9,206

Winchester, MA Homes

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  • /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 $1,730,966

      Not Listed For Sale

      31 Girard Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 3,158 Sq Ft
      • Built 1975
      31 Girard Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Philip Vita Compass

  • /37

    $1,749,000

    Open Sat 11:30AM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 3,508 Sq Ft

    17 Churchill Rd, Winchester, MA 01890

    A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with

    Domingo Medina Coldwell Banker Realty - Lexington

    17 Churchill Rd, 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
    • /40

      Est $2,174,236

      Not Listed For Sale

      99 Ridge St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,567 Sq Ft
      • Built 2004
      99 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Doug Hills Compass

  • /42

    $1,599,000

    Open Sat 11AM - 12PM
    • 5 Beds
    • 3 Baths
    • 2,944 Sq Ft

    143 Arlington St, Winchester, MA 01890

    JOIN US FOR AN OPEN HOUSE SATURDAY 9/19 11-12;30! Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases

    Kim Covino Compass

    143 Arlington St, 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
    • /42

      Est $1,248,155

      Not Listed For Sale

      119 Ridge St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,542 Sq Ft
      • Built 1956
      119 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Charles Jolin Keller Williams Realty

  • /20

    $675,000

    • 2 Beds
    • 1.5 Baths
    • 1,190 Sq Ft

    60 Lake St Unit E, Winchester, MA 01890

    Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all

    Shaundize Moosavizadeh Coldwell Banker Realty - Boston

    60 Lake St Unit E, Winchester, MA 01890
  • /38

    $1,655,000

    Sold Aug 13, 2026

    11 Carriage Ln, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,707 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Below List Price
    • $611/SF
    • 9 Days On Market

    Current Estimated Value $1,646,501

    Last Listing Agent Kim Covino Compass

    11 Carriage Ln, Winchester, MA 01890
    • /42

      Est $1,733,152

      Not Listed For Sale

      50 Johnson Rd, Winchester, MA 01890

      • 3 Beds
      • 4 Baths
      • 2,646 Sq Ft
      • Built 1957
      50 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 18 Days On Market

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

  • /41

    $3,200,000

    Open Sat 1PM - 2:30PM
    • 8 Beds
    • 6.5 Baths
    • 5,750 Sq Ft

    30 Willowdale Rd, Winchester, MA 01890

    A rare expression of quality, craftsmanship, and enduring style, 30 Willowdale Road presents an exceptional opportunity to own a newly constructed residence in one of Winchester’s most coveted neighborhoods. Set on a beautifully proportioned, large and level lot, this remarkable home has been thoughtfully conceived to offer the space, sophistication, and effortless lifestyle expected of a truly

    Nancy Pallotta Gibson Sotheby's International Realty

    30 Willowdale Rd, 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
    • /40

      Est $1,427,756

      Not Listed For Sale

      25 Lockeland Rd, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 2,456 Sq Ft
      • Built 1954
      25 Lockeland Rd, Winchester, MA 01890

      Last Sold Summary

      • 12 Days On Market

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

  • /42

    $1,075,000

    Open Sat 1PM - 2PM $150K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    53 Lake St, Winchester, MA 01890

    Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming

    Kim Covino Compass

    53 Lake St, 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 $2,302,733

      Not Listed For Sale

      7 Plymouth Rd, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 2,770 Sq Ft
      • Built 1959
      7 Plymouth Rd, Winchester, MA 01890

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /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
  • /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
    • /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

  • /42

    $3,199,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 5,406 Sq Ft

    10 Rangeley Rd, Winchester, MA 01890

    Exceptionally rare property on prestigious Rangeley Road, steps to downtown Winchester. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Brand NEW Roof+HVAC. Grand, sun drenched

    Karima Alami Compass

    10 Rangeley Rd, 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
    • /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

  • /38

    $1,195,000

    Open Sun 11:30AM - 1PM
    • 3 Beds
    • 1.5 Baths
    • 2,239 Sq Ft

    4 Stone Ave, Winchester, MA 01890

    Introducing 4 Stone Ave, a charming 3 bed, 1.5 bath Colonial Style home, one block from Muraco School, and minutes from the Middlesex Fells Reservation, offering over 2,575 acres of pristine woodlands, reservoirs, and scenic trails perfect for outdoor recreation. Beautiful updates complement the home’s original oak woodwork, including stained oak Harvey windows with tilt in sashes. The spacious

    Paul Cirignano The Synergy Group

    4 Stone Ave, 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
    • /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

  • /42

    $1,549,000

    Open Sat 12:30PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    50 Holland St, Winchester, MA 01890

    Private showings available this weekend~call to schedule! Resort living just steps from the town center! Completely remodeled with 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

    Kim Covino Compass

    50 Holland St, 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
    • /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

  • /42

    $3,295,000

    Pending
    • 6 Beds
    • 6.5 Baths
    • 6,100 Sq Ft

    2 Atherton Rd, Winchester, MA 01890

    Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an

    Peter Kasseris Serhant

    2 Atherton Rd, 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
    • /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

  • /38

    $775,000

    Open Sun 2:30PM - 4PM
    • 3 Beds
    • 2 Baths
    • 1,643 Sq Ft

    189 Washington St Unit 2, Winchester, MA 01890

    Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym,

    Kim Covino Compass

    189 Washington St Unit 2, 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
    • /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

  • /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

    $2,400,000

    Sold Aug 31, 2026

    112 Highland Ave, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 5,121 Sq Ft
    • Built 1890

    Last Sold Summary

    • 4% Below List Price
    • $469/SF
    • 20 Days On Market

    Current Estimated Value $2,422,400

    Last Listing Agent Kim Covino Compass

    112 Highland Ave, 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

  • /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
  • /42

    $1,090,000

    Sold Feb 06, 2026

    16 Ridge St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft
    • Built 1965

    Last Sold Summary

    • 9% Below List Price
    • $591/SF
    • 82 Days On Market

    Current Estimated Value $1,150,221

    Last Listing Agent Kim Covino Compass

    16 Ridge St, Winchester, MA 01890

Showing Results 201 - 240, Page 6 of 18

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