9,208

Winchester, MA Homes

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  • /2

    $389,900

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    20 Arthur St, Winchester, MA 01890

    Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

    Dan O'Connell LAER Realty Partners

    20 Arthur St, Winchester, MA 01890
  • /39

    $2,200,000 Sold Jul 14, 2025

    • 3,896 Sq Ft
    • $565/SF
    • 11 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2016

    4 Fairfield Place, Winchester, MA 01890

    NEWER CONSTRUCTION 4 bed 3.5 bath colonial located in a great neighborhood right outside Winchester center! Enjoy all the area has to offer just outside your door including restaurants, shops, schools, train to Boston, the Tri-Community bike path, Horn Pond, Packer tennis courts & Wedge pond! This warm and welcoming, gently lived in home showcases 3900sf of space on 3 levels with 4 large

    Kim Covino Compass

    4 Fairfield Place, Winchester, MA 01890
    • /41

      Est $2,239,405 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 4,925 Sq Ft

      6 Cambridge St, Winchester, MA 01890

      6 Cambridge St, Winchester, MA 01890
  • /26

    $2,160,000 Sold Jul 14, 2025

    • 4,023 Sq Ft
    • $537/SF
    • 37 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1998

    19 Sussex Rd, Winchester, MA 01890

    Ideally located in a very desirable neighborhood that abuts the town forest and surrounded by cul-de-sacs, this elegant well-designed 4-bedroom, 3.5-bathroom colonial home has been meticulously maintained by the original owners and features a spacious layout with ample room for comfortable living. The floorplan is thoughtfully designed, with a nice flow from one room to the next. The family room

    Ida Bianco Coldwell Banker Realty - Lexington

    19 Sussex Rd, Winchester, MA 01890
    • /42

      Est $4,773,263 Not Listed For Sale

      • 7 Beds
      • 8.5 Baths
      • 10,146 Sq Ft

      3 Myopia Rd, Winchester, MA 01890

      3 Myopia Rd, Winchester, MA 01890
  • /39

    $1,400,000 Sold Jul 14, 2025

    • 2,282 Sq Ft
    • $613/SF
    • 38 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    20 Fletcher St Unit 20, Winchester, MA 01890

    Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication

    Kim Covino Compass

    20 Fletcher St Unit 20, Winchester, MA 01890
    • /42

      Est $1,955,060 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,243 Sq Ft

      10 Taft Dr, Winchester, MA 01890

      10 Taft Dr, Winchester, MA 01890
  • /42

    $2,500,000 Sold Jul 14, 2025

    • 3,719 Sq Ft
    • $672/SF
    • 7 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1952

    17 Harrison St, Winchester, MA 01890

    Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized

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

    17 Harrison St, Winchester, MA 01890
    • /41

      Est $2,622,022 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,333 Sq Ft

      17 Swan Rd, Winchester, MA 01890

      17 Swan Rd, Winchester, MA 01890
  • /40

    $1,635,000 Sold Jul 11, 2025

    • 2,470 Sq Ft
    • $662/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2012

    35 Rumford St Unit 35, Winchester, MA 01890

    This sun-filled 2012 townhouse, with its spacious layout, backyard oasis & attached garage, lives like a single-family home. Spend weekends lounging on the private deck, unwinding under the pergola, or playing on the lush, fenced lawn. Inside, the inviting open layout is made for gathering—whether around the gas fireplace on cozy evenings or at the kitchen island while entertaining friends. High

    Elena Langlois Compass

    35 Rumford St Unit 35, Winchester, MA 01890
    • /42

      Est $2,243,582 Not Listed For Sale

      • 7 Beds
      • 3 Baths
      • 4,090 Sq Ft

      5 Swan Rd, Winchester, MA 01890

      5 Swan Rd, Winchester, MA 01890
  • /42

    $1,540,000 Sold Jul 11, 2025

    • 2,814 Sq Ft
    • $547/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1970

    21 Johnson Rd, Winchester, MA 01890

    This lovingly maintained Colonial home is ideally situated just a 1/2 mile from Vinson-Owen Elementary School. Featuring all 4 bedrooms on the second floor, the layout includes a spacious primary w/ an en-suite bath as well as a fully updated hall bath. The main level offers an elegant family room w/ soaring ceilings, a cozy fireplace, recessed lighting & a slider leading to the deck. The

    Stefanie Clifford Keller Williams Realty Boston Northwest

    21 Johnson Rd, Winchester, MA 01890
    • /39

      Est $1,211,826 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,664 Sq Ft

      10 Chesterford Rd E, Winchester, MA 01890

      10 Chesterford Rd E, Winchester, MA 01890
  • /16

    $1,050,000 Sold Jul 11, 2025

    • 2,621 Sq Ft
    • $401/SF
    • 48 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1952

    61 Westland Ave, Winchester, MA 01890

    Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    61 Westland Ave, Winchester, MA 01890
    • /42

      Est $1,139,828 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,657 Sq Ft

      8 Chesterford Rd E, Winchester, MA 01890

      8 Chesterford Rd E, Winchester, MA 01890
  • /38

    $1,924,000 Sold Jul 10, 2025

    • 4,195 Sq Ft
    • $459/SF
    • 4 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1995

    5 Hastings Rd, Winchester, MA 01890

    Rare opportunity on a peaceful cul-de-sac. This extraordinary 4-bedroom, 4-bathroom home is nestled in one of Winchester's most sought-after neighborhoods. For the first time ever, this meticulously maintained residence is available on a street where properties rarely change hands. Bathed in abundant natural light, the thoughtfully designed floor plan showcases generously sized living spaces that

    Nancy Pallotta Gibson Sotheby's International Realty

    5 Hastings Rd, Winchester, MA 01890
    • /35

      Est $1,974,747 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,846 Sq Ft

      12 Ardley Place, Winchester, MA 01890

      12 Ardley Place, Winchester, MA 01890
  • /37

    $2,200,000 Sold Jul 09, 2025

    • 3,901 Sq Ft
    • $564/SF
    • 4 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 2011

    20 Elm St, Winchester, MA 01890

    Nestled in the highly sought-after "heart" of Winchester Center, this Newer Construction single-family (slightly attached) home offers space & finishes you typically find in 2.5M+ homes! With 10' ceilings and high end finishes throughout, this stunning 5-6 bedroom, 3.5 bath home is just two blocks from the vibrant town center, train station, schools, restaurants & shops! 5190 total sf w/ 3900sf

    Kim Covino Compass

    20 Elm St, Winchester, MA 01890
    • /37

      Est $1,378,073 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,350 Sq Ft

      8 Parker Rd, Winchester, MA 01890

      8 Parker Rd, Winchester, MA 01890
  • /41

    $1,500,000 Sold Jun 30, 2025

    • 2,189 Sq Ft
    • $685/SF
    • 1 Day On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    23 Elmwood Ave Unit C, Winchester, MA 01890

    Welcome to Elmwood condos with over 2,100 SF of stunning single-level luxury living in vibrant downtown Winchester! This sparkling, modern condo offers a beautifully open floor plan designed for today's discerning buyer with the kitchen, dining & living areas seamlessly integrated for both comfort and style. Enjoy high end/ top-of-the-line, rich finishes throughout, including gleaming hardwood

    Kim Covino Compass

    23 Elmwood Ave Unit C, Winchester, MA 01890
    • /39

      Est $1,621,419 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,592 Sq Ft

      59 Woodside Rd, Winchester, MA 01890

      59 Woodside Rd, Winchester, MA 01890
  • /39

    $2,200,000 Sold Jun 30, 2025

    • 3,818 Sq Ft
    • $576/SF
    • 0 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1967

    1 Saint Augustine Ct, Winchester, MA 01890

    Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and gleaming hardwood floors throughout, it strikes the perfect balance between timeless charm and fresh, move-in-ready style. The front-to-back living room is flooded with natural light—ideal for everything from morning coffee to impromptu

    Nancy Pallotta Gibson Sotheby's International Realty

    1 Saint Augustine Ct, Winchester, MA 01890
    • /29

      Est $1,043,916 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,630 Sq Ft

      7 Brantwood Rd, Winchester, MA 01890

      7 Brantwood Rd, Winchester, MA 01890
  • /40

    $1,877,000 Sold Jun 30, 2025

    • 2,813 Sq Ft
    • $667/SF
    • 26 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    20 Seneca Rd, Winchester, MA 01890

    Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

    Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

    20 Seneca Rd, Winchester, MA 01890
    • /40

      Est $1,238,881 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 2,202 Sq Ft

      71 Woodside Rd, Winchester, MA 01890

      71 Woodside Rd, Winchester, MA 01890
  • /41

    $1,500,000 Sold Jun 30, 2025

    • 4,214 Sq Ft
    • $356/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1995

    7 Wainwright Rd Unit 117, Winchester, MA 01890

    Welcome to the largest unit at The Ledges! This stunning F unit boasts soaring ceilings and an expansive open floor plan, perfect for entertaining or relaxing in style. Custom decorated in a perfect, custom Palm Beach vibe, but easy to change if you don't love it. Sunlight floods the large formal living room, with an attached deck, bifurcated by a gas fireplace that leads to the dining room. A

    Nancy Pallotta Gibson Sotheby's International Realty

    7 Wainwright Rd Unit 117, Winchester, MA 01890
    • /42

      Est $2,595,923 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 4,659 Sq Ft

      10 Norfolk Rd, Winchester, MA 01890

      10 Norfolk Rd, Winchester, MA 01890
  • /32

    $1,250,000 Sold Jun 30, 2025

    • 2,759 Sq Ft
    • $453/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1973

    80 Harvard St, Winchester, MA 01890

    Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3 bedrooms and a bathroom.

    Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

    80 Harvard St, Winchester, MA 01890
    • /42

      Est $1,713,271 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,180 Sq Ft

      85 Pond St, Winchester, MA 01890

      85 Pond St, Winchester, MA 01890
  • /42

    $2,359,000 Sold Jun 30, 2025

    • 3,274 Sq Ft
    • $721/SF
    • 8 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1985

    57 Jefferson Rd, Winchester, MA 01890

    Situated on a picturesque corner lot, this exceptional home is nestled in a very desirable neighborhood! Step into a light-filled, open-concept 1st floor, where a soaring beamed ceiling enhances the inviting ambiance. The living room boasts built-in shelves, while the kitchen impresses w/timeless white cabinetry, soapstone counters, SS appliances, large island, & pantry. The dining area, warmed

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    57 Jefferson Rd, Winchester, MA 01890
    • /41

      Est $1,968,720 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,011 Sq Ft

      67 Wildwood St, Winchester, MA 01890

      67 Wildwood St, Winchester, MA 01890
  • /28

    $1,260,000 Sold Jun 30, 2025

    • 2,705 Sq Ft
    • $466/SF
    • 41 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1885

    261 Cambridge St Unit 261 G, Winchester, MA 01890

    Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms,

    Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

    261 Cambridge St Unit 261 G, Winchester, MA 01890
    • /41

      Est $2,557,946 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,676 Sq Ft

      79 Yale St, Winchester, MA 01890

      79 Yale St, Winchester, MA 01890
  • /30

    $1,330,000 Sold Jun 27, 2025

    • 1,629 Sq Ft
    • $816/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1941

    17 Mason St, Winchester, MA 01890

    Nestled on a quiet, tree-lined street near Winchester’s vibrant town center, this delightful storybook colonial offers charm, character, and exceptional potential. Beautifully sited on a 10,000+ sq ft wooded lot, this three-bedroom, two-bath home invites your vision to blend timeless architectural details with thoughtful updates. A fireplaced front-to-back living room flows seamlessly into a

    Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

    17 Mason St, Winchester, MA 01890
    • /42

      Est $2,539,943 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,775 Sq Ft

      76 Yale St, Winchester, MA 01890

      76 Yale St, Winchester, MA 01890
  • /35

    $1,100,000 Sold Jun 27, 2025

    • 3,157 Sq Ft
    • $348/SF
    • 20 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1866

    63 Church St, Winchester, MA 01890

    Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

    Nancy McLaughlin Redfin Corp.

    63 Church St, Winchester, MA 01890
    • /32

      Est $1,989,123 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,350 Sq Ft

      57 Wildwood St, Winchester, MA 01890

      57 Wildwood St, Winchester, MA 01890
  • /25

    $715,000 Sold Jun 27, 2025

    • 1,539 Sq Ft
    • $465/SF
    • 33 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1999

    7 Conant Rd Unit 37, Winchester, MA 01890

    Welcome to this beautifully updated corner unit townhouse-style condo, offering ample-sized rooms, abundant natural light, & hardwood floors throughout! The layout includes 5 well proportioned rooms. Kitchen, living room w/gas fireplace w/marble surround, dining room & 2.5 bathrooms, creating a comfortable & functional living space. Both bedrooms are en-suite, providing privacy & convenience,

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Conant Rd Unit 37, Winchester, MA 01890
    • /42

      Est $2,051,472 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,003 Sq Ft

      12 Woodside Rd, Winchester, MA 01890

      12 Woodside Rd, Winchester, MA 01890
  • /17

    $299,000 Sold Jun 27, 2025

    • 450 Sq Ft
    • $664/SF
    • 10 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1966

    200 Swanton St Unit T4, Winchester, MA 01890

    Immaculate, recently renovated Jumbo Studio Condominium with a private/direct-entry terrace level. This unit is spacious and bright, featuring a slider that leads to a private patio overlooking scenic duck ponds and lush landscaping. The large eat-in kitchen features white cabinets, with a white tiled backsplash and granite countertops. The bathroom was recently updated with new fixtures,

    Michael Masci North Atlantic Realty Group

    200 Swanton St Unit T4, Winchester, MA 01890

Showing Results 281 - 320, Page 8 of 18

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