Winchester, MA Real Estate & Homes For Sale

32 homes

  • 50 Lorena Rd, Winchester, MA 01890
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    NEWOPEN FRI, 12-1:30PM0.35 ACRES
    $3,299,000
    5bd
    5ba
    7,242 sqft (on 0.35 acres)
    50 Lorena Rd,
    Winchester, MA 01890
    Leigh Ventura, Compass
  • 7 Bradford #7, Winchester, MA 01890
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    NEWOPEN SAT, 11:30-1PM
    $549,000
    3bd
    2ba
    1,210 sqft
    7 Bradford #7,
    Winchester, MA 01890
    Alina Wang Team, Coldwell Banker Realty - Lexington
  • 29 Kenwin Rd, Winchester, MA 01890
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    NEWOPEN SAT, 12-1:30PM0.36 ACRES
    $1,150,000
    4bd
    2ba
    2,132 sqft (on 0.36 acres)
    29 Kenwin Rd,
    Winchester, MA 01890
    Judith Moore, Barrett Sotheby's International Realty
  • 22 Baldwin St, Winchester, MA 01890
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    NEWOPEN SUN, 11-1PM
    $999,000
    3bd
    2ba
    1,678 sqft
    22 Baldwin St,
    Winchester, MA 01890
    Michael Lissack, The Virtual Realty Group
  • 9 Robinson Park, Winchester, MA 01890
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    NEWOPEN SAT, 12-1:30PM0.28 ACRES
    $1,599,000
    4bd
    4ba
    3,224 sqft (on 0.28 acres)
    9 Robinson Park,
    Winchester, MA 01890
    Paula R. Sughrue, Better Homes and Gardens Real Estate - The Shanahan Group
  • 7 Chisholm Rd, Winchester, MA 01890
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    NEWOPEN FRI, 11:30-1PM
    $899,000
    3bd
    1ba
    1,227 sqft
    7 Chisholm Rd,
    Winchester, MA 01890
    Pirani & Wile Group, Leading Edge Real Estate
  • 50 Allen Rd, Winchester, MA 01890
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    OPEN FRI, 11:30-1PM
    $1,429,000
    3bd
    3ba
    2,769 sqft
    50 Allen Rd,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 28 Garfield Ave, Winchester, MA 01890
    NEWOPEN THU, 5-7PM
    Elizabeth Darby, Berkshire Hathaway HomeServices Commonwealth Real Estate
  • 83 Church St #6, Winchester, MA 01890
    OPEN SUN, 1-2:30PM
    Carolyn Vernaglia, Better Homes and Gardens Real Estate - The Shanahan Group
  • 41 White St, Winchester, MA 01890
    $1,549,900
    4bd
    4ba
    2,442 sqft
    41 White St,
    Winchester, MA 01890
    Sharon Tang, U3 Realty, LLC
  • 40 Wainwright Rd, Winchester, MA 01890
    0.48 ACRES
    $1,699,000
    4bd
    3ba
    2,853 sqft (on 0.48 acres)
    40 Wainwright Rd,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 7 Conant Rd #41, Winchester, MA 01890
    OPEN SAT, 11-1PM
    The Diamond Group, Keller Williams Realty-Merrimack
  • 235 Forest St, Winchester, MA 01890
    0.29 ACRES
    $949,000
    3bd
    2ba
    2,212 sqft (on 0.29 acres)
    235 Forest St,
    Winchester, MA 01890
    Lin Wu, JW Real Estate Services, LLC
  • 48 Edward Dr, Winchester, MA 01890
    OPEN SAT, 1:30-3PM
    $1,050,000
    3bd
    3ba
    2,774 sqft
    48 Edward Dr,
    Winchester, MA 01890
    Alina Wang Team, Coldwell Banker Realty - Lexington
  • 204 Highland Ave, Winchester, MA 01890
    0.29 ACRES
    $1,999,000
    5bd
    4ba
    4,274 sqft (on 0.29 acres)
    204 Highland Ave,
    Winchester, MA 01890
    The Pallotta Group, Leading Edge Real Estate
  • 67 Wildwood St, Winchester, MA 01890
    0.29 ACRES
    $1,649,500
    3bd
    4ba
    3,011 sqft (on 0.29 acres)
    67 Wildwood St,
    Winchester, MA 01890
    Dorothea Feffer, Coldwell Banker Realty - Lexington
  • 3 Cambridge St, Arlington, MA 02474
    0.86 ACRES
    The Synergy Group, The Synergy Group
  • 116 Forest St, Winchester, MA 01890
    $959,000
    4bd
    3ba
    2,106 sqft
    116 Forest St,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 49 Oxford St, Winchester, MA 01890
    0.32 ACRES
    $2,599,000
    7bd
    4ba
    5,616 sqft (on 0.32 acres)
    49 Oxford St,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 4 Abby Rd, Winchester, MA 01890
    OPEN SUN, 12-1:30PM
    $2,798,000
    4bd
    5ba
    5,471 sqft
    4 Abby Rd,
    Winchester, MA 01890
    Vita Realty Group, Compass
  • 68 Harvard St #68, Winchester, MA 01890
    OPEN SUN, 11:30-1PM
    $1,269,000
    4bd
    4ba
    2,181 sqft
    68 Harvard St #68,
    Winchester, MA 01890
    William Copithorne, Keller Williams Realty Boston Northwest
  • 3 Cambridge St, Winchester, MA 01890
    0.86 ACRES
    The Synergy Group, The Synergy Group
  • 43 Mayflower Rd, Winchester, MA 01890
    0.46 ACRES
    $1,550,000
    4bd
    3ba
    4,190 sqft (on 0.46 acres)
    43 Mayflower Rd,
    Winchester, MA 01890
    Annie Youssoufian, Boston Brownstones Realty PLLC
  • 27 Everett Ave, Winchester, MA 01890
    0.64 ACRES
    $4,199,000
    6bd
    6ba
    7,431 sqft (on 0.64 acres)
    27 Everett Ave,
    Winchester, MA 01890
    The Pallotta Group, Leading Edge Real Estate
  • 6 Lakeview Rd, Winchester, MA 01890
    0.27 ACRES
    $2,449,000
    5bd
    4ba
    4,300 sqft (on 0.27 acres)
    6 Lakeview Rd,
    Winchester, MA 01890
    Michelle Geissler, Century 21 Property Central Inc.
  • 37 Canterbury Rd, Winchester, MA 01890
    0.38 ACRES
    $1,599,000
    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 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
  • 1 Alice Ln, Winchester, MA 01890
    0.25 ACRES
    $2,699,000
    6bd
    6ba
    5,524 sqft (on 0.25 acres)
    1 Alice Ln,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 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
  • 89 Wildwood St, Winchester, MA 01890
    NEW CONSTRUCTION
    $2,499,000
    7bd
    6ba
    4,800 sqft
    89 Wildwood St,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 276 High St, Winchester, MA 01890
    OPEN SAT, 3-5PM0.46 ACRES
    $2,870,000
    5bd
    4ba
    6,595 sqft (on 0.46 acres)
    276 High St,
    Winchester, MA 01890
    Barbie Wallis, MLSMOVES
  • 20 Bellevue Ave, Winchester, MA 01890
    $2,699,000
    6bd
    7ba
    6,300 sqft
    20 Bellevue Ave,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass

Homes Near Winchester, MA

We found 30 more homes matching your filters just outside Winchester

  • 18 Rindge Ave, Lexington, MA 02420
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    NEWOPEN FRI, 11-12:30PM
    $899,000
    3bd
    3ba
    1,407 sqft
    18 Rindge Ave,
    Lexington, MA 02420
    Mark Lesses Group, Coldwell Banker Realty - Lexington
  • 105-107 Pleasant St, Woburn, MA 01801
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    NEW - 6 HRS AGO
    $950,000
    10bd
    5ba
    4,035 sqft
    105-107 Pleasant St,
    Woburn, MA 01801
    Magalie Jean-Michel, Keller Williams Realty Evolution
  • 46-46 Pine St #48, Stoneham, MA 02180
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    NEWOPEN THU, 4:30-6PM
    Julie Darcangelo, Coldwell Banker Realty
  • 4 Stratton Dr   #303, Woburn, MA 01801
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    NEW - 7 HRS AGO
    $838,680
    2bd
    2ba
    1,643 sqft
    4 Stratton Dr #303,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 19 Emerson St, Stoneham, MA 02180
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    NEWOPEN FRI, 1-2PM
    $614,999
    3bd
    2ba
    1,266 sqft
    19 Emerson St,
    Stoneham, MA 02180
    The Pittella Properties Team, GDP Real Estate Group, LLC
  • 29 Montague St, Arlington, MA 02474
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    NEW - 1 DAY AGO
    $1,219,000
    3bd
    3ba
    2,200 sqft
    29 Montague St,
    Arlington, MA 02474
    Derek Greene, The Greene Realty Group
  • 255 Mountain Ave, Arlington, MA 02474
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    NEWOPEN FRI, 11-12:30PM
    Steve McKenna & The Home Advantage Team, Gibson Sotheby's International Realty
  • 8 Appletree Ln, Lexington, MA 02420
    NEWOPEN FRI, 4-6PM0.5 ACRES
    $1,300,000
    3bd
    2ba
    1,948 sqft (on 0.50 acres)
    8 Appletree Ln,
    Lexington, MA 02420
    Frances Walker, Coldwell Banker Realty - Concord
  • 299 Lexington St #99, Woburn, MA 01801
    NEWOPEN FRI, 5-6:30PM
    Andrew Martini, Compass
  • Gordon Rd, Medford, MA 02155
    Chuck Andre, RE/MAX Andrew Realty Services
  • 4 Stratton Dr #2203, Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 4 Stratton Dr   #305, Woburn, MA 01801
    NEW CONSTRUCTION
    $1,000,000
    2bd
    2ba
    1,796 sqft
    4 Stratton Dr #305,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 59 Fowle St, Woburn, MA 01801
    OPEN FRI, 4:30-6PM
    $849,000
    5bd
    2ba
    2,406 sqft
    59 Fowle St,
    Woburn, MA 01801
    Gayle Winters & Co. Team, Compass
  • Wheaton Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
  • Belmont Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
  • 120 Harrison Ave, Woburn, MA 01801
    0.64 ACRES
    $1,750,000
    4bd
    4ba
    4,600 sqft (on 0.64 acres)
    120 Harrison Ave,
    Woburn, MA 01801
    Ari Koufos, Realty Executives
  • 14 Goodwin Dr #41, Woburn, MA 01801
    $1,272,295
    3bd
    3ba
    2,300 sqft
    14 Goodwin Dr #41,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • Bailey St, Medford, MA 02155
    Cosmopolitan Team, Realty ONE Group Cosmopolitan
  • 137 Fern Rd, Medford, MA 02155
    $689,900
    3bd
    2ba
    1,218 sqft
    137 Fern Rd,
    Medford, MA 02155
    Devin Rogers, ERA Key Realty Services
  • 12 Skyview Ln, Woburn, MA 01801
    $619,900
    3bd
    1ba
    975 sqft
    12 Skyview Ln,
    Woburn, MA 01801
    Marissa Whitten, J. Mulkerin Realty
  • Eldridge Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
  • 9 Goodwin Dr #52, Woburn, MA 01801
    $1,275,315
    3bd
    3ba
    2,300 sqft
    9 Goodwin Dr #52,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • 35 Wright St, Stoneham, MA 02180
    OPEN THU, 5-6PM
    $699,999
    3bd
    2ba
    1,056 sqft
    35 Wright St,
    Stoneham, MA 02180
    Jason Saphire, www.HomeZu.com
  • 43 Samoset Rd, Woburn, MA 01801
    0.34 ACRES
    $1,599,000
    4bd
    4ba
    3,200 sqft (on 0.34 acres)
    43 Samoset Rd,
    Woburn, MA 01801
    Mary L. Lawton, Lawton Real Estate, Inc
  • 17 Goodwin Dr #56, Woburn, MA 01801
    NEW CONSTRUCTION
    $1,338,740
    3bd
    4ba
    3,500 sqft
    17 Goodwin Dr #56,
    Woburn, MA 01801
    Erin Sullivan, Pulte Homes of New England
  • Southbrook Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
  • Jackson Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
  • 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
  • Ashford Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
  • Desmond Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION

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 $1,480,501
MonthMedian home value
April 2023$1.35M
May 2023$1.37M
June 2023$1.39M
July 2023$1.42M
August 2023$1.43M
September 2023$1.44M
October 2023$1.45M
November 2023$1.46M
December 2023$1.46M
January 2024$1.46M
February 2024$1.47M
March 2024$1.48M
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 8 new listings and 32 homes for sale in Winchester.
Home SizeHome Value*
1 bedroom (See homes)$343,176
2 bedrooms (3 homes)$779,807
3 bedrooms (6 homes)$1,257,276
4 bedrooms (10 homes)$1,655,158
*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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