The median home in New Windsor, New York is valued at $427,153, up 3.9% year over year. Typical monthly rent is $2,338, producing a price-to-rent ratio of 15.2x — near the national average of 18x. New Windsor is part of the Poughkeepsie-Newburgh-Middletown, NY metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$427,153

+3.9%

Rent$2,338/mo

Prices rising — worse for buyers.

Affordability

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Income (annual)

Down Payment

$85,431 on $427,153

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

Out of reach46.8% of income

Need $125,229/yr to afford.

PITI$2,922

P/I46.8%

Afford$256K

Gap-$171K

P&I $2,160Tax $612Ins $150

Renting $584/mo cheaper ($2,338 rent)6.50% 30yr, 20% down, county tax + NY ins. 28% per HUD.

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

Other cities in New York

Compare New Windsor with other housing markets across New York.

Sagaponack$7.21M Water Mill$4.54M Bridgehampton$4.44M Wainscott$3.78M Sands Point$3.18M Amagansett$2.97M Old Westbury$2.85M Quogue$2.77M

Full Poughkeepsie-Newburgh-Middletown, NY analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Poughkeepsie-Newburgh-Middletown, NY metro.

View Poughkeepsie-Newburgh-Middletown, NY metro

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New Windsor, NY