Cost of living in Winter Park, FL — Housing, Rent & Index

The median home value in Winter Park, FL is $465,527 as of 2026-04. That places Winter Park above the US average for housing cost, with a cost index of approximately 131 versus a national baseline of 100.

Over the past 12 months, the median home value in Winter Park has moved sideways, and over the past five years it has averaged +5.7% annual growth. The current price sits -3.0% from its 5-year peak in 2024-05.

Renters pay a median of $1,845 per month in Winter Park. Rents have changed -0.8% over the last year and averaged +5.4% per year over five years.

Beyond housing, day-to-day costs in Winter Park are shaped by state and local taxes, utility rates, transportation, and groceries. This page focuses on the housing component, which is the largest single line in most household budgets and the easiest to compare across cities using consistent national data.