Homes for Sale in Winter Park, FL
323 homes are for sale in Winter Park, FL as of 2026-09-06, with 21 more under contract. The median list price is $639,500 ($389/sq ft), most homes list between $185K to $2.50M, and the median listing has been on the market 41 days. 68 homes came on the market this week and 357 sold in the last 12 months at a median of $447,000.
Newest homes 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 homes for sale by price
Every active listing in Winter Park grouped by price, with the newest listings in each band. The median is $639,500; the busiest band is $1M and up.
Under $200K: 42 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: 30 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: 22 homes
- $305,000 · 3 bd / 2 ba / 1,467 sq ft · 2370 BARBADOS DRIVE
- $309,900 · 3 bd / 2.5 ba / 1,545 sq ft · 7530 CRANES CREEK COURT
- $335,000 · 3 bd / 2.5 ba / 1,790 sq ft · 2526 PASSAMONTE DRIVE #10F
- $349,000 · 2 bd / 1 ba / 749 sq ft · 811 OVERSPIN DRIVE (Dubsdread Heights)
$400K – $500K: 31 homes
- $495,000 · 3 bd / 2 ba / 1,380 sq ft · 5316 HALYARD COURT
- $430,000 · 3 bd / 2 ba / 1,620 sq ft · 2765 ABBEY ROAD
- $460,000 · 3 bd / 2 ba / 1,521 sq ft · 2826 AMBERGATE ROAD
- $449,000 · 3 bd / 2 ba / 1,154 sq ft · 2007 CORNELL AVENUE (Stansbury Estates)
$500K – $750K: 58 homes
- $575,000 · 2 bd / 2.5 ba / 1,851 sq ft · 1071 ARAGON AVENUE
- $510,000 · 3 bd / 2.5 ba / 1,669 sq ft · 1061 ARAGON AVENUE #1061
- $549,000 · 4 bd / 2 ba / 1,845 sq ft · 2211 KING RICHARDS COURT
- $700,000 · 4 bd / 3 ba / 2,016 sq ft · 1592 ARBOR PARK DRIVE
$750K – $1M: 24 homes
- $799,000 · 3 bd / 2.5 ba / 1,957 sq ft · 1278 S PENNSYLVANIA AVENUE #13
- $899,000 · 3 bd / 2.5 ba / 2,022 sq ft · 1621 CHESTNUT AVENUE (Lake Knowles Terrace)
- $995,999 · 4 bd / 3 ba / 2,528 sq ft · 471 HOLT AVENUE (Winter Park Villas)
- $839,000 · 5 bd / 3 ba / 2,132 sq ft · 730 W SWOOPE AVENUE (Carver Town First Add)
$1M and up: 116 homes
- $1.20M · 3 bd / 2 ba / 1,487 sq ft · 1220 HOWELL BRANCH ROAD
- $1.30M · 3 bd / 2.5 ba / 1,873 sq ft · 1922 HAMMERLIN AVENUE
- $2.50M · 5 bd / 5.5 ba / 3,656 sq ft · 2812 MULFORD AVENUE
- $3.15M · 3 bd / 4 ba / 3,244 sq ft · 125 S INTERLACHEN AVENUE #2
Homes 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 homes 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 |
|---|---|---|---|---|
| Winter Park Pines | 9 | $639,500 | — | — |
| The Enclave Winter Park | 7 | $2.27M | — | — |
| Winter Park Village | 5 | $1.10M | — | — |
| Charmont | 5 | $2.30M | — | — |
| Stratford A Winter Park Condo | 4 | $186,400 | — | — |
| Colonies | 4 | $149,500 | — | — |
| Killarney Estates | 4 | $1.26M | — | — |
| Lake Knowles Terrace Add 02 | 4 | $1.56M | — | — |
| Lawndale | 4 | $1.41M | — | — |
| Orwin Manor Westminster | 3 | $549,000 | — | — |
| Parkview Village | 3 | $144,500 | — | — |
| Sylvan Heights | 3 | $1.75M | — | — |
| Winter Park Villas | 3 | $1.59M | — | — |
| Lake Forest Park | 3 | $1.70M | — | — |
| Lake Knowles Terrace | 3 | $899,000 | — | — |
| Lakeview Terrace | 3 | $725,000 | — | — |
| Park Grove | 2 | $4.62M | — | — |
| South Lakemont Shores | 2 | $1.42M | — | — |
| Swoope Park | 2 | $697,000 | — | — |
| Sylvan Lake Shores | 2 | $2.62M | — | — |
| Townhomes/Harper Place | 2 | $557,500 | — | — |
| Virginia Heights | 2 | $1.30M | — | — |
| Waterfall Cove | 2 | $144,950 | — | — |
| Winter Park Estates | 2 | $575,000 | — | — |
| Winter Park Pines Merrie Oaks | 2 | $497,450 | — | — |
| Aloma | 2 | $499,000 | — | — |
| Chateaux Du Lac | 2 | $202,450 | — | — |
| Orange County | 2 | $3.25M | — | — |
| Comstock Park | 2 | $3.82M | — | — |
| Conwill Estates | 2 | $1.34M | — | — |
What is for sale in Winter Park: property types
- Single-family homes: 219
- Condos: 80
- Townhouses: 24
Another 3 listings in Winter Park are land, commercial or other non-residential property and are not counted above.
Browse by type: Condos for sale in Winter Park (80) · Townhomes for sale in Winter Park (24).
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 323 homes for sale against that sales pace, months of supply is 10.9, a buyer’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 $639,500 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $3,305/month. Orange County’s typical millage of 16.67 puts property tax near $9,829/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 $4,241/month plus any HOA or CDD assessment.
Explore Winter Park
- All homes 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
- All Florida cities and counties
Homes for sale near Winter Park
- Homes for sale in Orlando, FL — 4128 listings
- Homes for sale in Winter Garden, FL — 725 listings
- Homes for sale in Apopka, FL — 543 listings
- Homes for sale in Windermere, FL — 261 listings
- Homes for sale in Ocoee, FL — 150 listings
- Homes for sale in Maitland, FL — 114 listings
- Homes for sale in Zellwood, FL — 50 listings
- Homes for sale in Oakland, FL — 30 listings
- Homes for sale in Belle Isle, FL — 18 listings
- Homes for sale in Gotha, FL — 14 listings
- Homes for sale in Golden Oak, FL — 6 listings
Common questions
How many homes are for sale in Winter Park, FL?
What is the median home price in Winter Park?
How long do homes take to sell in Winter Park?
What does a $639,500 home in Winter Park cost per month?
Which Winter Park neighborhoods have the most homes for sale?
How do I see a home for sale in Winter Park?
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.