.5 3.2 2,509 $1,416,195 $528 80 days
Viewing 1 - 50 of 69
Viewing 1 - 50 of 69
Sold Properties
Address Beds Baths Living ft2 List Price Sold Price Cost per ft2 DOM Sold Date
1221 Richmond Road 5 6 5,164 $4,995,000 $5,125,000 $992 3 days 6/24/26
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
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
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
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 $3,150,000 $831 15 days 6/29/26
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
1724 Pine Avenue 3 5 4,425 $3,095,000 $2,875,000 $649 6 days 7/15/26
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
436 N Knowles Avenue N/A N/A N/A $2,450,000 $2,280,000 Unknown 0 days 6/8/26
2015 N Park Avenue 5 5 3,963 $2,295,000 $2,250,000 $567 74 days 6/2/26
2550 Venetian Way 4 5 5,051 $2,399,000 $2,200,000 $435 63 days 6/16/26
230 E Rockwood Way 5 4 3,374 $2,189,000 $2,150,000 $637 5 days 7/20/26
800 Juanita Rael 5 4 4,021 $2,300,000 $2,150,000 $534 56 days 7/14/26
2503 Versailles Avenue 5 4 4,026 $2,184,000 $2,100,000 $521 138 days 6/11/26
2423 Via Sienna 4 4 3,472 $2,200,000 $2,080,000 $599 35 days 6/26/26
1636 Elizabeths Walk 4 5 3,412 $2,195,000 $2,050,000 $600 29 days 6/18/26
872 Granville Drive 4 4 3,195 $2,200,000 $2,032,850 $636 5 days 5/28/26
1711 Barcelona Way 5 3 3,669 $2,100,000 $2,010,000 $547 92 days 6/15/26
1624 Barcelona Way 3 3 3,818 $2,235,000 $2,000,000 $523 211 days 7/24/26
1760 Alabama Drive 4 3 2,841 $2,198,000 $1,900,000 $668 75 days 6/3/26
543 E Lake Sue Avenue 4 5 3,657 $1,875,000 $1,875,000 $512 3 days 6/5/26
640 Arjay Way 5 5 3,953 $1,890,000 $1,840,000 $465 107 days 6/9/26
1177 Kenwood Avenue 5 5 4,363 $1,800,000 $1,776,000 $407 69 days 6/26/26
1813 Harland Park Drive 4 4 3,551 $1,875,000 $1,755,000 $494 67 days 7/24/26
1181 Via Capri N/A N/A N/A $1,800,000 $1,700,000 Unknown 24 days 5/29/26
1110 Alabama Drive 3 3 2,488 $1,699,000 $1,699,000 $682 78 days 7/14/26
1510 Miller Avenue 5 5 3,252 $1,599,900 $1,599,900 $491 278 days 7/23/26
1516 Miller Avenue 4 4 3,144 $1,549,900 $1,549,900 $492 0 days 6/30/26
1340 Place Picardy 3 4 3,459 $1,599,000 $1,500,000 $433 50 days 6/29/26
1311 W Webster Avenue N/A N/A 3,412 $1,450,000 $1,450,000 $424 0 days 7/13/26
1220 Woodmere Drive 4 4 2,815 $1,700,000 $1,400,000 $497 5 days 7/17/26
234 Detmar Drive 4 6 3,609 $1,599,000 $1,400,000 $387 106 days 6/25/26
433 Carolina Avenue 5 4 2,771 $1,395,000 $1,395,000 $503 0 days 6/1/26
2408 Lafayette Avenue 4 4 2,838 $1,495,000 $1,395,000 $491 60 days 6/30/26
1780 Mondrian Circle 3 4 2,310 $1,395,000 $1,300,000 $562 48 days 5/29/26
220 W Reading Way N/A N/A N/A $1,195,000 $1,295,100 Unknown 4 days 6/22/26
1723 Chestnut Avenue 3 3 2,608 $1,125,000 $1,201,000 $460 1 day 6/18/26
1321 Fairview Avenue N/A N/A N/A $1,200,000 $1,200,000 Unknown 0 days 7/10/26
106 S Interlachen Avenue Unit 118 3 2 1,834 $1,295,000 $1,200,000 $654 151 days 7/24/26
1807 Magnolia Avenue 5 3 2,618 $1,199,000 $1,199,000 $457 9 days 6/9/26
1651 Westchester Avenue 3 3 2,426 $1,175,000 $1,125,000 $463 67 days 6/23/26
250 Cortland Avenue 3 2 2,114 $950,000 $920,000 $435 73 days 7/22/26
1960 Winter Park Road 3 3 1,864 $899,000 $892,500 $478 13 days 6/25/26
Average: 3.4 3.2 2,471 $1,407,903 $1,352,094 $487 52 days
Viewing 1 - 50 of 103
Viewing 1 - 50 of 103
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