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.

See the full metro analysis: Boston-Cambridge-Newton, MA-NH stress score, crash risk, and 12-month forecast →

Home Value$1,496,625

+2.3%

Rent$3,175/mo

AFFORDABILITY

Enter your income for Winchester.

Income (annual)

Down Payment

$299,325 on $1,496,625

Out of reach — 147.4% of income

Need $394,886/yr to afford.

PITI$9,214

P/I147.4%

Afford$284K

Gap-$1212K

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

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.

View Boston-Cambridge-Newton, MA-NH metro →

WINCHESTER, MA