Active Listings in Winter Park, FL
Search homes, rentals, and properties in Winter Park, FL. Filter by price, bedrooms, square feet, and features.
Winter Park, FL offers an active real estate market with 167 available listings, including 131 homes for sale and 36 rentals based on the current property database.
Winter Park, FL stands out for combining active inventory, varied housing styles, and opportunities across different budgets. It is a useful city for comparing buy, rent, and investment options based on lifestyle, location, and property type.
Visible property types in this market include Single Family Residence, Condominium, Townhouse, giving buyers, renters, and investors a practical way to compare different housing styles.
The database also shows activity in local areas and communities such as STRATFORD A WINTER PARK CONDO, THE ENCLAVE WINTER PARK, WINTER PARK ESTATES, which can help narrow the search within the city.
Listings with MLS details show an approximate 3.0 bedroom average and about 2,479 average square feet.
Updated from active MLS data
Winter Park, FL Real Estate Market Velocity & Pricing Dynamics
As of May 15, 2026, Winter Park presents a fast-moving real estate market with notable dynamics worth considering:
- Average Days on Market: 33.6 days
- Median Price per Square Foot: $320.36
- Trailing 30-Day Price Drop Percentage: 5.5%
- Sale-to-List Price Ratio: 94.1%
The market is currently active with 346 listings, 293 sales in the last month, and an average sale price of approximately $948,067. With a median property price of $549,500, properties are receiving competitive offers at an average sale-to-list price ratio of nearly 93.9%.
These metrics indicate a vibrant local market, driven by demand and momentum in various neighborhoods throughout Winter Park.
Neighborhood schema mapped from active MLS inventory
Winter Park: Top local areas are ranked by active MLS inventory, with quick links into the city search.
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