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.

See the full metro analysis: Pittsfield, MA stress score, crash risk, and 12-month forecast →

Home Value$342,371

+3.9%

AFFORDABILITY

Enter your income for Cheshire.

Income (annual)

Down Payment

$68,474 on $342,371

Stretch — 35.6% 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$2970K Chilmark$2283K Weston$2182K Wellesley$1946K Edgartown$1773K Aquinnah$1729K Dover$1715K West Tisbury$1597K

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 →

CHESHIRE, MA