9,202

Winchester, MA Homes

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  • /36

    $1,945,000

    Sold Sep 16, 2025

    20 Grayson Rd, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 3,825 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Above List Price
    • $508/SF
    • 7 Days On Market

    Current Estimated Value $1,916,269

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    20 Grayson Rd, Winchester, MA 01890
    • /42

      Est $3,002,895

      Not Listed For Sale

      6 Pocahontas Dr, Winchester, MA 01890

      • 5 Beds
      • 5.5 Baths
      • 5,600 Sq Ft
      • Built 2022
      6 Pocahontas Dr, Winchester, MA 01890

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  • /30

    $349,900

    $15K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 613 Sq Ft

    200 Swanton St Unit 717, Winchester, MA 01890

    Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for

    Cameron Moniz Coldwell Banker Realty - Lexington

    200 Swanton St Unit 717, Winchester, MA 01890
  • /31

    $1,170,000

    Sold Jul 30, 2026

    6 Hancock St, Winchester, MA 01890

    • 5 Beds
    • 1.5 Baths
    • 2,688 Sq Ft
    • Built 1890

    Last Sold Summary

    • 6% Below List Price
    • $435/SF
    • 35 Days On Market

    Current Estimated Value $1,201,488

    Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

    6 Hancock St, Winchester, MA 01890
    • /36

      Est $1,655,308

      Not Listed For Sale

      43 Mayflower Rd, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 4,190 Sq Ft
      • Built 1970
      43 Mayflower Rd, Winchester, MA 01890

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Annie Youssoufian Boston Brownstones Realty PLLC

  • /42

    $1,549,000

    • 3 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    50 Holland St, Winchester, MA 01890

    Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted

    Kim Covino Compass

    50 Holland St, Winchester, MA 01890
  • /31

    $1,965,000

    Sold Jan 27, 2026

    46 Church St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,475 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $565/SF
    • 13 Days On Market

    Current Estimated Value $1,984,380

    Last Listing Agent Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

    46 Church St, Winchester, MA 01890
    • /38

      Est $1,988,615

      Not Listed For Sale

      11 Plymouth Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,611 Sq Ft
      • Built 1984
      11 Plymouth Rd, Winchester, MA 01890

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Darryl Brian RE/MAX Bentley's

  • /37

    $649,900

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft

    666 Main St Unit 315, Winchester, MA 01890

    Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features

    Kim Covino Compass

    666 Main St Unit 315, Winchester, MA 01890
  • /42

    $2,300,000

    Sold Jul 21, 2026

    30 Rangeley Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,744 Sq Ft
    • Built 1929

    Last Sold Summary

    • 5% Above List Price
    • $485/SF
    • 8 Days On Market

    Current Estimated Value $2,194,809

    Last Listing Agent Kim Covino Compass

    30 Rangeley Rd, Winchester, MA 01890
    • /35

      Est $1,993,644

      Not Listed For Sale

      34 Mayflower Rd, Winchester, MA 01890

      • 4 Beds
      • 4.5 Baths
      • 4,439 Sq Ft
      • Built 1970
      34 Mayflower Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Janice Vazquez United Brokers

  • /28

    $1,150,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,004 Sq Ft

    52 Salem St Unit 52, Winchester, MA 01890

    Completely renovated in 2021, this stunning 3-bedroom, 2.5-bath townhouse offers the comfort and feel of a single-family home with three levels of beautifully finished living space. The open and inviting floor plan features hardwood floors throughout, modern finishes, and abundant natural light. The spacious third-floor primary suite provides a private retreat with spacious walk in closet and its

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

    52 Salem St Unit 52, Winchester, MA 01890
  • /23

    $1,440,150

    Sold Jun 01, 2026

    65 High St, Winchester, MA 01890

    • 6 Beds
    • 3 Baths
    • 2,658 Sq Ft
    • Built 1949

    Last Sold Summary

    • 3% Above List Price
    • $542/SF
    • 5 Days On Market

    Current Estimated Value $1,449,275

    Last Listing Agent Anna Jung K Stadium Realty INC

    65 High St, Winchester, MA 01890
    • /40

      Est $1,539,797

      Not Listed For Sale

      57 Hutchinson Rd, Winchester, MA 01890

      • 2 Beds
      • 3 Baths
      • 2,874 Sq Ft
      • Built 1952
      57 Hutchinson Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

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

  • /12

    $789,000

    $40K PRICE DROP
    • Land
    • 19,166 Sq Ft
    • $1,793,182 per Acre

    14 Cross St, Woburn, MA 01801

    Improved Land Opportunity - Developers, Contractors, Investors and Future single-family 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 residential structure permitted.)

    Donna Bozza Barrett Sotheby's International Realty

    14 Cross St, Woburn, MA 01801
  • /28

    $710,000

    Sold Sep 10, 2025

    666 Main St Unit 206, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $607/SF
    • 50 Days On Market

    Current Estimated Value $733,491

    Last Listing Agent Sveta Vakhitova Berkshire Hathaway HomeServices Warren Residential

    666 Main St Unit 206, Winchester, MA 01890
    • /33

      Est $1,330,434

      Not Listed For Sale

      132 Cambridge St, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 1,636 Sq Ft
      • Built 1980
      132 Cambridge St, Winchester, MA 01890

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Emmanuel Garcia Elia Realty Group, Inc

  • /42

    $2,299,000

    Pending
    • 7 Beds
    • 4.5 Baths
    • 4,930 Sq Ft

    42 Wildwood St, Winchester, MA 01890

    Exceptional craftsmanship defines this majestic home in The Flats, where beautifully-preserved architectural details blend seamlessly w/ modern livability. A showstopping foyer welcomes you w/ a sweeping staircase, exquisite millwork, graceful arched openings & leaded glass windows. You’ll find quarter-sawn oak floors, rich woodwork, generously scaled windows & impressive ceiling height

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

    42 Wildwood St, Winchester, MA 01890
  • /40

    $2,895,000

    Sold Oct 30, 2025

    6 Abby Rd, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,716 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $506/SF
    • 28 Days On Market

    Last Listing Agent Philip Vita Compass

    6 Abby Rd, Winchester, MA 01890
    • /42

      Est $2,458,204

      Not Listed For Sale

      7 Russett Ln, Winchester, MA 01890

      • 5 Beds
      • 7 Baths
      • 7,292 Sq Ft
      • Built 1974
      7 Russett Ln, Winchester, MA 01890

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Reliable Results Realty Coldwell Banker Realty - Westford

  • /23

    $719,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,494 Sq Ft

    247 Washington St Unit 11, Winchester, MA 01890

    Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for

    Heejeong Joo Coldwell Banker Realty - Lexington

    247 Washington St Unit 11, Winchester, MA 01890
  • /34

    $2,100,000

    Sold Mar 19, 2026

    10 Hawthorne Rd, Winchester, MA 01890

    • 5 Beds
    • 6 Baths
    • 3,191 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Above List Price
    • $658/SF
    • 7 Days On Market

    Current Estimated Value $2,020,776

    Last Listing Agent Susan Kadilak Fiv Realty Co.

    10 Hawthorne Rd, Winchester, MA 01890
    • /42

      Est $2,353,484

      Not Listed For Sale

      8 Johnson Rd, Winchester, MA 01890

      • 6 Beds
      • 5.5 Baths
      • 5,800 Sq Ft
      • Built 2016
      8 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  • /28

    $288,750

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft

    200 Swanton St Unit L8, Winchester, MA 01890

    Welcome to effortless living in the most desirable community of Winchester. This beautifully updated studio condominium at The Parkview Condominiums offers an exceptional opportunity to own the most affordable home in Winchester. Rarely offered sunny side lobby level. You'll find a thoughtfully renovated interior featuring a stunning new kitchen with white shaker cabinetry, gleaming quartz

    Stephen DeConto Cameron Real Estate Group

    200 Swanton St Unit L8, Winchester, MA 01890
  • /11

    $270,000

    Sold Mar 02, 2026

    200 Swanton St Unit 636, Winchester, MA 01890

    • 1 Bed
    • 1 Bath
    • 394 Sq Ft
    • Built 1966

    Last Sold Summary

    • 10% Below List Price
    • $685/SF
    • 26 Days On Market

    Current Estimated Value $273,825

    Last Listing Agent Michael Masci North Atlantic Realty Group

    200 Swanton St Unit 636, Winchester, MA 01890
    • /40

      Est $2,975,617

      Not Listed For Sale

      50 Emerson Rd, Winchester, MA 01890

      • 4 Beds
      • 5 Baths
      • 4,051 Sq Ft
      • Built 2005
      50 Emerson Rd, Winchester, MA 01890

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Steve Leavey Keller Williams Realty

  • /41

    $1,195,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,303 Sq Ft

    52 Middlesex St Unit 52, Winchester, MA 01890

    Newly renovated 4-bedroom, 3-bath townhome offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy new white oak hardwood floors, a stunning chef's kitchen with quartz countertops and

    The North Star Group Keller Williams Realty Evolution

    52 Middlesex St Unit 52, Winchester, MA 01890
  • /35

    $1,015,000

    Sold Mar 20, 2026

    320 Washington St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,749 Sq Ft
    • Built 1850

    Last Sold Summary

    • 2% Above List Price
    • $580/SF
    • 6 Days On Market

    Current Estimated Value $1,010,444

    Last Listing Agent John Conroy East Coast Realty, Inc.

    320 Washington St, Winchester, MA 01890
    • /37

      Est $1,955,405

      Not Listed For Sale

      36 Robinhood Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 3,689 Sq Ft
      • Built 1959
      36 Robinhood Rd, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /42

    $1,699,000

    Pending
    • 3 Beds
    • 3.5 Baths
    • 2,513 Sq Ft

    2 Olde Lyme Rd, Winchester, MA 01890

    Beautifully updated & impeccably maintained 3 BR, 3.5 bath home on a sought-after cul-de-sac w/lovely front & side yards, abutting conservation land for exceptional privacy. The main level features a spacious living room, updated sunroom, granite kitchen w/newer SS appliances, abundant cabinetry, peninsula seating, & dining room w/ access to an inviting deck. Two 1st floor bedrooms & two full

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

    2 Olde Lyme Rd, Winchester, MA 01890
  • /42

    $1,082,000

    Sold May 01, 2026

    38 Pickering St Unit A, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,056 Sq Ft
    • Built 1890

    Last Sold Summary

    • 8% Above List Price
    • $526/SF
    • 5 Days On Market

    Current Estimated Value $1,060,442

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    38 Pickering St Unit A, Winchester, MA 01890
    • /42

      Est $1,699,062

      Not Listed For Sale

      9 Blossom Hill Rd, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 2,635 Sq Ft
      • Built 1955
      9 Blossom Hill Rd, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /40

    $2,300,000

    $80K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,881 Sq Ft

    14 Hillside Ave, Winchester, MA 01890

    Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom

    Rebecca Huang William Raveis R.E. & Home Services

    14 Hillside Ave, Winchester, MA 01890
  • /38

    $1,558,200

    Sold Jan 05, 2026

    82 Hillcrest Pkwy, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft
    • Built 1936

    Last Sold Summary

    • 6% Below List Price
    • $828/SF
    • 8 Days On Market

    Current Estimated Value $1,583,049

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

    82 Hillcrest Pkwy, Winchester, MA 01890
    • /37

      Est $1,567,992

      Not Listed For Sale

      4 Albamont Rd, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 2,793 Sq Ft
      • Built 1958
      4 Albamont Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent The Ridick Revis Group Compass

  • /38

    $2,195,000

    $104K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 5,006 Sq Ft

    276 High St, Winchester, MA 01890

    Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

    Kim Covino Compass

    276 High St, Winchester, MA 01890
  • /42

    $1,199,000

    Sold Nov 21, 2025

    162 Swanton St Unit 162, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,459 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $488/SF
    • 73 Days On Market

    Last Listing Agent Kim Covino Compass

    162 Swanton St Unit 162, Winchester, MA 01890
    • /33

      Est $1,546,358

      Not Listed For Sale

      10 Albamont Rd, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,920 Sq Ft
      • Built 1958
      10 Albamont Rd, Winchester, MA 01890

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Dorothea Feffer Coldwell Banker Realty - Lexington

  • /33

    $1,110,000

    $40K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,186 Sq Ft

    63-65 Harvard St, Winchester, MA 01890

    Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home.

    Beth Sager Group Keller Williams Realty Boston Northwest

    63-65 Harvard St, Winchester, MA 01890
  • /38

    $1,950,000

    Sold Jul 29, 2026

    9 Wilson St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,943 Sq Ft
    • Built 1890

    Last Sold Summary

    • 3% Above List Price
    • $663/SF
    • 6 Days On Market

    Current Estimated Value $1,898,774

    Last Listing Agent Elena Langlois Compass

    9 Wilson St, Winchester, MA 01890

Showing Results 201 - 240, Page 6 of 18

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