Homes for Sale in Winter Park, FL
361 listings available right now — swipe to find your perfect match.
Updated daily ·
361
Active Listings
$1,115,230
Avg. Price
$75,000
Starting From
$8,950,000
Up To
How much do homes cost in Winter Park?
The median home price in Winter Park is $600,000, with listings ranging from $75,000 to $8,950,000. Buyers can expect to pay around $419/sqft on average. Homes typically spend 75 days on market.
Price Distribution
Recent Price Drops in Winter Park
39 Winter Park homes dropped price in the last 30 days · average drop -3.0%.
676 Dunblane Dr
$750,000 → $699,000 · 2026-05-12
423 Ololu Dr
$589,000 → $549,000 · 2026-05-14
1809 Hammerlin Ave
$585,000 → $549,000 · 2026-05-05
1565 Forest Ave
$1,750,000 → $1,650,000 · 2026-05-11
1903 N Park Ave
$1,795,000 → $1,695,000 · 2026-05-14
1651 Westchester Ave
$1,349,000 → $1,275,000 · 2026-05-08
And 33 more — sorted by largest drop first.
Featured Listings in Winter Park
Swipe all 361 →Browse all 361 Winter Park homes on the map
Open map →Top-Rated Schools in Winter Park
Schools serving multiple Winter Park listings, rated 7+ on a 10-point scale.
AUDUBON PARK SCHOOL
Dommerich Elementary School
Princeton Elementary School
Baldwin Park Elementary School
Tuskawilla Middle School
Winter Park High School
Glenridge Middle School
Lake Howell High School
What types of homes are for sale in Winter Park?
Winter Park listings average 3.2 bedrooms, 2.9 bathrooms, and 2,199 square feet. The average year built is 1981. Single Family homes are the most common property type, making up 65% of available inventory.
Popular Neighborhoods in Winter Park
Find Your Dream Home in Winter Park
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Start Swiping in Winter ParkAbout Living in Winter Park, Florida
Winter Park, part of the Orlando area, has 361 active listings. The median home is priced at $600,000, averaging $419 per square foot, with the full range running from $75,000 to $8,950,000. Most listings (65%) are single family homes. Condo (25%) and Townhouse (8%) round out the mix.
Expect 3.2 bedrooms, 2.9 bathrooms, 2,199 square feet on an average listing in Winter Park. Average year built: 1981. Homes typically go under contract after 75 days on market.
Active listings in Winter Park skew toward Eastbrook, Kenilworth Shores, Stratford Winter Park, Winter Park Pines. Prices and property types vary meaningfully between them, so a tour across neighborhoods usually surfaces more range than a single one.
Rather than scrolling endless grids, you can swipe Winter Park homes on HomeSwipr one at a time. The more you swipe, the better it gets at surfacing homes you'd actually tour.
Frequently asked questions about homes for sale in Winter Park
How many homes are for sale in Winter Park, FL?
There are 361 homes for sale in Winter Park, FL right now, with prices ranging from $75,000 to $8,950,000. Inventory is refreshed daily from live listing feeds.
What is the median home price in Winter Park?
The median home price in Winter Park is $600,000, with an average of $1,115,230. Prices span $75,000 to $8,950,000 across 361 current listings.
What is the average price per square foot in Winter Park?
The average price per square foot in Winter Park is $419 based on current listings. Per-sqft varies meaningfully by neighborhood and property type within the city.
What types of homes are for sale in Winter Park?
Single Family homes dominate Winter Park inventory at 65% of listings. Condo (25%) and Townhouse (8%) round out the mix.
What does a typical Winter Park home look like?
A typical Winter Park listing offers 3.2 bedrooms, 2.9 bathrooms, and 2,199 square feet, with an average year built of 1981.
Which neighborhoods have the most listings in Winter Park?
Active inventory in Winter Park is concentrated in Eastbrook, Kenilworth Shores, Stratford Winter Park, Winter Park Pines. Each neighborhood differs on price and property type, so comparing across them usually surfaces more range than a single one.
How long do Winter Park homes stay on the market?
Winter Park homes have been on the market an average of 75 days. Newer listings (under 7 days) typically indicate fresh inventory worth early attention.
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