Winter Garden today
| Typical value | Typical rent | Gross yield | |
|---|---|---|---|
| Single family house | $579,000 | $2,970 | 6.2% |
| Condo or townhome (apartment rent) | $239,000 | $2,150 | 10.8% |
What this means
Winter Garden prices barely moved in the past year (−0.5%), now 5.2% below the May 2024 peak.
A typical house here rents for 6.2% of its value each year, below the state figure of 8.1%. In this market, rentals are mostly a growth play.
Builders are busier: 117 homes permitted so far in 2026, up 83%.
Rents are area estimates; check comps for the exact house. Sources and method: how these figures are built.
Go deeper: Dane's detailed guides for this area: Buying a Home in Winter Garden.
Quick facts
| Winter Garden | vs Orange County | vs Florida | |
|---|---|---|---|
| Population | 48,063 (2025 estimate) | ||
| Growth since 2020 | 1.4% | −5.5 pts | −7.5 pts |
| Median home value | $476,000 | 22% higher | 33% higher |
| Median gross rent | $1,963 | 11% higher | 18% higher |
| Median household income | $106,495 | 34% higher | 43% higher |
| Gross rent yield | 4.95% | −0.5 pts | −0.6 pts |
| Owner occupied homes | 65.7% | +8.9 pts | −1.9 pts |
| Residents 65 and older | 13.8% | +0.8 pts | −7.5 pts |
| Average commute (minutes) | 27 | 2% lower | 2% lower |
| Homes built 2010 or later | 26% | +6.7 pts | +11.8 pts |
| Median property tax paid | $3,527 | 19% higher | 29% higher |
Census survey figures are 2020 to 2024 averages; methods.
Living in Winter Garden
West Orange County city about 14 miles west of downtown Orlando, settled in the 1850s and grown on citrus, turpentine and lumber.
As an incorporated city, Winter Garden sets its own zoning inside Orange County.
Known for: historic downtown; West Orange Trail; Garden Theatre
Getting around and growth: State Road 429 links Interstate 4 and the Turnpike; growth has continued since 2000.
Against the Orange County averages, household incomes are higher ($106,495 vs $79,719); less of the housing is in apartment and condo buildings (13% vs 29.9%); homes are pricier than the county median ($476,000 vs $390,100) and more homes are owner occupied (65.7% vs 56.8%).
Among the 150 Florida cities in these guides, Winter Garden ranks 42 for home value, 96 for rent yield and 17 for household income (1 is highest).
Closest matches on price and rent: Cutler Bay ($472,700, $1,978), Tamiami ($482,100, $1,939), Destin ($490,300, $1,936).
Growth and housing
The Census estimates 48,063 residents in 2025, up from 47,399 in 2020: 1.4% growth.
| 2025 building permits | Winter Garden |
|---|---|
| Single family | 78 |
| 5 or more units | 0 |
| Total units | 78 |
| Per 1,000 residents | 1.6 |
Newer housing (26% built since 2010) often comes with HOA and CDD fees that lenders count. CDD fees
Half the homes are older than 2004. Most housing is single family (68.9%). Average household size is 2.96.
Each year about 1.8% of residents arrive from other states.
Risks to price in
| Risk item | Detail |
|---|---|
| County average homeowners insurance with wind | $3,610 a year |
Flood, storms and jobs
No CRS flood discount applies inside Winter Garden city limits. Insured homes in the city filed 29 flood claims since 2000, with $185,435 paid. For county flood claims, disaster history and jobs, see the Orange County guide (2.3% of homes there are in high risk zones).
Buying a home in Winter Garden
| 2026 loan limits (county) | Amount |
|---|---|
| FHA, one unit | $541,287 |
| Conforming, one unit | $832,750 |
| Median home value here | $476,000 |
Price to income: 4.5x, compared with 4.9x for the county.
- Conventional: mortgage insurance drops off as equity builds.
- FHA: works for the typical $476,000 home here.
Sample FHA payment at $476,000
| Item | Monthly |
|---|---|
| Principal and interest (7.32%, 3.5% down) | $3,211 |
| Property tax (0.74%) | $294 |
| Insurance (county average) | $301 |
| FHA mortgage insurance | $214 |
| Total before HOA or CDD | $4,019 |
| Income needed at a 45% debt ratio | $107,177 a year |
Example, not a quote. Assumptions. Down payment help: Florida Housing.
Investing in Winter Garden
| Rental math at the median | Value |
|---|---|
| Price / rent | $476,000 / $1,963 |
| Estimated net cap rate | 2.3% to 3% |
| DSCR at 25% down | 0.64 |
| Down payment for DSCR 1.0 | 59% down |
| Down payment for DSCR 1.25 | 71% down |
Long term rentals
| Winter Garden | vs Orange County | |
|---|---|---|
| Renter occupied homes | 34.3% | −8.9 pts |
| Rental vacancy | 5.5% | −3.8 pts |
| Rent as share of renter income | 30.8% | −4.0 pts |
Short term rentals
Vacation home share is above the county (3.2% vs 2.4%), so nightly demand here is stronger.
| 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 | 68.9% |
| Buildings with 5+ units | 13% |
| Manufactured homes | 4.2% |
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.
- Wikipedia article for this place (history, setting, roads). checked October 2026.
- Zillow Observed Rent Index (ZORI), all homes and apartments, smoothed. September 2026.
- Zillow Home Value Index (ZHVI), all homes, middle tier, smoothed and seasonally adjusted. September 2026.
- Federal Housing Finance Agency House Price Index (county annual, metro and state quarterly, all transactions). through Q2 2026.
- U.S. Census Bureau, Building Permits Survey, January to September 2026 and 2025. September 2026.
- FEMA OpenFEMA, NFIP Residential Penetration Rates. as of August 2026.
- FEMA OpenFEMA, FIMA NFIP Redacted Claims (2000 to 2026). as of September 2026.
- FEMA OpenFEMA, NFIP Community Status Book (Community Rating System class). August 2026.
- FEMA OpenFEMA, Disaster Declarations Summaries (2000 to 2026). October 2026.
- U.S. Census Bureau, County Business Patterns 2023. 2023.
- U.S. Census Bureau, ACS 2020 to 2024, median gross rent by bedrooms (B25031). 2020 to 2024.
- 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.