City

CHESTERTOWN, MD

Baltimore-Columbia-Towson, MD

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.

See the full metro analysis: Baltimore-Columbia-Towson, MD stress score, crash risk, and 12-month forecast →

Home Value$378,817

+1.4%

AFFORDABILITY

Enter your income for Chestertown.

Income (annual)

Down Payment

$75,763 on $378,817

Out of reach — 38.1% 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$2941K Chevy Chase View$1431K Potomac$1352K Glen Echo$1286K Cabin John$1246K Chevy Chase$1199K Bethesda$1110K Dayton$1056K

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.

View Baltimore-Columbia-Towson, MD metro →