In September 2026, the median home sale price in Winter Park, FL was $524,990, with homes selling in an average of 64 days — slower than the 58-day average last year, suggesting buyers have more negotiating room. A total of 1037 homes sold in this period, down from 1079 last year.
The median list price of Winter Park, FL, was $630,000 in September 2026, compared to $519,990 in September 2025.
Winter Park, FL Market Trend for Houses
Median List Price
The median list price of houses in Winter Park, FL, was $854,500 in September 2026, compared to $739,000 in September 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 $270,000 in September 2026, compared to $214,900 in September 2025.
Winter Park, FL Market Trend for Lots/Land
Median List Price
The median list price of lots/land in Winter Park, FL, was $1,449,000 in September 2026, compared to $774,500 in September 2025.
Winter Park, FL Market Trend for Commercial
Median List Price
The median list price of commercial in Winter Park, FL, was $499,000 in September 2026, compared to $695,500 in September 2025.
Winter Park, FL Housing Market Analysis
There are currently 381 homes listed for sale in Winter Park, FL, an increase of 45.98% compared to 2025. With inventory tight relative to sales volume, sellers are in a strong position. The median asking price is $1,070,652 (up 7.42% year-over-year), and the average price per square foot is $349 compared to $304 in 2025. Properties spend an average of 105 days on the market before going under contract.
