The median home in Chestertown, Maryland is valued at $378,817, up 1.4% year over year. Chestertown is part of the Baltimore-Columbia-Towson, MD metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$378,817

+1.4%

Prices rising — worse for buyers.

Affordability

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Income (annual)

Down Payment

$75,763 on $378,817

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

Out of reach38.1% of income

Need $102,000/yr to afford.

PITI$2,380

P/I38.1%

Afford$279K

Gap-$100K

P&I $1,916Tax $331Ins $133

6.50% 30yr, 20% down, county tax + MD ins. 28% per HUD.

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

Other cities in Maryland

Compare Chestertown with other housing markets across Maryland.

Gibson Island$2.94M Chevy Chase View$1.43M Potomac$1.35M Glen Echo$1.29M Cabin John$1.25M Chevy Chase$1.2M Bethesda$1.11M Dayton$1.06M

Full Baltimore-Columbia-Towson, MD analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Baltimore-Columbia-Towson, MD metro.

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Chestertown, MD