9,246

Homes in ZIP Code 01890

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  • 12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury Rd, Winchester, MA 01890
    /33

    $1,200,000 Open Thu 4:30PM - 5:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft

    12 Canterbury Rd, Winchester, MA 01890

    Tucked along a quiet side street in the sought-after Ambrose School district, this spacious ranch offers comfort, convenience, and endless possibilities. With nearly 2,000 square feet of living space, the home features seven rooms, including a large living room w/ fireplace that anchors the easy, natural flow. Three spacious bedrooms and two and a half full baths make one-level living effortless,

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

    12 Canterbury Rd, Winchester, MA 01890
  • 6 Skillings Rd Unit 2, Winchester, MA 01890
    6 Skillings Rd Unit 2, Winchester, MA 01890
    6 Skillings Rd Unit 2, Winchester, MA 01890
    /8

    $2,350 total monthly price

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    6 Skillings Rd Unit 2, Winchester, MA 01890

    Great two bedroom with hardwood floors, super sunny, updated kitchen and bath, in unit laundry, central A/C, good size bedrooms, one off street parking spot. Great location. 9/1 move in no pets.

    Kristen Day RE/MAX Realty Plus

    6 Skillings Rd Unit 2, Winchester, MA 01890
  • 5 Emerson Ct, Winchester, MA 01890
    5 Emerson Ct, Winchester, MA 01890
    5 Emerson Ct, Winchester, MA 01890
    /30

    $1,185,000 Sold Oct 08, 2025

    • 2,000 Sq Ft
    • $592/SF
    • 5 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1870

    5 Emerson Ct, Winchester, MA 01890

    Gut renovated charming home sets back on a private way near downtown. This sun drenched home features hardwood floor, custom tile work, meticulous woodwork, wainscot, skylights, cathedral ceiling, marble bath, amazing custom mantles FP along w/all 3.5 designer baths w/all the fancy stone work and unique vanities. Open floor plan 1st fl. features large LivRm w/lots of custom touch which leads to

    Elaine Song Coldwell Banker Realty - Lexington

    5 Emerson Ct, 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 $1,666,208 Not Listed For Sale

      • 2 Beds
      • 4 Baths
      • 3,655 Sq Ft

      7 Wainwright Rd Unit 37, Winchester, MA 01890

      7 Wainwright Rd Unit 37, Winchester, MA 01890
  • 5A Wood Ln, Winchester, MA 01890
    5A Wood Ln, Winchester, MA 01890
    5A Wood Ln, Winchester, MA 01890
    /42

    $1,950,000

    • Land
    • 1.05 Acres
    • $1,857,143 per Acre

    5A Wood Ln, Winchester, MA 01890

    Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cypress shingle exterior, and classic New England design. Inside, three magnificent fireplaces, exquisite

    Kim Covino Compass

    5A Wood Ln, Winchester, MA 01890
  • 211 Forest St, Winchester, MA 01890
    211 Forest St, Winchester, MA 01890
    211 Forest St, Winchester, MA 01890
    /41

    $7,500 total monthly price

    • 5 Beds
    • 3.5 Baths
    • 3,474 Sq Ft
    • House for Rent

    211 Forest St, Winchester, MA 01890

    FURNISHED ONLY 3 MONTH WINTER RENTAL. If you’ve been thinking of a kitchen renovation or addition but dread the chaos of construction, or maybe you're visiting one of our world renowned hospitals, our stunning 5-bedroom, 3.5-bathroom, 3,500-square-foot home in the coveted Muraco school district is available for a 3-month winter rental (January through March) while my family snowbirds in Florida.

    Michael Gilbert Stuart St James, Inc.

    211 Forest St, Winchester, MA 01890
  • 162 Forest St, Winchester, MA 01890
    162 Forest St, Winchester, MA 01890
    162 Forest St, Winchester, MA 01890
    /33

    $1,280,000 Sold Oct 03, 2025

    • 1,900 Sq Ft
    • $674/SF
    • 9 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1930

    162 Forest St, Winchester, MA 01890

    Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining

    Paul Cirignano The Synergy Group

    162 Forest St, 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 $1,757,606 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,901 Sq Ft

      7 Wainwright Rd Unit 5, Winchester, MA 01890

      7 Wainwright Rd Unit 5, Winchester, MA 01890
  • 446 Highland Ave, Winchester, MA 01890
    446 Highland Ave, Winchester, MA 01890
    446 Highland Ave, Winchester, MA 01890
    /38

    $999,000 Open Sat 11AM - 12PM

    • 2 Beds
    • 1.5 Baths
    • 2,033 Sq Ft

    446 Highland Ave, Winchester, MA 01890

    Charming Spanish-style home in desirable Winchester! This unique property features a beautiful terracotta roof and timeless architectural details. The first floor welcomes you with a foyer which leads to an astounding great room, perfect for entertaining or hosting family gatherings. The kitchen opens seamlessly to the dining area. Additionally an inviting enclosed patio provides space to relax

    Andersen Group Realty Keller Williams Realty Boston Northwest

    446 Highland Ave, Winchester, MA 01890
  • 10 Farrow St, Winchester, MA 01890
    10 Farrow St, Winchester, MA 01890
    10 Farrow St, Winchester, MA 01890
    /33

    $6,950 total monthly price

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    10 Farrow St, Winchester, MA 01890

    Single Family Home Rental in Winchester. NO BROKERS FEE. Available 11/1 or 11/15. Completely rebuilt from ground up in 2019 w/Attached 1 Car Garage. 4 Beds, 3.5 baths & 3500SF w/ 2 dedicated home offices. Modern kitchen w/Quartz Countertops, Stainless Steel Appliances & Venting for cooking. Open concept has an Island connecting dining & living spaces. Sundrenched Living Room offers a wood burning

    Collin Bray Century 21 Cityside

    10 Farrow St, Winchester, MA 01890
  • 171 Swanton St Unit 60, Winchester, MA 01890
    171 Swanton St Unit 60, Winchester, MA 01890
    171 Swanton St Unit 60, Winchester, MA 01890
    /27

    $738,000 Sold Sep 26, 2025

    • 1,824 Sq Ft
    • $405/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    171 Swanton St Unit 60, Winchester, MA 01890

    Well kept, end-unit townhouse at The Village offering a blank slate for new owners to update or renovate to their precise desire! End unit means you have more windows, more natural light and 3 parking spots (1 garage spot w direct access into the home & EVSE charging unit, 1 spot in front of your garage AND 1 spot adjacent)! Kitchen has an opening to the dining room that has fabulous, vaulted

    Michaela Hellman Redfin Corp.

    171 Swanton St Unit 60, 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 $1,579,732 Not Listed For Sale

      • 2 Beds
      • 4 Baths
      • 5,564 Sq Ft

      7 Wainwright Rd Unit 41, Winchester, MA 01890

      7 Wainwright Rd Unit 41, Winchester, MA 01890
  • 209 Washington St, Winchester, MA 01890
    209 Washington St, Winchester, MA 01890
    209 Washington St, Winchester, MA 01890
    /35

    $1,499,000

    • 5 Beds
    • 3.5 Baths
    • 3,141 Sq Ft

    209 Washington St, Winchester, MA 01890

    Charm and character meet modern living in this beautifully renovated & expanded Victorian townhome just steps from Winchester Center. Fully updated in 2013/14 with new kitchen, baths, wiring, all systems, roof, and windows—and enhanced in 2023 with a redesigned patio, landscaping, fencing, and flower beds—in the exclusive yard. This home offers four levels of sun-filled space. The main level

    Kim Covino Compass

    209 Washington St, Winchester, MA 01890
  • 35 Thornberry Rd, Winchester, MA 01890
    35 Thornberry Rd, Winchester, MA 01890
    35 Thornberry Rd, Winchester, MA 01890
    /26

    $8,000 total monthly price

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    35 Thornberry Rd, Winchester, MA 01890

    No Broker Fee! Large Sun-filled Windows, Contemporary, Minimalist, and Modern Design. A truly rare opportunity to rent this magnificent single-family home in one of Winchester’s most desirable neighborhoods. The home was ground-up construction in 2010 with over 3,500 square feet of living space. Its open concept, large loft-style office / second living room area, four bedrooms, three and a half

    Frank Celeste Gibson Sotheby's International Realty

    35 Thornberry Rd, Winchester, MA 01890
  • 17 Baldwin St, Winchester, MA 01890
    17 Baldwin St, Winchester, MA 01890
    17 Baldwin St, Winchester, MA 01890
    /19

    $878,000 Sold Sep 26, 2025

    • 1,672 Sq Ft
    • $525/SF
    • 2 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1890

    17 Baldwin St, Winchester, MA 01890

    Here's your chance to get into Winchester! Currently the only home under a million dollar! A short distance off Route 93 montvale exit, makes this location great for commuting to Boston; route 2 or NH! Charming 3-bedroom, 1.5-bath single-family home located on a quiet dead-end street, offering peace and privacy. This property boasts a spacious yard—perfect for gardening, outdoor

    Dennis Oliveira JDS Realty Group

    17 Baldwin St, Winchester, MA 01890
    • 40 Wainwright Rd, Winchester, MA 01890
      40 Wainwright Rd, Winchester, MA 01890
      40 Wainwright Rd, Winchester, MA 01890
      /42

      Est $1,962,870 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,853 Sq Ft

      40 Wainwright Rd, Winchester, MA 01890

      40 Wainwright Rd, Winchester, MA 01890
  • 32 Woodside Rd, Winchester, MA 01890
    32 Woodside Rd, Winchester, MA 01890
    32 Woodside Rd, Winchester, MA 01890
    /42

    $1,549,000

    • 3 Beds
    • 2.5 Baths
    • 2,587 Sq Ft

    32 Woodside Rd, Winchester, MA 01890

    Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc..along with serenity and privacy so hard to find. This home offers ample living

    Kim Covino Compass

    32 Woodside Rd, Winchester, MA 01890
  • 60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    /39

    $1,475,000 Sold Sep 26, 2025

    • 1,947 Sq Ft
    • $758/SF
    • 7 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2011

    60 Graystone Cir Unit 60, Winchester, MA 01890

    Meticulously maintained, 2-bedroom, 2.5-bath townhome with 2 car garage. The kitchen features custom cabinets, granite countertops, high-end stainless steel appliances and gleaming hardwood floors. The living/dining room combo features hardwood floors, gas fireplace, cathedral ceilings along with french doors that open to a private patio with gas grill. Spacious first floor primary suite boasts a

    Pirani & Wile Group Gibson Sotheby's International Realty

    60 Graystone Cir Unit 60, Winchester, MA 01890
    • 19 Socrates Way, Winchester, MA 01890
      19 Socrates Way, Winchester, MA 01890
      19 Socrates Way, Winchester, MA 01890
      /42

      Est $2,912,938 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 5,678 Sq Ft

      19 Socrates Way, Winchester, MA 01890

      19 Socrates Way, Winchester, MA 01890
  • 82 Hillcrest Pkwy, Winchester, MA 01890
    82 Hillcrest Pkwy, Winchester, MA 01890
    82 Hillcrest Pkwy, Winchester, MA 01890
    /38

    $1,650,000

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft

    82 Hillcrest Pkwy, Winchester, MA 01890

    Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly hardwood floors throughout, a brand-new roof, and a newer heating and AC system. The second floor

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

    82 Hillcrest Pkwy, 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

    • 3,002 Sq Ft
    • $571/SF
    • 53 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1983

    44 Amberwood Dr, Winchester, MA 01890

    Picture your family in this unique colonial, just one street over from the amazing Vinson-Owen school! 2 sizeable, private yards with lush grass, flagstone patios and even a dining room deck! Lots of upgrades include a new family room with brick wall, computer cubby, cathedral ceiling & mahogany deck. There's 3 bedrooms to start, including a spacious Primary Suite with walk-in closet, large

    Hudson Santana Keller Williams Realty Boston Northwest

    44 Amberwood Dr, Winchester, MA 01890
    • 40 Amberwood Dr, Winchester, MA 01890
      40 Amberwood Dr, Winchester, MA 01890
      40 Amberwood Dr, Winchester, MA 01890
      /42

      Est $2,736,623 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 5,713 Sq Ft

      40 Amberwood Dr, Winchester, MA 01890

      40 Amberwood Dr, Winchester, MA 01890
  • 7 Wainwright Rd Unit 29, Winchester, MA 01890
    7 Wainwright Rd Unit 29, Winchester, MA 01890
    7 Wainwright Rd Unit 29, Winchester, MA 01890
    /42

    $1,425,000

    • 3 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    7 Wainwright Rd Unit 29, Winchester, MA 01890

    Welcome to The Ledges, Winchester’s premier hilltop community offering refined, resort-style living with modern convenience. This sun-filled, beautifully updated home features an open layout with cathedral ceilings, hardwood floors, and newly landscaped courtyard space by Mahoney’s. The gourmet kitchen with premium appliances. Living Room opens to a private wooded deck, ideal for entertaining or

    Joanne Sexeny Coldwell Banker Realty - Lexington

    7 Wainwright Rd Unit 29, Winchester, MA 01890
  • 10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, Winchester, MA 01890
    /42

    $1,768,500 Sold Sep 25, 2025

    • 3,838 Sq Ft
    • $461/SF
    • 10 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1951

    10 Blossom Hill Rd, Winchester, MA 01890

    Welcome to 10 Blossom Hill Road. Tucked away in a cozy and desirable West Side Winchester neighborhood, this enchanting storybook home is full of warmth, charm, and heart. Here you will find a lovingly cared-for 4-bedroom home with a guest or in-law suite offering wonderful flexibility to suit your needs. Inside, you’ll find light-filled spaces, thoughtful updates, and timeless character that

    Stephen DeConto Cameron Real Estate Group

    10 Blossom Hill Rd, Winchester, MA 01890
    • 45 Amberwood Dr, Winchester, MA 01890
      45 Amberwood Dr, Winchester, MA 01890
      45 Amberwood Dr, Winchester, MA 01890
      /38

      Est $1,869,213 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 4,008 Sq Ft

      45 Amberwood Dr, Winchester, MA 01890

      45 Amberwood Dr, Winchester, MA 01890
  • 53 Bacon St, Winchester, MA 01890
    53 Bacon St, Winchester, MA 01890
    53 Bacon St, Winchester, MA 01890
    /34

    $1,499,000

    • 3 Beds
    • 2.5 Baths
    • 2,865 Sq Ft

    53 Bacon St, Winchester, MA 01890

    Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering

    Taleen Chiofaro Leading Edge Real Estate

    53 Bacon St, Winchester, MA 01890
  • 4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    /36

    $1,950,000 Sold Sep 25, 2025

    • 4,378 Sq Ft
    • $445/SF
    • 40 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1987

    4 Fieldstone Dr, Winchester, MA 01890

    Nestled in a desirable Westside neighborhood, this stunning California contemporary/colonial home sits on a quiet cul-de-sac and offers 5 bedrooms, 3.5 baths, and over 20,000 sq ft of beautifully landscaped grounds. The sun-drenched interior features an open-concept kitchen and dining room with five fully opening doors leading to a bright four-seasons sunroom—perfect for gatherings year-round.

    Wenli Zheng Fairview Partners International LLC

    4 Fieldstone Dr, Winchester, MA 01890
    • 9 Amberwood Dr, Winchester, MA 01890
      9 Amberwood Dr, Winchester, MA 01890
      9 Amberwood Dr, Winchester, MA 01890
      /36

      Est $2,362,141 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,257 Sq Ft

      9 Amberwood Dr, Winchester, MA 01890

      9 Amberwood Dr, Winchester, MA 01890
  • 16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    /42

    $1,199,000

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

    16 Ridge St, Winchester, MA 01890

    ATTENTION CONTRACTORS/BUILDERS & BUYERS LOOKING TO BUILD EQUITY~whether you do a light update/ expand or completely renovate; this well maintained 3 bedroom split entry home on a stunning 27k+ lot with a great layout and an oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning

    Kim Covino Compass

    16 Ridge St, Winchester, MA 01890
  • 147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    /37

    $1,200,000 Sold Sep 25, 2025

    • 1,884 Sq Ft
    • $637/SF
    • 103 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1919

    147 Highland Ave, Winchester, MA 01890

    Call for a private showing anytime! Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you w/ a spacious living room w fplc that flows seamlessly into a sun-drenched updated

    Kim Covino Compass

    147 Highland Ave, Winchester, MA 01890
    • 27 Amberwood Dr, Winchester, MA 01890
      27 Amberwood Dr, Winchester, MA 01890
      27 Amberwood Dr, Winchester, MA 01890
      /38

      Est $1,838,847 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,218 Sq Ft

      27 Amberwood Dr, Winchester, MA 01890

      27 Amberwood Dr, Winchester, MA 01890
  • 80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    /37

    $3,099,000

    • 5 Beds
    • 3.5 Baths
    • 5,632 Sq Ft

    80 Arlington St, Winchester, MA 01890

    New roof. New landscaping. New exterior paint. New price! With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved home offers 11 rooms, 5 bedrooms and 3.5 baths. Enjoy views from the sun-splashed eat-in kitchen w/

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

    80 Arlington St, Winchester, MA 01890
  • 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

    • 388 Sq Ft
    • $740/SF
    • 7 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1966

    200 Swanton St Unit 402, Winchester, MA 01890

    Immaculate, studio condominium within the desirable Parkview Condominiums in Winchester. This unit is located on the east side of the building, where it is filled with natural sunlight. The large private balcony overlooks a beautiful wildlife pond, and the grounds are meticulously landscaped. The kitchen features tile flooring, updated granite countertops, and a breakfast bar. The Condominium

    Michael Masci North Atlantic Realty Group

    200 Swanton St Unit 402, Winchester, MA 01890
    • 9 Buckman Dr, Winchester, MA 01890
      9 Buckman Dr, Winchester, MA 01890
      9 Buckman Dr, Winchester, MA 01890
      /42

      Est $2,200,203 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 4,124 Sq Ft

      9 Buckman Dr, Winchester, MA 01890

      9 Buckman Dr, Winchester, MA 01890
  • 44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    /39

    $3,099,000 Open Sun 12PM - 1PM

    • 6 Beds
    • 6.5 Baths
    • 6,028 Sq Ft

    44 Cabot St, Winchester, MA 01890

    Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

    Andersen Group Realty Keller Williams Realty Boston Northwest

    44 Cabot St, Winchester, MA 01890
  • 9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, Winchester, MA 01890
    /42

    $1,725,000 Sold Sep 19, 2025

    • 2,541 Sq Ft
    • $679/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1960

    9 Pilgrim Dr, Winchester, MA 01890

    Welcome to this beautiful split-level home nestled on a desirable corner lot in Winchester’s sought after west side. Featuring gleaming hardwood floors throughout, this home offers a perfect blend of comfort and style. The main level boasts an open floor plan connecting the dining room, kitchen, and living room, and seamlessly flows into a stunning vaulted family room, perfect for both everyday

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    9 Pilgrim Dr, Winchester, MA 01890
    • 5 Pilgrim Dr, Winchester, MA 01890
      5 Pilgrim Dr, Winchester, MA 01890
      5 Pilgrim Dr, Winchester, MA 01890
      /42

      Est $2,446,135 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 4,138 Sq Ft

      5 Pilgrim Dr, Winchester, MA 01890

      5 Pilgrim Dr, Winchester, MA 01890
  • 104 Church St, Winchester, MA 01890
    104 Church St, Winchester, MA 01890
    104 Church St, Winchester, MA 01890
    /42

    $1,285,000

    • 4 Beds
    • 1.5 Baths
    • 2,696 Sq Ft

    104 Church St, Winchester, MA 01890

    This charming colonial in prime flats location is full of surprises! Showcasing a stunning rear 3 story addition duplex with walls of windows & 4 rooms! Use as the primary, home office, art studio or let your children enjoy this unique space~ The first floor offers a classic layout with an expanded updated kitchen & family area open to gorgeous deck overlooking the beacon hill style yard

    Kim Covino Compass

    104 Church St, Winchester, MA 01890
  • 6 Highland Ave, Winchester, MA 01890
    6 Highland Ave, Winchester, MA 01890
    6 Highland Ave, Winchester, MA 01890
    /31

    $1,465,000 Sold Sep 18, 2025

    • 2,506 Sq Ft
    • $585/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1974

    6 Highland Ave, Winchester, MA 01890

    4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is

    Peter Rooney Compass

    6 Highland Ave, Winchester, MA 01890
    • 15 Pilgrim Dr, Winchester, MA 01890
      15 Pilgrim Dr, Winchester, MA 01890
      15 Pilgrim Dr, Winchester, MA 01890
      /42

      Est $2,020,403 Not Listed For Sale

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

      15 Pilgrim Dr, Winchester, MA 01890

      15 Pilgrim Dr, Winchester, MA 01890

Showing Results 81 - 120, Page 3 of 18

Massachusetts Middlesex County Winchester 01890

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