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.

See the full metro analysis: Glens Falls, NY stress score, crash risk, and 12-month forecast →

Home Value$358,071

+4.6%

AFFORDABILITY

Enter your income for Chestertown.

Income (annual)

Down Payment

$71,614 on $358,071

Out of reach — 39.6% 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$7210K Water Mill$4535K Bridgehampton$4439K Wainscott$3780K Sands Point$3176K Amagansett$2966K Old Westbury$2853K Quogue$2769K

Full Glens Falls, NY analysis

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

View Glens Falls, NY metro →

CHESTERTOWN, NY