284

Recently Sold Winchester, MA Homes

Section Image
  • /35

    $1,100,000 Sold Jun 27, 2025

    • 3,157 Sq Ft
    • $348/SF
    • 20 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1866

    63 Church St, Winchester, MA 01890

    Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

    Nancy McLaughlin Redfin Corp.

    63 Church St, Winchester, MA 01890
  • /25

    $715,000 Sold Jun 27, 2025

    • 1,539 Sq Ft
    • $465/SF
    • 33 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1999

    7 Conant Rd Unit 37, Winchester, MA 01890

    Welcome to this beautifully updated corner unit townhouse-style condo, offering ample-sized rooms, abundant natural light, & hardwood floors throughout! The layout includes 5 well proportioned rooms. Kitchen, living room w/gas fireplace w/marble surround, dining room & 2.5 bathrooms, creating a comfortable & functional living space. Both bedrooms are en-suite, providing privacy & convenience,

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Conant Rd Unit 37, Winchester, MA 01890
  • /42

    $1,350,000 Sold Jun 27, 2025

    • 2,141 Sq Ft
    • $631/SF
    • 40 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1880

    117 Mount Vernon St, Winchester, MA 01890

    Available for the first time in over four decades and nestled just footsteps from Winchester Center, welcome to 117 Mount Vernon Street! As you enter, you are greeted by tall ceilings adorned with beautiful molding and a flood of natural light that fills the space with warmth and tranquility. The home offers three spacious bedrooms, including a flexible primary suite that boasts an adjoining

    Philip Vita Compass

    117 Mount Vernon St, Winchester, MA 01890
  • /9

    $2,899,000 Sold Jun 27, 2025

    • 5,658 Sq Ft
    • $512/SF
    • 25 Days On Market
    • 6 Beds
    • 7.5 Baths
    • Built 2025

    5 Clearwater Rd, Winchester, MA 01890

    Welcome to a rare opportunity to select the final finishes in your dream home right within Winchester’s most coveted neighborhoods. 5 Clearwater presents a luxurious canvas for your vision, offering 6 bedrooms, 7.5 baths, and 5,658 sq. ft. of meticulously planned living space. The spectacular floor plan seamlessly combines modern sophistication with timeless elegance, offering the perfect

    Monte Marrocco Coldwell Banker Realty - Lexington

    5 Clearwater Rd, Winchester, MA 01890
  • /22

    $4,200,000 Sold Jun 26, 2025

    • 5,208 Sq Ft
    • $806/SF
    • 4 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2025

    3 Foxcroft Rd, Winchester, MA 01890

    Nearing completion! Welcome to this exquisite 6-bedroom, 5-1/2 bath residence nestled in one of Winchesters most prestigious neighborhoods. This completely rebuilt, expanded & tastefully renovated home is one of a kind, offering a perfect blend of elegance & modern sophistication for a lifestyle of luxury & comfort. Step inside to discover a beautifully designed interior that exudes charm & style

    Kim Covino Compass

    3 Foxcroft Rd, Winchester, MA 01890
  • /19

    $3,450,000 Sold Jun 26, 2025

    • 5,500 Sq Ft
    • $627/SF
    • 54 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 2025

    2 Chestnut St, Winchester, MA 01890

    Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering

    Mark Donnellan Advisors Living - Winchester

    2 Chestnut St, Winchester, MA 01890
  • /39

    $1,425,000 Sold Jun 25, 2025

    • 2,496 Sq Ft
    • $571/SF
    • 6 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1957

    9 Thornberry Rd, Winchester, MA 01890

    Nestled on a picturesque lot with lush landscaping and mature trees, 9 Thornberry Road offers a perfect blend of natural beauty and refined living. Sunlight pours into this thoughtfully designed home, featuring an open-concept layout ideal for comfortable living and entertaining. The main level includes a welcoming fireplace, hardwood floors, large living room, dining area, and an updated kitchen

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

    9 Thornberry Rd, Winchester, MA 01890
  • /34

    $2,450,000 Sold Jun 24, 2025

    • 5,218 Sq Ft
    • $470/SF
    • 19 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    31 Lawson Rd, Winchester, MA 01890

    Welcome to this gracious Colonial, seamlessly blending traditional charm with modern amenities, perfect for today’s lifestyle. Located in one of Winchester’s most desirable neighborhoods, you’ll enjoy easy access to top-rated schools, the commuter rail, and downtown. This home showcases deep moldings along w/ a stunning kitchen that naturally flows into the living/dining area & family room,

    Monte Marrocco Coldwell Banker Realty - Lexington

    31 Lawson Rd, Winchester, MA 01890
  • /39

    $904,000 Sold Jun 23, 2025

    • 1,528 Sq Ft
    • $592/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1954

    703 Washington St, Winchester, MA 01890

    Delightful ranch, well maintained and located conveniently near the major routes. The kitchen is spacious and opens to the comfortable dining area with large built in hutch. It has been updated and features a tile backsplash, stainless steel appliances and recessed lighting. The living room is fireplaced and is nicely appointed with hardwood floors. Easy one level living with two first floor

    Michael Barrett Barrett, Chris. J., REALTORS®

    703 Washington St, Winchester, MA 01890
  • /16

    $650,000 Sold Jun 23, 2025

    • 1,007 Sq Ft
    • $645/SF
    • 7 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1900

    27 Elm St, Winchester, MA 01890

    Attention investors, contractors, and handy owner occupants looking to build sweat equity! This single family home is in need of major renovation and is the perfect opportunity for a contractor to make a profitable investment or an owner occupant to unlock instant sweat equity. Dream location just around the corner to Winchester Center's shops and restaurants, less than 0.3 miles to the top rated

    Shao Realty Group RE/MAX Executive Realty

    27 Elm St, Winchester, MA 01890
  • /42

    $1,890,000 Sold Jun 23, 2025

    • 3,148 Sq Ft
    • $600/SF
    • 5 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1993

    15 Kendall St, Winchester, MA 01890

    Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lot with slider to patio & expansive rear yard, this captivating home has an absolutely beautiful setting w/natural stone walls, raised planting beds w/flowering trees, perennials & a spectacular rose garden! Enjoy the lovely farmers porch & desirable layout w/sun-drenched kitchen

    Kim Covino Compass

    15 Kendall St, Winchester, MA 01890
  • /42

    $2,950,000 Sold Jun 23, 2025

    • 4,279 Sq Ft
    • $689/SF
    • 23 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1914

    51 Wedgemere Ave, Winchester, MA 01890

    Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-placed foyer welcomes you into the home, enhanced by a new chefs kitchen w/ 10' island, custom cabinetry, & adjacent family room overlooking yard. With four floors of beautifully finished spaces, there's room for every lifestyle need. Enjoy

    Kim Covino Compass

    51 Wedgemere Ave, Winchester, MA 01890
  • /15

    $930,000 Sold Jun 20, 2025

    • 2,333 Sq Ft
    • $399/SF
    • 25 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1959

    48 Tremont St, Winchester, MA 01890

    Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living

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

    48 Tremont St, Winchester, MA 01890
  • /42

    $1,187,000 Sold Jun 18, 2025

    • 1,906 Sq Ft
    • $623/SF
    • 12 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1926

    44 Forest St, Winchester, MA 01890

    This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living

    Kim Covino Compass

    44 Forest St, Winchester, MA 01890
  • /35

    $1,750,000 Sold Jun 17, 2025

    • 2,597 Sq Ft
    • $674/SF
    • 2 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1925

    18 Englewood Rd, Winchester, MA 01890

    OFFER ACCEPTED - Open Houses CANCELED This stunning, sun-filled home welcomes you with a front porch facing southwest for sunset views! Move right in and enjoy so many updates - new windows, new kitchen, new shared bath, new heating and cooling systems, new exercise/mudroom, new landscaping and so much more!!! With fabulous detail and a focus on energy efficiency, this home will win your heart

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    18 Englewood Rd, Winchester, MA 01890
  • /42

    $2,350,000 Sold Jun 16, 2025

    • 4,212 Sq Ft
    • $558/SF
    • 15 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1880

    19 Yale St, Winchester, MA 01890

    Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom

    Nancy Pallotta Advisors Living - Winchester

    19 Yale St, Winchester, MA 01890
  • /36

    $749,900 Sold Jun 13, 2025

    • 1,545 Sq Ft
    • $485/SF
    • 8 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1999

    7 Conant Rd Unit 34, Winchester, MA 01890

    Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of

    Melanie Lentini Leading Edge Real Estate

    7 Conant Rd Unit 34, Winchester, MA 01890
  • /40

    $3,025,000 Sold Jun 13, 2025

    • 5,198 Sq Ft
    • $582/SF
    • 50 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1910

    21 Sheffield W, Winchester, MA 01890

    Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

    Kim Covino Compass

    21 Sheffield W, Winchester, MA 01890
  • /37

    $1,535,000 Sold Jun 12, 2025

    • 2,525 Sq Ft
    • $608/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1965

    65 Thornberry Rd, Winchester, MA 01890

    Beautifully updated 4-bed, 2.5-bath ranch on a landscaped half-acre lot with attached 2-car garage. Enjoy single-level living with an open floor plan, cathedral-ceiling kitchen with granite counters, island seating, and stainless appliances. Living and dining areas flow seamlessly; cozy family room with fireplace. Sunroom with wall of windows overlooks the expansive backyard. Primary suite

    Hongmei Wang HMW Real Estate, LLC

    65 Thornberry Rd, Winchester, MA 01890
  • /40

    $1,510,000 Sold Jun 09, 2025

    • 3,406 Sq Ft
    • $443/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1959

    7 Hutchinson Rd, Winchester, MA 01890

    A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l

    Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
  • /23

    $1,182,000 Sold Jun 09, 2025

    • 1,520 Sq Ft
    • $778/SF
    • 24 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1929

    10 Allen Rd, Winchester, MA 01890

    Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the

    Sally Baldwin Coldwell Banker Realty - Lexington

    10 Allen Rd, Winchester, MA 01890
  • /41

    $2,850,000 Sold Jun 09, 2025

    • 4,325 Sq Ft
    • $659/SF
    • 8 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1953

    45 Brooks St, Winchester, MA 01890

    Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4BD 4 BA home offering a classic exterior with a stunning "must see" interior; featuring formal spaces great for entertaining blended w/casual living areas both inside & out w/ walls of floor to ceiling windows capturing the elements of

    Kim Covino Compass

    45 Brooks St, Winchester, MA 01890
  • /19

    $690,000 Sold Jun 06, 2025

    • 1,634 Sq Ft
    • $422/SF
    • 20 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1999

    7 Conant Rd Unit 60, Winchester, MA 01890

    OPEN HOUSE Sunday, May 18: 1-3:30PM. Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and

    Irene Novia Loka Matahari Real Estate LLC

    7 Conant Rd Unit 60, Winchester, MA 01890
  • /33

    $1,650,000 Sold Jun 06, 2025

    • 3,338 Sq Ft
    • $494/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1980

    34 Coolidge Rd, Winchester, MA 01890

    A chance to update and create your personal design that is located in Winchester's sought after Vinson Owen School district. Set on a impressive massive manicured corner lot that has been maintained since it has been custom built by its original owners. Scenic backyard with a patio off the kitchen that spills on a large private backyard that has an inground pool. Set the stage with a large foyer

    Pauline Marino Coldwell Banker Realty - Lexington

    34 Coolidge Rd, Winchester, MA 01890
  • /38

    $1,475,000 Sold Jun 05, 2025

    • 2,897 Sq Ft
    • $509/SF
    • 15 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1934

    195 Mystic Valley Pkwy, Winchester, MA 01890

    Lovely brick home just up the road from EVERYTHING!!! Commuter Rail, Library, Schools, Shopping, Restaurants, Town Hall. Less than 9 miles to Boston! So close to the Middlesex Fells and the Tri-Community Greenway. Location, location, location - CHECK! Now the structure...classic brick home built to stand the test of time with BIG IMPROVEMENTS. Grand front to back living room with fireplace leads

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    195 Mystic Valley Pkwy, Winchester, MA 01890
  • /42

    $2,111,000 Sold Jun 05, 2025

    • 4,744 Sq Ft
    • $445/SF
    • 6 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1922

    14 Grove St, Winchester, MA 01890

    Located just outside the town center near Brooks neighborhood & the train to Boston! This spacious home has it all! Situated on a lovely level lot w/ 2 car garage & private yard, this updated move in ready home boasts an abundance of space w/ideal layout & large sun drenched eat in kitchen with skylights & bay window, adjacent family room, living room w/ fplc, formal dining, office, laundry & 2

    Kim Covino Compass

    14 Grove St, Winchester, MA 01890
  • /11

    $1,269,000 Sold Jun 04, 2025

    • 2,136 Sq Ft
    • $594/SF
    • 1 Day On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2025

    158 Swanton St Unit 160, Winchester, MA 01890

    Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

    Monte Marrocco Coldwell Banker Realty - Lexington

    158 Swanton St Unit 160, Winchester, MA 01890
  • /24

    $1,084,000 Sold Jun 04, 2025

    • 2,290 Sq Ft
    • $473/SF
    • 30 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2025

    160 Swanton St Unit 160, Winchester, MA 01890

    Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

    Monte Marrocco Coldwell Banker Realty - Lexington

    160 Swanton St Unit 160, Winchester, MA 01890
  • /26

    $1,140,000 Sold Jun 03, 2025

    • 1,646 Sq Ft
    • $693/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1955

    7 Indian Hill Rd, Winchester, MA 01890

    This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood floors, a gas fireplace, and arched doorways add character and warmth to the space. The well-equipped kitchen features granite countertops, glass-front cabinetry and access to a side deck for al fresco dining. Three bright bedrooms and a

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

    7 Indian Hill Rd, Winchester, MA 01890
  • /34

    $2,000,000 Sold Jun 02, 2025

    • 3,039 Sq Ft
    • $658/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1927

    11 Chesterford Rd E, Winchester, MA 01890

    Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly

    Joseph Pollack Redfin Corp.

    11 Chesterford Rd E, Winchester, MA 01890
  • /33

    $699,900 Sold May 30, 2025

    • 1,326 Sq Ft
    • $528/SF
    • 4 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1890

    32 Clark St, Winchester, MA 01890

    A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

    Rodrigo Serrano Leading Edge Real Estate

    32 Clark St, Winchester, MA 01890
  • /42

    $1,350,000 Sold May 30, 2025

    • 3,351 Sq Ft
    • $403/SF
    • 38 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1946

    34 Fells Rd, Winchester, MA 01890

    Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

    Andersen Group Realty Keller Williams Realty Boston Northwest

    34 Fells Rd, Winchester, MA 01890
  • /37

    $1,450,000 Sold May 30, 2025

    • 3,763 Sq Ft
    • $385/SF
    • 34 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1988

    7 Wainwright Rd Unit 8, Winchester, MA 01890

    Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large

    Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

    7 Wainwright Rd Unit 8, Winchester, MA 01890
  • /25

    $1,881,900 Sold May 30, 2025

    • 3,488 Sq Ft
    • $540/SF
    • 34 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1980

    4 Olde Lyme Rd, Winchester, MA 01890

    This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace and an open-concept design, this spacious home is bathed in natural beauty. The gourmet kitchen is pristine and boasts high-end appliances, quartz countertops, a prep sink and secondary dishwasher, and a large island—ideal for

    Nancy Pallotta Advisors Living - Winchester

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

    $1,558,000 Sold May 29, 2025

    • 2,792 Sq Ft
    • $558/SF
    • 9 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1993

    24 Eugene Dr, Winchester, MA 01890

    Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layout plus amenities like central air, 1st floor laundry room, direct indoor access to a 2-car garage, and delightful wooded back yard are more outstanding details. The kitchen & family room at the back of the house will be everyone’s favorite gathering spot. The eat-in kitchen

    Andrea O'Reilly Keller Williams Realty Evolution

    24 Eugene Dr, Winchester, MA 01890
  • /31

    $948,000 Sold May 29, 2025

    • 1,469 Sq Ft
    • $645/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1928

    79 Sylvester Ave, Winchester, MA 01890

    Discover where form meets function in this beautifully maintained home, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a quintessential location. Thoughtfully updated, the kitchen, exterior, and bedrooms reflect pride of ownership, showcasing care and attention

    Anne Spry Barrett Sotheby's International Realty

    79 Sylvester Ave, Winchester, MA 01890
  • /31

    $380,000 Sold May 23, 2025

    • 613 Sq Ft
    • $620/SF
    • 15 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1966

    200 Swanton St Unit 722, Winchester, MA 01890

    Top-Floor Penthouse Condo with Scenic Views at Parkview Condominiums Move right into this beautifully updated 1-bedroom, 1-bath top-floor unit at the highly desirable Parkview Condominiums in Winchester. Centrally located on the 7th floor, this penthouse offers stunning treetop and pond views from your private balcony—perfect for enjoying peaceful moments all year round. Inside, you'll find a

    Yang Liu Weston Realty LLC

    200 Swanton St Unit 722, Winchester, MA 01890
  • /33

    $1,785,000 Sold May 22, 2025

    • 2,848 Sq Ft
    • $627/SF
    • 13 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1968

    85 Thornberry Rd, Winchester, MA 01890

    Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,000 sqft lot with professional landscaping. The living room features a charming wood-burning fireplace, while the sun-filled formal dining room is centered with an elegant chandelier. The kitchen has granite countertops, stainless steel appliances, and an adjacent eat-in area

    Diane Basemera Coldwell Banker Realty - Newton

    85 Thornberry Rd, Winchester, MA 01890
  • /42

    $2,750,000 Sold May 19, 2025

    • 5,263 Sq Ft
    • $523/SF
    • 12 Days On Market
    • 6 Beds
    • 6 Baths
    • Built 1920

    35 Lawson Rd, Winchester, MA 01890

    Welcome 35 Lawson where elegance meets modern luxury in this exquisite 6-bedroom 4F, 2H bathroom residence. A stunning marble mudroom welcomes you into the home w/ heated floors leading into fabulous new custom kitchen featuring a large dining island, inset cabinets, Wolf/Sub-Zero appliances (2 dishwashers, 2 ovens/ steam oven, 2 fridge drawers) a sleek gas fireplace, built-in banquette & direct

    Kim Covino Compass

    35 Lawson Rd, Winchester, MA 01890
  • /42

    $2,499,000 Sold May 19, 2025

    • 4,270 Sq Ft
    • $585/SF
    • 0 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2024

    50 Winford Way, Winchester, MA 01890

    Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace, open dining leads to sitting room & out to a deck

    Kim Covino Compass

    50 Winford Way, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 8

Frequently Asked Questions

What is the average home price in Winchester, MA?
Homes for sale in Winchester, MA have an average home price of $1,814,418.
What is the average time to sell a house in Winchester, MA?
The houses for sale in Winchester, MA spend an average of 23 days on the market.
What is the number of active homes for sale in Winchester, MA?
There are 50 active homes for sale in Winchester, MA.
How many homes have sold over the last 12 months in Winchester, MA?
225 homes have sold in Winchester, MA over the last 12 months.

Home Trends in Winchester, MA

Housing Trends

Median Sale Price
$1,558,000
Median Single Family Sale Price
$1,910,000
Median Townhouse Sale Price
$1,330,000
Median 2 Bedroom Sale Price
$719,999
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$550
Number of Homes for Sale
50
Last 12 months Home Sales
225
Months of Supply
2.70
Median List Price
$1,599,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
How to Buy a Home How to Sell a Home How to Rent a Home