289

Recently Sold Winchester, MA Homes

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  • 18 Brookside Ave, Winchester, MA 01890
    18 Brookside Ave, Winchester, MA 01890
    18 Brookside Ave, Winchester, MA 01890
    /30

    $1,207,500 Sold Jul 24, 2025

    • 1,573 Sq Ft
    • $768/SF
    • 20 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1910

    18 Brookside Ave, Winchester, MA 01890

    Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to a bright bow front living room w/ high ceilings, that flows into the dining room & beautifully updated kitchen w/ stainless appliances & custom cabinetry w/ generous counter space. Off the kitchen, there’s a half bath and a bonus room—great as an office, playroom, or casual

    Kim Covino Compass

    18 Brookside Ave, Winchester, MA 01890
  • 6 Francis Circuit Unit 6, Winchester, MA 01890
    6 Francis Circuit Unit 6, Winchester, MA 01890
    6 Francis Circuit Unit 6, Winchester, MA 01890
    /39

    $950,000 Sold Jul 17, 2025

    • 1,540 Sq Ft
    • $617/SF
    • 10 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1875

    6 Francis Circuit Unit 6, Winchester, MA 01890

    Submerge yourself in historic elegance in this meticulously detailed Victorian home, brimming with classic design. Located on one of Winchester’s most serene and desirable cul-de-sacs, this stunning gem overflows with rich architectural details. Inside, you'll find three stately fireplaces, two oversized pocket doors, exquisite antique leaded light fixtures, stained glass, gleaming hardwood

    Katherine Waters-Clark Compass

    6 Francis Circuit Unit 6, Winchester, MA 01890
  • 7 Conant Rd Unit 23, Winchester, MA 01890
    7 Conant Rd Unit 23, Winchester, MA 01890
    7 Conant Rd Unit 23, Winchester, MA 01890
    /34

    $680,000 Sold Jul 17, 2025

    • 1,160 Sq Ft
    • $586/SF
    • 18 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2000

    7 Conant Rd Unit 23, Winchester, MA 01890

    Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts’ top-rated school districts. Located in the desirable Lynch Elementary district, which will open a brand-new school building this fall. This move-in ready home has just been freshly painted, with brand-new kitchen appliances and new carpeting throughout. The open-concept living and dining area

    Xin Cui Hooli Homes Boston

    7 Conant Rd Unit 23, Winchester, MA 01890
  • 18 Hemingway St, Winchester, MA 01890
    18 Hemingway St, Winchester, MA 01890
    18 Hemingway St, Winchester, MA 01890
    /32

    $1,280,000 Sold Jul 16, 2025

    • 2,137 Sq Ft
    • $599/SF
    • 21 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2015

    18 Hemingway St, Winchester, MA 01890

    This COMPLETEDLY GUTTED AND REBUILT IN 2015 5B3.5B colonia-preserving a portion of original foundation, is located in a quiet neighborhood yet just minutes to Town Center, Elementary & High School, Town beach, Horn Pond, Fells Reservation, commuter rail station/Bus 134 to Wellington T. The architect-designed home features hardwood flooring throughout, high ceiling & abundant natural light. 1st

    Julia Xie Keller Williams Realty-Merrimack

    18 Hemingway St, Winchester, MA 01890
  • 8 Ware Rd, Winchester, MA 01890
    8 Ware Rd, Winchester, MA 01890
    8 Ware Rd, Winchester, MA 01890
    /25

    $1,226,000 Sold Jul 15, 2025

    • 2,534 Sq Ft
    • $484/SF
    • 6 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1980

    8 Ware Rd, Winchester, MA 01890

    Tucked into the desirable Winchester Highlands and abutting the Middlesex Fells, 8 Ware Road offers space, comfort, and a flexible footprint. This well-maintained ranch features 3 bedrooms on the main level, including a primary suite with full bath, plus a finished basement with a spacious family room, walk-out sliding patio door, large flex space, & bonus 4th bedroom. The kitchen includes modern

    Alex Navarro Coldwell Banker Realty - Beverly

    8 Ware Rd, Winchester, MA 01890
  • 48 Winford Way, Winchester, MA 01890
    48 Winford Way, Winchester, MA 01890
    48 Winford Way, Winchester, MA 01890
    /32

    $1,115,000 Sold Jul 15, 2025

    • 1,978 Sq Ft
    • $564/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1951

    48 Winford Way, Winchester, MA 01890

    Welcome to 48 Winford Way, a three bed, two bath Cape on a lovely level lot with a family room addition and a garage. A perfect starter home or downsizer with a full bath on each floor. Living room with large windows and a fireplace, dining room with an impressive chandelier and built-in china cabinet, eat-in kitchen with quartz countertops, tiled backsplash, and pantry closet. First floor family

    Rebecca Brennan Better Homes and Gardens Real Estate - The Shanahan Group

    48 Winford Way, Winchester, MA 01890
  • 25 Canterbury Rd, Winchester, MA 01890
    25 Canterbury Rd, Winchester, MA 01890
    25 Canterbury Rd, Winchester, MA 01890
    /32

    $1,280,000 Sold Jul 15, 2025

    • 2,349 Sq Ft
    • $545/SF
    • 6 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1948

    25 Canterbury Rd, Winchester, MA 01890

    Don't miss your opportunity to own on Canterbury Road! This sun-drenched, 4-bedroom home with hardwood flooring offers an open and classic layout. Enjoy the spacious living room with built-ins, four, second floor bedrooms, and an expansive .37 acre lot. The versatile family room provides flexible space for a home office, playroom, or guest space! Imagine evenings on the covered porch or patio,

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

    25 Canterbury Rd, Winchester, MA 01890
  • 7 Wainwright Rd Unit 13, Winchester, MA 01890
    7 Wainwright Rd Unit 13, Winchester, MA 01890
    7 Wainwright Rd Unit 13, Winchester, MA 01890
    /40

    $1,551,000 Sold Jul 15, 2025

    • 3,186 Sq Ft
    • $487/SF
    • 5 Days On Market
    • 3 Beds
    • 4.5 Baths
    • Built 1988

    7 Wainwright Rd Unit 13, Winchester, MA 01890

    Welcome to The Ledges, Winchester’s premier townhouse community! This extraordinary F Style corner unit is truly one of a kind with soaring ceilings, sun-filled spaces, and rare flat backyard space with two decks. A landscaped courtyard leads to a gracious foyer and transitions into an expansive open layout. The chef’s kitchen opens to the dining rm and features ss appliances, granite countertops

    Nancy Pallotta Advisors Living - Winchester

    7 Wainwright Rd Unit 13, Winchester, MA 01890
  • 26 Ridge St, Winchester, MA 01890
    26 Ridge St, Winchester, MA 01890
    26 Ridge St, Winchester, MA 01890
    /37

    $1,390,000 Sold Jul 15, 2025

    • 2,388 Sq Ft
    • $582/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1963

    26 Ridge St, Winchester, MA 01890

    Set on a generous, beautifully landscaped lot, this meticulously maintained home showcases numerous recent upgrades, and offers both comfort and style. The newly renovated kitchen features upscale appliances and custom quartz countertops, perfect for everyday living and entertaining alike.Hardwood floors, two fireplaces, a sunlit living room, and a separate family room create inviting spaces

    Dream Team Dreamega International Realty LLC

    26 Ridge St, Winchester, MA 01890
  • 4 Fairfield Place, Winchester, MA 01890
    4 Fairfield Place, Winchester, MA 01890
    4 Fairfield Place, Winchester, MA 01890
    /39

    $2,200,000 Sold Jul 14, 2025

    • 3,896 Sq Ft
    • $565/SF
    • 11 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2016

    4 Fairfield Place, Winchester, MA 01890

    NEWER CONSTRUCTION 4 bed 3.5 bath colonial located in a great neighborhood right outside Winchester center! Enjoy all the area has to offer just outside your door including restaurants, shops, schools, train to Boston, the Tri-Community bike path, Horn Pond, Packer tennis courts & Wedge pond! This warm and welcoming, gently lived in home showcases 3900sf of space on 3 levels with 4 large

    Kim Covino Compass

    4 Fairfield Place, Winchester, MA 01890
  • 19 Sussex Rd, Winchester, MA 01890
    19 Sussex Rd, Winchester, MA 01890
    19 Sussex Rd, Winchester, MA 01890
    /26

    $2,160,000 Sold Jul 14, 2025

    • 4,023 Sq Ft
    • $537/SF
    • 37 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1998

    19 Sussex Rd, Winchester, MA 01890

    Ideally located in a very desirable neighborhood that abuts the town forest and surrounded by cul-de-sacs, this elegant well-designed 4-bedroom, 3.5-bathroom colonial home has been meticulously maintained by the original owners and features a spacious layout with ample room for comfortable living. The floorplan is thoughtfully designed, with a nice flow from one room to the next. The family room

    Ida Bianco Coldwell Banker Realty - Lexington

    19 Sussex Rd, Winchester, MA 01890
  • 20 Fletcher St Unit 20, Winchester, MA 01890
    20 Fletcher St Unit 20, Winchester, MA 01890
    20 Fletcher St Unit 20, Winchester, MA 01890
    /39

    $1,400,000 Sold Jul 14, 2025

    • 2,282 Sq Ft
    • $613/SF
    • 38 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    20 Fletcher St Unit 20, Winchester, MA 01890

    Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication

    Kim Covino Compass

    20 Fletcher St Unit 20, Winchester, MA 01890
  • 17 Harrison St, Winchester, MA 01890
    17 Harrison St, Winchester, MA 01890
    17 Harrison St, Winchester, MA 01890
    /42

    $2,500,000 Sold Jul 14, 2025

    • 3,719 Sq Ft
    • $672/SF
    • 7 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1952

    17 Harrison St, Winchester, MA 01890

    Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized

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

    17 Harrison St, Winchester, MA 01890
  • 35 Rumford St Unit 35, Winchester, MA 01890
    35 Rumford St Unit 35, Winchester, MA 01890
    35 Rumford St Unit 35, Winchester, MA 01890
    /40

    $1,635,000 Sold Jul 11, 2025

    • 2,470 Sq Ft
    • $662/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2012

    35 Rumford St Unit 35, Winchester, MA 01890

    This sun-filled 2012 townhouse, with its spacious layout, backyard oasis & attached garage, lives like a single-family home. Spend weekends lounging on the private deck, unwinding under the pergola, or playing on the lush, fenced lawn. Inside, the inviting open layout is made for gathering—whether around the gas fireplace on cozy evenings or at the kitchen island while entertaining friends. High

    Elena Langlois Compass

    35 Rumford St Unit 35, Winchester, MA 01890
  • 21 Johnson Rd, Winchester, MA 01890
    21 Johnson Rd, Winchester, MA 01890
    21 Johnson Rd, Winchester, MA 01890
    /42

    $1,540,000 Sold Jul 11, 2025

    • 2,814 Sq Ft
    • $547/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1970

    21 Johnson Rd, Winchester, MA 01890

    This lovingly maintained Colonial home is ideally situated just a 1/2 mile from Vinson-Owen Elementary School. Featuring all 4 bedrooms on the second floor, the layout includes a spacious primary w/ an en-suite bath as well as a fully updated hall bath. The main level offers an elegant family room w/ soaring ceilings, a cozy fireplace, recessed lighting & a slider leading to the deck. The

    Stefanie Clifford Keller Williams Realty Boston Northwest

    21 Johnson Rd, Winchester, MA 01890
  • 61 Westland Ave, Winchester, MA 01890
    61 Westland Ave, Winchester, MA 01890
    61 Westland Ave, Winchester, MA 01890
    /16

    $1,050,000 Sold Jul 11, 2025

    • 2,621 Sq Ft
    • $401/SF
    • 48 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1952

    61 Westland Ave, Winchester, MA 01890

    Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    61 Westland Ave, Winchester, MA 01890
  • 5 Hastings Rd, Winchester, MA 01890
    5 Hastings Rd, Winchester, MA 01890
    5 Hastings Rd, Winchester, MA 01890
    /38

    $1,924,000 Sold Jul 10, 2025

    • 4,195 Sq Ft
    • $459/SF
    • 4 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1995

    5 Hastings Rd, Winchester, MA 01890

    Rare opportunity on a peaceful cul-de-sac. This extraordinary 4-bedroom, 4-bathroom home is nestled in one of Winchester's most sought-after neighborhoods. For the first time ever, this meticulously maintained residence is available on a street where properties rarely change hands. Bathed in abundant natural light, the thoughtfully designed floor plan showcases generously sized living spaces that

    Nancy Pallotta Advisors Living - Winchester

    5 Hastings Rd, Winchester, MA 01890
  • 20 Elm St, Winchester, MA 01890
    20 Elm St, Winchester, MA 01890
    20 Elm St, Winchester, MA 01890
    /37

    $2,200,000 Sold Jul 09, 2025

    • 3,901 Sq Ft
    • $564/SF
    • 4 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 2011

    20 Elm St, Winchester, MA 01890

    Nestled in the highly sought-after "heart" of Winchester Center, this Newer Construction single-family (slightly attached) home offers space & finishes you typically find in 2.5M+ homes! With 10' ceilings and high end finishes throughout, this stunning 5-6 bedroom, 3.5 bath home is just two blocks from the vibrant town center, train station, schools, restaurants & shops! 5190 total sf w/ 3900sf

    Kim Covino Compass

    20 Elm 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

    $1,500,000 Sold Jun 30, 2025

    • 2,189 Sq Ft
    • $685/SF
    • 1 Day On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    23 Elmwood Ave Unit C, Winchester, MA 01890

    Welcome to Elmwood condos with over 2,100 SF of stunning single-level luxury living in vibrant downtown Winchester! This sparkling, modern condo offers a beautifully open floor plan designed for today's discerning buyer with the kitchen, dining & living areas seamlessly integrated for both comfort and style. Enjoy high end/ top-of-the-line, rich finishes throughout, including gleaming hardwood

    Kim Covino Compass

    23 Elmwood Ave Unit C, Winchester, MA 01890
  • 1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, Winchester, MA 01890
    /39

    $2,200,000 Sold Jun 30, 2025

    • 3,818 Sq Ft
    • $576/SF
    • 0 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1967

    1 Saint Augustine Ct, Winchester, MA 01890

    Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and gleaming hardwood floors throughout, it strikes the perfect balance between timeless charm and fresh, move-in-ready style. The front-to-back living room is flooded with natural light—ideal for everything from morning coffee to impromptu

    Nancy Pallotta Advisors Living - Winchester

    1 Saint Augustine Ct, Winchester, MA 01890
  • 20 Seneca Rd, Winchester, MA 01890
    20 Seneca Rd, Winchester, MA 01890
    20 Seneca Rd, Winchester, MA 01890
    /40

    $1,877,000 Sold Jun 30, 2025

    • 2,813 Sq Ft
    • $667/SF
    • 26 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    20 Seneca Rd, Winchester, MA 01890

    Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

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

    20 Seneca Rd, Winchester, MA 01890
  • 7 Wainwright Rd Unit 117, Winchester, MA 01890
    7 Wainwright Rd Unit 117, Winchester, MA 01890
    7 Wainwright Rd Unit 117, Winchester, MA 01890
    /41

    $1,500,000 Sold Jun 30, 2025

    • 4,214 Sq Ft
    • $356/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1995

    7 Wainwright Rd Unit 117, Winchester, MA 01890

    Welcome to the largest unit at The Ledges! This stunning F unit boasts soaring ceilings and an expansive open floor plan, perfect for entertaining or relaxing in style. Custom decorated in a perfect, custom Palm Beach vibe, but easy to change if you don't love it. Sunlight floods the large formal living room, with an attached deck, bifurcated by a gas fireplace that leads to the dining room. A

    Nancy Pallotta Advisors Living - Winchester

    7 Wainwright Rd Unit 117, Winchester, MA 01890
  • 80 Harvard St, Winchester, MA 01890
    80 Harvard St, Winchester, MA 01890
    80 Harvard St, Winchester, MA 01890
    /32

    $1,250,000 Sold Jun 30, 2025

    • 2,759 Sq Ft
    • $453/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1973

    80 Harvard St, Winchester, MA 01890

    Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3 bedrooms and a bathroom.

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

    80 Harvard St, Winchester, MA 01890
  • 57 Jefferson Rd, Winchester, MA 01890
    57 Jefferson Rd, Winchester, MA 01890
    57 Jefferson Rd, Winchester, MA 01890
    /42

    $2,359,000 Sold Jun 30, 2025

    • 3,274 Sq Ft
    • $721/SF
    • 8 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1985

    57 Jefferson Rd, Winchester, MA 01890

    Situated on a picturesque corner lot, this exceptional home is nestled in a very desirable neighborhood! Step into a light-filled, open-concept 1st floor, where a soaring beamed ceiling enhances the inviting ambiance. The living room boasts built-in shelves, while the kitchen impresses w/timeless white cabinetry, soapstone counters, SS appliances, large island, & pantry. The dining area, warmed

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    57 Jefferson Rd, 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

    $1,260,000 Sold Jun 30, 2025

    • 2,705 Sq Ft
    • $466/SF
    • 41 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1885

    261 Cambridge St Unit 261 G, Winchester, MA 01890

    Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms,

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

    261 Cambridge St Unit 261 G, Winchester, MA 01890
  • 17 Mason St, Winchester, MA 01890
    17 Mason St, Winchester, MA 01890
    17 Mason St, Winchester, MA 01890
    /30

    $1,330,000 Sold Jun 27, 2025

    • 1,629 Sq Ft
    • $816/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1941

    17 Mason St, Winchester, MA 01890

    Nestled on a quiet, tree-lined street near Winchester’s vibrant town center, this delightful storybook colonial offers charm, character, and exceptional potential. Beautifully sited on a 10,000+ sq ft wooded lot, this three-bedroom, two-bath home invites your vision to blend timeless architectural details with thoughtful updates. A fireplaced front-to-back living room flows seamlessly into a

    Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

    17 Mason St, Winchester, MA 01890
  • 63 Church St, Winchester, MA 01890
    63 Church St, Winchester, MA 01890
    63 Church St, Winchester, MA 01890
    /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
  • 7 Conant Rd Unit 37, Winchester, MA 01890
    7 Conant Rd Unit 37, Winchester, MA 01890
    7 Conant Rd Unit 37, 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
  • 200 Swanton St Unit T4, Winchester, MA 01890
    200 Swanton St Unit T4, Winchester, MA 01890
    200 Swanton St Unit T4, Winchester, MA 01890
    /17

    $299,000 Sold Jun 27, 2025

    • 450 Sq Ft
    • $664/SF
    • 10 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1966

    200 Swanton St Unit T4, Winchester, MA 01890

    Immaculate, recently renovated Jumbo Studio Condominium with a private/direct-entry terrace level. This unit is spacious and bright, featuring a slider that leads to a private patio overlooking scenic duck ponds and lush landscaping. The large eat-in kitchen features white cabinets, with a white tiled backsplash and granite countertops. The bathroom was recently updated with new fixtures,

    Michael Masci North Atlantic Realty Group

    200 Swanton St Unit T4, Winchester, MA 01890
  • 117 Mount Vernon St, Winchester, MA 01890
    117 Mount Vernon St, Winchester, MA 01890
    117 Mount Vernon St, 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
  • 5 Clearwater Rd, Winchester, MA 01890
    5 Clearwater Rd, Winchester, MA 01890
    5 Clearwater Rd, 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
  • 3 Foxcroft Rd, Winchester, MA 01890
    3 Foxcroft Rd, Winchester, MA 01890
    3 Foxcroft 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
  • 2 Chestnut St, Winchester, MA 01890
    2 Chestnut St, Winchester, MA 01890
    2 Chestnut St, 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
  • 9 Thornberry Rd, Winchester, MA 01890
    9 Thornberry Rd, Winchester, MA 01890
    9 Thornberry Rd, 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
  • 31 Lawson Rd, Winchester, MA 01890
    31 Lawson Rd, Winchester, MA 01890
    31 Lawson 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
  • 703 Washington St, Winchester, MA 01890
    703 Washington St, Winchester, MA 01890
    703 Washington St, 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
  • 27 Elm St, Winchester, MA 01890
    27 Elm St, Winchester, MA 01890
    27 Elm 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
  • 15 Kendall St, Winchester, MA 01890
    15 Kendall St, Winchester, MA 01890
    15 Kendall 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
  • 51 Wedgemere Ave, Winchester, MA 01890
    51 Wedgemere Ave, Winchester, MA 01890
    51 Wedgemere Ave, 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
  • 48 Tremont St, Winchester, MA 01890
    48 Tremont St, Winchester, MA 01890
    48 Tremont St, 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

Showing Results 1 - 40, Page 1 of 8

Massachusetts Winchester

Recently Sold Real Estate & Homes in Winchester, MA

Frequently Asked Questions

What is the average home price in Winchester, MA?
Homes for sale in Winchester, MA have an average home price of $1,342,522.
What is the average time to sell a house in Winchester, MA?
The houses for sale in Winchester, MA spend an average of 28 days on the market.
What is the number of active homes for sale in Winchester, MA?
There are 0 active homes for sale in Winchester, MA.
How many homes have sold over the last 12 months in Winchester, MA?
53 homes have sold in Winchester, MA over the last 12 months.

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 28 days on the market compared to the national average of 70 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,300,000, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,300,000
Median Single Family Sale Price
$2,750,000
Median Townhouse Sale Price
$1,635,000
Median 2 Bedroom Sale Price
$630,000
Median 1 Bedroom Sale Price
$995,000
Average Price Per Sq Ft
$559
Number of Homes for Sale
0
Last 12 months Home Sales
53
Months of Supply
0.00
Median List Price
$1,458,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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