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.

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

Home Value$453,292

-2.9%

Rent$1,869/mo

AFFORDABILITY

Enter your income for Winter Park.

Income (annual)

Down Payment

$90,658 on $453,292

Out of reach — 47.5% 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$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 PARK, FL