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.
Median sold: $1.1M · Median DOM: 25 · Sold-to-list: 96.6% · Source: Stellar MLS
About 4.9 months of inventory — supply and demand are roughly even, so neither side has a clear edge (4–6 months = balanced).
Aggregate statistics from recent Stellar MLS closed sales and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Ryan's Take on Winter Park
Winter Park is the oldest established luxury address in Central Florida — a historic city laid out in 1887 by New England industrialists on a chain of six spring-fed lakes, with red-brick streets, Rollins College on Lake Virginia, and a Park Avenue dining and gallery corridor that doesn't need a theme park nearby to justify its existence. The Isle of Sicily on Lake Maitland — 11 private homes accessible over a single bridge — is the trophy waterfront position, with closing prices that can reach $17M. Via Lugano and Via Tuscany shadow-price it on the lake's eastern shore. Interlachen Country Club, designed by Joe Lee with a Steve Smyers renovation and a 1986 U.S. Senior Amateur Championship on its resume, sits embedded in the old-money residential core. Winter Park High's IB Diploma Programme has been running for decades, carries a 97.5% pass rate with 500+ participants, and is one of the heavyweight academic programs in the state.
The buyers I represent here either grew up in Winter Park, know someone who did, or have spent enough time on Park Avenue to understand that this kind of walkable, architecturally controlled, culture-forward community doesn't exist anywhere else in the metro. The Morse Museum holds the world's largest Tiffany glass collection. The Bach Festival Society has been performing on the Rollins campus since 1935. The Sidewalk Art Festival draws 250,000 visitors every March and ranks top 10 nationally in Art Fair profitability. These are not amenities you bolt onto a subdivision; they're the product of 140 years of intentional community building. The honest tradeoff: Winter Park is largely built out, the housing stock is mostly 1960s–1990s, and the architectural review board has real teeth. Buyers who want the newest smart-home tech or a truly private gated estate should look at Lake Nona or Windermere. Buyers who want to walk to dinner and feel like they live somewhere, this is the answer.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
20 homes pending in Winter Park · Avg. $1.6M
Winter Park · 2nd Quarter 2026
397 sales · Stellar MLS · last 12 mo
$1.1M
Median Sale Price
25 days
Median Days on Market
96.6%
Sold-to-List
$490
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Winter Park · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 5,022 | — | 12/1/25 | — | $6,111,000 | $1,217 | — |
| — | — | 6,699 | — | 12/1/25 | — | $4,800,000 | $717 | — |
| — | — | 5,082 | — | 12/1/25 | — | $4,450,000 | $876 | — |
| — | — | 4,635 | — | 12/1/25 | — | $3,325,000 | $717 | — |
| — | — | 2,503 | — | 12/1/25 | — | $2,288,300 | $914 | — |
| — | — | 4,328 | — | 12/1/25 | — | $2,078,500 | $480 | — |
| — | — | 3,314 | — | 12/1/25 | — | $1,875,000 | $566 | — |
| — | — | 3,153 | — | 12/1/25 | — | $1,850,000 | $587 | — |
| — | — | 2,898 | — | 12/1/25 | — | $1,850,000 | $638 | — |
| — | — | 3,297 | — | 12/1/25 | — | $1,600,000 | $485 | — |
| — | — | 2,662 | — | 12/1/25 | — | $1,589,000 | $597 | — |
| — | — | 1,458 | — | 12/1/25 | — | $1,525,000 | $1,046 | — |
| — | — | 3,145 | — | 12/1/25 | — | $1,350,000 | $429 | — |
| — | — | 2,630 | — | 12/1/25 | — | $1,300,000 | $494 | — |
| — | — | 2,395 | — | 12/1/25 | — | $1,250,000 | $522 | — |
| — | — | 2,615 | — | 12/1/25 | — | $1,129,000 | $432 | — |
| — | — | 2,841 | — | 12/1/25 | — | $1,100,000 | $387 | — |
| — | — | 1,577 | — | 12/1/25 | — | $1,050,000 | $666 | — |
| — | — | 2,316 | — | 12/1/25 | — | $1,042,500 | $450 | — |
| — | — | 1,431 | — | 12/1/25 | — | $1,000,500 | $699 | — |
| — | — | 2,515 | — | 12/1/25 | — | $920,000 | $366 | — |
| — | — | 1,808 | — | 12/1/25 | — | $895,000 | $495 | — |
| — | — | 2,041 | — | 12/1/25 | — | $850,000 | $416 | — |
| — | — | 1,213 | — | 12/1/25 | — | $655,000 | $540 | — |
| — | — | 1,399 | — | 12/1/25 | — | $645,000 | $461 | — |
| — | — | 1,984 | — | 12/1/25 | — | $610,000 | $307 | — |
| — | — | 1,284 | — | 12/1/25 | — | $575,000 | $448 | — |
| — | — | 1,453 | — | 12/1/25 | — | $567,500 | $391 | — |
| — | — | 1,870 | — | 12/1/25 | — | $540,000 | $289 | — |
| — | — | 901 | — | 12/1/25 | — | $535,000 | $594 | — |
| — | — | 1,771 | — | 12/1/25 | — | $530,000 | $299 | — |
| — | — | 1,263 | — | 12/1/25 | — | $505,000 | $400 | — |
| — | — | 1,630 | — | 12/1/25 | — | $490,000 | $301 | — |
| — | — | 1,182 | — | 12/1/25 | — | $479,000 | $405 | — |
| — | — | 1,645 | — | 12/1/25 | — | $470,000 | $286 | — |
| — | — | 1,886 | — | 12/1/25 | — | $435,000 | $231 | — |
| — | — | 945 | — | 12/1/25 | — | $427,000 | $452 | — |
| — | — | 1,685 | — | 12/1/25 | — | $417,500 | $248 | — |
| — | — | 1,804 | — | 12/1/25 | — | $410,000 | $227 | — |
| — | — | 969 | — | 12/1/25 | — | $405,000 | $418 | — |
| — | — | 6,708 | — | 11/1/25 | — | $5,125,000 | $764 | — |
| — | — | 3,635 | — | 11/1/25 | — | $2,835,000 | $780 | — |
| — | — | 4,315 | — | 11/1/25 | — | $2,325,000 | $539 | — |
| — | — | 3,883 | — | 11/1/25 | — | $2,285,000 | $588 | — |
| — | — | 4,319 | — | 11/1/25 | — | $2,250,000 | $521 | — |
| — | — | 3,461 | — | 11/1/25 | — | $2,175,000 | $628 | — |
| — | — | 3,882 | — | 11/1/25 | — | $2,037,500 | $525 | — |
| — | — | 2,976 | — | 11/1/25 | — | $1,720,000 | $578 | — |
| — | — | 3,292 | — | 11/1/25 | — | $1,475,000 | $448 | — |
| — | — | 3,014 | — | 11/1/25 | — | $1,305,000 | $433 | — |
| — | — | 2,953 | — | 11/1/25 | — | $1,300,000 | $440 | — |
| — | — | 1,942 | — | 11/1/25 | — | $1,095,000 | $564 | — |
| — | — | 2,388 | — | 11/1/25 | — | $1,030,000 | $431 | — |
| — | — | 1,843 | — | 11/1/25 | — | $975,000 | $529 | — |
| — | — | 2,227 | — | 11/1/25 | — | $879,000 | $395 | — |
| — | — | 1,738 | — | 11/1/25 | — | $810,000 | $466 | — |
| — | — | 1,714 | — | 11/1/25 | — | $765,000 | $446 | — |
| — | — | 1,446 | — | 11/1/25 | — | $750,000 | $519 | — |
| — | — | 2,582 | — | 11/1/25 | — | $700,000 | $271 | — |
| — | — | 1,442 | — | 11/1/25 | — | $675,000 | $468 | — |
Currently For Sale
50 active listings in Winter Park
$749/sqft
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$706/sqft
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$1,087/sqft
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$373/sqft
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$446/sqft
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$289/sqft
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$521/sqft
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$528/sqft
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$719/sqft
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$691/sqft
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$286/sqft
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$852/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 3 | 2 | 1,734 | $1,299,000 | $749 | 128 | — | ✓ | Lake Osceola |
| 3 | 2 | 1,834 | $1,295,000 | $706 | 141 | — | ✓ | Lake Osceola |
| 5 | 6 | 5,152 | $5,600,000 | $1,087 | 0 | ✓ | — | — |
| 3 | 2 | 1,248 | $465,500 | $373 | 1 | — | — | — |
| 3 | 3 | 1,904 | $849,000 | $446 | 12 | — | — | — |
| 3 | 4 | 1,937 | $560,000 | $289 | 24 | — | — | — |
| 3 | 2 | 2,015 | $1,050,000 | $521 | 36 | — | — | — |
| 4 | 4 | 3,551 | $1,875,000 | $528 | 57 | ✓ | — | — |
| 4 | 4 | 3,130 | $2,249,000 | $719 | 72 | ✓ | — | — |
| 4 | 2 | 2,163 | $1,495,000 | $691 | 74 | — | — | Water |
| 3 | 2 | 1,606 | $460,000 | $286 | 77 | — | — | — |
| 3 | 4 | 3,286 | $2,800,000 | $852 | 2 | — | — | — |
| 4 | 2 | 1,536 | $429,900 | $280 | 3 | — | — | — |
| 5 | 4 | 2,351 | $1,429,000 | $608 | 17 | ✓ | — | — |
| 4 | 6 | 4,683 | $3,393,000 | $725 | 107 | ✓ | — | — |
| 4 | 5 | 2,812 | $1,449,900 | $516 | 249 | ✓ | — | — |
| 5 | 5 | 3,252 | $1,599,900 | $492 | 262 | ✓ | — | — |
| — | 0 | — | $650,000 | — | 36 | — | ✓ | Lake Bell |
| 5 | 5 | 3,520 | $2,499,000 | $710 | 3 | ✓ | — | — |
| 3 | 4 | 1,824 | $899,000 | $493 | 5 | — | — | — |
| 5 | 5 | 2,889 | $2,250,000 | $779 | 16 | ✓ | — | — |
| 3 | 3 | 1,411 | $699,900 | $496 | 26 | — | — | — |
| 3 | 2 | 1,467 | $650,000 | $443 | 36 | — | ✓ | Lake Bell |
| 5 | 4 | 2,964 | $1,900,000 | $641 | 94 | ✓ | — | — |
| 5 | 7 | 4,520 | $3,390,000 | $750 | 230 | ✓ | — | — |
| 3 | 1 | 1,101 | $649,000 | $589 | 2 | — | — | — |
| 3 | 3 | 2,434 | $1,050,000 | $431 | 1 | — | — | — |
| 4 | 2 | 1,511 | $799,000 | $529 | 58 | — | — | — |
| 2 | 1 | 857 | $535,000 | $624 | 1 | — | — | — |
| 4 | 3 | 2,075 | $1,300,000 | $627 | 1 | — | — | — |
| 4 | 3 | 2,431 | $995,000 | $409 | 102 | ✓ | — | — |
| 5 | 4 | 3,691 | $2,225,000 | $603 | 209 | ✓ | — | — |
| 4 | 4 | 3,223 | $1,299,900 | $403 | 98 | ✓ | — | — |
| 3 | 3 | 2,046 | $1,299,000 | $635 | 89 | — | — | — |
| 4 | 6 | 3,850 | $4,195,000 | $1,090 | 363 | ✓ | — | — |
| 4 | 3 | 1,647 | $735,000 | $446 | 19 | — | — | — |
| 4 | 4 | 3,294 | $2,460,000 | $747 | 44 | ✓ | — | — |
| 5 | 5 | 4,018 | $2,829,000 | $704 | 102 | ✓ | — | — |
| 4 | 4 | 3,676 | $2,899,900 | $789 | 165 | ✓ | — | — |
| 4 | 4 | 3,578 | $1,550,000 | $433 | 14 | — | — | — |
| 3 | 5 | 3,272 | $2,095,000 | $640 | 131 | ✓ | — | — |
| — | 0 | — | $649,000 | — | 0 | — | — | — |
| 4 | 5 | 4,775 | $5,500,000 | $1,152 | 10 | ✓ | ✓ | Sylvan Lake |
| 4 | 4 | 3,249 | $1,820,000 | $560 | 87 | ✓ | — | — |
| 4 | 4 | 2,916 | $1,070,000 | $367 | 56 | — | — | — |
| 3 | 2 | 1,287 | $625,000 | $486 | 70 | — | — | — |
| 4 | 5 | 3,460 | $1,950,000 | $564 | 6 | ✓ | — | — |
| 4 | 4 | 2,916 | $1,665,000 | $571 | 42 | ✓ | — | — |
| 3 | 2 | 1,669 | $649,000 | $389 | 36 | — | — | — |
| 4 | 4 | 3,450 | $2,095,000 | $607 | 62 | ✓ | — | — |
Winter Park Market — Common Questions
Is Winter Park a buyer's or seller's market in 2026?+
Winter Park is currently a balanced market with about 4.9 months of inventory. About 4.9 months of inventory — supply and demand are roughly even, so neither side has a clear edge (4–6 months = balanced).
What is the median home sale price in Winter Park?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Winter Park is approximately $1.1M, up about 21.2% from a year earlier.
How many homes are for sale in Winter Park?+
There are currently 162 active listings in Winter Park, with homes selling at roughly 33.1 per month. That works out to about 4.9 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 27, 2026 at 6:52 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 Florida Department of Revenue public property 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 27, 2026 at 5:56 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 27, 2026 at 5:56 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.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA