Quick facts
| Winter Park | vs Orange County | vs Florida | |
|---|---|---|---|
| Population | 30,444 (2025 estimate) | ||
| Growth since 2020 | 2.1% | -4.8 pts | -6.8 pts |
| Median home value | $731,400 | 87% higher | 104% higher |
| Median gross rent | $1,738 | 2% lower | 4% higher |
| Median household income | $105,724 | 33% higher | 42% higher |
| Owner occupied homes | 66.2% | +9.4 pts | -1.4 pts |
Census survey figures are 2020 to 2024 averages; methods.
Living in Winter Park
Winter Park is a city in Orange County. The Census counted a 2025 estimate of 30,444 residents.
As an incorporated city, Winter Park sets its own zoning inside Orange County.
Known for: Rollins College, founded in 1885 by the Congregational Assembly of Florida; Winter Park Public Library, opened late 2021 on a campus designed by architect David Adjaye
Development and roads: Incorporated as a town on October 21, 1887, and reincorporated as a city in 1925. Source: Wikipedia, Winter Park, Florida, accessed October 29, 2026.
Against the Orange County averages, homes are pricier than the county median ($731,400 vs $390,100); household incomes are higher ($105,724 vs $79,719); more homes are owner occupied (66.2% vs 56.8%) and it grew slower than the county since 2020 (2.1% vs 6.9%).
If you like the numbers here, also look at Marathon ($725,800, $1,633), Indian Rocks Beach ($738,800, $1,863), St. Pete Beach ($675,700, $1,811).
Growth and housing
Winter Park changed 2.1% in population from 2020 to 2025 (county 6.9%, Florida 8.9%).
The housing mix is 0% detached houses and 0% larger buildings.
Risks to price in
| Risk item | Detail |
|---|---|
| County average homeowners insurance with wind | $3,610 a year |
Buying a home in Winter Park
| 2026 loan limits (county) | Amount |
|---|---|
| FHA, one unit | $541,287 |
| Conforming, one unit | $832,750 |
| Median home value here | $731,400 |
Homes cost 6.9 times median household income here (Orange County 4.9, Florida 4.8).
- Conventional: the default for buyers with solid credit and 5% or more down.
- Jumbo: many homes here run near or past the $832,750 conforming limit.
Investing in Winter Park
Long term rentals
| Winter Park | vs Orange County | |
|---|---|---|
| Renter occupied homes | 33.8% | -9.4 pts |
Short term rentals
Seasonal and vacation homes: 0% of the stock, against 2.4% countywide.
| Short term rental taxes | Rate |
|---|---|
| County tourist development tax | 6% |
| State sales tax | 6% plus any county surtax |
Check the address against local zoning and the HOA documents first. State rules
Property types
| Housing stock | Share |
|---|---|
| Single family detached | 0% |
| Buildings with 5+ units | 0% |
| Manufactured homes | 0% |
Nearby
Other Florida markets
Sources
- U.S. Census Bureau, American Community Survey 2020 to 2024 5 year estimates. 2020 to 2024.
- U.S. Census Bureau, Population Estimates, Vintage 2025. July 1, 2025.
- U.S. Census Bureau, Building Permits Survey, 2025 annual. 2025.
- FFIEC HMDA Data Browser, originated loans. 2025 and 2024.
- LendingTree: 2026 FHA loan limits in Florida by county (HUD figures). 2026.
- Florida Realtors: FHFA sets 2026 conforming loan limits. 2026.
- Florida Office of Economic and Demographic Research: 2026 local option tourist tax rates. 2026.
- Florida Office of Insurance Regulation, July 2026 Insurance Stability Unit report (average homeowners premium with wind, as of March 31, 2026). March 31, 2026.
- Freddie Mac Primary Mortgage Market Survey. week of October 22, 2026.
- Wikipedia: List of counties in Florida. checked October 2026.
- U.S. Census Bureau county adjacency file. 2024.
- Wikipedia county article and statewide lists (colleges, teams, airports); Florida Defense Support Task Force installation map. checked October 2026.
- Hurricane landfalls: Wikipedia, List of Florida hurricanes (2000 to present). checked October 2026.
Estimates from public data; they change over time. General information, not investment, tax or legal advice, and not a loan offer. Methods and assumptions.