The median home in Winchester, Massachusetts is valued at $1,496,625, up 2.3% year over year. Typical monthly rent is $3,175, producing a price-to-rent ratio of 39.3x — well above the national average of 18x. Winchester is part of the Boston-Cambridge-Newton, MA-NH metropolitan area, which CrashWatch tracks daily with real-time stress scores and crash risk analysis.

Home Value$1,496,625

+2.3%

Rent$3,175/mo

Prices rising — worse for buyers.

Affordability

Enter your income for Winchester.

Income (annual)

Down Payment

$299,325 on $1,496,625

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

Out of reach147.4% of income

Need $394,886/yr to afford.

PITI$9,214

P/I147.4%

Afford$284K

Gap-$1.21M

P&I $7,568Tax $1,497Ins $150

Renting $6,039/mo cheaper ($3,175 rent)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 Winchester 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 Boston-Cambridge-Newton, MA-NH analysis

Stress scores, crash risk, early warning signals, and 12-month price forecasts for the Boston-Cambridge-Newton, MA-NH metro.

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Winchester, MA