1,780

West Side Homes

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  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /40

    $3,379,000

    • 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
  • 20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    /36

    $15,000 Per Month

    • 6 Beds
    • 7 Baths
    • 8,866 Sq Ft
    • House for Rent

    20 Amberwood Dr, Winchester, MA 01890

    New construction 6 bedrooms and 7 full baths, 2 Car garage. Located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador appliances, custom cabinetry,

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    (781) 992-2320

    20 Amberwood Dr, Winchester, MA 01890
  • 15 Edward Dr Unit 15, Winchester, MA 01890
    15 Edward Dr Unit 15, Winchester, MA 01890
    15 Edward Dr Unit 15, Winchester, MA 01890
    /42

    $1,055,000

    Sold May 15, 2026

    15 Edward Dr Unit 15, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,082 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Above List Price
    • $507/SF
    • 5 Days On Market

    Last Listing Agent Alina Wang Coldwell Banker Realty - Lexington

    15 Edward Dr Unit 15, Winchester, MA 01890
    • 34 Coolidge Rd, Winchester, MA 01890
      34 Coolidge Rd, Winchester, MA 01890
      34 Coolidge Rd, Winchester, MA 01890
      /33

      Est $1,724,539

      Not Listed For Sale

      34 Coolidge Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,338 Sq Ft
      • Built 1980
      34 Coolidge Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

  • 94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    /40

    $1,799,000

    • 4 Beds
    • 3 Baths
    • 3,366 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated

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

    94 Johnson Rd, Winchester, MA 01890
  • 282 High St, Winchester, MA 01890
    282 High St, Winchester, MA 01890
    282 High St, Winchester, MA 01890
    /27

    $10,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 6,583 Sq Ft
    • House for Rent

    282 High St, Winchester, MA 01890

    Fabulous 6 month rental opportunity with full additional in-law suite with private kitchen, bedroom, bath, and laundry. Very generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and

    Anthony Marino The Marino Group Collection

    282 High St, Winchester, MA 01890
  • 12 Thornberry Rd, Winchester, MA 01890
    12 Thornberry Rd, Winchester, MA 01890
    12 Thornberry Rd, Winchester, MA 01890
    /31

    $1,240,000

    Sold Apr 27, 2026

    12 Thornberry Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 2,087 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Above List Price
    • $594/SF
    • 6 Days On Market

    Current Estimated Value $1,234,197

    Last Listing Agent Kim Covino Compass

    12 Thornberry Rd, Winchester, MA 01890
    • 7 Hutchinson Rd, Winchester, MA 01890
      7 Hutchinson Rd, Winchester, MA 01890
      7 Hutchinson Rd, Winchester, MA 01890
      /40

      Est $1,598,982

      Not Listed For Sale

      7 Hutchinson Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 3,406 Sq Ft
      • Built 1959
      7 Hutchinson Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

  • 9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    /10

    $3,200,000

    $200K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 6,100 Sq Ft

    9 Albamont Rd, Winchester, MA 01890

    Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept

    Kim Covino Compass

    9 Albamont Rd, Winchester, MA 01890
  • 416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    /20

    Starting at $2,773 Plus Fees

    • Studio - 3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West is crafted to elevate every moment of your day—from morning workouts in the fully equipped fitness center to productive afternoons in private work-from-home pods and inviting gathering spaces. Whether you're entertaining in the chef-inspired kitchen and lounge, relaxing by the fire with neighbors, or enjoying the convenience of Whole Foods and local shops just

    Sanctuary Winchester West

    (339) 214-9536

    416 Cambridge St, Winchester, MA 01890
  • 1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, Winchester, MA 01890
    /39

    $2,200,000

    Sold Jun 30, 2025

    1 Saint Augustine Ct, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 3,818 Sq Ft
    • Built 1967

    Last Sold Summary

    • 10% Above List Price
    • $576/SF
    • 0 Days On Market

    Current Estimated Value $2,140,394

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    1 Saint Augustine Ct, 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 $1,415,551

      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

  • 15 Thornberry Rd, Winchester, MA 01890
    15 Thornberry Rd, Winchester, MA 01890
    15 Thornberry Rd, Winchester, MA 01890
    /41

    $1,350,000

    Pending
    • 4 Beds
    • 3 Baths
    • 4,062 Sq Ft

    15 Thornberry Rd, Winchester, MA 01890

    Located on a level corner lot in the desirable Vinson Owen School district and nearby Winchester Swim & Tennis Club, this ranch-style home offers abundant space and a flexible floor plan. The main level features three bedrooms, a full bath, hardwood floors, and a fireplace living room that flows into the dining area and kitchen. A heated sunroom/mudroom with skylights and exposed beams connects

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

    15 Thornberry Rd, Winchester, MA 01890
  • 186 Ridge St, Winchester, MA 01890
    186 Ridge St, Winchester, MA 01890
    186 Ridge St, Winchester, MA 01890
    /28

    $15,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 5,820 Sq Ft
    • House for Rent

    186 Ridge St, Winchester, MA 01890

    Stunning 2020-built residence, fully furnished, beautifully maintained and located atop a hill on the West Side of Town, proudly situated on over an acre of land and offering gorgeous panoramic views. 5 bedroom 4.5 bath, 5,820SF custom built colonial with three-car attached garage with side entrance into oversized mudroom. Main level features gourmet kitchen with high-end appliances, oversized

    Anzor Sidamonidze Skylight Real Estate, LLC

    186 Ridge St, Winchester, MA 01890
  • 7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, Winchester, MA 01890
    /42

    $1,055,000

    Sold Feb 26, 2026

    7 Trinity Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft
    • Built 1963

    Last Sold Summary

    • 11% Below List Price
    • $495/SF
    • 24 Days On Market

    Current Estimated Value $1,208,480

    Last Listing Agent Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
    • 6 Vinson Cir, Winchester, MA 01890
      6 Vinson Cir, Winchester, MA 01890
      6 Vinson Cir, Winchester, MA 01890
      /42

      Est $4,086,100

      Not Listed For Sale

      6 Vinson Cir, Winchester, MA 01890

      • 6 Beds
      • 7.5 Baths
      • 7,500 Sq Ft
      • Built 2025
      6 Vinson Cir, Winchester, MA 01890

      Last Sold Summary

      • 71 Days On Market

  • 1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    /35

    $3,299,000

    Open Sat 11AM - 12:30PM $100K PRICE DROP
    • 7 Beds
    • 7.5 Baths
    • 7,226 Sq Ft

    1 Plymouth Rd, Winchester, MA 01890

    Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    1 Plymouth Rd, Winchester, MA 01890
  • 37 Emerson Rd, Winchester, MA 01890
    37 Emerson Rd, Winchester, MA 01890
    37 Emerson Rd, Winchester, MA 01890
    /26

    $6,500 Per Month

    • 4 Beds
    • 4 Baths
    • 3,436 Sq Ft
    • House for Rent

    37 Emerson Rd, Winchester, MA 01890

    This sunlit, upgraded Winchester single-family home offers a perfect blend of comfort and elegance. The versatile 4-bedrooms & 4-Bathrooms layout features a convenient 1st-floor full bath alongside a formal living room, dining room, office, and spacious family room. The primary suite is located on the 2nd floor with a private ensuite. Skylights brighten the living areas, which open to a wide

    Hao Wang Dreamega International Realty LLC

    37 Emerson Rd, Winchester, MA 01890
  • 10 Trinity Rd, Winchester, MA 01890
    10 Trinity Rd, Winchester, MA 01890
    10 Trinity Rd, Winchester, MA 01890
    /42

    $1,580,000

    Sold Feb 26, 2026

    10 Trinity Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • Built 1963

    Last Sold Summary

    • 11% Above List Price
    • $748/SF
    • 5 Days On Market

    Current Estimated Value $1,574,903

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Trinity Rd, Winchester, MA 01890
    • 228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      /42

      Est $2,929,783

      Not Listed For Sale

      228 Ridge St, Winchester, MA 01890

      • 5 Beds
      • 5.5 Baths
      • 6,265 Sq Ft
      • Built 2023
      228 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 142 Days On Market

  • 14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    /36

    $2,799,000

    Open Sat 2PM - 3PM $51K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 6,968 Sq Ft

    14 Nassau Dr, Winchester, MA 01890

    Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, Winchester, MA 01890
  • 26 Ridge St, Winchester, MA 01890
    26 Ridge St, Winchester, MA 01890
    26 Ridge St, Winchester, MA 01890
    /37

    $1,390,000

    Sold Jul 15, 2025

    26 Ridge St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,388 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $582/SF
    • 6 Days On Market

    Current Estimated Value $1,436,052

    Last Listing Agent Dream Team Dreamega International Realty LLC

    26 Ridge St, Winchester, MA 01890
    • 15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      /40

      Est $1,368,438

      Not Listed For Sale

      15 Wincrest Dr, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,529 Sq Ft
      • Built 1957
      15 Wincrest Dr, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

  • 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

    Pending
    • 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
  • 64 Westland Ave, Winchester, MA 01890
    64 Westland Ave, Winchester, MA 01890
    64 Westland Ave, Winchester, MA 01890
    /39

    $2,050,000

    Sold Oct 15, 2025

    64 Westland Ave, Winchester, MA 01890

    • 4 Beds
    • 5 Baths
    • 3,716 Sq Ft
    • Built 1931

    Last Sold Summary

    • $552/SF
    • 2 Days On Market

    Current Estimated Value $2,042,361

    Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

    64 Westland Ave, Winchester, MA 01890
    • 10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      /33

      Est $1,429,411

      Not Listed For Sale

      10 Carriage Ln, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,034 Sq Ft
      • Built 1957
      10 Carriage Ln, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

  • 8 Hawthorne Rd, Winchester, MA 01890
    8 Hawthorne Rd, Winchester, MA 01890
    8 Hawthorne Rd, Winchester, MA 01890
    /27

    $1,885,000

    Open Sat 12PM - 1:15PM $40K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,315 Sq Ft

    8 Hawthorne Rd, Winchester, MA 01890

    Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees.

    Elaine Song Coldwell Banker Realty - Lexington

    8 Hawthorne Rd, Winchester, MA 01890
  • 5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    /38

    $1,525,000

    Sold Sep 12, 2025

    5 Thornton Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,755 Sq Ft
    • Built 1929

    Last Sold Summary

    • 12% Below List Price
    • $554/SF
    • 30 Days On Market

    Current Estimated Value $1,825,321

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

    5 Thornton Rd, Winchester, MA 01890
    • 28 Thornberry Rd, Winchester, MA 01890
      28 Thornberry Rd, Winchester, MA 01890
      28 Thornberry Rd, Winchester, MA 01890
      /29

      Est $1,307,499

      Not Listed For Sale

      28 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,245 Sq Ft
      • Built 1959
      28 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 117 Days On Market

  • 105 Thornberry Rd, Winchester, MA 01890
    105 Thornberry Rd, Winchester, MA 01890
    105 Thornberry Rd, Winchester, MA 01890
    /35

    $1,899,000

    Pending
    • 5 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    105 Thornberry Rd, Winchester, MA 01890

    Perfectly situated on Winchester’s sought-after Westside, this beautifully updated Colonial offers 5 bedrooms, 2.5 baths, and exceptional indoor-outdoor living. A recent renovation transformed and expanded the first floor, featuring an updated kitchen with oversized mahogany topped center island, family room, dining room, mudroom, and half bath. The kitchen opens seamlessly to a spacious family

    Monte Marrocco Coldwell Banker Realty - Lexington

    105 Thornberry Rd, Winchester, MA 01890
  • 21 Johnson Rd, Winchester, MA 01890
    21 Johnson Rd, Winchester, MA 01890
    21 Johnson Rd, Winchester, MA 01890
    /42

    $1,540,000

    Sold Jul 11, 2025

    21 Johnson Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,814 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Above List Price
    • $547/SF
    • 5 Days On Market

    Current Estimated Value $1,569,630

    Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

    21 Johnson Rd, Winchester, MA 01890
    • 16 Nassau Dr, Winchester, MA 01890
      16 Nassau Dr, Winchester, MA 01890
      16 Nassau Dr, Winchester, MA 01890
      /35

      Est $1,669,314

      Not Listed For Sale

      16 Nassau Dr, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,926 Sq Ft
      • Built 1960
      16 Nassau Dr, Winchester, MA 01890

      Last Sold Summary

      • 20 Days On Market

  • 7 Wainwright Rd Unit 47, Winchester, MA 01890
    7 Wainwright Rd Unit 47, Winchester, MA 01890
    7 Wainwright Rd Unit 47, Winchester, MA 01890
    /32

    $1,330,000

    Open Sat 11AM - 12:30PM
    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft

    7 Wainwright Rd Unit 47, Winchester, MA 01890

    Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub.

    Felicity Tuttle Better Homes and Gardens Real Estate - The Shanahan Group

    7 Wainwright Rd Unit 47, Winchester, MA 01890
  • 257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    /40

    $3,150,000

    Sold May 28, 2026

    257 High St, Winchester, MA 01890

    • 5 Beds
    • 7 Baths
    • 7,101 Sq Ft
    • Built 1994

    Last Sold Summary

    • 3% Below List Price
    • $444/SF
    • 2 Days On Market

    Current Estimated Value $3,191,342

    Last Listing Agent Kim Covino Compass

    257 High St, Winchester, MA 01890
    • 104 Thornberry Rd, Winchester, MA 01890
      104 Thornberry Rd, Winchester, MA 01890
      104 Thornberry Rd, Winchester, MA 01890
      /32

      Est $1,574,026

      Not Listed For Sale

      104 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,622 Sq Ft
      • Built 1973
      104 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

  • 2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    /38

    $3,600,000

    Open Sat 12:30PM - 1:45PM
    • 6 Beds
    • 6.5 Baths
    • 7,400 Sq Ft

    2 Atherton Rd, Winchester, MA 01890

    This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is

    Brooke Zarbano Regatta Realty

    2 Atherton Rd, Winchester, MA 01890
  • 7 Wainwright Rd Unit 13, Winchester, MA 01890
    7 Wainwright Rd Unit 13, Winchester, MA 01890
    7 Wainwright Rd Unit 13, Winchester, MA 01890
    /24

    $2,155,000

    Sold Oct 21, 2025

    7 Wainwright Rd Unit 13, Winchester, MA 01890

    • 3 Beds
    • 4.5 Baths
    • 3,186 Sq Ft
    • Built 1988

    Last Sold Summary

    • $676/SF
    • 1 Day On Market

    Current Estimated Value $1,872,868

    Last Listing Agent Isabella Bruno William Raveis R.E. & Home Services

    7 Wainwright Rd Unit 13, Winchester, MA 01890
    • 22 Berkshire Dr, Winchester, MA 01890
      22 Berkshire Dr, Winchester, MA 01890
      22 Berkshire Dr, Winchester, MA 01890
      /35

      Est $1,763,660

      Not Listed For Sale

      22 Berkshire Dr, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 3,224 Sq Ft
      • Built 1967
      22 Berkshire Dr, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

  • 7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    /39

    $1,499,000

    Open Sat 12PM - 2PM $51K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 3,360 Sq Ft

    7 Ridge St, Winchester, MA 01890

    Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds

    Paul Cirignano The Synergy Group

    7 Ridge St, Winchester, MA 01890
  • 114 Johnson Rd, Winchester, MA 01890
    114 Johnson Rd, Winchester, MA 01890
    114 Johnson Rd, Winchester, MA 01890
    /42

    $1,700,000

    Sold May 01, 2026

    114 Johnson Rd, Winchester, MA 01890

    • 3 Beds
    • 3 Baths
    • 3,182 Sq Ft
    • Built 1880

    Last Sold Summary

    • 5% Below List Price
    • $534/SF
    • 22 Days On Market

    Current Estimated Value $1,764,234

    Last Listing Agent Rosemary Kelleher LAER Realty Partners

    114 Johnson Rd, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18

Massachusetts Middlesex County Winchester West Side

Real Estate & Homes

Learn more about living in West Side

Home Prices in West Side, MA

The median home sale price in West Side, Winchester is $1,627,000, down 1% year-over-year. Homes in West Side sell in 23 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$1,627,000
Median Single Family Sale Price
$1,713,000
Median Townhouse Sale Price
$1,055,000
Median 2 Bedroom Sale Price
$805,000
Average Price Per Sq Ft
$527
Number of Homes for Sale
11
Last 12 months Home Sales
59
Months of Supply
2.20
Median List Price
$1,737,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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