The median home in Winter Park, Florida is valued at $453,292, down 2.9% year over year. Typical monthly rent is $1,869, producing a price-to-rent ratio of 20.2x — well above the national average of 18x. Winter Park 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$453,292

-2.9%

Rent$1,869/mo

Prices falling — better for buyers.

Affordability

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Income (annual)

Down Payment

$90,658 on $453,292

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

Out of reach47.5% of income

Need $127,157/yr to afford.

PITI$2,967

P/I47.5%

Afford$267K

Gap-$186K

P&I $2,292Tax $325Ins $350

Renting $1,098/mo cheaper ($1,869 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 Park 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 Park, FL