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.

See the full metro analysis: Orlando-Kissimmee-Sanford, FL stress score, crash risk, and 12-month forecast →

Home Value$559,942

-4.0%

Rent$2,441/mo

AFFORDABILITY

Enter your income for Winter Garden.

Income (annual)

Down Payment

$111,988 on $559,942

Out of reach — 57.3% 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$9494K Golden Beach$7499K Fisher Island$6393K Lake Buena Vista$6088K Jupiter Inlet Colony$3619K Manalapan$3569K Golf$2871K Boca Grande$2635K

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.

View Orlando-Kissimmee-Sanford, FL metro →

WINTER GARDEN, FL