In August 2026, the median home sale price in Winter Park, FL was $500,000, with homes selling in an average of 64 days — slower than the 59-day average last year, suggesting buyers have more negotiating room. A total of 1057 homes sold in this period, down from 1083 last year.
The median list price of Winter Park, FL, was $599,500 in August 2026, compared to $519,950 in August 2025.
Winter Park, FL Market Trend for Houses
Median List Price
The median list price of houses in Winter Park, FL, was $920,000 in August 2026, compared to $700,000 in August 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 $249,900 in August 2026, compared to $207,500 in August 2025.
Winter Park, FL Market Trend for Lots/Land
Median List Price
The median list price of lots/land in Winter Park, FL, was $1,462,500 in August 2026, compared to $499,000 in August 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 August 2026, compared to $612,000 in August 2025.
Winter Park, FL Housing Market Analysis
There are currently 356 homes listed for sale in Winter Park, FL, an increase of 26.24% compared to 2025. With inventory tight relative to sales volume, sellers are in a strong position. The median asking price is $1,134,537 (up 23.26% year-over-year), and the average price per square foot is $344 compared to $304 in 2025. Properties spend an average of 108 days on the market before going under contract.
