PARK AVENUE · CHAIN OF LAKES · OLD-MONEY FLORIDA
Winter Park
Winter Park is the rare Florida address where wealth does not announce itself — red brick streets, 100-year-old oak canopies, and a walkable Park Avenue of galleries and white-tablecloth restaurants that has not changed character in three generations. Residents kayak the Venice-of-America canal system to dinner, and the Morse Museum's Tiffany glass is a ten-minute walk from the city's finest lakefront estates.
Avg. sold: $1.5M · Avg. DOM: 56 · Sold-to-list: 96.5% · Source: Stellar MLS
Currently For Sale
50 active listings in Winter Park
$649/sqft
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$458/sqft
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$521/sqft
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$528/sqft
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$377/sqft
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$484/sqft
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$289/sqft
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$492/sqft
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$884/sqft
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$384/sqft
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$486/sqft
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$1,054/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 5 | 4 | 3,374 | $2,189,000 | $649 | 3 | ✓ | — | — |
| 4 | 4 | 3,046 | $1,395,000 | $458 | 10 | — | — | — |
| 3 | 3 | 2,304 | $1,200,000 | $521 | 2 | ✓ | — | — |
| 5 | 4 | 3,028 | $1,599,000 | $528 | 24 | ✓ | — | — |
| 4 | 4 | 2,916 | $1,100,000 | $377 | 38 | — | — | — |
| 3 | 3 | 2,426 | $1,175,000 | $484 | 56 | — | — | — |
| 3 | 3 | 1,818 | $525,000 | $289 | 82 | — | — | — |
| 5 | 5 | 3,252 | $1,599,900 | $492 | 242 | ✓ | — | — |
| 3 | 4 | 3,048 | $2,695,000 | $884 | 1 | — | — | — |
| 3 | 2 | 1,433 | $550,000 | $384 | 1 | — | — | — |
| 4 | 4 | 2,469 | $1,200,000 | $486 | 9 | — | — | — |
| 4 | 6 | 4,066 | $4,285,000 | $1,054 | 53 | ✓ | — | — |
| 4 | 3 | 1,647 | $735,000 | $446 | 0 | — | — | — |
| 5 | 7 | 4,520 | $3,390,000 | $750 | 209 | ✓ | — | — |
| 4 | 3 | 2,431 | $1,000,000 | $411 | 82 | ✓ | — | — |
| 3 | 4 | 2,767 | $1,895,000 | $685 | 16 | — | — | — |
| 2 | 2 | 2,304 | $1,995,000 | $866 | 29 | — | ✓ | Lake Osceola |
| 4 | 4 | 3,551 | $1,875,000 | $528 | 36 | ✓ | — | — |
| 4 | 2 | 2,640 | $1,695,000 | $642 | 37 | — | — | — |
| 4 | 2 | 2,163 | $1,650,000 | $763 | 53 | — | — | Water |
| 3 | 2 | 1,606 | $460,000 | $286 | 56 | — | — | — |
| 4 | 6 | 4,356 | $2,699,000 | $620 | 66 | ✓ | — | — |
| 3 | 3 | 2,433 | $1,980,000 | $814 | 71 | ✓ | — | Water |
| 5 | 6 | 4,389 | $2,695,000 | $614 | 46 | ✓ | — | — |
| 4 | 3 | 3,696 | $1,995,000 | $540 | 8 | ✓ | — | — |
| 5 | 4 | 3,691 | $2,225,000 | $603 | 189 | ✓ | — | — |
| 3 | 3 | 1,411 | $749,900 | $531 | 5 | — | — | — |
| — | 0 | — | $699,000 | — | 15 | — | ✓ | Lake Bell |
| 3 | 2 | 1,467 | $699,000 | $476 | 15 | — | ✓ | Lake Bell |
| 5 | 6 | 4,572 | $2,500,000 | $547 | 36 | ✓ | — | — |
| 4 | 4 | 2,249 | $1,569,000 | $698 | 40 | ✓ | — | — |
| 3 | 2 | 1,491 | $455,000 | $305 | 63 | — | — | — |
| 5 | 4 | 2,964 | $1,900,000 | $641 | 73 | ✓ | — | — |
| 4 | 4 | 2,916 | $1,665,000 | $571 | 23 | ✓ | — | — |
| 5 | 7 | 4,782 | $3,875,000 | $810 | 86 | ✓ | — | — |
| 3 | 4 | 1,937 | $560,000 | $289 | 3 | — | — | — |
| 3 | 4 | 2,213 | $1,095,000 | $495 | 11 | — | — | — |
| 3 | 2 | 2,015 | $1,095,000 | $543 | 15 | — | — | — |
| 4 | 4 | 2,756 | $1,495,000 | $542 | 9 | — | — | — |
| 3 | 5 | 4,425 | $3,095,000 | $699 | 1 | ✓ | — | — |
| 4 | 4 | 4,036 | $3,500,000 | $867 | 1 | ✓ | ✓ | Howell.Creek.Into.Lake Maitlan |
| 3 | 2 | 1,669 | $687,000 | $412 | 17 | — | — | — |
| 3 | 2 | 1,528 | $709,000 | $464 | 36 | — | — | — |
| 4 | 4 | 2,810 | $1,949,999 | $694 | 113 | ✓ | — | — |
| 4 | 6 | 3,850 | $4,195,000 | $1,090 | 342 | ✓ | — | — |
| 4 | 2 | 1,877 | $699,000 | $372 | 19 | ✓ | — | — |
| 2 | 2 | 1,305 | $739,000 | $566 | 1 | — | — | — |
| 5 | 3 | 2,242 | $825,000 | $368 | 113 | — | — | — |
| 3 | 4 | 2,467 | $1,650,000 | $669 | 8 | — | ✓ | Lake Spier |
| 4 | 4 | 3,065 | $2,000,000 | $653 | 7 | — | — | — |
Under Contract
17 homes pending in Winter Park · Avg. $1.5M
Recent Sales Analysis
392 homes sold in Winter Park over the past 12 months · Stellar MLS
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold | List Price | Sold Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 3 | 2 | 1,762 | 5/28/26 | 6/5/26 | $725,000 | $695,000 | $394 | 8 | ✓ | — | — |
| 4 | 5 | 3,657 | 6/2/26 | 6/5/26 | $1,875,000 | $1,875,000 | $513 | 3 | ✓ | — | — |
| 4 | 2 | 1,048 | 6/2/26 | 6/4/26 | $400,000 | $406,000 | $387 | 2 | — | — | — |
| 4 | 3 | 2,841 | 3/29/26 | 6/3/26 | $2,198,000 | $1,900,000 | $669 | 66 | — | — | — |
| 3 | 2 | 1,304 | 5/22/26 | 6/3/26 | $670,000 | $625,090 | $479 | 12 | — | — | — |
| — | 0 | — | 5/20/26 | 6/3/26 | $485,000 | $450,000 | — | 14 | — | — | — |
| 5 | 5 | 3,963 | 3/20/26 | 6/2/26 | $2,295,000 | $2,250,000 | $568 | 74 | ✓ | — | — |
| 3 | 2 | 2,556 | 5/15/26 | 6/1/26 | $599,000 | $599,900 | $235 | 17 | — | — | — |
| 5 | 4 | 2,771 | 6/1/26 | 6/1/26 | $1,395,000 | $1,395,000 | $503 | 0 | — | — | — |
| 4 | 5 | 3,181 | 2/12/26 | 6/1/26 | $4,595,000 | $4,250,000 | $1,336 | 109 | ✓ | ✓ | Lake Virginia |
| 3 | 2 | 1,627 | 12/10/25 | 5/30/26 | $995,000 | $800,000 | $492 | 171 | — | — | — |
| 3 | 4 | 2,310 | 4/11/26 | 5/29/26 | $1,395,000 | $1,300,000 | $563 | 48 | — | ✓ | Lake Killarney |
| 4 | 7 | 6,242 | 5/10/26 | 5/29/26 | $4,650,000 | $4,300,000 | $689 | 19 | ✓ | — | — |
| — | 0 | — | 5/5/26 | 5/29/26 | $1,800,000 | $1,700,000 | — | 24 | — | — | — |
| 4 | 5 | 3,922 | 5/29/26 | 5/29/26 | $4,500,000 | $4,500,000 | $1,147 | 0 | ✓ | ✓ | Lake Sylvan |
| 4 | 4 | 3,195 | 5/23/26 | 5/28/26 | $2,200,000 | $2,032,850 | $636 | 5 | ✓ | — | — |
| — | 0 | — | 5/26/26 | 5/28/26 | $825,000 | $825,000 | — | 2 | — | — | — |
| 4 | 3 | 1,378 | 5/19/26 | 5/28/26 | $490,000 | $482,000 | $350 | 9 | — | — | — |
| 3 | 2 | 1,356 | 4/3/26 | 5/27/26 | $525,000 | $500,000 | $369 | 54 | — | — | — |
| 4 | 2 | 2,479 | 5/20/26 | 5/22/26 | $850,000 | $841,500 | $339 | 2 | — | — | — |
| 1 | 1 | 673 | 1/26/26 | 5/22/26 | $450,000 | $420,000 | $624 | 116 | ✓ | — | — |
| 4 | 2 | 2,112 | 5/20/26 | 5/22/26 | $790,000 | $775,000 | $367 | 2 | — | — | — |
| 2 | 2 | 1,900 | 2/9/26 | 5/21/26 | $2,100,000 | $1,969,000 | $1,036 | 101 | — | — | Water |
| 3 | 4 | 3,174 | 4/15/26 | 5/21/26 | $1,450,000 | $1,000,000 | $315 | 36 | — | — | — |
| 5 | 5 | 3,334 | 2/25/26 | 5/21/26 | $2,289,000 | $2,185,000 | $655 | 85 | ✓ | — | — |
| 4 | 5 | 3,897 | 5/19/26 | 5/20/26 | $3,295,000 | $3,278,530 | $841 | 1 | ✓ | — | — |
| 2 | 2 | 2,281 | 5/17/26 | 5/19/26 | $1,500,000 | $1,500,000 | $658 | 2 | ✓ | — | — |
| 4 | 3 | 2,306 | 5/15/26 | 5/19/26 | $1,425,000 | $1,425,000 | $618 | 4 | ✓ | — | — |
| — | 0 | — | 5/17/26 | 5/19/26 | $1,500,000 | $1,500,000 | — | 2 | — | — | — |
| 4 | 5 | 4,665 | 5/14/26 | 5/18/26 | $4,195,000 | $3,978,550 | $853 | 4 | ✓ | — | — |
| 3 | 1 | 1,318 | 5/18/26 | 5/18/26 | $830,000 | $830,000 | $630 | 0 | — | — | — |
| 5 | 7 | 5,006 | 5/10/26 | 5/15/26 | $6,997,000 | $7,164,000 | $1,431 | 5 | ✓ | ✓ | Lake Maitland |
| 3 | 4 | 3,215 | 5/15/26 | 5/15/26 | $1,300,000 | $1,300,000 | $404 | 0 | — | — | — |
| 5 | 6 | 4,738 | 11/14/25 | 5/15/26 | $4,995,000 | $4,720,000 | $996 | 182 | ✓ | — | — |
| 5 | 6 | 4,296 | 2/13/26 | 5/15/26 | $3,250,000 | $3,000,000 | $698 | 91 | ✓ | — | — |
| 3 | 2 | 1,119 | 5/8/26 | 5/14/26 | $450,000 | $475,000 | $424 | 6 | — | — | — |
| 4 | 4 | 3,031 | 3/17/26 | 5/14/26 | $1,695,000 | $1,655,000 | $546 | 58 | ✓ | — | — |
| 2 | 2 | 1,609 | 4/29/26 | 5/13/26 | $490,090 | $450,000 | $280 | 14 | — | — | — |
| 3 | 3 | 2,667 | 5/5/26 | 5/12/26 | $2,540,000 | $2,570,000 | $964 | 7 | — | — | — |
| 4 | 4 | 3,470 | 2/1/26 | 5/11/26 | $1,895,000 | $1,635,000 | $471 | 99 | — | — | — |
| 5 | 5 | 3,851 | 4/22/26 | 5/8/26 | $1,850,000 | $1,675,000 | $435 | 16 | ✓ | — | — |
| 3 | 2 | 1,618 | 4/8/26 | 5/8/26 | $600,000 | $560,000 | $346 | 30 | ✓ | — | — |
| 3 | 2 | 1,566 | 5/3/26 | 5/7/26 | $775,000 | $776,533 | $496 | 4 | — | — | — |
| — | 0 | — | 12/6/25 | 5/7/26 | $1,795,000 | $1,700,000 | — | 152 | — | ✓ | Lake Berry |
| 4 | 3 | 3,142 | 4/24/26 | 5/1/26 | $1,699,000 | $1,650,000 | $525 | 7 | — | ✓ | Howell Creek, Lake Maitland |
| 3 | 2 | 1,893 | 4/5/26 | 4/30/26 | $825,000 | $795,000 | $420 | 25 | — | — | — |
| 3 | 2 | 1,800 | 4/30/26 | 4/30/26 | $899,000 | $800,000 | $444 | 0 | — | — | — |
| — | 0 | — | 2/14/26 | 4/30/26 | $2,249,900 | $2,050,000 | — | 75 | — | — | — |
| 6 | 6 | 5,759 | 9/20/25 | 4/30/26 | $5,000,000 | $4,500,000 | $781 | 222 | ✓ | — | — |
| 2 | 2 | 986 | 3/30/26 | 4/30/26 | $550,000 | $550,000 | $558 | 31 | — | — | — |
| 4 | 5 | 3,253 | 8/19/25 | 4/30/26 | $1,390,000 | $1,390,000 | $427 | 254 | — | — | — |
| 3 | 2 | 1,930 | 1/20/26 | 4/30/26 | $824,900 | $800,000 | $415 | 100 | — | — | — |
| 4 | 4 | 2,544 | 4/20/26 | 4/27/26 | $1,400,000 | $1,425,000 | $560 | 7 | ✓ | — | — |
| 4 | 3 | 3,263 | 7/27/25 | 4/22/26 | $1,675,000 | $1,600,000 | $490 | 269 | — | — | — |
| 3 | 4 | 2,714 | 12/9/25 | 4/17/26 | $2,195,000 | $2,232,000 | $822 | 129 | — | ✓ | Lake Virginia |
| 2 | 2 | 1,402 | 1/30/26 | 4/16/26 | $1,195,000 | $1,100,000 | $785 | 76 | — | ✓ | Lake Maitland |
| 2 | 2 | 1,220 | 2/23/26 | 4/15/26 | $1,165,000 | $1,100,000 | $902 | 51 | — | — | Water |
| 4 | 4 | 3,670 | 4/15/26 | 4/15/26 | $1,850,000 | $1,850,000 | $504 | 0 | ✓ | — | — |
| 4 | 5 | 3,022 | 1/6/26 | 4/15/26 | $1,525,000 | $1,500,000 | $496 | 99 | ✓ | — | — |
| 5 | 5 | 4,686 | 4/7/26 | 4/13/26 | $2,995,000 | $3,100,001 | $662 | 6 | ✓ | — | — |
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What Is Your Winter Park Home Worth?
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 7, 2026 at 3:23 PM ET· Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Stellar MLS closed-sale records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Winter Parkor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of June 7, 2026 at 3:06 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 7, 2026 at 3:06 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA