In October 2026, the median home sale price in Winter Park, FL was $510,000, with homes selling in an average of 77 days — . A total of 72 homes sold in this period.
The median list price of Winter Park, FL, was $672,450 in October 2026, compared to $619,500 in October 2025.
Winter Park, FL Market Trend for Houses
Median List Price
The median list price of houses in Winter Park, FL, was $899,000 in October 2026, compared to $764,500 in October 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 $285,000 in October 2026, compared to $179,990 in October 2025.
Winter Park, FL Market Trend for Lots/Land
Median List Price
The median list price of lots/land in Winter Park, FL, was $762,000 in October 2026, compared to $0 in October 2025.
Winter Park, FL Market Trend for Commercial
Median List Price
The median list price of commercial in Winter Park, FL, was $882,500 in October 2026, compared to $0 in October 2025.
Winter Park, FL Housing Market Analysis
There are currently 282 homes listed for sale in Winter Park, FL, an increase of 1780.00% compared to 2025. With more homes on the market than are selling each month, buyers may find more options and room to negotiate. The median asking price is $1,191,832 (up 23.82% year-over-year), and the average price per square foot is $369 compared to $403 in 2025. Properties spend an average of 82 days on the market before going under contract.
