9,208

Winchester, MA Homes

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    • /42

      Est $2,655,887

      Not Listed For Sale

      6 Agawam Rd, Winchester, MA 01890

      • 4 Beds
      • 4.5 Baths
      • 5,315 Sq Ft
      • Built 1930
      6 Agawam Rd, Winchester, MA 01890

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Leigh Ventura Compass

  • /39

    $1,850,000

    Open Sat 11AM - 12:30PM
    • 4 Beds
    • 2.5 Baths
    • 3,092 Sq Ft

    1 Overlook Way, Winchester, MA 01890

    Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone

    Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

    1 Overlook Way, Winchester, MA 01890
  • /39

    $2,255,000

    Sold Jul 30, 2026

    2 York Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,494 Sq Ft
    • Built 1950

    Last Sold Summary

    • 16% Above List Price
    • $645/SF
    • 6 Days On Market

    Current Estimated Value $1,912,876

    Last Listing Agent Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

    2 York Rd, Winchester, MA 01890
    • /39

      Est $1,555,231

      Not Listed For Sale

      21 Samoset Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,428 Sq Ft
      • Built 1949
      21 Samoset Rd, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • /37

    $2,250,000

    $250K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 4,071 Sq Ft

    9 Plymouth Rd, Winchester, MA 01890

    Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for

    Stephanie Crawford Real Broker MA, LLC

    9 Plymouth Rd, Winchester, MA 01890
  • /2

    $2,793,000

    Sold Jul 21, 2026

    74 Wedgemere Ave, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 4,581 Sq Ft
    • Built 1938

    Last Sold Summary

    • 15% Below List Price
    • $610/SF
    • 57 Days On Market

    Current Estimated Value $2,875,732

    Last Listing Agent Kim Covino Compass

    74 Wedgemere Ave, Winchester, MA 01890
    • /42

      Est $2,155,474

      Not Listed For Sale

      88 Arlington St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,097 Sq Ft
      • Built 1939
      88 Arlington St, Winchester, MA 01890

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Kim Covino Compass

  • /28

    $1,713,000

    Sold Sep 26, 2025

    44 Amberwood Dr, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 3,002 Sq Ft
    • Built 1983

    Last Sold Summary

    • 11% Below List Price
    • $571/SF
    • 53 Days On Market

    Current Estimated Value $1,824,555

    Last Listing Agent Hudson Santana Keller Williams Realty Boston Northwest

    44 Amberwood Dr, Winchester, MA 01890
    • /36

      Est $2,278,090

      Not Listed For Sale

      111 Arlington St, Winchester, MA 01890

      • 3 Beds
      • 4 Baths
      • 2,871 Sq Ft
      • Built 1950
      111 Arlington St, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

  • /37

    $1,610,000

    Sold Nov 10, 2025

    166 Forest St, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 3,508 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $459/SF
    • 11 Days On Market

    Current Estimated Value $1,730,394

    Last Listing Agent Ning Sun United Real Estate, LLC

    166 Forest St, Winchester, MA 01890
    • /41

      Est $2,758,706

      Not Listed For Sale

      108 Arlington St, Winchester, MA 01890

      • 5 Beds
      • 7 Baths
      • 5,830 Sq Ft
      • Built 2023
      108 Arlington St, Winchester, MA 01890

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Friel Estate FrielEstate

  • /42

    $1,700,000

    Sold Jul 31, 2026

    41 Sunset Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 3,090 Sq Ft
    • Built 2023

    Last Sold Summary

    • 1% Above List Price
    • $550/SF
    • 8 Days On Market

    Current Estimated Value $1,663,172

    Last Listing Agent Kim Covino Compass

    41 Sunset Rd, Winchester, MA 01890
    • /26

      Est $1,501,244

      Not Listed For Sale

      7 Indian Hill Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,646 Sq Ft
      • Built 1955
      7 Indian Hill Rd, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

  • /42

    $3,450,000

    Sold Jun 26, 2026

    40 Foxcroft Rd, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 6,460 Sq Ft
    • Built 2025

    Last Sold Summary

    • 8% Below List Price
    • $534/SF
    • 67 Days On Market

    Current Estimated Value $3,296,042

    Last Listing Agent The Boston ONE Team Serhant

    40 Foxcroft Rd, Winchester, MA 01890
    • /38

      Est $1,578,135

      Not Listed For Sale

      36 Oneida Rd, Winchester, MA 01890

      • 3 Beds
      • 4 Baths
      • 2,376 Sq Ft
      • Built 1927
      36 Oneida Rd, Winchester, MA 01890

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Philip Vita Compass

  • /36

    $2,750,000

    Sold Oct 29, 2025

    11 Taft Dr, Winchester, MA 01890

    • 5 Beds
    • 5.5 Baths
    • 4,627 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $594/SF
    • 30 Days On Market

    Current Estimated Value $2,493,188

    Last Listing Agent Rose Hall Blue Ocean Realty, LLC

    11 Taft Dr, Winchester, MA 01890
    • /38

      Est $1,680,649

      Not Listed For Sale

      32 Oneida Rd, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 2,853 Sq Ft
      • Built 1930
      32 Oneida Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

  • /24

    $1,165,000

    Sold Oct 14, 2025

    59 Johnson Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,458 Sq Ft
    • Built 1958

    Last Sold Summary

    • 10% Below List Price
    • $474/SF
    • 43 Days On Market

    Current Estimated Value $1,248,283

    Last Listing Agent Angela Zhang Greatland Real Estate LLC

    59 Johnson Rd, Winchester, MA 01890
    • /41

      Est $2,246,460

      Not Listed For Sale

      6 Cambridge St, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,925 Sq Ft
      • Built 1999
      6 Cambridge St, Winchester, MA 01890

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Kim Covino Compass

  • /40

    $2,030,000

    Sold Dec 01, 2025

    58 Bacon St, Winchester, MA 01890

    • 6 Beds
    • 5.5 Baths
    • 5,791 Sq Ft
    • Built 1925

    Last Sold Summary

    • 3% Below List Price
    • $351/SF
    • 8 Days On Market

    Current Estimated Value $2,188,459

    Last Listing Agent Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

    58 Bacon St, Winchester, MA 01890
    • /42

      Est $4,448,393

      Not Listed For Sale

      3 Myopia Rd, Winchester, MA 01890

      • 7 Beds
      • 8.5 Baths
      • 10,146 Sq Ft
      • Built 2024
      3 Myopia Rd, Winchester, MA 01890

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Kim Covino Compass

  • /41

    $2,150,000

    Sold Nov 05, 2025

    7 Wainwright Rd Unit 72, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,512 Sq Ft
    • Built 1989

    Last Sold Summary

    • 10% Above List Price
    • $612/SF
    • 7 Days On Market

    Current Estimated Value $2,121,373

    Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

    7 Wainwright Rd Unit 72, Winchester, MA 01890
    • /42

      Est $1,874,877

      Not Listed For Sale

      10 Taft Dr, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 3,243 Sq Ft
      • Built 1960
      10 Taft Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Cindy Cai Cindy Cai Realty LLC

  • /42

    $2,090,000

    Sold Jan 06, 2026

    5 Bacon St, Winchester, MA 01890

    • 6 Beds
    • 4 Baths
    • 4,385 Sq Ft
    • Built 1910

    Last Sold Summary

    • 9% Below List Price
    • $477/SF
    • 72 Days On Market

    Current Estimated Value $2,141,775

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    5 Bacon St, Winchester, MA 01890
    • /41

      Est $2,462,329

      Not Listed For Sale

      17 Swan Rd, Winchester, MA 01890

      • 4 Beds
      • 4.5 Baths
      • 4,333 Sq Ft
      • Built 1926
      17 Swan Rd, Winchester, MA 01890

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Peter Rooney Compass

  • /42

    $2,900,000

    Sold Dec 01, 2025

    26 Swan Rd, Winchester, MA 01890

    • 6 Beds
    • 6.5 Baths
    • 8,463 Sq Ft
    • Built 2006

    Last Sold Summary

    • 19% Below List Price
    • $343/SF
    • 83 Days On Market

    Current Estimated Value $3,285,566

    Last Listing Agent Kim Covino Compass

    26 Swan Rd, Winchester, MA 01890
    • /42

      Est $2,149,578

      Not Listed For Sale

      5 Swan Rd, Winchester, MA 01890

      • 7 Beds
      • 3 Baths
      • 4,090 Sq Ft
      • Built 1890
      5 Swan Rd, Winchester, MA 01890

      Last Sold Summary

      • 164 Days On Market

      Last Listing Agent Kim Covino Compass

  • /36

    $980,000

    Sold Aug 11, 2026

    339-341 Washington St, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1926

    Last Sold Summary

    • 11% Below List Price
    • $454/SF
    • 21 Days On Market

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    339-341 Washington St, Winchester, MA 01890
    • /38

      Est $2,526,007

      Not Listed For Sale

      30 Swan Rd, Winchester, MA 01890

      • 6 Beds
      • 4.5 Baths
      • 4,323 Sq Ft
      • Built 1929
      30 Swan Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jay Noble Lamacchia Realty, Inc.

  • /33

    $1,502,500

    Sold Jan 10, 2026

    7 Wainwright Rd Unit 118, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 3,807 Sq Ft
    • Built 1995

    Last Sold Summary

    • $395/SF
    • 5 Days On Market

    Current Estimated Value $1,565,871

    Last Listing Agent Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Wainwright Rd Unit 118, Winchester, MA 01890
    • /42

      Est $2,711,462

      Not Listed For Sale

      34 Swan Rd, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,704 Sq Ft
      • Built 1954
      34 Swan Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Laurie Cappuccio Classified Realty Group

  • /42

    $1,825,000

    Sold Dec 08, 2025

    19 Glengarry Rd, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 3,521 Sq Ft
    • Built 1897

    Last Sold Summary

    • 13% Below List Price
    • $518/SF
    • 86 Days On Market

    Current Estimated Value $1,899,030

    Last Listing Agent Kim Covino Compass

    19 Glengarry Rd, Winchester, MA 01890
    • /42

      Est $2,969,905

      Not Listed For Sale

      21 Fernway, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 5,386 Sq Ft
      • Built 1963
      21 Fernway, Winchester, MA 01890

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kim Covino Compass

  • /35

    $1,310,000

    Sold Dec 24, 2025

    7 Thornberry Rd, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 3,033 Sq Ft
    • Built 1957

    Last Sold Summary

    • 5% Below List Price
    • $432/SF
    • 73 Days On Market

    Current Estimated Value $1,350,775

    Last Listing Agent Kim Covino Compass

    7 Thornberry Rd, Winchester, MA 01890
    • /42

      Est $3,592,577

      Not Listed For Sale

      6 Robinson Park, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 6,900 Sq Ft
      • Built 1949
      6 Robinson Park, Winchester, MA 01890

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

  • /31

    $3,100,000

    Sold Sep 02, 2026

    25 Myopia Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,847 Sq Ft
    • Built 2005

    Last Sold Summary

    • 9% Below List Price
    • $640/SF
    • 99 Days On Market

    Current Estimated Value $3,347,151

    Last Listing Agent Wenjun Cao Engel & Volkers Boston

    25 Myopia Rd, Winchester, MA 01890
    • /42

      Est $1,771,908

      Not Listed For Sale

      9 Robinson Park, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,224 Sq Ft
      • Built 1945
      9 Robinson Park, Winchester, MA 01890

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Paul Reardon William Raveis R.E. & Home Services

  • /42

    $3,500,000

    Sold Jun 26, 2026

    50 Oxford St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 5,128 Sq Ft
    • Built 1917

    Last Sold Summary

    • 1% Above List Price
    • $683/SF
    • 1 Day On Market

    Current Estimated Value $3,399,726

    Last Listing Agent Kim Covino Compass

    50 Oxford St, Winchester, MA 01890
    • /39

      Est $2,159,465

      Not Listed For Sale

      5 Woodside Rd, Winchester, MA 01890

      • 6 Beds
      • 2.5 Baths
      • 3,487 Sq Ft
      • Built 1910
      5 Woodside Rd, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Kim Covino Compass

  • /39

    $1,330,000

    Sold May 28, 2026

    1 Orient St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 2,222 Sq Ft
    • Built 1932

    Last Sold Summary

    • 2% Above List Price
    • $599/SF
    • 7 Days On Market

    Current Estimated Value $1,325,889

    Last Listing Agent Julie Gibson Gibson Sotheby's International Realty

    1 Orient St, Winchester, MA 01890

Showing Results 281 - 320, Page 8 of 18

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