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Cost of Living in Winchester, MA — June 2026

What it costs to buy and own a home in Winchester, Massachusetts — prices, monthly payments, and property taxes.

Updated June 2026 · Live MLS data
Median Home Price
$1.9M
Est. Monthly Payment
$9,854
Price / Sq Ft
$549
Property Tax Rate
$11.09/$1k
Est. Monthly Tax
$1,755

Cost of Living in Winchester

The biggest cost-of-living factor in Winchester, Massachusetts is housing. The median home is priced around $1.9M, or about $549 per square foot.

With 20% down on a median-priced home, the estimated monthly mortgage payment (principal and interest) is about $9,854, plus roughly $1,755 per month in property taxes. Rates and down payment change this figure significantly.

Winchester's FY2025 residential property tax rate is $11.09 per $1,000 of assessed value. Combined with home prices, that gives a clear picture of the monthly cost of owning in Winchester.

Browse homes for sale in Winchester → See every active listing with photos, pricing, and full details.

Frequently Asked Questions

How much does it cost to buy a home in Winchester, MA?

The median home in Winchester is about $1.9M. With 20% down, the estimated monthly mortgage (principal & interest) is around $9,854.

What are property taxes like in Winchester?

Winchester's FY2025 residential rate is $11.09 per $1,000 — roughly $1,755 per month on a median-priced home.

Is Winchester an expensive place to live?

Housing is the main driver. At a $1.9M median price, Winchester is best compared against nearby towns — browse current listings to see your options.

Market figures are derived from live MLS data and are provided for informational purposes only. They are not an appraisal or a guarantee of value. Last updated June 2026.