In October 2026, the median home sale price in Winter Park, FL was $522,000, 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 1038 homes sold in this period, down from 1112 last year.
The median list price of Winter Park, FL, was $605,000 in October 2026, compared to $525,000 in October 2025.
Winter Park, FL Market Trend for Houses
Median List Price
The median list price of houses in Winter Park, FL, was $842,500 in October 2026, compared to $650,000 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 $277,000 in October 2026, compared to $217,000 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 $949,500 in October 2026, compared to $897,500 in October 2025.
Winter Park, FL Market Trend for Commercial
Median List Price
The median list price of commercial in Winter Park, FL, was $620,000 in October 2026, compared to $695,500 in October 2025.
Winter Park, FL Housing Market Analysis
There are currently 387 homes listed for sale in Winter Park, FL, an increase of 39.21% compared to 2025. With inventory tight relative to sales volume, sellers are in a strong position. The median asking price is $1,105,798 (up 20.30% year-over-year), and the average price per square foot is $338 compared to $301 in 2025. Properties spend an average of 106 days on the market before going under contract.
