1,774

West Side Homes

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    • /42

      Est $2,109,436 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 4,256 Sq Ft

      15 Pilgrim Dr, Winchester, MA 01890

      15 Pilgrim Dr, Winchester, MA 01890
  • /42

    $1,517,500 Sold Jan 09, 2025

    • 3,091 Sq Ft
    • $491/SF
    • 7 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1957

    14 Henry St, Winchester, MA 01890

    Incredible value! Don’t miss this 6 BR, 3 full bathroom expanded colonial w/ over 3,000 square feet of living space tucked away in a charming Vinson Owen School neighborhood. This expansive home features an open concept, eat-in kitchen/family room w/ granite countertops, double ovens, large island, recessed lighting & cozy family room. The sunny kitchen also opens to a private backyard w/ stone

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

    14 Henry St, Winchester, MA 01890
    • /40

      Est $1,459,220 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,142 Sq Ft

      16 Johnson Rd, Winchester, MA 01890

      16 Johnson Rd, Winchester, MA 01890
  • /29

    $1,335,000 Sold Dec 27, 2024

    • 2,245 Sq Ft
    • $595/SF
    • 117 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1959

    28 Thornberry Rd, Winchester, MA 01890

    Welcome to 28 Thornberry! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining,

    Shaundize Moosavizadeh Coldwell Banker Realty - Boston

    28 Thornberry Rd, Winchester, MA 01890
    • /33

      Est $2,019,973 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,603 Sq Ft

      8 Olde Lyme Rd, Winchester, MA 01890

      8 Olde Lyme Rd, Winchester, MA 01890
  • /25

    $1,000,000 Sold Dec 19, 2024

    • 1,840 Sq Ft
    • $543/SF
    • 8 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1937

    15 Westland Ave, Winchester, MA 01890

    A dIamond in the rough!!! Are you a contractor or handy end user looking for a project in sought after WInchester? Look no further than this 1937, 4 bedroom Colonial brimming with potential. The charm of yesteryear shows through with custom built-ins, crown moldings, hardwood flooring and so much more. Full walk out unfinished basement with double soapstone sink and a full walk up attic lends

    Libby Rankin Hamill Berkshire Hathaway HomeServices Stephan Real Estate

    15 Westland Ave, Winchester, MA 01890
    • /42

      Est $1,804,317 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,315 Sq Ft

      8 Hawthorne Rd, Winchester, MA 01890

      8 Hawthorne Rd, Winchester, MA 01890
  • /38

    $1,650,000 Sold Dec 11, 2024

    • 3,158 Sq Ft
    • $522/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1975

    31 Girard Rd, Winchester, MA 01890

    Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you’ll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen, seamlessly connected to a bright and airy dining area. This space is perfect for hosting

    Philip Vita Compass

    31 Girard Rd, Winchester, MA 01890
    • /42

      Est $2,403,779 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,473 Sq Ft

      239 Ridge St, Winchester, MA 01890

      239 Ridge St, Winchester, MA 01890
  • /40

    $1,225,000 Sold Dec 09, 2024

    • 3,350 Sq Ft
    • $366/SF
    • 27 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1988

    7 Wainwright Rd Unit 29, Winchester, MA 01890

    Imagine arriving home to peace & serenity at The Ledges, a hilltop oasis on Winchester's West side. This tranquil retreat offers carefree living & your private sanctuary. Relax in the fireplace living room, sliders to your private deck & expansive views. The main bedroom en suite, is conveniently located on the first floor. Second level finds a loft, skylit bonus room perfect for a home office,

    Joanne Sexeny Coldwell Banker Realty - Lexington

    7 Wainwright Rd Unit 29, Winchester, MA 01890
    • /26

      Est $1,142,566 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,826 Sq Ft

      75 Dunster Ln, Winchester, MA 01890

      75 Dunster Ln, Winchester, MA 01890
  • /30

    $900,000 Sold Nov 21, 2024

    • 1,857 Sq Ft
    • $485/SF
    • 6 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1985

    62 Edward Dr, Winchester, MA 01890

    Welcome to 62 Edward Drive in the sought-after Pepper Hill Estates. This spacious townhouse-style condo features two bedrooms and a versatile bonus room on the lower level, perfect for a home office, guest space, or playroom. The well-maintained home boasts an open living and dining area filled with natural light and a beautiful fireplace. The updated kitchen includes granite countertops, newer

    Melissa Perrone Better Homes and Gardens Real Estate - The Shanahan Group

    62 Edward Dr, Winchester, MA 01890
    • /42

      Est $3,230,157 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 5,676 Sq Ft

      222 High St, Winchester, MA 01890

      222 High St, Winchester, MA 01890
  • /42

    $2,035,000 Sold Nov 19, 2024

    • 4,730 Sq Ft
    • $430/SF
    • 12 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1953

    43 Emerson Rd, Winchester, MA 01890

    See it to believe it! Don’t miss this sprawling 5 bed, 4 full bath Cape-style home in an idyllic Ambrose school neighborhood. 1st floor features mudroom w/entry from attached garage, laundry room w/sink, living room w/fireplace, bedroom, full bath, & dining area w/French doors to a deck. But the jewel of this floor is the recent addition of a stunning eat-in kitchen & sun-filled primary suite.

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

    43 Emerson Rd, Winchester, MA 01890
    • /27

      Est $1,080,646 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,859 Sq Ft

      46 Edward Dr, Winchester, MA 01890

      46 Edward Dr, Winchester, MA 01890
  • /2

    $1,910,000 Sold Nov 04, 2024

    • 5,287 Sq Ft
    • $361/SF
    • 9 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1977

    5 Thoreau Cir, Winchester, MA 01890

    Welcome to this custom-built oversized ranch, cherished & meticulously maintained by the current owners. This idyllic property is situated on a large lot at the end of a cul-de-sac, abutting peaceful conservation land. The main level features grand scale rooms including a spacious eat in kitchen, 2 beautiful living rooms w/ wood burning fireplaces, a stunning dining room for holidays & dinner

    Kim Covino Compass

    5 Thoreau Cir, Winchester, MA 01890
    • /42

      Est $1,053,270 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,738 Sq Ft

      41 Edward Dr, Winchester, MA 01890

      41 Edward Dr, Winchester, MA 01890
  • /40

    $1,500,000 Sold Nov 01, 2024

    • 2,874 Sq Ft
    • $522/SF
    • 6 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1952

    57 Hutchinson Rd, Winchester, MA 01890

    Calling all nature enthusiasts! This property is perfect for you, whether you're a passionate gardener or a devoted golfer. From the front yard, you'll relish a stunning view of the thirteenth fairway at Winchester Country Club. The backyard features mature plantings, vibrant perennials, a charming koi pond, and a relaxing patio. This single-story home is designed for easy living, with a

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

    57 Hutchinson Rd, Winchester, MA 01890
    • /38

      Est $1,060,091 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,754 Sq Ft

      34 Edward Dr, Winchester, MA 01890

      34 Edward Dr, Winchester, MA 01890
  • /37

    $1,421,000 Sold Oct 30, 2024

    • 2,793 Sq Ft
    • $509/SF
    • 6 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1958

    4 Albamont Rd, Winchester, MA 01890

    Beautiful and spacious 5 bedroom, 2.5 bathroom contemporary Cape in one of Winchester’s nicest west side neighborhoods, situated on lovely landscaped grounds. A well cared-for home with so many updates! Newer quartz countertop kitchen with island and stainless steel appliances, beautiful hardwood floors throughout, bright living room with fireplace, dining room with built-in corner cabinet,

    The Ridick Revis Group Compass

    4 Albamont Rd, Winchester, MA 01890
    • /37

      Est $881,723 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,920 Sq Ft

      47 Edward Dr, Winchester, MA 01890

      47 Edward Dr, Winchester, MA 01890
  • /42

    $2,400,000 Sold Oct 28, 2024

    • 4,138 Sq Ft
    • $580/SF
    • 5 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1962

    5 Pilgrim Dr, Winchester, MA 01890

    Welcome to your dream home, nestled in a tranquil cul-de-sac! This property combines luxury and functionality, featuring multiple living areas perfect for entertaining. At the heart of the home is a gourmet kitchen with a Wolf cooktop, dual ovens, two Sub Zero refrigerators, and butler's pantry with a wine cooler—ideal for culinary enthusiasts. The family room boasts cathedral ceilings with a

    Andersen Group Realty Keller Williams Realty Boston Northwest

    5 Pilgrim Dr, Winchester, MA 01890
    • /31

      Est $1,877,678 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 4,028 Sq Ft

      56 Ridge St, Winchester, MA 01890

      56 Ridge St, Winchester, MA 01890
  • /2

    $915,000 Sold Oct 24, 2024

    • 2,020 Sq Ft
    • $453/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    49 Edward Dr Unit 49, Winchester, MA 01890

    Welcome to this stunning townhouse in Pepper Hill Estates. It features an open floor plan with beautiful hardwood floors and abundant natural light. The kitchen with stainless steel appliances, flows into a spacious living area. With 3 bedrooms plus a guest room/office or playroom, the flexible floor plan caters to your needs.The home also boasts 2 fireplaces, 2.5 bathrooms, and central A/C and

    Alina Wang Coldwell Banker Realty - Lexington

    49 Edward Dr Unit 49, Winchester, MA 01890
    • /23

      Est $989,245 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,548 Sq Ft

      12 James St, Winchester, MA 01890

      12 James St, Winchester, MA 01890
  • /42

    $1,225,000 Sold Oct 15, 2024

    • 2,958 Sq Ft
    • $414/SF
    • 9 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 1994

    7 Wainwright Rd Unit 97, Winchester, MA 01890

    Unbeatable value and exceptional living in The Ledges! Unit #97 is a “B-style” townhouse with a flexible floorplan offering great potential. An entryway w/ soaring ceiling leads to a first floor bonus room which is perfect as a home office or extra bedroom, eat-in kitchen, half bath, laundry area, and open concept dining room/living room w/ gas fireplace & vaulted ceiling. From the dining room

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

    7 Wainwright Rd Unit 97, Winchester, MA 01890
    • /38

      Est $1,234,474 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,827 Sq Ft

      10 James St, Winchester, MA 01890

      10 James St, Winchester, MA 01890
  • /30

    $1,200,000 Sold Oct 15, 2024

    • 2,145 Sq Ft
    • $559/SF
    • 6 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1994

    7 Wainwright Rd Unit 94, Winchester, MA 01890

    Enjoy the relaxing life style at the Ledges Condominium set atop a quiet natural preserve on the West side of Winchester, close to major highways and shopping. Condo amenities include in-ground swimming pool, club house, and tennis courts. This attractive, well-maintained and laid out "A-style" unit offers three bedrooms, two with private full baths, vaulted ceilings, and walk-in closets.

    Joseph Farragher JPF Real Estate Services

    7 Wainwright Rd Unit 94, Winchester, MA 01890
    • /42

      Est $935,425 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 3,890 Sq Ft

      25 Henry St, Winchester, MA 01890

      25 Henry St, Winchester, MA 01890
  • /42

    $1,740,000 Sold Oct 04, 2024

    • 2,635 Sq Ft
    • $660/SF
    • 8 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1955

    9 Blossom Hill Rd, Winchester, MA 01890

    This newly renovated home (2023) has been refreshed with all new electrical, plumbing, HVAC, water heater, and appliances, ensuring modern comfort and efficiency. Beautiful 3/4" oak flooring throughout the main level, including bedrooms, creates a warm and inviting atmosphere. The main bathroom features a Kohler steam shower and dual shower heads. The electric fireplace in the living room is

    Andersen Group Realty Keller Williams Realty Boston Northwest

    9 Blossom Hill Rd, Winchester, MA 01890
    • /26

      Est $841,280 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,279 Sq Ft

      28 Henry St, Winchester, MA 01890

      28 Henry St, Winchester, MA 01890
  • /42

    $3,100,000 Sold Oct 03, 2024

    • 5,600 Sq Ft
    • $554/SF
    • 24 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2022

    6 Pocahontas Dr, Winchester, MA 01890

    Indulge in luxury living at its finest at 6 Pocahontas, Winchester! This exceptional residence, meticulously crafted by its owner, boasts modern sophistication and convenience. Enter & discover top-of-the-line features, including an open & expansive floor plan with elegant 6” white oak flooring throughout & complemented by Canadian fir beams. A gourmet kitchen w/ premium appliances, dual islands,

    Monte Marrocco Coldwell Banker Realty - Lexington

    6 Pocahontas Dr, Winchester, MA 01890
    • /20

      Est $1,082,908 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,432 Sq Ft

      14 Locke St, Winchester, MA 01890

      14 Locke St, Winchester, MA 01890
  • /40

    $1,980,000 Sold Sep 30, 2024

    • 6,259 Sq Ft
    • $316/SF
    • 136 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1976

    280 High St, Winchester, MA 01890

    Winchester Estate on Lexington line with your choice of Schools! This Mediterranean inspired home provides the ultimate in large,private,charming space!15 rooms on three living levels.Generous rooms throughout.2 car attached garage with lots of outdoor parking.Large,well appointed 2-tier kitchen ideal for large gatherings and entertaining.Over-sized Dining room with beamed ceiling and connecting

    Anthony Marino The Marino Group Collection

    280 High St, Winchester, MA 01890
    • /17

      Est $2,127,153 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,578 Sq Ft

      21 Dunster Ln, Winchester, MA 01890

      21 Dunster Ln, Winchester, MA 01890
  • /40

    $1,771,049 Sold Sep 27, 2024

    • 3,158 Sq Ft
    • $561/SF
    • 7 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1941

    49 Westland Ave, Winchester, MA 01890

    Curb appeal envelops this charming Colonial w/Dutch Gambrel roof line in desirable West Side neighborhood! About 3 blocks to sought-after Ambrose Elem! The generous 2nd bedrm has potential to convert to two. The foyer showcases a streamlined interior, flanked by a formal living room where you'll enjoy relaxing around a wood burning fireplace, and a dining room w/classic built-in corner cabinet.

    Michaela Mahtani Leading Edge Real Estate

    49 Westland Ave, Winchester, MA 01890
    • /38

      Est $1,207,244 Not Listed For Sale

      • 5 Beds
      • 1.5 Baths
      • 2,383 Sq Ft

      18 Ridge St, Winchester, MA 01890

      18 Ridge St, Winchester, MA 01890
  • /42

    $3,000,000 Sold Sep 17, 2024

    • 6,805 Sq Ft
    • $441/SF
    • 6 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 2009

    232 High St, Winchester, MA 01890

    Welcome to this expansive colonial home, epitomizing elegance and modern living. The grand entrance leads to an open floor concept with luxurious details throughout. The first floor features a spacious living room with an impressive fireplace, an elegant dining room, and a modern kitchen with high-end appliances and an adjacent dining area. A massive family room above the garage includes another

    Andersen Group Realty Keller Williams Realty Boston Northwest

    232 High St, Winchester, MA 01890
    • /41

      Est $2,088,251 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,730 Sq Ft

      2 Tanglewood Ln, Winchester, MA 01890

      2 Tanglewood Ln, Winchester, MA 01890
  • /36

    $975,000 Sold Sep 16, 2024

    • 2,568 Sq Ft
    • $380/SF
    • 6 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1987

    55 Edward Dr, Winchester, MA 01890

    Discover this exquisite condo in the heart of Winchester, where form meets function seamlessly. Nestled in a well-established neighborhood near Whipple Hill’s walking paths & green spaces, this residence is designed for modern living. The spacious first floor features a cozy fireplace family room or office & an inviting kitchen with updated appliances, granite counters, & under-cabinet lighting.

    Anne Spry Barrett Sotheby's International Realty

    55 Edward Dr, Winchester, MA 01890

Showing Results 81 - 120, Page 3 of 18

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