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.

Home Value$338,567

+1.4%

Prices rising — worse for buyers.

Affordability

Enter your income for Windsor.

Income (annual)

Down Payment

$67,713 on $338,567

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

Stretch35.2% 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$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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Windsor, MA