1,783

West Side Homes

Section Image
  • 10 Hawthorne Rd, Winchester, MA 01890
    10 Hawthorne Rd, Winchester, MA 01890
    10 Hawthorne Rd, Winchester, MA 01890
    /34

    $2,100,000 Sold Mar 19, 2026

    10 Hawthorne Rd, Winchester, MA 01890

    • 5 Beds
    • 6 Baths
    • 3,191 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Above List Price
    • $658/SF
    • 7 Days On Market

    Current Estimated Value $1,974,960

    Last Listing Agent Susan Kadilak Fiv Realty Co.

    10 Hawthorne Rd, Winchester, MA 01890
    • 233 High St, Winchester, MA 01890
      233 High St, Winchester, MA 01890
      233 High St, Winchester, MA 01890
      /11

      Est $1,254,065 Not Listed For Sale

      233 High St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,218 Sq Ft
      • Built 1952
      233 High St, Winchester, MA 01890

      Last Sold Summary

      • 8% Above List Price
      • $523/SF
      • 7 Days On Market

      Last Sold Price $1,161,000

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

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

    $1,349,000 Pending

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

    28 Emerson Rd, Winchester, MA 01890

    Set on a picturesque corner lot in Winchester’s coveted West Side near the Ambrose School, this beautifully preserved mid-century modern home is defined by clean lines, a thoughtful layout, and so many meaningful updates throughout. The main level features a sun-filled, fireplaced living room and a formal dining room with built-ins that flow to an inviting kitchen with stainless-steel appliances.

    Nancy Pallotta Gibson Sotheby's International Realty

    28 Emerson Rd, 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 $1,127,679

    Last Listing Agent Kim Covino Compass

    16 Ridge St, Winchester, MA 01890
    • 134 Johnson Rd, Winchester, MA 01890
      134 Johnson Rd, Winchester, MA 01890
      134 Johnson Rd, Winchester, MA 01890
      /40

      Est $1,308,441 Not Listed For Sale

      134 Johnson Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,430 Sq Ft
      • Built 1977
      134 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $484/SF
      • 3 Days On Market

      Last Sold Price $1,175,000

      Last Listing Agent Steve Savarese Senne

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

    $1,750,000 Pending

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

    12 Wincrest Dr, Winchester, MA 01890

    West Side! Set on a beautiful, serene oversized 1/2 acre lot, this turn key 2006* 5–6 bedroom, 4.5 BA home offers the perfect blend of space, comfort, & style. This home was completely renovated & expanded in 2004 offering an open floor plan w/ kitchen & dining area that flow seamlessly into an oversized family room w/ walls of windows showcasing the gorgeous yard. The main floor also offers

    Kim Covino Compass

    12 Wincrest Dr, Winchester, MA 01890
  • 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 $1,786,529

    Last Listing Agent Hudson Santana Keller Williams Realty Boston Northwest

    44 Amberwood Dr, Winchester, MA 01890
    • 7 Wainwright Rd Unit 98, Winchester, MA 01890
      7 Wainwright Rd Unit 98, Winchester, MA 01890
      7 Wainwright Rd Unit 98, Winchester, MA 01890
      /42

      Est $1,765,522 Not Listed For Sale

      7 Wainwright Rd Unit 98, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,361 Sq Ft
      • Built 1995
      7 Wainwright Rd Unit 98, Winchester, MA 01890

      Last Sold Summary

      • 12% Below List Price
      • $595/SF
      • 6 Days On Market

      Last Sold Price $2,000,000

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

  • 7 Wainwright Rd Unit 107, Winchester, MA 01890
    7 Wainwright Rd Unit 107, Winchester, MA 01890
    7 Wainwright Rd Unit 107, Winchester, MA 01890
    /40

    $1,350,000 Open Tue 11AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 2,907 Sq Ft

    7 Wainwright Rd Unit 107, Winchester, MA 01890

    Move right into this spacious, light-filled townhouse at The Ledges! This upscale condominium community right outside Winchester center offers the ease of low maintenance living with the feel of a single family home & with the added bonus of a private club w/swimming pool and tennis court! This sought after layout offers a grand FIRST FLOOR PRIMARY bedroom & bath suite. Easy access main floor w/

    Kim Covino Compass

    7 Wainwright Rd Unit 107, Winchester, MA 01890
  • 7 Wainwright Rd Unit 55, Winchester, MA 01890
    7 Wainwright Rd Unit 55, Winchester, MA 01890
    /2

    $1,675,000 Sold Jul 11, 2025

    7 Wainwright Rd Unit 55, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 4,228 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Above List Price
    • $396/SF
    • 8 Days On Market

    Current Estimated Value $1,733,565

    Last Listing Agent Ngoc Anh Goldstein Leading Edge Real Estate

    7 Wainwright Rd Unit 55, Winchester, MA 01890
    • 7 Wainwright Rd Unit 37, Winchester, MA 01890
      7 Wainwright Rd Unit 37, Winchester, MA 01890
      7 Wainwright Rd Unit 37, Winchester, MA 01890
      /39

      Est $1,754,274 Not Listed For Sale

      7 Wainwright Rd Unit 37, Winchester, MA 01890

      • 2 Beds
      • 4 Baths
      • 3,655 Sq Ft
      • Built 1988
      7 Wainwright Rd Unit 37, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $431/SF
      • 6 Days On Market

      Last Sold Price $1,575,000

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

  • 94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    /37

    $1,899,999

    • 4 Beds
    • 3 Baths
    • 3,512 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    This quintessential Colonial blends timeless charm with modern updates, offering a truly move-in ready home in a unique location! Directly across the street, the Winchester Swim and Tennis Club presents a rare opportunity for immediate membership—enjoy your own private club lifestyle just in time for summer! Just a few doors from Vinson-Owen Elementary, morning drop-offs couldn’t be easier.

    Philip Vita Compass

    94 Johnson Rd, Winchester, MA 01890
  • 59 Johnson Rd, Winchester, MA 01890
    59 Johnson Rd, Winchester, MA 01890
    59 Johnson Rd, Winchester, MA 01890
    /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 $1,215,348

    Last Listing Agent Angela Zhang Greatland Real Estate LLC

    59 Johnson Rd, Winchester, MA 01890
    • 7 Wainwright Rd Unit 5, Winchester, MA 01890
      7 Wainwright Rd Unit 5, Winchester, MA 01890
      7 Wainwright Rd Unit 5, Winchester, MA 01890
      /42

      Est $1,801,676 Not Listed For Sale

      7 Wainwright Rd Unit 5, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,901 Sq Ft
      • Built 1988
      7 Wainwright Rd Unit 5, Winchester, MA 01890

      Last Sold Summary

      • 3% Above List Price
      • $449/SF
      • 7 Days On Market

      Last Sold Price $1,750,000

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /42

    $3,537,000

    • 7 Beds
    • 7.5 Baths
    • 8,540 Sq Ft

    37 Mayflower Rd, Winchester, MA 01890

    Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

    Kim Covino Compass

    37 Mayflower Rd, Winchester, MA 01890
  • 7 Wainwright Rd Unit 72, Winchester, MA 01890
    7 Wainwright Rd Unit 72, Winchester, MA 01890
    7 Wainwright Rd Unit 72, Winchester, MA 01890
    /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 $2,047,510

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

    7 Wainwright Rd Unit 72, Winchester, MA 01890
    • 7 Wainwright Rd Unit 41, Winchester, MA 01890
      7 Wainwright Rd Unit 41, Winchester, MA 01890
      7 Wainwright Rd Unit 41, Winchester, MA 01890
      /41

      Est $1,579,265 Not Listed For Sale

      7 Wainwright Rd Unit 41, Winchester, MA 01890

      • 2 Beds
      • 4 Baths
      • 5,564 Sq Ft
      • Built 1988
      7 Wainwright Rd Unit 41, Winchester, MA 01890

      Last Sold Summary

      • 5% Above List Price
      • $270/SF
      • 7 Days On Market

      Last Sold Price $1,500,000

      Last Listing Agent Jill Citrano Leading Edge Real Estate

  • 15 Gershon Way Unit 15, Winchester, MA 01890
    15 Gershon Way Unit 15, Winchester, MA 01890
    15 Gershon Way Unit 15, Winchester, MA 01890
    /35

    $2,395,000

    • 3 Beds
    • 3.5 Baths
    • 4,087 Sq Ft

    15 Gershon Way Unit 15, Winchester, MA 01890

    Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual

    Moira Lown Coldwell Banker Realty - Wellesley

    15 Gershon Way Unit 15, Winchester, MA 01890
  • 7 Wainwright Rd Unit 118, Winchester, MA 01890
    7 Wainwright Rd Unit 118, Winchester, MA 01890
    7 Wainwright Rd Unit 118, Winchester, MA 01890
    /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 $1,515,969

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

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

      Est $1,929,994 Not Listed For Sale

      40 Wainwright Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,853 Sq Ft
      • Built 1992
      40 Wainwright Rd, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $669/SF
      • 7 Days On Market

      Last Sold Price $1,910,000

      Last Listing Agent Kim Covino Compass

  • 2 Gershon Way, Winchester, MA 01890
    2 Gershon Way, Winchester, MA 01890
    2 Gershon Way, Winchester, MA 01890
    /34

    $1,899,000

    • 3 Beds
    • 2.5 Baths
    • 2,306 Sq Ft

    2 Gershon Way, Winchester, MA 01890

    Welcome to Winning Farm of Winchester —an award-winning 55+ community and one of Winchester’s most sought-after addresses for effortless, elevated living. This meticulously maintained and lightly lived-in 3-bedroom, 2.5-bath townhome offers 2,306 sq ft of thoughtfully designed living, showcasing fine craftsmanship & timeless finishes throughout. Sun-drenched interiors highlight gorgeous hardwood

    Monte Marrocco Coldwell Banker Realty - Lexington

    2 Gershon Way, Winchester, MA 01890
  • 7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    /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 $1,331,671

    Last Listing Agent Kim Covino Compass

    7 Thornberry Rd, Winchester, MA 01890
    • 19 Socrates Way, Winchester, MA 01890
      19 Socrates Way, Winchester, MA 01890
      19 Socrates Way, Winchester, MA 01890
      /42

      Est $2,899,151 Not Listed For Sale

      19 Socrates Way, Winchester, MA 01890

      • 5 Beds
      • 6 Baths
      • 5,678 Sq Ft
      • Built 1994
      19 Socrates Way, Winchester, MA 01890

      Last Sold Summary

      • 9% Above List Price
      • $467/SF
      • 12 Days On Market

      Last Sold Price $2,650,000

      Last Listing Agent Lucille Murray Gibson Sotheby's International Realty

  • 11 Ridge St, Winchester, MA 01890
    11 Ridge St, Winchester, MA 01890
    11 Ridge St, Winchester, MA 01890
    /40

    $1,200,000

    • 3 Beds
    • 2 Baths
    • 1,888 Sq Ft

    11 Ridge St, Winchester, MA 01890

    Discover this beautifully updated 3-bedroom, 2-bath single-story ranch offering 1,888 sf of stylish, comfortable living – perfect for first-time buyers or those looking to downsize! Primary bedroom includes an en-suite bathroom and spacious closet. Wood floors, vaulted ceilings, recessed lighting, and abundant natural light throughout. Updated kitchen boasts modern appliances, a pantry, and

    Yvonne Logan Coldwell Banker Realty - Lexington

    11 Ridge St, Winchester, MA 01890
  • 50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, Winchester, MA 01890
    /42

    $1,650,000 Sold Jul 30, 2025

    50 Johnson Rd, Winchester, MA 01890

    • 3 Beds
    • 4 Baths
    • 2,646 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Below List Price
    • $624/SF
    • 18 Days On Market

    Current Estimated Value $1,660,119

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

    50 Johnson Rd, Winchester, MA 01890
    • 40 Amberwood Dr, Winchester, MA 01890
      40 Amberwood Dr, Winchester, MA 01890
      40 Amberwood Dr, Winchester, MA 01890
      /42

      Est $2,707,511 Not Listed For Sale

      40 Amberwood Dr, Winchester, MA 01890

      • 6 Beds
      • 3.5 Baths
      • 5,713 Sq Ft
      • Built 1983
      40 Amberwood Dr, Winchester, MA 01890

      Last Sold Summary

      • 18% Above List Price
      • $403/SF
      • 8 Days On Market

      Last Sold Price $2,300,000

      Last Listing Agent Kim Covino Compass

  • 34 Robinhood Rd, Winchester, MA 01890
    34 Robinhood Rd, Winchester, MA 01890
    34 Robinhood Rd, Winchester, MA 01890
    /37

    $1,524,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,380 Sq Ft

    34 Robinhood Rd, Winchester, MA 01890

    This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main

    Janet Halloran RE/MAX Real Estate Center

    34 Robinhood Rd, Winchester, MA 01890
  • 65 Thornberry Rd, Winchester, MA 01890
    65 Thornberry Rd, Winchester, MA 01890
    65 Thornberry Rd, Winchester, MA 01890
    /37

    $1,535,000 Sold Jun 12, 2025

    65 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,525 Sq Ft
    • Built 1965

    Last Sold Summary

    • 10% Above List Price
    • $608/SF
    • 5 Days On Market

    Current Estimated Value $1,564,290

    Last Listing Agent Jun Zhang HMW Real Estate, LLC

    65 Thornberry Rd, Winchester, MA 01890
    • 45 Amberwood Dr, Winchester, MA 01890
      45 Amberwood Dr, Winchester, MA 01890
      45 Amberwood Dr, Winchester, MA 01890
      /38

      Est $1,806,075 Not Listed For Sale

      45 Amberwood Dr, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 4,008 Sq Ft
      • Built 1983
      45 Amberwood Dr, Winchester, MA 01890

      Last Sold Summary

      • 17% Above List Price
      • $387/SF
      • 3 Days On Market

      Last Sold Price $1,550,000

      Last Listing Agent Kim Covino Compass

  • 6 Samoset Rd, Winchester, MA 01890
    6 Samoset Rd, Winchester, MA 01890
    6 Samoset Rd, Winchester, MA 01890
    /42

    $1,987,000 Sold Nov 18, 2025

    6 Samoset Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,731 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $420/SF
    • 16 Days On Market

    Current Estimated Value $2,092,069

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    6 Samoset Rd, Winchester, MA 01890
    • 9 Amberwood Dr, Winchester, MA 01890
      9 Amberwood Dr, Winchester, MA 01890
      9 Amberwood Dr, Winchester, MA 01890
      /36

      Est $2,191,333 Not Listed For Sale

      9 Amberwood Dr, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,257 Sq Ft
      • Built 2021
      9 Amberwood Dr, Winchester, MA 01890

      Last Sold Summary

      • 14% Above List Price
      • $451/SF
      • 195 Days On Market

      Last Sold Price $1,920,000

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

  • 85 Thornberry Rd, Winchester, MA 01890
    85 Thornberry Rd, Winchester, MA 01890
    85 Thornberry Rd, Winchester, MA 01890
    /33

    $1,785,000 Sold May 22, 2025

    85 Thornberry Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 2,848 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Below List Price
    • $627/SF
    • 13 Days On Market

    Current Estimated Value $1,774,958

    Last Listing Agent Diane Basemera Coldwell Banker Realty - Newton

    85 Thornberry Rd, Winchester, MA 01890
    • 9 Buckman Dr, Winchester, MA 01890
      9 Buckman Dr, Winchester, MA 01890
      9 Buckman Dr, Winchester, MA 01890
      /42

      Est $2,155,326 Not Listed For Sale

      9 Buckman Dr, Winchester, MA 01890

      • 6 Beds
      • 3.5 Baths
      • 4,124 Sq Ft
      • Built 1970
      9 Buckman Dr, Winchester, MA 01890

      Last Sold Summary

      • 13% Above List Price
      • $461/SF
      • 4 Days On Market

      Last Sold Price $1,900,000

      Last Listing Agent Philip Vita Compass

  • 109 Thornberry Rd, Winchester, MA 01890
    109 Thornberry Rd, Winchester, MA 01890
    109 Thornberry Rd, Winchester, MA 01890
    /19

    $1,820,000 Sold Aug 19, 2025

    109 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,784 Sq Ft
    • Built 1974

    Last Sold Summary

    • 1% Above List Price
    • $481/SF
    • 5 Days On Market

    Current Estimated Value $1,870,616

    Last Listing Agent Andrew Martini Compass

    109 Thornberry Rd, Winchester, MA 01890
    • 5 Pilgrim Dr, Winchester, MA 01890
      5 Pilgrim Dr, Winchester, MA 01890
      5 Pilgrim Dr, Winchester, MA 01890
      /42

      Est $2,388,816 Not Listed For Sale

      5 Pilgrim Dr, Winchester, MA 01890

      • 6 Beds
      • 3.5 Baths
      • 4,138 Sq Ft
      • Built 1962
      5 Pilgrim Dr, Winchester, MA 01890

      Last Sold Summary

      • $580/SF
      • 5 Days On Market

      Last Sold Price $2,400,000

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    /42

    $2,218,500 Sold Aug 29, 2025

    17 Wagon Wheel Rd, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 3,940 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $563/SF
    • 74 Days On Market

    Current Estimated Value $2,285,847

    Last Listing Agent Yifei Wang Dreamega International Realty LLC

    17 Wagon Wheel Rd, Winchester, MA 01890
    • 15 Pilgrim Dr, Winchester, MA 01890
      15 Pilgrim Dr, Winchester, MA 01890
      15 Pilgrim Dr, Winchester, MA 01890
      /42

      Est $1,996,548 Not Listed For Sale

      15 Pilgrim Dr, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 4,256 Sq Ft
      • Built 1959
      15 Pilgrim Dr, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $441/SF
      • 13 Days On Market

      Last Sold Price $1,875,000

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 322 Cambridge St, Winchester, MA 01890
    322 Cambridge St, Winchester, MA 01890
    322 Cambridge St, Winchester, MA 01890
    /15

    $1,088,000 Sold May 08, 2025

    322 Cambridge St, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 2,172 Sq Ft
    • Built 1985

    Last Sold Summary

    • 18% Above List Price
    • $501/SF
    • 6 Days On Market

    Current Estimated Value $1,170,788

    Last Listing Agent Joanne McDonnell RE/MAX Real Estate Center

    322 Cambridge St, Winchester, MA 01890
    • 16 Johnson Rd, Winchester, MA 01890
      16 Johnson Rd, Winchester, MA 01890
      16 Johnson Rd, Winchester, MA 01890
      /40

      Est $1,410,454 Not Listed For Sale

      16 Johnson Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 3,142 Sq Ft
      • Built 1958
      16 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 1% Below List Price
      • $452/SF
      • 6 Days On Market

      Last Sold Price $1,420,000

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • 7 Wainwright Rd Unit 15, Winchester, MA 01890
    7 Wainwright Rd Unit 15, Winchester, MA 01890
    7 Wainwright Rd Unit 15, Winchester, MA 01890
    /37

    $1,427,000 Sold Feb 26, 2026

    7 Wainwright Rd Unit 15, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,996 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Above List Price
    • $476/SF
    • 2 Days On Market

    Current Estimated Value $1,376,947

    Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Wainwright Rd Unit 15, Winchester, MA 01890

Showing Results 41 - 80, Page 2 of 18

Massachusetts Middlesex County Winchester West Side

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group