Winchester, MA Real Estate & Homes For Sale

42 homes

  • 114 Pond St, Winchester, MA 01890
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    NEWOPEN THU, 4:30-5:30PM0.27 ACRES
    $1,199,000
    3bd
    3ba
    1,894 sqft (on 0.27 acres)
    114 Pond St,
    Winchester, MA 01890
    Jennifer Ryer, Better Homes and Gardens Real Estate - The Shanahan Group
  • 22 Albamont Rd, Winchester, MA 01890
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    NEWOPEN TUE, 10:30-11:30AM0.27 ACRES
    $1,199,000
    3bd
    2ba
    2,597 sqft (on 0.27 acres)
    22 Albamont Rd,
    Winchester, MA 01890
    The Pallotta Group, Leading Edge Real Estate
  • 118 Wendell St, Winchester, MA 01890
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    NEW - 1 DAY AGO
    $1,699,000
    5bd
    3ba
    3,415 sqft
    118 Wendell St,
    Winchester, MA 01890
    Mark Donnellan, Better Homes and Gardens Real Estate - The Shanahan Group
  • 111 Arlington St, Winchester, MA 01890
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    0.31 ACRES
    $1,249,000
    3bd
    4ba
    2,871 sqft (on 0.31 acres)
    111 Arlington St,
    Winchester, MA 01890
    Carolyn Vernaglia, Better Homes and Gardens Real Estate - The Shanahan Group
  • 30 Glen Rd, Winchester, MA 01890
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    0.56 ACRES
    $2,099,000
    6bd
    3ba
    3,892 sqft (on 0.56 acres)
    30 Glen Rd,
    Winchester, MA 01890
    Paula R. Sughrue, Better Homes and Gardens Real Estate - The Shanahan Group
  • 4 Abby Rd, Winchester, MA 01890
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    $2,798,000
    4bd
    5ba
    5,471 sqft
    4 Abby Rd,
    Winchester, MA 01890
    Vita Realty Group, Compass
  • 14 Goodwin Dr #41, Woburn, MA 01801
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    $1,272,295
    3bd
    3ba
    2,300 sqft
    14 Goodwin Dr #41,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 9 S Gtwy, Winchester, MA 01890
    $1,599,000
    6bd
    4ba
    3,250 sqft
    9 S Gtwy,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 43 Mayflower Rd, Winchester, MA 01890
    0.46 ACRES
    $1,725,000
    4bd
    3ba
    4,190 sqft (on 0.46 acres)
    43 Mayflower Rd,
    Winchester, MA 01890
    Annie Youssoufian, Boston Brownstones Realty PLLC
  • 10-10 Winthrop St #A, Winchester, MA 01890
    Derek Greene, The Greene Realty Group
  • 23 Hancock St, Winchester, MA 01890
    0.34 ACRES
    $1,599,000
    3bd
    2ba
    2,128 sqft (on 0.34 acres)
    23 Hancock St,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 2 Chestnut St, Winchester, MA 01890
    0.25 ACRES
    $1,699,000
    4bd
    4ba
    3,171 sqft (on 0.25 acres)
    2 Chestnut St,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 3 Lagrange St, Winchester, MA 01890
    $1,599,000
    5bd
    2ba
    3,018 sqft
    3 Lagrange St,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 44 Cabot St, Winchester, MA 01890
    $1,699,000
    4bd
    2ba
    3,691 sqft
    44 Cabot St,
    Winchester, MA 01890
    Andersen Group Realty, Keller Williams Realty Boston Northwest
  • 4 Stratton Dr   #205, Woburn, MA 01801
    NEW CONSTRUCTION
    $907,535
    2bd
    2ba
    1,796 sqft
    4 Stratton Dr #205,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 4 Stratton Dr   #101, Woburn, MA 01801
    NEW CONSTRUCTION
    $827,920
    2bd
    2ba
    1,667 sqft
    4 Stratton Dr #101,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 143 Horn Pond Brook Rd, Winchester, MA 01890
    0.34 ACRES
    $969,000
    4bd
    2ba
    1,764 sqft (on 0.34 acres)
    143 Horn Pond Brook Rd,
    Winchester, MA 01890
    Mark Donnellan, Better Homes and Gardens Real Estate - The Shanahan Group
  • 19 Socrates Way, Winchester, MA 01890
    0.49 ACRES
    $2,799,000
    5bd
    6ba
    5,678 sqft (on 0.49 acres)
    19 Socrates Way,
    Winchester, MA 01890
    Lucille Murray, Compass
  • 200 Swanton St #322, Winchester, MA 01890
    Matthew Basteri, Flow Realty, Inc.
  • 27 Everett Ave, Winchester, MA 01890
    0.64 ACRES
    $4,399,000
    6bd
    6ba
    7,431 sqft (on 0.64 acres)
    27 Everett Ave,
    Winchester, MA 01890
    The Pallotta Group, Leading Edge Real Estate
  • 3 Sheffield Rd, Winchester, MA 01890
    0.47 ACRES
    $2,369,000
    6bd
    4ba
    3,755 sqft (on 0.47 acres)
    3 Sheffield Rd,
    Winchester, MA 01890
    Nannette Shanahan, Better Homes and Gardens Real Estate - The Shanahan Group
  • 17 Goodwin Dr #56, Woburn, MA 01801
    NEW CONSTRUCTION
    $1,316,740
    3bd
    4ba
    2,143 sqft
    17 Goodwin Dr #56,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 3 Cambridge St, Arlington, MA 02474
    0.86 ACRES
    The Synergy Group, The Synergy Group
  • 19 Gershon Way  #19, Winchester, MA 01890
    Michelle Faust, Coldwell Banker Realty - Westwood
  • 11 Brooks St, Winchester, MA 01890
    0.79 ACRES
    $2,899,000
    5bd
    5ba
    5,208 sqft (on 0.79 acres)
    11 Brooks St,
    Winchester, MA 01890
    Michaela Pixie Mahtani, Leading Edge Real Estate
  • 6 Lakeview Rd, Winchester, MA 01890
    0.27 ACRES
    $2,650,000
    5bd
    4ba
    4,300 sqft (on 0.27 acres)
    6 Lakeview Rd,
    Winchester, MA 01890
    Michelle Geissler, Century 21 Property Central Inc.
  • 50 Lorena Rd, Winchester, MA 01890
    0.35 ACRES
    $3,499,000
    5bd
    5ba
    7,200 sqft (on 0.35 acres)
    50 Lorena Rd,
    Winchester, MA 01890
    Leigh Ventura, Compass
  • 64 Highland Ave #5, Winchester, MA 01890
    Ann Norberg, Coldwell Banker Realty - Lexington
  • 204 Highland Ave, Winchester, MA 01890
    0.29 ACRES
    $2,199,000
    5bd
    4ba
    4,274 sqft (on 0.29 acres)
    204 Highland Ave,
    Winchester, MA 01890
    The Pallotta Group, Leading Edge Real Estate
  • 37 Canterbury Rd, Winchester, MA 01890
    0.38 ACRES
    $1,649,000
    4bd
    3ba
    3,527 sqft (on 0.38 acres)
    37 Canterbury Rd,
    Winchester, MA 01890
    Paula R. Sughrue, Better Homes and Gardens Real Estate - The Shanahan Group
  • 15 Dix St #10, Winchester, MA 01890
    $1,599,000
    2bd
    2ba
    2,066 sqft
    15 Dix St #10,
    Winchester, MA 01890
    Vita Realty Group, Compass
  • 3 Cambridge St, Winchester, MA 01890
    0.86 ACRES
    The Synergy Group, The Synergy Group
  • 5 Gershon Way  #5, Winchester, MA 01890
    $1,699,000
    3bd
    3ba
    2,549 sqft
    5 Gershon Way #5,
    Winchester, MA 01890
    The Marrocco Group, Coldwell Banker Realty - Lexington
  • 4 Stratton Dr   #308, Woburn, MA 01801
    NEW CONSTRUCTION
    $834,350
    2bd
    2ba
    1,444 sqft
    4 Stratton Dr #308,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 4 Stratton Dr   #403, Woburn, MA 01801
    NEW CONSTRUCTION
    $874,695
    2bd
    2ba
    1,643 sqft
    4 Stratton Dr #403,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 20 Fletcher St   #2, Winchester, MA 01890
    Gary J. Litchfield, Mass. Real Estate Solutions, LLC
  • 1 Alice Ln, Winchester, MA 01890
    0.25 ACRES
    $2,799,000
    6bd
    6ba
    5,524 sqft (on 0.25 acres)
    1 Alice Ln,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 276 High St, Winchester, MA 01890
    0.46 ACRES
    $2,930,000
    5bd
    4ba
    6,595 sqft (on 0.46 acres)
    276 High St,
    Winchester, MA 01890
    Barbie Wallis, MLSMOVES
  • 15 Vinson Circle 227, Winchester, MA 01890
    NEW CONSTRUCTION0.98 ACRES
    $6,500,000
    6bd
    7ba
    8,805 sqft (on 0.98 acres)
    15 Vinson Circle 227,
    Winchester, MA 01890
    Anthony Marino, The Marino Group Collection
  • 10 Norfolk Rd, Winchester, MA 01890
    $2,395,000
    5bd
    6ba
    4,659 sqft
    10 Norfolk Rd,
    Winchester, MA 01890
    Stephen Stratford, William Raveis R.E. & Home Services

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 $1,382,160
MonthMedian home value
February 2023$1.26M
March 2023$1.26M
April 2023$1.27M
May 2023$1.29M
June 2023$1.32M
July 2023$1.34M
August 2023$1.35M
September 2023$1.36M
October 2023$1.37M
November 2023$1.38M
December 2023$1.38M
January 2024$1.38M
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 10 new listings and 42 homes for sale in Winchester.
Home SizeHome Value*
1 bedroom (2 homes)$326,068
2 bedrooms (5 homes)$739,492
3 bedrooms (8 homes)$1,174,028
4 bedrooms (8 homes)$1,542,333
*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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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
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