1,759

West Side Homes

Section Image
  • /42

    $1,925,000

    $75K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,286 Sq Ft

    15 Fieldstone Dr, Winchester, MA 01890

    Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless

    Anne Spry Barrett Sotheby's International Realty

    15 Fieldstone Dr, Winchester, MA 01890
  • /20

    Starting at $2,620 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

    416 Cambridge St, 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
    • /42

      Est $3,598,589

      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

      Last Listing Agent Peter Kasseris Serhant

  • /37

    $1,599,000

    • 4 Beds
    • 4 Baths
    • 2,480 Sq Ft

    241 Ridge St, Winchester, MA 01890

    New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new

    Team Lillian Montalto Lillian Montalto Signature Properties

    241 Ridge St, Winchester, MA 01890
  • /38

    $6,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,443 Sq Ft
    • House for Rent

    25 Berkshire Dr, Winchester, MA 01890

    This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail

    Nadia Mounsif McCaul & Mounsif Real Estate Group LLC

    25 Berkshire Dr, 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 $1,238,250

    Last Listing Agent Kim Covino Compass

    12 Thornberry Rd, Winchester, MA 01890
    • /42

      Est $2,903,722

      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

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

  • /4

    $3,200,000

    • 5 Beds
    • 5.5 Baths
    • 5,295 Sq Ft

    18 Ridge St, Winchester, MA 01890

    Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort.

    Gayle Winters Compass

    18 Ridge St, Winchester, MA 01890
  • /30

    $3,200 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    7 Ridge St, Winchester, MA 01890

    Welcome to this charming 2-bedroom, 1.5-bath rental located on the desirable west side of Winchester. Offering three levels of living space, this home provides plenty of room to spread out and enjoy a comfortable, flexible layout. Beautiful hardwood floors add warmth and character throughout, while the level, partially fenced backyard provides a wonderful private outdoor space for relaxing,

    Shannon Jenkins RE/MAX Realty Experts

    7 Ridge St, 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 $1,191,098

    Last Listing Agent Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
    • /40

      Est $1,357,776

      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

      Last Listing Agent Kim Covino Compass

  • /40

    $3,179,000

    $200K PRICE DROP
    • 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
  • /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 $1,543,175

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Trinity Rd, Winchester, MA 01890
    • /33

      Est $1,459,872

      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

      Last Listing Agent Peter Kasseris Serhant

  • /40

    $1,799,000

    Pending
    • 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
  • /41

    $1,360,000

    Sold Jul 29, 2026

    15 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 4,062 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Above List Price
    • $335/SF
    • 7 Days On Market

    Current Estimated Value $1,365,421

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

    15 Thornberry Rd, Winchester, MA 01890
    • /39

      Est $1,377,940

      Not Listed For Sale

      9 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 1957
      9 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

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

  • /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
  • /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 $2,039,319

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

    64 Westland Ave, Winchester, MA 01890
    • /29

      Est $1,335,559

      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

      Last Listing Agent Shaundize Moosavizadeh Coldwell Banker Realty - Boston

  • /37

    $3,299,000

    $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
  • /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 $1,787,828

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

    5 Thornton Rd, Winchester, MA 01890
    • /37

      Est $1,504,318

      Not Listed For Sale

      65 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,525 Sq Ft
      • Built 1965
      65 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jun Zhang HMW Real Estate, LLC

  • /30

    $2,799,000

    $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
  • /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 $3,118,023

    Last Listing Agent Kim Covino Compass

    257 High St, Winchester, MA 01890
    • /35

      Est $1,705,406

      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

      Last Listing Agent Timothy Morgan RE/MAX Innovative Properties

  • /38

    $1,699,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,707 Sq Ft

    11 Carriage Ln, Winchester, MA 01890

    15K LOT!! Move right into this beautifully updated 4 BR 3 BA open concept home w/stunning rear addition/primary bedroom suite! This impeccably maintained, nicely updated home has a bright & airy open layout w/ abundant natural light streaming through oversized windows. The main living area flows seamlessly from the spacious living room w/beautiful fireplace into the dining room & kitchen. The

    Kim Covino Compass

    11 Carriage Ln, Winchester, MA 01890
  • /33

    $1,936,000

    Sold Jun 23, 2026

    2 Gershon Way Unit 2, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,306 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Above List Price
    • $840/SF
    • 7 Days On Market

    Current Estimated Value $1,902,667

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    2 Gershon Way Unit 2, Winchester, MA 01890
    • /33

      Est $1,762,821

      Not Listed For Sale

      85 Thornberry Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 2,848 Sq Ft
      • Built 1968
      85 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Diane Basemera Coldwell Banker Realty - Newton

  • /42

    $3,450,000

    • 6 Beds
    • 4.5 Baths
    • 5,735 Sq Ft

    7 Hutchinson Rd, Winchester, MA 01890

    Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the oversized three car garage into the

    Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
  • /42

    $1,700,000

    Sold Jun 29, 2026

    29 Pilgrim Dr, Winchester, MA 01890

    • 5 Beds
    • 3 Baths
    • 3,271 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Below List Price
    • $520/SF
    • 20 Days On Market

    Current Estimated Value $1,737,516

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    29 Pilgrim Dr, Winchester, MA 01890
    • /40

      Est $2,008,813

      Not Listed For Sale

      3 Berkshire Dr, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 3,344 Sq Ft
      • Built 1967
      3 Berkshire Dr, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Allison Shannon Charlesgate Realty Group, llc

  • /27

    $1,825,000

    $100K PRICE DROP Pending
    • 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
  • /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 $1,856,310

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

    7 Wainwright Rd Unit 13, Winchester, MA 01890
    • /11

      Est $1,301,828

      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

      • 7 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /42

    $2,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    7 Wainwright Rd Unit 113, Winchester, MA 01890

    Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home

    Kim Covino Compass

    7 Wainwright Rd Unit 113, 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 $1,696,035

    Last Listing Agent Rosemary Kelleher LAER Realty Partners

    114 Johnson Rd, Winchester, MA 01890
    • /40

      Est $1,340,210

      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

      • 3 Days On Market

      Last Listing Agent Steve Savarese Senne

  • /32

    $1,125,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,736 Sq Ft

    38 Robinhood Rd, Winchester, MA 01890

    Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open

    Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

    38 Robinhood Rd, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,699,500
Median Single Family Sale Price
$1,713,000
Median Townhouse Sale Price
$2,130,500
Median 2 Bedroom Sale Price
$825,000
Average Price Per Sq Ft
$535
Number of Homes for Sale
12
Last 12 months Home Sales
58
Months of Supply
2.50
Median List Price
$1,785,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
7%
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