9,206

Winchester, MA Homes

Section Image
    • /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

  • /30

    $1,289,000

    Open Sun 1PM - 3PM $211K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,459 Sq Ft

    110 Thornberry Rd, Winchester, MA 01890

    Key upgrades include 200-amp electrical service, a 2021 Brute natural gas boiler and replacement windows. The updated kitchen features stone counters, stainless appliances and a double oven. On Winchester's West Side, this 3-bedroom, 2.5-bath home offers 2,459 sq. ft., including a finished lower level. Enjoy hardwood floors, two fireplaces, central air and a year-round sunroom.The 0.46-acre

    Mark Kiklis Kiklis Real Estate, LLC

    110 Thornberry Rd, Winchester, MA 01890
  • /32

    $1,475,000

    Sold Apr 29, 2026

    28 Emerson Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 2,344 Sq Ft
    • Built 1952

    Last Sold Summary

    • 9% Above List Price
    • $629/SF
    • 4 Days On Market

    Current Estimated Value $1,466,943

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    28 Emerson Rd, 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

  • /35

    $1,000,000

    Open Sat 11:30AM - 1PM
    • 3 Beds
    • 1 Bath
    • 1,908 Sq Ft

    23 Stone Ave, Winchester, MA 01890

    Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light

    Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

    23 Stone Ave, Winchester, MA 01890
  • /35

    $2,975,000

    Sold Jul 09, 2026

    115 Church St, Winchester, MA 01890

    • 7 Beds
    • 6 Baths
    • 5,888 Sq Ft
    • Built 1888

    Last Sold Summary

    • $505/SF
    • 8 Days On Market

    Current Estimated Value $2,940,994

    Last Listing Agent Jennifer Ryer Better Homes and Gardens Real Estate - The Shanahan Group

    115 Church 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

  • /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
  • /42

    $1,350,000

    Sold Mar 06, 2026

    95 Irving St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,490 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $542/SF
    • 61 Days On Market

    Current Estimated Value $1,352,394

    Last Listing Agent Kim Covino Compass

    95 Irving St, 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

  • /42

    $2,450,000

    Open Sat 12PM - 1:30PM $49K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,450 Sq Ft

    54 Squire Rd, Winchester, MA 01890

    Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with

    Anthony Marino The Marino Group Collection

    54 Squire Rd, Winchester, MA 01890
  • /24

    $2,300,000

    Sold Sep 18, 2026

    53 Winford Way, Winchester, MA 01890

    • 5 Beds
    • 4 Baths
    • 5,083 Sq Ft
    • Built 2025

    Last Sold Summary

    • 18% Below List Price
    • $452/SF
    • 80 Days On Market

    Current Estimated Value $2,348,089

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    53 Winford Way, 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

  • /31

    $1,325,000

    • 4 Beds
    • 2 Baths
    • 1,922 Sq Ft

    9 Priscilla Ln, Winchester, MA 01890

    UNRIVALED ACCESS! PRIVATE VIEWINGS ONLY! Timeless New England charm meets prime Winchester living at 9 Priscilla Lane. Tucked along a quiet, tree-lined neighborhood on Winchester’s East side, this inviting 4-bedroom home offers the perfect balance of suburban tranquility, outdoor adventure, and seamless connectivity.Inside, the sun-drenched home features rich hardwood floors, a gorgeous kitchen,

    Robert Del Greco Compass

    9 Priscilla Ln, Winchester, MA 01890
  • /27

    $1,225,000

    Sold Nov 14, 2025

    10 Winchester Place Unit 301, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,531 Sq Ft
    • Built 2002

    Last Sold Summary

    • 14% Above List Price
    • $800/SF
    • 1 Day On Market

    Current Estimated Value $1,291,593

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    10 Winchester Place Unit 301, 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

  • /28

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 2,666 Sq Ft

    465 Washington St Unit 467, Winchester, MA 01890

    Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is

    Nancy Pallotta Gibson Sotheby's International Realty

    465 Washington St Unit 467, Winchester, MA 01890
  • /41

    $815,000

    Sold Mar 09, 2026

    49 Spruce St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,710 Sq Ft
    • Built 1860

    Last Sold Summary

    • 2% Below List Price
    • $477/SF
    • 16 Days On Market

    Current Estimated Value $843,783

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    49 Spruce St, Winchester, MA 01890
    • /37

      Est $1,401,664

      Not Listed For Sale

      22 Albamont Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,597 Sq Ft
      • Built 1959
      22 Albamont Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /37

    $2,049,000

    • 4 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    26 N Gateway, Winchester, MA 01890

    Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the

    Pirani & Wile Group Gibson Sotheby's International Realty

    26 N Gateway, Winchester, MA 01890
  • /42

    $2,650,000

    Sold Jul 17, 2026

    21 Bellevue Ave, Winchester, MA 01890

    • 5 Beds
    • 4 Baths
    • 5,950 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $445/SF
    • 5 Days On Market

    Current Estimated Value $2,685,014

    Last Listing Agent Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    21 Bellevue Ave, Winchester, MA 01890
    • /31

      Est $1,254,957

      Not Listed For Sale

      23 New Meadows Rd, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 2,321 Sq Ft
      • Built 1941
      23 New Meadows Rd, Winchester, MA 01890

      Last Sold Summary

      • 33 Days On Market

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

  • /2

    $1,080,000

    • 3 Beds
    • 1 Bath
    • 1,382 Sq Ft

    6 Reservoir St, Winchester, MA 01890

    Opportunities and possibilities for builders or handyman!! At 6 Reservoir Street, Winchester, a distinguished single-family residence on an expansive 10818 square foot lot. This property represents a unique opportunity for refined living within a desirable community. The residence encompasses three well-proportioned bedrooms plus walk-up to a generously sized attic and one full bathroom.

    Dongjun Lou HMW Real Estate, LLC

    6 Reservoir St, Winchester, MA 01890
  • /2

    $3,242,250

    Sold Oct 17, 2025

    4 Norwood St, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,250 Sq Ft
    • Built 1870

    Last Sold Summary

    • 5% Below List Price
    • $618/SF
    • 25 Days On Market

    Current Estimated Value $3,098,659

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    4 Norwood St, Winchester, MA 01890
    • /38

      Est $1,787,828

      Not Listed For Sale

      5 Thornton Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,755 Sq Ft
      • Built 1929
      5 Thornton Rd, Winchester, MA 01890

      Last Sold Summary

      • 30 Days On Market

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

  • /40

    $1,050,000

    Open Sat 12:30PM - 1:30PM
    • 5 Beds
    • 2.5 Baths
    • 2,801 Sq Ft

    257 Cross St, Winchester, MA 01890

    Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath,

    Kim Covino Compass

    257 Cross St, Winchester, MA 01890
  • /40

    $1,755,000

    Sold May 01, 2026

    35 Hollywood Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,906 Sq Ft
    • Built 1963

    Last Sold Summary

    • 7% Below List Price
    • $449/SF
    • 14 Days On Market

    Current Estimated Value $1,779,509

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    35 Hollywood Rd, Winchester, MA 01890
    • /36

      Est $1,822,389

      Not Listed For Sale

      21 Westland Ave, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,432 Sq Ft
      • Built 1925
      21 Westland Ave, Winchester, MA 01890

      Last Sold Summary

      • 9 Days On Market

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

  • /36

    $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

    $2,150,000

    Sold Feb 02, 2026

    7 Appalachian Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,263 Sq Ft
    • Built 1927

    Last Sold Summary

    • 8% Above List Price
    • $659/SF
    • 3 Days On Market

    Current Estimated Value $2,122,442

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    7 Appalachian Rd, Winchester, MA 01890
    • /40

      Est $1,834,240

      Not Listed For Sale

      20 Seneca Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,813 Sq Ft
      • Built 1930
      20 Seneca Rd, Winchester, MA 01890

      Last Sold Summary

      • 26 Days On Market

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

  • /33

    $1,110,000

    Open Sun 12PM - 1:30PM $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
  • /10

    $425,000

    Sold Mar 18, 2026

    13 Nelson St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,783 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 66 Days On Market

    Current Estimated Value $473,463

    Last Listing Agent Karen Morand MCO Realty Service, LLC

    13 Nelson St, Winchester, MA 01890
    • /40

      Est $1,834,886

      Not Listed For Sale

      49 Westland Ave, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 3,158 Sq Ft
      • Built 1941
      49 Westland Ave, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Michaela Mahtani Leading Edge Real Estate

  • /42

    $450,000

    Open Sat 11AM - 1PM $65K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 810 Sq Ft

    200 Swanton St Unit T35, Winchester, MA 01890

    BACK ON MARKET DUE TO FINANCING ! PARKVIEW WINCHESTER CONDOMINIUMS! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great

    Nuri Tirana Tirana Real Estate Group

    200 Swanton St Unit T35, Winchester, MA 01890
  • /41

    $1,810,000

    Sold May 18, 2026

    12 Wincrest Dr, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 3,833 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Above List Price
    • $472/SF
    • 5 Days On Market

    Current Estimated Value $1,801,279

    Last Listing Agent Kim Covino Compass

    12 Wincrest Dr, Winchester, MA 01890
    • /42

      Est $2,187,734

      Not Listed For Sale

      43 Emerson Rd, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 4,730 Sq Ft
      • Built 1953
      43 Emerson Rd, Winchester, MA 01890

      Last Sold Summary

      • 12 Days On Market

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

  • /36

    $3,600,000

    Open Sat 12PM - 1PM
    • 7 Beds
    • 7.5 Baths
    • 7,429 Sq Ft

    11 Viking Rd, Winchester, MA 01890

    Spectacular ground-up NEW construction set on an expansive, level lot of 24,688 square foot lot at the end of a quiet Winchester cul-de-sac. Newly completed and ready for immediate occupancy, this exceptional residence offers more than 7,000 square feet of beautifully finished living space, combining impressive scale, refined design, privacy and convenience just moments from Winchester Country

    Valerie Post Engel & Volkers Boston

    11 Viking Rd, Winchester, MA 01890
  • /39

    $960,000

    Sold Apr 06, 2026

    8 Russell Rd Unit 10, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1922

    Last Sold Summary

    • 4% Below List Price
    • $533/SF
    • 17 Days On Market

    Current Estimated Value $992,220

    Last Listing Agent Rajive Dogra Coldwell Banker Realty - Lexington

    8 Russell Rd Unit 10, Winchester, MA 01890
    • /42

      Est $2,655,887

      Not Listed For Sale

      6 Agawam Rd, Winchester, MA 01890

      • 4 Beds
      • 4.5 Baths
      • 5,315 Sq Ft
      • Built 1930
      6 Agawam Rd, Winchester, MA 01890

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Leigh Ventura Compass

Showing Results 241 - 280, Page 7 of 18

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