The median home in Chestertown, New York is valued at $358,071, up 4.6% year over year. Chestertown is part of the Glens Falls, NY metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$358,071

+4.6%

Prices rising — worse for buyers.

Affordability

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Income (annual)

Down Payment

$71,614 on $358,071

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

Out of reach39.6% of income

Need $106,029/yr to afford.

PITI$2,474

P/I39.6%

Afford$253K

Gap-$105K

P&I $1,811Tax $513Ins $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 Chestertown 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 Glens Falls, NY analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Glens Falls, NY metro.

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Chestertown, NY