9,202

Winchester, MA Homes

Section Image
    • 22 Albamont Rd, Winchester, MA 01890
      22 Albamont Rd, Winchester, MA 01890
      22 Albamont Rd, Winchester, MA 01890
      /37

      Est $1,401,664

      Not Listed For Sale

      22 Albamont Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,597 Sq Ft
      • Built 1959
      22 Albamont Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 200 Swanton St Unit T35, Winchester, MA 01890
    200 Swanton St Unit T35, Winchester, MA 01890
    200 Swanton St Unit T35, Winchester, MA 01890
    /39

    $400,000

    $115K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 810 Sq Ft

    200 Swanton St Unit T35, Winchester, MA 01890

    SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of

    Nuri Tirana Tirana Real Estate Group

    200 Swanton St Unit T35, Winchester, MA 01890
  • 16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    /42

    $1,090,000

    Sold Feb 06, 2026

    16 Ridge St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft
    • Built 1965

    Last Sold Summary

    • 9% Below List Price
    • $591/SF
    • 82 Days On Market

    Current Estimated Value $1,150,221

    Last Listing Agent Kim Covino Compass

    16 Ridge St, Winchester, MA 01890
    • 23 New Meadows Rd, Winchester, MA 01890
      23 New Meadows Rd, Winchester, MA 01890
      23 New Meadows Rd, Winchester, MA 01890
      /31

      Est $1,254,957

      Not Listed For Sale

      23 New Meadows Rd, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 2,321 Sq Ft
      • Built 1941
      23 New Meadows Rd, Winchester, MA 01890

      Last Sold Summary

      • 33 Days On Market

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

  • 11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    /36

    $3,600,000

    • 7 Beds
    • 7.5 Baths
    • 7,429 Sq Ft

    11 Viking Rd, Winchester, MA 01890

    Spectacular ground-up new construction estate on a quiet Winchester cul-de-sac near Wright Locke Farm. Newly completed, this exceptional residence spans more than 7,000 square feet across four impeccably finished levels. Ideally positioned on a quiet cul-de-sac in one of Winchester’s most desirable locations, the home offers an extraordinary combination of new construction, refined design,

    Valerie Post Engel & Volkers Boston

    11 Viking Rd, Winchester, MA 01890
  • 28 Emerson Rd, Winchester, MA 01890
    28 Emerson Rd, Winchester, MA 01890
    28 Emerson Rd, Winchester, MA 01890
    /32

    $1,475,000

    Sold Apr 29, 2026

    28 Emerson Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 2,344 Sq Ft
    • Built 1952

    Last Sold Summary

    • 9% Above List Price
    • $629/SF
    • 4 Days On Market

    Current Estimated Value $1,466,943

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    28 Emerson Rd, Winchester, MA 01890
    • 21 Westland Ave, Winchester, MA 01890
      21 Westland Ave, Winchester, MA 01890
      21 Westland Ave, Winchester, MA 01890
      /36

      Est $1,822,389

      Not Listed For Sale

      21 Westland Ave, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,432 Sq Ft
      • Built 1925
      21 Westland Ave, Winchester, MA 01890

      Last Sold Summary

      • 9 Days On Market

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

  • 9 Plymouth Rd, Winchester, MA 01890
    9 Plymouth Rd, Winchester, MA 01890
    9 Plymouth Rd, Winchester, MA 01890
    /37

    $2,500,000

    • 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
  • 115 Church St, Winchester, MA 01890
    115 Church St, Winchester, MA 01890
    115 Church St, Winchester, MA 01890
    /35

    $2,975,000

    Sold Jul 09, 2026

    115 Church St, Winchester, MA 01890

    • 7 Beds
    • 6 Baths
    • 5,888 Sq Ft
    • Built 1888

    Last Sold Summary

    • $505/SF
    • 8 Days On Market

    Current Estimated Value $2,940,994

    Last Listing Agent Jennifer Ryer Better Homes and Gardens Real Estate - The Shanahan Group

    115 Church St, Winchester, MA 01890
    • 20 Seneca Rd, Winchester, MA 01890
      20 Seneca Rd, Winchester, MA 01890
      20 Seneca Rd, Winchester, MA 01890
      /40

      Est $1,834,240

      Not Listed For Sale

      20 Seneca Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,813 Sq Ft
      • Built 1930
      20 Seneca Rd, Winchester, MA 01890

      Last Sold Summary

      • 26 Days On Market

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

  • 95 Irving St, Winchester, MA 01890
    95 Irving St, Winchester, MA 01890
    95 Irving St, Winchester, MA 01890
    /42

    $1,350,000

    Sold Mar 06, 2026

    95 Irving St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,490 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $542/SF
    • 61 Days On Market

    Current Estimated Value $1,279,170

    Last Listing Agent Kim Covino Compass

    95 Irving St, Winchester, MA 01890
    • 49 Westland Ave, Winchester, MA 01890
      49 Westland Ave, Winchester, MA 01890
      49 Westland Ave, Winchester, MA 01890
      /40

      Est $1,834,886

      Not Listed For Sale

      49 Westland Ave, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 3,158 Sq Ft
      • Built 1941
      49 Westland Ave, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Michaela Mahtani Leading Edge Real Estate

  • 10 Winchester Place Unit 301, Winchester, MA 01890
    10 Winchester Place Unit 301, Winchester, MA 01890
    10 Winchester Place Unit 301, Winchester, MA 01890
    /27

    $1,225,000

    Sold Nov 14, 2025

    10 Winchester Place Unit 301, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,531 Sq Ft
    • Built 2002

    Last Sold Summary

    • 14% Above List Price
    • $800/SF
    • 1 Day On Market

    Current Estimated Value $1,281,846

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    10 Winchester Place Unit 301, Winchester, MA 01890
    • 43 Emerson Rd, Winchester, MA 01890
      43 Emerson Rd, Winchester, MA 01890
      43 Emerson Rd, Winchester, MA 01890
      /42

      Est $2,187,734

      Not Listed For Sale

      43 Emerson Rd, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 4,730 Sq Ft
      • Built 1953
      43 Emerson Rd, Winchester, MA 01890

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

  • 49 Spruce St, Winchester, MA 01890
    49 Spruce St, Winchester, MA 01890
    49 Spruce St, Winchester, MA 01890
    /41

    $815,000

    Sold Mar 09, 2026

    49 Spruce St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,710 Sq Ft
    • Built 1860

    Last Sold Summary

    • 2% Below List Price
    • $477/SF
    • 16 Days On Market

    Current Estimated Value $843,783

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    49 Spruce St, Winchester, MA 01890
    • 6 Agawam Rd, Winchester, MA 01890
      6 Agawam Rd, Winchester, MA 01890
      6 Agawam Rd, Winchester, MA 01890
      /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

  • 21 Bellevue Ave, Winchester, MA 01890
    21 Bellevue Ave, Winchester, MA 01890
    21 Bellevue Ave, Winchester, MA 01890
    /42

    $2,650,000

    Sold Jul 17, 2026

    21 Bellevue Ave, Winchester, MA 01890

    • 5 Beds
    • 4 Baths
    • 5,950 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $445/SF
    • 5 Days On Market

    Current Estimated Value $2,685,014

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

    21 Bellevue Ave, Winchester, MA 01890
    • 21 Samoset Rd, Winchester, MA 01890
      21 Samoset Rd, Winchester, MA 01890
      21 Samoset 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

  • 60 Lake St Unit I, Winchester, MA 01890
    60 Lake St Unit I, Winchester, MA 01890
    60 Lake St Unit I, Winchester, MA 01890
    /30

    $640,000

    Sold Aug 15, 2025

    60 Lake St Unit I, Winchester, MA 01890

    • 2 Beds
    • 1.5 Baths
    • 1,464 Sq Ft
    • Built 1976

    Last Sold Summary

    • 2% Above List Price
    • $437/SF
    • 8 Days On Market

    Current Estimated Value $666,331

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

    60 Lake St Unit I, Winchester, MA 01890
    • 88 Arlington St, Winchester, MA 01890
      88 Arlington St, Winchester, MA 01890
      88 Arlington St, 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

  • 200 Swanton St Unit 402, Winchester, MA 01890
    200 Swanton St Unit 402, Winchester, MA 01890
    200 Swanton St Unit 402, Winchester, MA 01890
    /14

    $287,000

    Sold Sep 19, 2025

    200 Swanton St Unit 402, Winchester, MA 01890

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft
    • Built 1966

    Last Sold Summary

    • 4% Below List Price
    • $740/SF
    • 7 Days On Market

    Current Estimated Value $295,282

    Last Listing Agent Michael Masci North Atlantic Realty Group

    200 Swanton St Unit 402, Winchester, MA 01890
    • 111 Arlington St, Winchester, MA 01890
      111 Arlington St, Winchester, MA 01890
      111 Arlington St, 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

  • 4 Norwood St, Winchester, MA 01890
    4 Norwood St, Winchester, MA 01890
    /2

    $3,242,250

    Sold Oct 17, 2025

    4 Norwood St, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,250 Sq Ft
    • Built 1870

    Last Sold Summary

    • 5% Below List Price
    • $618/SF
    • 25 Days On Market

    Current Estimated Value $3,098,659

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    4 Norwood St, Winchester, MA 01890
    • 108 Arlington St, Winchester, MA 01890
      108 Arlington St, Winchester, MA 01890
      108 Arlington 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

  • 35 Hollywood Rd, Winchester, MA 01890
    35 Hollywood Rd, Winchester, MA 01890
    35 Hollywood Rd, Winchester, MA 01890
    /40

    $1,755,000

    Sold May 01, 2026

    35 Hollywood Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,906 Sq Ft
    • Built 1963

    Last Sold Summary

    • 7% Below List Price
    • $449/SF
    • 14 Days On Market

    Current Estimated Value $1,779,509

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    35 Hollywood Rd, Winchester, MA 01890
    • 7 Indian Hill Rd, Winchester, MA 01890
      7 Indian Hill Rd, Winchester, MA 01890
      7 Indian Hill 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

  • 7 Appalachian Rd, Winchester, MA 01890
    7 Appalachian Rd, Winchester, MA 01890
    7 Appalachian Rd, Winchester, MA 01890
    /42

    $2,150,000

    Sold Feb 02, 2026

    7 Appalachian Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,263 Sq Ft
    • Built 1927

    Last Sold Summary

    • 8% Above List Price
    • $659/SF
    • 3 Days On Market

    Current Estimated Value $2,122,442

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    7 Appalachian Rd, Winchester, MA 01890
    • 36 Oneida Rd, Winchester, MA 01890
      36 Oneida Rd, Winchester, MA 01890
      36 Oneida 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

  • 13 Nelson St, Winchester, MA 01890
    13 Nelson St, Winchester, MA 01890
    13 Nelson St, Winchester, MA 01890
    /10

    $425,000

    Sold Mar 18, 2026

    13 Nelson St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,783 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 66 Days On Market

    Current Estimated Value $473,463

    Last Listing Agent Karen Morand MCO Realty Service, LLC

    13 Nelson St, Winchester, MA 01890
    • 32 Oneida Rd, Winchester, MA 01890
      32 Oneida Rd, Winchester, MA 01890
      32 Oneida Rd, 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

  • 12 Wincrest Dr, Winchester, MA 01890
    12 Wincrest Dr, Winchester, MA 01890
    12 Wincrest Dr, Winchester, MA 01890
    /41

    $1,810,000

    Sold May 18, 2026

    12 Wincrest Dr, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 3,833 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Above List Price
    • $472/SF
    • 5 Days On Market

    Current Estimated Value $1,801,279

    Last Listing Agent Kim Covino Compass

    12 Wincrest Dr, Winchester, MA 01890
    • 6 Cambridge St, Winchester, MA 01890
      6 Cambridge St, Winchester, MA 01890
      6 Cambridge St, 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

  • 8 Russell Rd Unit 10, Winchester, MA 01890
    8 Russell Rd Unit 10, Winchester, MA 01890
    8 Russell Rd Unit 10, Winchester, MA 01890
    /39

    $960,000

    Sold Apr 06, 2026

    8 Russell Rd Unit 10, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1922

    Last Sold Summary

    • 4% Below List Price
    • $533/SF
    • 17 Days On Market

    Current Estimated Value $992,220

    Last Listing Agent Rajive Dogra Coldwell Banker Realty - Lexington

    8 Russell Rd Unit 10, Winchester, MA 01890
    • 3 Myopia Rd, Winchester, MA 01890
      3 Myopia Rd, Winchester, MA 01890
      3 Myopia Rd, 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

  • 74 Wedgemere Ave, Winchester, MA 01890
    74 Wedgemere Ave, 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
    • 10 Taft Dr, Winchester, MA 01890
      10 Taft Dr, Winchester, MA 01890
      10 Taft Dr, 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

  • 2 York Rd, Winchester, MA 01890
    2 York Rd, Winchester, MA 01890
    2 York Rd, 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
    • 17 Swan Rd, Winchester, MA 01890
      17 Swan Rd, Winchester, MA 01890
      17 Swan Rd, 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

  • 44 Amberwood Dr, Winchester, MA 01890
    44 Amberwood Dr, Winchester, MA 01890
    44 Amberwood Dr, Winchester, MA 01890
    /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
    • 5 Swan Rd, Winchester, MA 01890
      5 Swan Rd, Winchester, MA 01890
      5 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

Showing Results 241 - 280, Page 7 of 18

Massachusetts Middlesex County

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