The median home in Winter Garden, Florida is valued at $559,942, down 4.0% year over year. Typical monthly rent is $2,441, producing a price-to-rent ratio of 19.1x — near the national average of 18x. Winter Garden is part of the Orlando-Kissimmee-Sanford, FL metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$559,942

-4.0%

Rent$2,441/mo

Prices falling — better for buyers.

Affordability

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Income (annual)

Down Payment

$111,988 on $559,942

Example: $75,000 household income. Change it above to see your own.

Out of reach57.3% of income

Need $153,557/yr to afford.

PITI$3,583

P/I57.3%

Afford$273K

Gap-$286K

P&I $2,831Tax $401Ins $350

Renting $1,142/mo cheaper ($2,441 rent)6.50% 30yr, 20% down, county tax + FL ins. 28% per HUD.

Home Buying Kit For Dummies (2025)Financing, negotiation, closing

Other cities in Florida

Compare Winter Garden with other housing markets across Florida.

Jupiter Island$9.49M Golden Beach$7.5M Fisher Island$6.39M Lake Buena Vista$6.09M Jupiter Inlet Colony$3.62M Manalapan$3.57M Golf$2.87M Boca Grande$2.63M

Full Orlando-Kissimmee-Sanford, FL analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Orlando-Kissimmee-Sanford, FL metro.

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Winter Garden, FL