Winchester, MA Real Estate & Homes For Sale

40 homes

Real Estate & Homes For Sale Near Winchester, MA

We found 30 more homes matching your filters just outside Winchester

Winchester, MA Real Estate Trends

Learn about the Winchester, MA housing market through trends and averages.

Affordability of Living in Winchester, MA

The median home value is $1,575,917
MonthMedian home value
May 2025$1.55M
June 2025$1.55M
July 2025$1.55M
August 2025$1.54M
September 2025$1.54M
October 2025$1.55M
November 2025$1.56M
December 2025$1.57M
January 2026$1.57M
February 2026$1.58M
March 2026$1.58M
April 2026$1.58M
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Winchester, MA, by Home Size

Currently, there are 7 new listings in Winchester, MA and 40 homes for sale.
Home SizeHome Value*
1 bedroom (3 homes)$360,357
2 bedrooms (5 homes)$793,397
3 bedrooms (4 homes)$1,346,956
4 bedrooms (8 homes)$1,748,355
*Home value over the past month

What Locals Say about Winchester

  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
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  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
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  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
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  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
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  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
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  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
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  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
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  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
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  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
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  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
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  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
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  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
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