9,215

Winchester, MA Homes

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

    $898,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,425 Sq Ft

    571 Washington St, Winchester, MA 01890

    Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for

    Ryan Wilson Keller Williams Realty

    571 Washington St, Winchester, MA 01890
  • 19 Rangeley Rd, Winchester, MA 01890
    19 Rangeley Rd, Winchester, MA 01890
    19 Rangeley Rd, Winchester, MA 01890
    /39

    $4,650,000 Sold May 01, 2025

    19 Rangeley Rd, Winchester, MA 01890

    • 5 Beds
    • 7 Baths
    • 7,779 Sq Ft
    • Built 1915

    Last Sold Summary

    • 3% Below List Price
    • $598/SF
    • 5 Days On Market

    Current Estimated Value $4,622,895

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    19 Rangeley Rd, Winchester, MA 01890
    • 7 Wainwright Rd Unit 72, Winchester, MA 01890
      7 Wainwright Rd Unit 72, Winchester, MA 01890
      7 Wainwright Rd Unit 72, Winchester, MA 01890
      /33

      Est $1,901,935 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,327 Sq Ft

      7 Wainwright Rd Unit 72, Winchester, MA 01890

      7 Wainwright Rd Unit 72, Winchester, MA 01890
  • 26 North Gateway, Winchester, MA 01890
    26 North Gateway, Winchester, MA 01890
    /2

    $999,999 Pending

    • 2 Beds
    • 1 Bath
    • 1,666 Sq Ft

    26 North Gateway, Winchester, MA 01890

    LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or restoration All offers must be on attached OFFER TO PURCHASE form and prior to entering property the attached " Hold Harmless" agreement must be signed. All offers must include the OTP, Proof of funds and/or preapproval and copy of $1,000.00

    Robert Dell Homes Unlimited

    26 North Gateway, Winchester, MA 01890
  • 48 Tremont St, Winchester, MA 01890
    48 Tremont St, Winchester, MA 01890
    48 Tremont St, Winchester, MA 01890
    /15

    $930,000 Sold Jun 20, 2025

    48 Tremont St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,333 Sq Ft
    • Built 1959

    Last Sold Summary

    • 7% Below List Price
    • $399/SF
    • 25 Days On Market

    Current Estimated Value $949,893

    Last Listing Agent Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

    48 Tremont St, 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 $1,665,638 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
  • 200 Swanton St Unit 234, Winchester, MA 01890
    200 Swanton St Unit 234, Winchester, MA 01890
    200 Swanton St Unit 234, Winchester, MA 01890
    /17

    $269,000

    • 1 Bath
    • 388 Sq Ft

    200 Swanton St Unit 234, Winchester, MA 01890

    Sunny studio unit overlooking the pond and courtyard at Parkview Condos in Winchester. Unit features include large private balcony with large sliding door that lets in lots of natural sun light. New LVP flooring in the living room/bedroom area and hallway. Freshly painted all throughout. Kitchen has granite countertops and a new refrigerator and electric range. The condominium amenities include

    Devin Caglayan All County Select Property Management

    200 Swanton St Unit 234, Winchester, MA 01890
  • 41 Foxcroft Rd, Winchester, MA 01890
    41 Foxcroft Rd, Winchester, MA 01890
    /2

    $2,222,500 Sold Mar 27, 2025

    41 Foxcroft Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,900 Sq Ft
    • Built 1932

    Last Sold Summary

    • 1% Above List Price
    • $766/SF
    • 0 Days On Market

    Current Estimated Value $2,096,440

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    41 Foxcroft Rd, 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 $1,784,242 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
  • 77A Brooks St, Winchester, MA 01890
    77A Brooks St, Winchester, MA 01890
    77A Brooks St, Winchester, MA 01890
    /42

    $2,100,000 Pending

    • 6 Beds
    • 3.5 Baths
    • 4,122 Sq Ft

    77A Brooks St, Winchester, MA 01890

    This stately Victorian offers an exceptional blend of preserved character and modern functionality across its generous, well-appointed layout. Sunlit rooms highlight hardwood floors, detailed millwork, bay windows, and a graceful fireplace, creating a warm and elegant flow throughout the main level. The expansive kitchen features stone counters, a central island, French doors, and direct access

    Anne Spry Barrett Sotheby's International Realty

    77A Brooks St, Winchester, MA 01890
  • 18 Englewood Rd, Winchester, MA 01890
    18 Englewood Rd, Winchester, MA 01890
    18 Englewood Rd, Winchester, MA 01890
    /35

    $1,750,000 Sold Jun 17, 2025

    18 Englewood Rd, Winchester, MA 01890

    • 5 Beds
    • 2.5 Baths
    • 2,597 Sq Ft
    • Built 1925

    Last Sold Summary

    • 6% Above List Price
    • $674/SF
    • 2 Days On Market

    Current Estimated Value $1,690,161

    Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    18 Englewood Rd, 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 $1,584,789 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
  • 237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    /35

    $1,995,000

    • 5 Beds
    • 4 Baths
    • 4,334 Sq Ft

    237 Swanton St, Winchester, MA 01890

    NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas

    Kim Covino Compass

    237 Swanton St, Winchester, MA 01890
  • 21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    /42

    $2,890,000 Sold Aug 14, 2025

    21 Fernway, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,386 Sq Ft
    • Built 1963

    Last Sold Summary

    • $537/SF
    • 9 Days On Market

    Current Estimated Value $2,872,914

    Last Listing Agent Kim Covino Compass

    21 Fernway, Winchester, MA 01890
    • 40 Wainwright Rd, Winchester, MA 01890
      40 Wainwright Rd, Winchester, MA 01890
      40 Wainwright Rd, Winchester, MA 01890
      /42

      Est $1,918,554 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
  • 21 Park Ave, Winchester, MA 01890
    21 Park Ave, Winchester, MA 01890
    21 Park Ave, Winchester, MA 01890
    /20

    $1,799,000

    • 3 Beds
    • 2.5 Baths
    • 2,136 Sq Ft

    21 Park Ave, Winchester, MA 01890

    Completely renovated home featuring a brand new kitchen, hvac, plumbing, electrical, flooring and exterior decks. First floor offers kitchen with island, mudroom, laundy/pantry, dining room, and fire-placed living room. Second floor offers 3 bedrooms and 2 baths including a primary en suite. The generous lot size of over 21,000 sq ft affords the new owners an abundance of options for expansion

    Mark Donnellan Gibson Sotheby's International Realty

    21 Park Ave, Winchester, MA 01890
  • 171 Swanton St Unit 5, Winchester, MA 01890
    171 Swanton St Unit 5, Winchester, MA 01890
    171 Swanton St Unit 5, Winchester, MA 01890
    /30

    $900,000 Sold Oct 20, 2025

    171 Swanton St Unit 5, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,843 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $488/SF
    • 8 Days On Market

    Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

    171 Swanton St Unit 5, Winchester, MA 01890
    • 19 Socrates Way, Winchester, MA 01890
      19 Socrates Way, Winchester, MA 01890
      19 Socrates Way, Winchester, MA 01890
      /42

      Est $2,870,165 Not Listed For Sale

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

      19 Socrates Way, Winchester, MA 01890

      19 Socrates Way, Winchester, MA 01890
  • 1 Copley St, Winchester, MA 01890
    1 Copley St, Winchester, MA 01890
    1 Copley St, Winchester, MA 01890
    /32

    $1,725,000 Pending

    • 7 Beds
    • 2.5 Baths
    • 2,998 Sq Ft

    1 Copley St, Winchester, MA 01890

    Gracious Center Entrance colonial situated in top Flats location on a desirable corner lot. This home has all the charm of yesteryear and has many custom features including a beautiful front staircase with window seats, hardwood floors and sunny rooms. Attractive cherry cabinet kitchen with granite island. Large front to back living room has fireplace and is situated next to enclosed porch.

    Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

    1 Copley St, Winchester, MA 01890
  • 235 Cross St, Winchester, MA 01890
    235 Cross St, Winchester, MA 01890
    235 Cross St, Winchester, MA 01890
    /32

    $868,000 Sold Sep 04, 2025

    235 Cross St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,931 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Above List Price
    • $450/SF
    • 8 Days On Market

    Current Estimated Value $867,404

    Last Listing Agent Melanie Lentini Leading Edge Real Estate

    235 Cross St, Winchester, MA 01890
    • 40 Amberwood Dr, Winchester, MA 01890
      40 Amberwood Dr, Winchester, MA 01890
      40 Amberwood Dr, Winchester, MA 01890
      /42

      Est $2,622,766 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
  • 19 Cox Rd, Winchester, MA 01890
    19 Cox Rd, Winchester, MA 01890
    19 Cox Rd, Winchester, MA 01890
    /40

    $1,499,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 2,351 Sq Ft

    19 Cox Rd, Winchester, MA 01890

    Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w

    Kim Covino Compass

    19 Cox Rd, Winchester, MA 01890
  • 9 South Gateway, Winchester, MA 01890
    9 South Gateway, Winchester, MA 01890
    /2

    $2,050,000 Sold Jan 24, 2025

    9 South Gateway, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,450 Sq Ft
    • Built 1953

    Last Sold Summary

    • 9% Below List Price
    • $594/SF
    • 89 Days On Market

    Current Estimated Value $2,061,284

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    9 South Gateway, Winchester, MA 01890
    • 45 Amberwood Dr, Winchester, MA 01890
      45 Amberwood Dr, Winchester, MA 01890
      45 Amberwood Dr, Winchester, MA 01890
      /38

      Est $1,853,494 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
  • 14 Cross St, Woburn, MA 01801
    14 Cross St, Woburn, MA 01801
    14 Cross St, Woburn, MA 01801
    /12

    $795,000 Pending

    • Land
    • 0.44 Acre
    • $1,806,818 per Acre

    14 Cross St, Woburn, MA 01801

    ATTENTION developers, contractors, investors and future homeowners – recently reconfigured 14 Cross Street located immediately over the WINCHESTER line is an attractive sized residential lot consisting of 19,277 square feet of land (see attached recorded plan, Lot 1) Lot is zoned R-2 (Per Building Department - single or 2 family structure permitted.) Currently situated on the lot is a building

    Donna Bozza Barrett Sotheby's International Realty

    14 Cross St, Woburn, MA 01801
  • 102 Hillcrest Pkwy, Winchester, MA 01890
    102 Hillcrest Pkwy, Winchester, MA 01890
    102 Hillcrest Pkwy, Winchester, MA 01890
    /39

    $1,425,000 Sold Dec 01, 2025

    102 Hillcrest Pkwy, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 1,755 Sq Ft
    • Built 1939

    Last Sold Summary

    • 19% Above List Price
    • $812/SF
    • 4 Days On Market

    Last Listing Agent Curtis Howe Howe Realty Group

    102 Hillcrest Pkwy, Winchester, MA 01890
    • 9 Amberwood Dr, Winchester, MA 01890
      9 Amberwood Dr, Winchester, MA 01890
      9 Amberwood Dr, Winchester, MA 01890
      /36

      Est $2,401,077 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
  • 26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    /41

    $1,460,000

    • 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
  • 205 Ridge St, Winchester, MA 01890
    205 Ridge St, Winchester, MA 01890
    205 Ridge St, Winchester, MA 01890
    /42

    $1,550,000 Sold Oct 31, 2025

    205 Ridge St, Winchester, MA 01890

    • 5 Beds
    • 3 Baths
    • 2,995 Sq Ft
    • Built 1960

    Last Sold Summary

    • $518/SF
    • 5 Days On Market

    Last Listing Agent Debby Valdes eXp Realty

    205 Ridge St, Winchester, MA 01890
    • 27 Amberwood Dr, Winchester, MA 01890
      27 Amberwood Dr, Winchester, MA 01890
      27 Amberwood Dr, Winchester, MA 01890
      /38

      Est $1,824,839 Not Listed For Sale

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

      27 Amberwood Dr, Winchester, MA 01890

      27 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 Pending

    • 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
  • 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

    115 Washington St Unit 3D, Winchester, MA 01890

    • 1 Bed
    • 1.5 Baths
    • 769 Sq Ft
    • Built 1988

    Last Sold Summary

    • $675/SF
    • 5 Days On Market

    Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    115 Washington St Unit 3D, Winchester, MA 01890
    • 9 Buckman Dr, Winchester, MA 01890
      9 Buckman Dr, Winchester, MA 01890
      9 Buckman Dr, Winchester, MA 01890
      /42

      Est $2,176,428 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
  • 257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    /42

    $3,299,000

    • 5 Beds
    • 7 Baths
    • 7,101 Sq Ft

    257 High St, Winchester, MA 01890

    Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

    Kim Covino Compass

    257 High St, Winchester, MA 01890
  • 5 Pine St, Winchester, MA 01890
    5 Pine St, Winchester, MA 01890
    5 Pine St, Winchester, MA 01890
    /41

    $2,350,000 Sold Apr 15, 2025

    5 Pine St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,273 Sq Ft
    • Built 1910

    Last Sold Summary

    • 4% Above List Price
    • $550/SF
    • 7 Days On Market

    Current Estimated Value $2,334,348

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

    5 Pine St, Winchester, MA 01890
    • 5 Pilgrim Dr, Winchester, MA 01890
      5 Pilgrim Dr, Winchester, MA 01890
      5 Pilgrim Dr, Winchester, MA 01890
      /42

      Est $2,387,141 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
  • 139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    /24

    $969,000

    • 3 Beds
    • 1.5 Baths
    • 1,302 Sq Ft

    139 High St, Winchester, MA 01890

    This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

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

    139 High St, Winchester, MA 01890
  • 18 Brookside Ave, Winchester, MA 01890
    18 Brookside Ave, Winchester, MA 01890
    18 Brookside Ave, Winchester, MA 01890
    /30

    $1,207,500 Sold Jul 24, 2025

    18 Brookside Ave, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,573 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Above List Price
    • $768/SF
    • 20 Days On Market

    Current Estimated Value $1,192,808

    Last Listing Agent Kim Covino Compass

    18 Brookside Ave, Winchester, MA 01890
    • 15 Pilgrim Dr, Winchester, MA 01890
      15 Pilgrim Dr, Winchester, MA 01890
      15 Pilgrim Dr, Winchester, MA 01890
      /42

      Est $2,037,678 Not Listed For Sale

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

      15 Pilgrim Dr, Winchester, MA 01890

      15 Pilgrim Dr, Winchester, MA 01890
  • 5 Wood Ln, Winchester, MA 01890
    5 Wood Ln, Winchester, MA 01890
    5 Wood Ln, Winchester, MA 01890
    /42

    $1,950,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,443 Sq Ft

    5 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

    5 Wood Ln, Winchester, MA 01890

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Massachusetts Middlesex County Winchester

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