9,206

Winchester, MA Homes

Section Image
  • /40

    $1,799,999

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,126 Sq Ft

    30 Allen Rd, Winchester, MA 01890

    Welcome to 30 Allen Road, a beautifully situated Colonial in one of Winchester’s most desirable and walkable neighborhoods. Ideally located within easy reach of top-rated schools, shops, restaurants, and the commuter rail, this inviting home offers the space, character, and flexibility today’s buyers are looking for. The first floor features a spacious kitchen equipped with a Sub-Zero

    Philip Vita Compass

    30 Allen Rd, Winchester, MA 01890
  • /40

    $645,000

    Sold Jun 16, 2026

    17 Charles Rd Unit 17, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,326 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Above List Price
    • $486/SF
    • 10 Days On Market

    Current Estimated Value $646,725

    Last Listing Agent Jessica Later JL+CoRE

    17 Charles Rd Unit 17, Winchester, MA 01890
    • /30

      Est $937,599

      Not Listed For Sale

      62 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,857 Sq Ft
      • Built 1985
      62 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Melissa Perrone Gibson Sotheby's International Realty

  • /42

    $2,100,000

    Open Sat 11AM - 12PM
    • 4 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    7 Wainwright Rd Unit 113, Winchester, MA 01890

    Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home

    Kim Covino Compass

    7 Wainwright Rd Unit 113, 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

    Current Estimated Value $1,462,947

    Last Listing Agent Curtis Howe Howe Realty Group

    102 Hillcrest Pkwy, Winchester, MA 01890
    • /27

      Est $1,088,503

      Not Listed For Sale

      46 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,859 Sq Ft
      • Built 1985
      46 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Sam Zhu Keller Williams Realty

  • /17

    $1,098,000

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

    17 Russell Rd, Winchester, MA 01890

    Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a

    KoKo Kwan Kwan Realty Inc.

    17 Russell Rd, 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

    Current Estimated Value $1,619,078

    Last Listing Agent Debby Valdes eXp Realty LLC

    205 Ridge St, Winchester, MA 01890
    • /36

      Est $1,023,075

      Not Listed For Sale

      55 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,568 Sq Ft
      • Built 1987
      55 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • /35

    $2,995,000

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

    8 Priscilla Ln, Winchester, MA 01890

    A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout

    The Pezzano Group Rise Signature Homes

    8 Priscilla Ln, 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

    Current Estimated Value $522,173

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

    115 Washington St Unit 3D, Winchester, MA 01890
    • /38

      Est $1,072,677

      Not Listed For Sale

      34 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,754 Sq Ft
      • Built 1985
      34 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /42

    $2,600,000

    • 6 Beds
    • 4 Baths
    • 3,534 Sq Ft

    7 Lakeview Terrace, Winchester, MA 01890

    RARE WATERFRONT OPPORTUNITY on Upper Mystic Lake with spectacular sunset views! Tucked away on Lakeview Terrace, this special 1910 home offers a combination rarely found in Winchester: waterfront living, privacy, beautiful southwest light and exceptional convenience. Gracious rooms, period details and quality craftsmanship give the home wonderful character, while its generous layout offers an

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Lakeview Terrace, Winchester, MA 01890
  • /35

    $1,375,000

    Sold Jan 23, 2026

    32 Oak St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,652 Sq Ft
    • Built 1963

    Last Sold Summary

    • 2% Above List Price
    • $518/SF
    • 6 Days On Market

    Current Estimated Value $1,367,838

    Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

    32 Oak St, Winchester, MA 01890
    • /37

      Est $902,763

      Not Listed For Sale

      47 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1985
      47 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /42

    $1,050,000

    $49K PRICE DROP Pending
    • 3 Beds
    • 1.5 Baths
    • 1,711 Sq Ft

    150 Cambridge St, Winchester, MA 01890

    Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for

    Diane Plunkett Plunkett Properties

    150 Cambridge St, Winchester, MA 01890
  • /22

    $2,400,000

    Sold Dec 18, 2025

    19 Laurel Hill Ln, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 3,700 Sq Ft
    • Built 1954

    Last Sold Summary

    • 4% Below List Price
    • $649/SF
    • 3 Days On Market

    Current Estimated Value $1,959,855

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    19 Laurel Hill Ln, Winchester, MA 01890
    • /42

      Est $921,607

      Not Listed For Sale

      25 Henry St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 3,890 Sq Ft
      • Built 2021
      25 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Karima Alami Compass

  • /37

    $1,295,000

    Open Fri 4PM - 6PM
    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft

    7 Wainwright Rd Unit 47, Winchester, MA 01890

    This Ledges "A" Style townhouse condo offers extensive single floor living with a spacious first floor primary suite as well as a separate second floor suite and loft area. The main bedroom is truly vast. The first floor den can be used as a third bedroom. The home is move-in ready with all new oak hardwood floors throughout the finished areas! Entirely freshly painted in Moore's attractive

    Felicity Tuttle Better Homes and Gardens Real Estate - The Shanahan Group

    7 Wainwright Rd Unit 47, Winchester, MA 01890
  • /42

    $2,450,000

    Sold Dec 16, 2025

    30 Prospect St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,519 Sq Ft
    • Built 1934

    Last Sold Summary

    • 17% Above List Price
    • $973/SF
    • 3 Days On Market

    Current Estimated Value $2,245,337

    Last Listing Agent Karima Alami Compass

    30 Prospect St, Winchester, MA 01890
    • /26

      Est $856,301

      Not Listed For Sale

      28 Henry St, Winchester, MA 01890

      • 2 Beds
      • 1 Bath
      • 1,279 Sq Ft
      • Built 1942
      28 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Alison Socha Leading Edge Real Estate

  • /36

    $2,100,000

    Open Sat 1:30PM - 2:30PM $100K PRICE INCREASE
    • 6 Beds
    • 5 Baths
    • 3,403 Sq Ft

    6 Ivy Cir, Winchester, MA 01890

    Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

    Valerie Post Engel & Volkers Boston

    6 Ivy Cir, Winchester, MA 01890
  • /4

    $700,000

    Sold Apr 28, 2026

    20 Charles Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,317 Sq Ft
    • Built 1962

    Last Sold Summary

    • 8% Above List Price
    • $532/SF
    • 8 Days On Market

    Current Estimated Value $692,080

    Last Listing Agent Wei Wenny Fu Phoenix Real Estate

    20 Charles Rd, Winchester, MA 01890
    • /42

      Est $1,498,166

      Not Listed For Sale

      14 Henry St, Winchester, MA 01890

      • 6 Beds
      • 3 Baths
      • 3,091 Sq Ft
      • Built 1957
      14 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

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

  • /40

    $1,299,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 3,307 Sq Ft

    253 Pond St, Winchester, MA 01890

    Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen

    Pirani & Wile Group Gibson Sotheby's International Realty

    253 Pond St, Winchester, MA 01890
  • /39

    $1,310,000

    Sold Jun 30, 2026

    12 Hancock St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 2,030 Sq Ft
    • Built 1907

    Last Sold Summary

    • 1% Above List Price
    • $645/SF
    • 6 Days On Market

    Current Estimated Value $1,293,171

    Last Listing Agent Elena Langlois Compass

    12 Hancock St, Winchester, MA 01890
    • /37

      Est $1,413,403

      Not Listed For Sale

      26 Ridge St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,388 Sq Ft
      • Built 1963
      26 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Dream Team Dreamega International Realty LLC

  • /25

    $2,249,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 4,368 Sq Ft

    11 Locke St, Winchester, MA 01890

    Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by

    Lesley Smith Barrett Sotheby's International Realty

    11 Locke St, Winchester, MA 01890
  • /37

    $665,000

    Sold Nov 14, 2025

    7 Conant Rd Unit 20, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • Built 2000

    Last Sold Summary

    • 8% Below List Price
    • $569/SF
    • 124 Days On Market

    Current Estimated Value $689,650

    Last Listing Agent Brian Woods Woods Properties Inc.

    7 Conant Rd Unit 20, Winchester, MA 01890
    • /40

      Est $2,363,468

      Not Listed For Sale

      280 High St, Winchester, MA 01890

      • 6 Beds
      • 5 Baths
      • 6,259 Sq Ft
      • Built 1976
      280 High St, Winchester, MA 01890

      Last Sold Summary

      • 136 Days On Market

      Last Listing Agent Anthony Marino The Marino Group Collection

  • /41

    $769,000

    Open Sat 10AM - 12PM
    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    666 Main St Unit 310, Winchester, MA 01890

    Don't miss this beautifully appointed 2-bedroom, 2 bath unit at Wedgewood Place, a waterfront condominium community that is centrally located in downtown Winchester. Magnificent new kitchen with custom cabinets, quartz counter tops and stainless-steel appliances that looks out at a bright and sunny, spacious open living and dining room and small home office area. Featuring a wood burning

    Darryl Brian RE/MAX Bentley's

    666 Main St Unit 310, Winchester, MA 01890
  • /42

    $4,450,000

    Sold Oct 24, 2025

    20 Foxcroft Rd, Winchester, MA 01890

    • 5 Beds
    • 7 Baths
    • 7,679 Sq Ft
    • Built 1937

    Last Sold Summary

    • 1% Above List Price
    • $580/SF
    • 1 Day On Market

    Current Estimated Value $4,611,547

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

    20 Foxcroft Rd, Winchester, MA 01890
    • /33

      Est $1,714,714

      Not Listed For Sale

      34 Coolidge Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,338 Sq Ft
      • Built 1980
      34 Coolidge Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Pauline Marino Coldwell Banker Realty - Lexington

  • /42

    $1,350,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,573 Sq Ft

    36 Elmwood Ave Unit 11, Winchester, MA 01890

    Introducing 36 Elmwood Avenue, Unit 11 - a penthouse residence at Allegro with Winchester Center's shops, restaurants & commuter rail right outside your door. Built in 2021, this 2 bedroom / 2.5 bath home w/ 2 GARAGE PARKING SPACES offers 1,573 sqft and the best layout in the building. Loads of upgrades throughout! The open living, dining & kitchen area is bright and great for entertaining, with

    The Rasner Group Keller Williams Realty Boston-Metro | Back Bay

    36 Elmwood Ave Unit 11, Winchester, MA 01890
  • /2

    $2,025,000

    Sold Jul 09, 2026

    36 Cambridge St, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 3,956 Sq Ft
    • Built 2026

    Last Sold Summary

    • 1% Above List Price
    • $512/SF
    • 5 Days On Market

    Current Estimated Value $1,178,362

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    36 Cambridge St, Winchester, MA 01890
    • /41

      Est $1,932,103

      Not Listed For Sale

      31 Coolidge Rd, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,650 Sq Ft
      • Built 1980
      31 Coolidge Rd, Winchester, MA 01890

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /24

    $799,000

    $50K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    15 Clark St Unit 15, Winchester, MA 01890

    Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated

    Jeffrey Hsu Coldwell Banker Realty - Milton

    15 Clark St Unit 15, 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
    • /42

      Est $2,090,287

      Not Listed For Sale

      23 Olde Village Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 4,997 Sq Ft
      • Built 1975
      23 Olde Village Dr, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /36

    $619,000

    Pending
    • 3 Beds
    • 4 Baths
    • 1,225 Sq Ft

    23 Shepard Ct Unit U23, Winchester, MA 01890

    Great opportunity to live on a quiet side street conveniently located near the town center and Elizabeth C. McDonald Field, featuring tennis courts, ball fields, basketball courts, and a playground. This well-maintained 3-bedroom, 3.5-bath townhouse offers 1,225 sq. ft. of comfortable living space. The charming home features high ceilings and a functional multi-level layout with a bright living

    Ning Sun United Real Estate, LLC

    23 Shepard Ct Unit U23, Winchester, MA 01890

Showing Results 161 - 200, Page 5 of 18

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