The median home in Chester, New York is valued at $513,571, up 2.8% year over year. Chester 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$513,571

+2.8%

Prices rising — worse for buyers.

Affordability

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Income (annual)

Down Payment

$102,714 on $513,571

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

Out of reach55.7% of income

Need $149,271/yr to afford.

PITI$3,483

P/I55.7%

Afford$258K

Gap-$256K

P&I $2,597Tax $736Ins $150

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 Chester 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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Chester, NY