The median home in Cheshire, Massachusetts is valued at $342,371, up 3.9% year over year. Cheshire is part of the Pittsfield, MA metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$342,371

+3.9%

Prices rising — worse for buyers.

Affordability

Enter your income for Cheshire.

Income (annual)

Down Payment

$68,474 on $342,371

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

Stretch35.6% of income

Above 28% but manageable with cuts.

PITI$2,224

P/I35.6%

Afford$269K

Gap-$73K

P&I $1,731Tax $342Ins $150

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

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

Other cities in Massachusetts

Compare Cheshire with other housing markets across Massachusetts.

Nantucket$2.97M Chilmark$2.28M Weston$2.18M Wellesley$1.95M Edgartown$1.77M Aquinnah$1.73M Dover$1.72M West Tisbury$1.6M

Full Pittsfield, MA analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Pittsfield, MA metro.

View Pittsfield, MA metro

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Cheshire, MA