9,208

Winchester, MA Homes

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  • 189 High St, Winchester, MA 01890
    189 High St, Winchester, MA 01890
    189 High St, Winchester, MA 01890
    /41

    $1,150,000 Open Sat 12:30PM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,126 Sq Ft

    189 High St, Winchester, MA 01890

    This classic Cape offers exceptional space, character, and room to make it your own. The first floor features a gracious front-to-back living room, formal dining room, and an inviting eat-in kitchen, all highlighted by hardwood floors, high ceilings, and a seamless circular layout ideal for everyday living. A charming breezeway connects directly to the one-car garage, adding easy functionality.

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

    189 High St, 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 Now. 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 stove!

    Collin Bray Century 21 Cityside

    10 Farrow St, Winchester, MA 01890
  • 10 Olde Lyme Rd, Winchester, MA 01890
    10 Olde Lyme Rd, Winchester, MA 01890
    10 Olde Lyme Rd, Winchester, MA 01890
    /33

    $1,600,000 Sold Oct 10, 2025

    • 3,478 Sq Ft
    • $460/SF
    • 57 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1960

    10 Olde Lyme Rd, Winchester, MA 01890

    Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state.

    Darryl Brian RE/MAX Bentley's

    10 Olde Lyme Rd, Winchester, MA 01890
    • 7 Wainwright Rd Unit 39, Winchester, MA 01890
      7 Wainwright Rd Unit 39, Winchester, MA 01890
      7 Wainwright Rd Unit 39, Winchester, MA 01890
      /38

      Est $1,614,216 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,368 Sq Ft

      7 Wainwright Rd Unit 39, Winchester, MA 01890

      7 Wainwright Rd Unit 39, Winchester, MA 01890
  • 6 Marchant Rd, Winchester, MA 01890
    6 Marchant Rd, Winchester, MA 01890
    6 Marchant Rd, Winchester, MA 01890
    /42

    $1,350,000 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,153 Sq Ft

    6 Marchant Rd, Winchester, MA 01890

    Beautiful 3 bed, 2.5 bath home set on a generous lot in a fantastic Winchester location/ Lincoln Elementary close to town, schools, the train, and route to Boston. The first floor offers an ideal layout with an updated kitchen, stainless steel appliances & island w seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc and dining room. A 3 season sunroom in

    Kim Covino Compass

    6 Marchant Rd, 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 Dennett Rd, Winchester, MA 01890
    17 Dennett Rd, Winchester, MA 01890
    17 Dennett Rd, Winchester, MA 01890
    /41

    $1,500,000 Sold Oct 09, 2025

    • 2,283 Sq Ft
    • $657/SF
    • 30 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1968

    17 Dennett Rd, Winchester, MA 01890

    Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized

    Kim Covino Compass

    17 Dennett Rd, 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
  • 26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    /41

    $1,475,000

    • 3 Beds
    • 2.5 Baths
    • 2,316 Sq Ft

    26 Berkshire Dr, Winchester, MA 01890

    Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

    DANIEL BEIRNE OpenDoor Brokerage LLC

    26 Berkshire Dr, Winchester, MA 01890
  • 115 Washington St Unit 3D, Winchester, MA 01890
    115 Washington St Unit 3D, Winchester, MA 01890
    115 Washington St Unit 3D, Winchester, MA 01890
    /36

    $519,000 Sold Oct 08, 2025

    • 769 Sq Ft
    • $675/SF
    • 5 Days On Market
    • 1 Bed
    • 1.5 Baths
    • Built 1988

    115 Washington St Unit 3D, Winchester, MA 01890

    Welcome to Church Place in Winchester. This light-filled one-bedroom condo offers a unique two-level layout with beautiful windows that frame picturesque views of the town. The main level features an airy, open-concept living and dining area, highlighted by a cathedral ceiling in the living room making it perfect for entertaining or enjoying a quiet evening at home. Upstairs, you’ll find a cozy

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    115 Washington St Unit 3D, 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
  • 18 Raymond Place, Winchester, MA 01890
    18 Raymond Place, Winchester, MA 01890
    18 Raymond Place, Winchester, MA 01890
    /16

    $899,900 Open Sat 11AM - 1PM

    • Land
    • 0.23 Acre
    • $3,912,609 per Acre

    18 Raymond Place, Winchester, MA 01890

    An opportunity awaits at 18 Raymond Place! This property offers a nearly 10,000 sq/ft lot, ample parking, and a large structure in a quaint, idyllic neighborhood. This freestanding building offers over 2 levels of space with direct exterior lower access for separate quarters. High ceilings, and lots of natural sunlight, this property awaits your customization. Each floor has 2 bathrooms, and the

    Kim Covino Compass

    18 Raymond Place, 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 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
  • 12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury Rd, Winchester, MA 01890
    /33

    $1,200,000 Open Sat 11:30AM - 1PM

    • 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
  • 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
    • 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
  • 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
  • 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
    • 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
  • 446 Highland Ave, Winchester, MA 01890
    446 Highland Ave, Winchester, MA 01890
    446 Highland Ave, Winchester, MA 01890
    /38

    $999,000 Open Sun 2PM - 3PM

    • 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
  • 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 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
  • 209 Washington St, Winchester, MA 01890
    209 Washington St, Winchester, MA 01890
    209 Washington St, Winchester, MA 01890
    /35

    $1,499,000 Open Sat 11AM - 12:30PM

    • 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
  • 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
    • 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
  • 8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    /5

    $3,250,000

    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    8 Priscilla Ln, Winchester, MA 01890

    Welcome to 8 Priscilla Ln, Winchester—a brand-new 5 bed, 5.5 bath luxury home designed by Salt & Stone Co where elevated craftsmanship meets everyday comfort. Spanning 6,500 ± sq ft, this home features a chef’s kitchen with custom cabinetry, premium appliances, and an oversized center island flowing into a dramatic two-story living room with fireplace and glass slider to the backyard. The

    The Pezzano Group Rise Signature Homes

    8 Priscilla Ln, 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
    • 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
  • 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
  • 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
    • 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
  • 16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    /42

    $1,149,000 Open Sat 11:30AM - 12:30PM

    • 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
  • 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 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
  • 80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    /37

    $3,099,000 Open Sun 11AM - 12PM

    • 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
  • 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
    • 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
  • 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
  • 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

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Massachusetts Middlesex County Winchester

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