The median home in Windsor, Massachusetts is valued at $338,567, up 1.4% year over year. Windsor 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$338,567

+1.4%

AFFORDABILITY

Enter your income for Windsor.

Income (annual)

Down Payment

$67,713 on $338,567

Stretch — 35.2% of income

Above 28% but manageable with cuts.

PITI$2,201

P/I35.2%

Afford$269K

Gap-$69K

P&I $1,712Tax $339Ins $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 Windsor 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 →

WINDSOR, MA