9,198

Winchester, MA Homes

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  • 258 Cross St, Winchester, MA 01890
    258 Cross St, Winchester, MA 01890
    258 Cross St, Winchester, MA 01890
    /39

    $999,900

    • 4 Beds
    • 2 Baths
    • 1,719 Sq Ft

    258 Cross St, Winchester, MA 01890

    A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth,

    Agent Photo

    Justin Blankenship

    Fiv Realty Co

    258 Cross St, Winchester, MA 01890
  • 200 Swanton St Unit 412, Winchester, MA 01890
    200 Swanton St Unit 412, Winchester, MA 01890
    200 Swanton St Unit 412, Winchester, MA 01890
    /7

    $2,100 Per Month

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 412, Winchester, MA 01890

    All utilities includes in the rent. Well-maintained 1-bedroom, 1-bathroom condo in the highly desirable Winchester Parkview community. Offering comfortable living at an affordable price, this inviting home is located in a professionally managed building with excellent amenities, including elevator service, on-site management, and an in-ground swimming pool. The HOA fee covers heat, AC, hot water,

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    200 Swanton St Unit 412, Winchester, MA 01890
  • 15 Edward Dr Unit 15, Winchester, MA 01890
    15 Edward Dr Unit 15, Winchester, MA 01890
    15 Edward Dr Unit 15, Winchester, MA 01890
    /42

    $1,055,000

    Sold May 15, 2026

    15 Edward Dr Unit 15, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,082 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Above List Price
    • $507/SF
    • 5 Days On Market

    Last Listing Agent Alina Wang Coldwell Banker Realty - Lexington

    15 Edward Dr Unit 15, Winchester, MA 01890
    • 25 Wedgemere Ave, Winchester, MA 01890
      25 Wedgemere Ave, Winchester, MA 01890
      25 Wedgemere Ave, Winchester, MA 01890
      /42

      Est $4,012,902

      Not Listed For Sale

      25 Wedgemere Ave, Winchester, MA 01890

      • 7 Beds
      • 8 Baths
      • 7,587 Sq Ft
      • Built 2010
      25 Wedgemere Ave, Winchester, MA 01890

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Prestige Homes Realty Team Prestige Homes Real Estate, LLC

  • 200 Swanton St Unit 303, Winchester, MA 01890
    200 Swanton St Unit 303, Winchester, MA 01890
    200 Swanton St Unit 303, Winchester, MA 01890
    /19

    $499,999

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 822 Sq Ft

    200 Swanton St Unit 303, Winchester, MA 01890

    Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and

    Agent Photo

    Joan Powell

    REMAX Andrew Realty Services

    200 Swanton St Unit 303, Winchester, MA 01890
  • 416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    /20

    Starting at $2,620 Plus Fees

    • Studio - 3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West is crafted to elevate every moment of your day—from morning workouts in the fully equipped fitness center to productive afternoons in private work-from-home pods and inviting gathering spaces. Whether you're entertaining in the chef-inspired kitchen and lounge, relaxing by the fire with neighbors, or enjoying the convenience of Whole Foods and local shops just

    Sanctuary Winchester West

    416 Cambridge St, Winchester, MA 01890
  • 12 Thornberry Rd, Winchester, MA 01890
    12 Thornberry Rd, Winchester, MA 01890
    12 Thornberry Rd, Winchester, MA 01890
    /31

    $1,240,000

    Sold Apr 27, 2026

    12 Thornberry Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 2,087 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Above List Price
    • $594/SF
    • 6 Days On Market

    Current Estimated Value $1,238,250

    Last Listing Agent Kim Covino Compass

    12 Thornberry Rd, Winchester, MA 01890
    • 38 Winthrop Street Extension, Winchester, MA 01890
      38 Winthrop Street Extension, Winchester, MA 01890
      38 Winthrop Street Extension, Winchester, MA 01890
      /39

      Est $2,348,551

      Not Listed For Sale

      38 Winthrop Street Extension, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 4,539 Sq Ft
      • Built 2020
      38 Winthrop Street Extension, Winchester, MA 01890

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Ryan Wilson Keller Williams Realty

  • 15 Fieldstone Dr, Winchester, MA 01890
    15 Fieldstone Dr, Winchester, MA 01890
    15 Fieldstone Dr, Winchester, MA 01890
    /42

    $1,925,000

    $75K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,286 Sq Ft

    15 Fieldstone Dr, Winchester, MA 01890

    Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless

    Anne Spry Barrett Sotheby's International Realty

    15 Fieldstone Dr, Winchester, MA 01890
  • 63 Holland St Unit 63, Winchester, MA 01890
    63 Holland St Unit 63, Winchester, MA 01890
    63 Holland St Unit 63, Winchester, MA 01890
    /9

    $3,500 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    63 Holland St Unit 63, Winchester, MA 01890

    Welcome to 63 Holland St in Winchester! This beautifully renovated 2-bedroom, 1-bath townhome offers the perfect blend of classic charm and modern updates, featuring hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom showcases a walk-in tiled shower with a custom glass

    Agent Photo

    Issam Dib

    Skyline Realty

    63 Holland St Unit 63, Winchester, MA 01890
  • 6 Wyman Ct Unit 6, Winchester, MA 01890
    6 Wyman Ct Unit 6, Winchester, MA 01890
    6 Wyman Ct Unit 6, Winchester, MA 01890
    /35

    $1,379,000

    Sold Jan 05, 2026

    6 Wyman Ct Unit 6, Winchester, MA 01890

    • 3 Beds
    • 4.5 Baths
    • 2,722 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $507/SF
    • 15 Days On Market

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    6 Wyman Ct Unit 6, Winchester, MA 01890
    • 897 Main St Unit 1, Winchester, MA 01890
      897 Main St Unit 1, Winchester, MA 01890
      897 Main St Unit 1, Winchester, MA 01890
      /34

      Est $846,698

      Not Listed For Sale

      897 Main St Unit 1, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,584 Sq Ft
      • Built 2014
      897 Main St Unit 1, Winchester, MA 01890

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 46 Clark St, Winchester, MA 01890
    46 Clark St, Winchester, MA 01890
    46 Clark St, Winchester, MA 01890
    /36

    $1,064,000

    $35K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,777 Sq Ft

    46 Clark St, Winchester, MA 01890

    Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as

    Andersen Group Realty Keller Williams Realty Boston Northwest

    46 Clark St, Winchester, MA 01890
  • 25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    /24

    Starting at $2,976 Plus Fees

    • 1 - 3 Beds

    25-35 River St, Winchester, MA 01890

    The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and

    Sanctuary Winchester North

    25-35 River St, Winchester, MA 01890
  • 104 Church St, Winchester, MA 01890
    104 Church St, Winchester, MA 01890
    104 Church St, Winchester, MA 01890
    /42

    $1,255,000

    Sold Jan 07, 2026

    104 Church St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,696 Sq Ft
    • Built 1897

    Last Sold Summary

    • 10% Below List Price
    • $466/SF
    • 46 Days On Market

    Current Estimated Value $1,397,049

    Last Listing Agent Kim Covino Compass

    104 Church St, Winchester, MA 01890
    • 23 Elmwood Ave Unit C, Winchester, MA 01890
      23 Elmwood Ave Unit C, Winchester, MA 01890
      23 Elmwood Ave Unit C, Winchester, MA 01890
      /41

      Est $1,478,334

      Not Listed For Sale

      23 Elmwood Ave Unit C, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,189 Sq Ft
      • Built 2017
      23 Elmwood Ave Unit C, Winchester, MA 01890

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Kim Covino Compass

  • 11 Williams Cir, Winchester, MA 01890
    11 Williams Cir, Winchester, MA 01890
    11 Williams Cir, Winchester, MA 01890
    /39

    $1,150,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,392 Sq Ft

    11 Williams Cir, Winchester, MA 01890

    Classic center-entrance Colonial set on a cul-de-sac with a wonderful sense of flow and everyday function. The main level offers formal living and dining rooms, a spacious front-to-back fireplaced family room with first-floor laundry and half bath, plus a bright kitchen with island, dining area, and direct access to the deck. Upstairs, the primary suite includes a walk-in closet and private bath,

    Anne Spry Barrett Sotheby's International Realty

    11 Williams Cir, Winchester, MA 01890
  • 171 Swanton St, Winchester, MA 01890
    171 Swanton St, Winchester, MA 01890
    171 Swanton St, Winchester, MA 01890
    /13

    $4,550 Plus Fees

    • 3 Beds
    • 2.5 Baths
    • 1,826 Sq Ft
    • Townhouse for Rent

    171 Swanton St, Winchester, MA 01890

    Property Id: 2604314 Welcome home to this rare opportunity to reside in the highly sought after " Village" community in Winchester. This sunny & spacious Townhome boasts of fresh paint, newer floors, updated kitchen with stainless steel appliances, oversized rooms with an abundance of windows perfect for natural light, 2.5 baths one in with primary suite with a walk in closet, washer/dryer

    171 Swanton St, Winchester, MA 01890
  • 200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    /17

    $330,000

    Sold Jul 28, 2026

    200 Swanton St Unit 228, Winchester, MA 01890

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

    Last Sold Summary

    • 17% Below List Price
    • $545/SF
    • 199 Days On Market

    Current Estimated Value $370,419

    Last Listing Agent Joan Powell REMAX Andrew Realty Services

    200 Swanton St Unit 228, Winchester, MA 01890
    • 261 Cambridge St Unit 261 G, Winchester, MA 01890
      261 Cambridge St Unit 261 G, Winchester, MA 01890
      261 Cambridge St Unit 261 G, Winchester, MA 01890
      /28

      Est $1,353,660

      Not Listed For Sale

      261 Cambridge St Unit 261 G, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,705 Sq Ft
      • Built 1885
      261 Cambridge St Unit 261 G, Winchester, MA 01890

      Last Sold Summary

      • 41 Days On Market

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

  • 171 Swanton St Unit 7, Winchester, MA 01890
    171 Swanton St Unit 7, Winchester, MA 01890
    171 Swanton St Unit 7, Winchester, MA 01890
    /30

    $729,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,431 Sq Ft

    171 Swanton St Unit 7, Winchester, MA 01890

    Easy living awaits at The Village, where this well-maintained, freshly painted, townhouse offers a functional layout, desirable amenities, and a convenient Winchester location. The main level features hardwood floors, an oversized living room with gas fireplace, an open dining area, and kitchen with direct access to a private patio overlooking the beautifully landscaped grounds. A half bath and

    Pirani & Wile Group Gibson Sotheby's International Realty

    171 Swanton St Unit 7, Winchester, MA 01890
  • 2 Elmwood Ave Unit 1, Winchester, MA 01890
    2 Elmwood Ave Unit 1, Winchester, MA 01890
    2 Elmwood Ave Unit 1, Winchester, MA 01890
    /7

    $2,050 Plus Fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 1, Winchester, MA 01890

    This nice 1 Bedroom 1 Bath place in the Winchester area is available for Now. Included Features are: Laundry in Basement.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect

    2 Elmwood Ave Unit 1, Winchester, MA 01890
  • 2 Edgewater Place, Winchester, MA 01890

    $2,575,000

    Sold Jun 16, 2026

    2 Edgewater Place, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,945 Sq Ft
    • Built 1959

    Last Sold Summary

    • 8% Below List Price
    • $653/SF
    • 34 Days On Market

    Current Estimated Value $2,624,187

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    2 Edgewater Place, Winchester, MA 01890
    • 6 Vinson Cir, Winchester, MA 01890
      6 Vinson Cir, Winchester, MA 01890
      6 Vinson Cir, Winchester, MA 01890
      /42

      Est $3,598,589

      Not Listed For Sale

      6 Vinson Cir, Winchester, MA 01890

      • 6 Beds
      • 7.5 Baths
      • 7,500 Sq Ft
      • Built 2025
      6 Vinson Cir, Winchester, MA 01890

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Peter Kasseris Serhant

  • 241 Ridge St, Winchester, MA 01890
    241 Ridge St, Winchester, MA 01890
    241 Ridge St, Winchester, MA 01890
    /37

    $1,599,000

    • 4 Beds
    • 4 Baths
    • 2,480 Sq Ft

    241 Ridge St, Winchester, MA 01890

    New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new

    Team Lillian Montalto Lillian Montalto Signature Properties

    241 Ridge St, Winchester, MA 01890
  • 10 Webster St Unit 1, Winchester, MA 01890
    10 Webster St Unit 1, Winchester, MA 01890
    10 Webster St Unit 1, Winchester, MA 01890
    /31

    $3,700

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,967 Sq Ft
    • Condo for Rent

    10 Webster St Unit 1, Winchester, MA 01890

    **NOT A SINGLE FAMILY HOME** Amazing 4 bed 2 bath located within close proximity of Winchester Center! This spacious apartment takes up the first floor and lower level of a 2 family, but it has a single-family feel to it! Inside on the first floor, you'll find hardwood floors throughout, a living room, a dining room, two spacious bedrooms, and a great eat-in kitchen featuring a new dishwasher and

    10 Webster St Unit 1, Winchester, MA 01890
  • 17 Cranston Rd, Winchester, MA 01890
    17 Cranston Rd, Winchester, MA 01890
    17 Cranston Rd, Winchester, MA 01890
    /39

    $1,560,000

    Sold Apr 30, 2026

    17 Cranston Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,578 Sq Ft
    • Built 1950

    Last Sold Summary

    • $605/SF
    • 5 Days On Market

    Current Estimated Value $1,558,066

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    17 Cranston Rd, Winchester, MA 01890
    • 228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      /42

      Est $2,903,722

      Not Listed For Sale

      228 Ridge St, Winchester, MA 01890

      • 5 Beds
      • 5.5 Baths
      • 6,265 Sq Ft
      • Built 2023
      228 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 142 Days On Market

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

  • 18 Ridge St, Winchester, MA 01890
    18 Ridge St, Winchester, MA 01890
    18 Ridge St, Winchester, MA 01890
    /4

    $3,200,000

    • 5 Beds
    • 5.5 Baths
    • 5,295 Sq Ft

    18 Ridge St, Winchester, MA 01890

    Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort.

    Gayle Winters Compass

    18 Ridge St, Winchester, MA 01890
  • 270 Cross St, Winchester, MA 01890
    270 Cross St, Winchester, MA 01890
    270 Cross St, Winchester, MA 01890
    /34

    $6,000

    Total Monthly Price

    • 4 Beds
    • 4 Baths
    • 2,700 Sq Ft
    • House for Rent

    270 Cross St, Winchester, MA 01890

    Winchester Gorgeous SF Home w/ Garage 4 Prkng, Big Deck, YardFully Renovated 4-BR+ 4BA Single-Family Home for Rent in WinchesterThree Levels of Living Space - Spacious and versatile, great home office space for remote work. 4BR, 4BA + bonus room/office + basement level walkout (potential in-law or au-pair suite). 2 Heating Zones (gas) with NEST thermostats. Attached 2-Car Garage +

    270 Cross St, Winchester, MA 01890
  • 7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, Winchester, MA 01890
    /42

    $1,055,000

    Sold Feb 26, 2026

    7 Trinity Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft
    • Built 1963

    Last Sold Summary

    • 11% Below List Price
    • $495/SF
    • 24 Days On Market

    Current Estimated Value $1,191,098

    Last Listing Agent Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
    • 15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      /40

      Est $1,357,776

      Not Listed For Sale

      15 Wincrest Dr, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,529 Sq Ft
      • Built 1957
      15 Wincrest Dr, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kim Covino Compass

  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /40

    $3,179,000

    $200K PRICE DROP
    • 7 Beds
    • 7.5 Baths
    • 8,540 Sq Ft

    37 Mayflower Rd, Winchester, MA 01890

    Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

    Kim Covino Compass

    37 Mayflower Rd, Winchester, MA 01890
  • 219 Washington St Unit 1, Winchester, MA 01890
    219 Washington St Unit 1, Winchester, MA 01890
    219 Washington St Unit 1, Winchester, MA 01890
    /21

    $1,950

    Total Monthly Price

    • Studio
    • 1 Bath
    • 250 Sq Ft
    • Condo for Rent

    219 Washington St Unit 1, Winchester, MA 01890

    Amazing location right in the heart of Winchester! Close walking distance to downtown. - Utilities INCLUDED! - Off-street parking available- Laundry on-site- Close to public transportation

    219 Washington St Unit 1, Winchester, MA 01890
  • 163 Main St, Winchester, MA 01890
    163 Main St, Winchester, MA 01890
    163 Main St, Winchester, MA 01890
    /36

    $1,175,000

    Sold Aug 18, 2025

    163 Main St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,335 Sq Ft
    • Built 1961

    Last Sold Summary

    • 18% Above List Price
    • $503/SF
    • 8 Days On Market

    Current Estimated Value $1,234,591

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    163 Main St, Winchester, MA 01890
    • 10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      /33

      Est $1,459,872

      Not Listed For Sale

      10 Carriage Ln, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,034 Sq Ft
      • Built 1957
      10 Carriage Ln, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Peter Kasseris Serhant

  • 2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    /41

    $3,475,000

    $272K PRICE DROP Pending
    • 7 Beds
    • 6 Baths
    • 7,043 Sq Ft

    2 Everett Ave, Winchester, MA 01890

    Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end

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

    2 Everett Ave, Winchester, MA 01890
  • 161 Highland Ave, Winchester, MA 01890
    161 Highland Ave, Winchester, MA 01890
    161 Highland Ave, Winchester, MA 01890
    /18

    $8,500

    Total Monthly Price

    • 6 Beds
    • 2.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    161 Highland Ave, Winchester, MA 01890

    Beautiful Colonial House in Prime Winchester Location steps from Middlesex Fells ReservationExperience comfort, space, and nature in this stunning 6-bedroom Colonial home in Winchester, MA, available August 1. Perfect for families or professionals seeking a peaceful retreat with convenient access to Boston.Nestled just steps from the Middlesex Fells Reservation (2,575 acres of hiking and

    161 Highland Ave, Winchester, MA 01890
  • 24 Hinds Rd, Winchester, MA 01890
    24 Hinds Rd, Winchester, MA 01890
    24 Hinds Rd, Winchester, MA 01890
    /42

    $1,750,000

    Sold Jul 09, 2026

    24 Hinds Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,814 Sq Ft
    • Built 1955

    Last Sold Summary

    • 3% Below List Price
    • $622/SF
    • 7 Days On Market

    Current Estimated Value $1,747,039

    Last Listing Agent Kim Covino Compass

    24 Hinds Rd, Winchester, MA 01890
    • 9 Thornberry Rd, Winchester, MA 01890
      9 Thornberry Rd, Winchester, MA 01890
      9 Thornberry Rd, Winchester, MA 01890
      /39

      Est $1,377,940

      Not Listed For Sale

      9 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 1957
      9 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

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

Showing Results 1 - 40, Page 1 of 18

Massachusetts Middlesex County

Real Estate & Homes

Home Prices in Winchester, MA

The median home sale price in Winchester, MA is $1,678,500, consistent with the median home sale price year-over-year. Homes in Winchester sell in 20 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$1,678,500
Median Single Family Sale Price
$1,750,000
Median Townhouse Sale Price
$1,412,500
Median 2 Bedroom Sale Price
$940,000
Average Price Per Sq Ft
$565
Number of Homes for Sale
28
Last 12 months Home Sales
181
Months of Supply
1.90
Median List Price
$1,725,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
0%
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