In June 2026, the median home sale price in Winter Park, FL was $499,000, with homes selling in an average of 63 days — slower than the 56-day average last year, suggesting buyers have more negotiating room. A total of 1061 homes sold in this period, up from 1049 last year — a sign of an active market.
The median list price of Winter Park, FL, was $680,000 in June 2026, compared to $499,000 in June 2025.
Winter Park, FL Market Trend for Houses
Median List Price
The median list price of houses in Winter Park, FL, was $1,070,000 in June 2026, compared to $697,000 in June 2025.
Winter Park, FL Market Trend for Condos / Townhouses / Penthouses
Median List Price
The median list price of condos/co-ops in Winter Park, FL, was $250,000 in June 2026, compared to $224,999 in June 2025.
Winter Park, FL Market Trend for Lots/Land
Median List Price
The median list price of lots/land in Winter Park, FL, was $1,350,000 in June 2026, compared to $482,000 in June 2025.
Winter Park, FL Market Trend for Commercial
Median List Price
The median list price of commercial in Winter Park, FL, was $399,000 in June 2026, compared to $725,000 in June 2025.
Winter Park, FL Housing Market Analysis
There are currently 354 homes listed for sale in Winter Park, FL, an increase of 6.31% compared to 2025. With inventory tight relative to sales volume, sellers are in a strong position. The median asking price is $1,210,607 (up 31.93% year-over-year), and the average price per square foot is $365 compared to $295 in 2025. Properties spend an average of 111 days on the market before going under contract.
