Condos for Sale in Winter Park, FL
80 condos are for sale in Winter Park, FL as of 2026-09-06. The median list price is $199,900 ($201/sq ft), most condos list between $135K to $635K, and the median listing has been on the market 48 days. 20 condos came on the market this week and 357 sold in the last 12 months at a median of $447,000.
Newest condos for sale in Winter Park
The most recently listed homes in Winter Park, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.
Winter Park condos for sale by price
Every active listing in Winter Park grouped by price, with the newest listings in each band. The median is $199,900; the busiest band is Under $200K.
Under $200K: 41 homes
- $130,000 · 1 bd / 1 ba / 645 sq ft · 2500 LEE ROAD #143
- $135,000 · 2 bd / 2 ba / 1,018 sq ft · 3020 ANTIQUE OAKS CIRCLE #129 (Parkview Village)
- $140,000 · 2 bd / 2.5 ba / 1,090 sq ft · 3021 AARON BURR AVENUE #3 (Colonies)
- $154,900 · 3 bd / 2 ba / 1,149 sq ft · 1695 LEE ROAD #A101 (Waterfall Cove)
$200K – $300K: 25 homes
- $245,000 · 2 bd / 2 ba / 913 sq ft · 1250 S DENNING DR #Unit 233
- $229,000 · 3 bd / 2.5 ba / 1,151 sq ft · 7454 WYNNEWOOD SQUARE #188
- $254,000 · 2 bd / 2 ba / 1,316 sq ft · 2477 TAHOE CIRCLE #2477
- $269,000 · 2 bd / 1 ba / 710 sq ft · 151 N ORLANDO AVENUE #242
$300K – $400K: 3 homes
- $335,000 · 3 bd / 2.5 ba / 1,790 sq ft · 2526 PASSAMONTE DRIVE #10F
- $349,500 · 2 bd / 1 ba / 709 sq ft · 500 N PENNSYLVANIA AVENUE #G
- $350,000 · 1 bd / 1 ba / 987 sq ft · 700 MELROSE AVENUE #J24 (Winter Park Gardens Condo)
$400K – $500K: 1 home
$500K – $750K: 5 homes
- $510,000 · 3 bd / 2.5 ba / 1,669 sq ft · 1061 ARAGON AVENUE #1061
- $739,000 · 2 bd / 2 ba / 1,311 sq ft · 250 CAROLINA AVENUE #205
- $635,000 · 3 bd / 2.5 ba / 2,015 sq ft · 565 HUNTINGTON AVENUE #565
- $525,000 · 3 bd / 3.5 ba / 2,195 sq ft · 1134 WASHINGTON AVENUE #13C
$750K – $1M: 2 homes
- $799,000 · 3 bd / 2.5 ba / 1,957 sq ft · 1278 S PENNSYLVANIA AVENUE #13
- $989,500 · 1 bd / 1.5 ba / 1,109 sq ft · 269 E CANTON AVENUE #269
$1M and up: 3 homes
- $1.85M · 3 bd / 3.5 ba / 3,112 sq ft · 101 S NEW YORK AVENUE #311 (Winter Park Residential)
- $1.79M · 3 bd / 2 ba / 1,807 sq ft · 106 S INTERLACHEN AVENUE #518
- $1.82M · 2 bd / 2 ba / 2,304 sq ft · 311 E MORSE BOULEVARD #1-3
Condos for sale in Winter Park by ZIP code
Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.
Winter Park communities with the most condos for sale
The Winter Park neighborhoods and subdivisions with active listings, the median asking price in each, and what homes there actually sold for over the last 12 months. Community names open the community guide with live inventory, sales history, HOA and schools.
| Community | For sale | Median list | Median sold (12 mo) | Days on market |
|---|---|---|---|---|
| Stratford A Winter Park Condo | 4 | $186,400 | — | — |
| Colonies | 4 | $149,500 | — | — |
| Parkview Village | 3 | $144,500 | — | — |
| Waterfall Cove | 2 | $144,950 | — | — |
| Chateaux Du Lac | 2 | $202,450 | — | — |
| Phillips Circle Rep | 1 | $279,000 | — | — |
| Waterfall Cove At Winter Park | 1 | $205,000 | — | — |
| Waterfall Cove/Winter Park | 1 | $108,000 | — | — |
| Winter Park Gardens Condo | 1 | $350,000 | — | — |
| Winter Park Residential | 1 | $1.85M | — | — |
| Winter Park Villas Condo | 1 | $199,900 | — | — |
| Winter Park Woods Condo | 1 | $109,400 | — | — |
| Lancelot/Winter Park | 1 | $169,900 | — | — |
The Winter Park housing market right now
Over the last 12 months 357 homes sold in Winter Park at a median of $447,000 (-3.3% year over year), $270 per square foot. Sellers received 95% of list price and homes took a median 32 days to go under contract. With 80 condos for sale against that sales pace, months of supply is 2.7, a seller’s market by the six-month rule. Cash buyers accounted for 41% of sales. New construction was 2% of sales.
Winter Park supply by price band
| Price band | Active | Sold, 12 mo | Months of supply | DOM |
|---|---|---|---|---|
| Under $300K | 23 | 76 | 3.6 | 55 |
| $300K–$500K | 20 | 55 | 4.4 | 26 |
| $500K–$750K | 22 | 97 | 2.7 | 30 |
| $750K+ | 27 | 129 | 2.5 | 38 |
Winter Park home prices by year
Median sold price, closed sales, days on market and sale-to-list ratio by year, from Momentum’s MLS record.
| Year | Median sold price | Homes sold | Days on market | Sale-to-list |
|---|---|---|---|---|
| 2019 | $473,163 | 64 | 100 | 93% |
| 2021 | $398,855 | 58 | 7 | 100% |
| 2022 | $475,714 | 1,277 | 9 | 99% |
| 2023 | $441,910 | 386 | 19 | 97% |
| 2024 | $616,104 | 929 | 19 | 96% |
| 2025 | $604,724 | 980 | 32 | 94% |
| 2026 | $596,865 | 845 | 32 | 95% |
What a home in Winter Park costs to own
Take the median $199,900 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $1,033/month. Orange County’s typical millage of 16.67 puts property tax near $2,499/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Orange County is about $1,409/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $1,359/month plus any HOA or CDD assessment.
Explore Winter Park
- All condos for sale in Orange County, FL
- Winter Park market intelligence: prices, supply and trends
- Moving to Winter Park: the data guide
- Cost of living in Winter Park
- New construction homes in Winter Park
- Best neighborhoods in Winter Park
- Orange County property tax guide
- Search every Winter Park community
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Common questions
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Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Winter Park as of 2026-09-06 and refresh as homes list and sell. Listings courtesy of Stellar MLS as distributed by MLS GRID. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.