Winchester, MA Real Estate & Homes For Sale

29 homes

  • 40 Wainwright Rd, Winchester, MA 01890
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    NEWOPEN FRI, 11-12:30PM0.48 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
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    NEWOPEN SAT, 12-2PM
    $740,000
    2bd
    3ba
    1,421 sqft
    7 Conant Rd #41,
    Winchester, MA 01890
    The Diamond Group, Keller Williams Realty-Merrimack
  • 171 Swanton St #63, Winchester, MA 01890
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    NEWOPEN SAT, 11:30-1PM
    $699,000
    2bd
    3ba
    1,823 sqft
    171 Swanton St #63,
    Winchester, MA 01890
    Paula R. Sughrue, Better Homes and Gardens Real Estate - The Shanahan Group
  • 7 Wainwright Rd #98, Winchester, MA 01890
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    NEW - 2 DAYS AGO
    $1,799,000
    4bd
    4ba
    3,361 sqft
    7 Wainwright Rd #98,
    Winchester, MA 01890
    Paula R. Sughrue, Better Homes and Gardens Real Estate - The Shanahan Group
  • 30 Graystone Cir #30, Winchester, MA 01890
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    NEWOPEN SAT, 11:30-1PM
    $1,650,000
    3bd
    4ba
    3,874 sqft
    30 Graystone Cir #30,
    Winchester, MA 01890
    Find Your Village Real Estate Team, Keller Williams Realty Boston Northwest
  • 235 Forest St, Winchester, MA 01890
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    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
  • 4 Davey Ln, Winchester, MA 01890
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    0.31 ACRES
    $2,600,000
    5bd
    5ba
    5,267 sqft (on 0.31 acres)
    4 Davey Ln,
    Winchester, MA 01890
    Gayle Winters & Co. Team, Compass
  • 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
    OPEN SAT, 11-1PM0.29 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
  • 116 Forest St, Winchester, MA 01890
    $959,000
    4bd
    3ba
    2,106 sqft
    116 Forest St,
    Winchester, MA 01890
    Kim Covino & Co. Team, Compass
  • 68 Harvard St #68, Winchester, MA 01890
    $1,299,000
    4bd
    4ba
    2,181 sqft
    68 Harvard St #68,
    Winchester, MA 01890
    William Copithorne, Keller Williams Realty Boston Northwest
  • 3 Cambridge St, Arlington, MA 02474
    0.86 ACRES
    $1,699,000
    3 Cambridge St,
    Arlington, MA 02474
    The Synergy Group, The Synergy Group
  • 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
  • 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
  • 19 Gershon Way #19, Winchester, MA 01890
    $2,249,000
    3bd
    3ba
    3,938 sqft
    19 Gershon Way #19,
    Winchester, MA 01890
    Michelle Faust, Coldwell Banker Realty - Westwood
  • 4 Abby Rd, Winchester, MA 01890
    $2,798,000
    4bd
    5ba
    5,471 sqft
    4 Abby Rd,
    Winchester, MA 01890
    Vita Realty Group, Compass
  • 3 Cambridge St, Winchester, MA 01890
    0.86 ACRES
    $1,699,000
    3 Cambridge St,
    Winchester, MA 01890
    The Synergy Group, The Synergy Group
  • 30 Glen Rd, Winchester, MA 01890
    OPEN SAT, 11:30-1PM0.56 ACRES
    $1,999,000
    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
  • 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
  • 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
  • 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
  • 6 Lakeview Rd, Winchester, MA 01890
    0.27 ACRES
    $2,499,000
    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
    0.46 ACRES
    $2,830,000
    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

  • 239 Mountain Ave, Arlington, MA 02474
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    NEW - 13 HRS AGO
    $829,000
    3bd
    3ba
    2,193 sqft
    239 Mountain Ave,
    Arlington, MA 02474
    Jennifer Schneider, Century 21 Elite Realty
  • 55 Mount Pleasant St, Woburn, MA 01801
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    NEWOPEN SAT, 10-11:30AM0.26 ACRES
    $699,000
    3bd
    2ba
    1,483 sqft (on 0.26 acres)
    55 Mount Pleasant St,
    Woburn, MA 01801
    Steve McKenna & The Home Advantage Team, Gibson Sotheby's International Realty
  • 147 Ridge St, Arlington, MA 02474
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    NEWOPEN THU, 5-6:30PM0.27 ACRES
    $749,900
    3bd
    2ba
    1,474 sqft (on 0.27 acres)
    147 Ridge St,
    Arlington, MA 02474
    Gary Blattberg, RE/MAX 360
  • 9 Marigold Way #9, Burlington, MA 01803
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    NEWOPEN SAT, 12-2PM
    $1,319,000
    3bd
    3ba
    3,286 sqft
    9 Marigold Way #9,
    Burlington, MA 01803
    Top Home Team, Coldwell Banker Realty
  • Gordon Rd, Medford, MA 02155
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    NEW - 1 DAY AGO
    $379,000
    Gordon Rd,
    Medford, MA 02155
    Chuck Andre, RE/MAX Andrew Realty Services
  • 35 Garden St, Woburn, MA 01801
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    NEWOPEN THU, 4-5:30PM
    $635,000
    3bd
    1ba
    1,152 sqft
    35 Garden St,
    Woburn, MA 01801
    Wendy Rocca, Keller Williams Realty Boston Northwest
  • 4 Stratton Dr #2203, Woburn, MA 01801
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    $811,260
    2bd
    2ba
    1,643 sqft
    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
    $875,000
    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
    $976,995+
    3bd
    3ba
    1,921 sqft
    Wheaton Plan in Highland at Vale,
    Woburn, MA 01801
  • Belmont Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
    $1,000,000+
    2bd
    2ba
    1,796 sqft
    Belmont Plan in Highland at Vale,
    Woburn, MA 01801
  • 137 Fern Rd, Medford, MA 02155
    $700,000
    3bd
    2ba
    1,218 sqft
    137 Fern Rd,
    Medford, MA 02155
    Devin Rogers, ERA Key Realty Services
  • 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
    $75,000
    Bailey St,
    Medford, MA 02155
    Cosmopolitan Team, Realty ONE Group Cosmopolitan
  • 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
    $811,260+
    2bd
    2ba
    1,643 sqft
    Eldridge Plan in Highland at Vale,
    Woburn, MA 01801
  • 61 Wright St #105, Stoneham, MA 02180
    OPEN SAT, 2-3PM
    $399,999
    2bd
    2ba
    796 sqft
    61 Wright St #105,
    Stoneham, MA 02180
    Francesca Driscoll, Redfin Corp.
  • 519 Summer St, Arlington, MA 02474
    OPEN FRI, 11:30-12:30PM
    $874,900
    3bd
    2ba
    1,400 sqft
    519 Summer St,
    Arlington, MA 02474
    Kathryn Hendy, Aikenhead Real Estate, Inc.
  • 11-13 Garfield Ave, Woburn, MA 01801
    OPEN SUN, 12-1:30PM
    $775,000
    5bd
    2ba
    2,841 sqft
    11-13 Garfield Ave,
    Woburn, MA 01801
    Karren Shaughnessy, J. Mulkerin Realty
  • 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
  • 9 Goodwin Dr #52, Woburn, MA 01801
    $1,325,315
    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 SAT, 12-1:30PM
    $699,999
    3bd
    2ba
    1,056 sqft
    35 Wright St,
    Stoneham, MA 02180
    Jason Saphire, www.HomeZu.com
  • 43 Samoset Rd, Woburn, MA 01801
    OPEN SAT, 11:30-1PM0.34 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
    $1,101,995+
    3bd
    3ba
    2,300 sqft
    Southbrook Plan in Highland at Vale,
    Woburn, MA 01801
  • Jackson Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
    $1,086,995+
    3bd
    3ba
    2,143 sqft
    Jackson Plan in Highland at Vale,
    Woburn, MA 01801
  • Ashford Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
    $827,920+
    2bd
    2ba
    1,667 sqft
    Ashford Plan in Highland at Vale,
    Woburn, MA 01801
  • Desmond Plan in Highland at Vale, Woburn, MA 01801
    NEW CONSTRUCTION
    $830,090+
    2bd
    2ba
    1,444 sqft
    Desmond Plan in Highland at Vale,
    Woburn, MA 01801
  • 5 Graystone Rd, Stoneham, MA 02180
    $499,000
    5 Graystone Rd,
    Stoneham, MA 02180
    Emma Fula, Coldwell Banker Realty - Boston

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 $1,429,091
MonthMedian home value
March 2023$1.3M
April 2023$1.31M
May 2023$1.33M
June 2023$1.36M
July 2023$1.38M
August 2023$1.4M
September 2023$1.41M
October 2023$1.41M
November 2023$1.42M
December 2023$1.42M
January 2024$1.42M
February 2024$1.43M
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 and 29 homes for sale in Winchester.
Home SizeHome Value*
1 bedroom (See homes)$328,290
2 bedrooms (3 homes)$757,252
3 bedrooms (5 homes)$1,215,494
4 bedrooms (8 homes)$1,596,346
*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."
    0
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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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