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Recently Sold Winchester, MA Homes

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  • 34 Rangeley Rd, Winchester, MA 01890
    34 Rangeley Rd, Winchester, MA 01890
    34 Rangeley Rd, Winchester, MA 01890
    /42

    $2,700,000 Sold Aug 18, 2025

    • 3,708 Sq Ft
    • $728/SF
    • 2 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1929

    34 Rangeley Rd, Winchester, MA 01890

    Welcome to this truly distinctive home nestled on a lush landscaped lot in historic & highly sought after Rangeley Estates neighborhood. Just moments from downtown Winchester, this hidden gem offers a unique blend of privacy and convenience! This stunning home boasts 5 bedrooms & 4 full baths, seamlessly blending original charm with modern amenities. Step inside to discover sun-filled rooms and a

    Kim Covino Compass

    34 Rangeley Rd, Winchester, MA 01890
  • 60 Lake St Unit I, Winchester, MA 01890
    60 Lake St Unit I, Winchester, MA 01890
    60 Lake St Unit I, Winchester, MA 01890
    /30

    $640,000 Sold Aug 15, 2025

    • 1,464 Sq Ft
    • $437/SF
    • 8 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1976

    60 Lake St Unit I, Winchester, MA 01890

    Enjoy the best of Winchester living in this spacious 2-bed, 1.5-bath townhouse at Wedge Pond Condominium, set along scenic Wedge Pond. The main level features hardwood floors, a sunny living room, dining room with charming bow window, half bath, and renovated kitchen with updated appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides flexible space for a

    Pirani & Wile Group Advisors Living - Winchester

    60 Lake St Unit I, Winchester, MA 01890
  • 19 Pilgrim Dr, Winchester, MA 01890
    19 Pilgrim Dr, Winchester, MA 01890
    19 Pilgrim Dr, Winchester, MA 01890
    /42

    $1,775,000 Sold Aug 15, 2025

    • 3,150 Sq Ft
    • $563/SF
    • 6 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1961

    19 Pilgrim Dr, Winchester, MA 01890

    Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –

    Gorfinkle Group eXp Realty

    19 Pilgrim Dr, Winchester, MA 01890
  • 21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    /42

    $2,890,000 Sold Aug 14, 2025

    • 5,386 Sq Ft
    • $537/SF
    • 9 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1963

    21 Fernway, Winchester, MA 01890

    Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day

    Kim Covino Compass

    21 Fernway, Winchester, MA 01890
  • 9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    /40

    $2,175,000 Sold Aug 14, 2025

    • 4,667 Sq Ft
    • $466/SF
    • 18 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1895

    9 Prospect St, Winchester, MA 01890

    Step into timeless elegance with this Colonial Revival, a true celebration of classic architecture, refined style, and exceptional craftsmanship. From the moment you arrive, the home's rich character makes a striking first impression, setting the stage for everything that follows. Inside, you’ll discover a harmonious blend of historic charm and modern comfort. Gleaming hardwood floors, intricate

    Nancy Pallotta Advisors Living - Winchester

    9 Prospect St, Winchester, MA 01890
  • 4 Winslow Rd, Winchester, MA 01890
    4 Winslow Rd, Winchester, MA 01890
    4 Winslow Rd, Winchester, MA 01890
    /42

    $2,215,000 Sold Aug 12, 2025

    • 3,607 Sq Ft
    • $614/SF
    • 5 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1895

    4 Winslow Rd, Winchester, MA 01890

    Situated in a coveted Winchester neighborhood, this classical five-bedroom home unfolds across 3 levels above grade—boasting sunlit living & dining spaces framed by walls of windows overlooking lush greenery, a chef’s kitchen appointed with an expansive butcher-block island & dual fuel oven & a serene primary suite featuring a private bath & walk-in closet. 2 additional bedrooms occupy the second

    Anne Spry Barrett Sotheby's International Realty

    4 Winslow Rd, Winchester, MA 01890
  • 540-542 Washington St, Winchester, MA 01890
    540-542 Washington St, Winchester, MA 01890
    540-542 Washington St, Winchester, MA 01890
    /6

    $1,120,000 Sold Aug 11, 2025

    • 2,060 Sq Ft
    • $544/SF
    • 2 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1917

    540-542 Washington St, Winchester, MA 01890

    Great Two-Family Home in a Desirable Location! This well-maintained two-family property features a total of 4 bedrooms and 2 full bathrooms, with beautiful hardwood floors throughout. Each unit offers spacious living areas filled with natural light. The basement includes laundry hookups with washer and dryer included. Enjoy the convenience of 6 off-street parking spaces—a rare find! Situated just

    Wei Wang WW Real Estate LLC

    540-542 Washington St, Winchester, MA 01890
  • 22 Grove Place Unit 4, Winchester, MA 01890
    22 Grove Place Unit 4, Winchester, MA 01890
    22 Grove Place Unit 4, Winchester, MA 01890
    /37

    $770,000 Sold Aug 11, 2025

    • 1,123 Sq Ft
    • $686/SF
    • 44 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1986

    22 Grove Place Unit 4, Winchester, MA 01890

    Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect opportunity to enjoy the lovely town of Winchester and keep costs down. Near Symmes corner, downtown Winchester & Wedgemere train station, this wonderful 2 bedroom, 1 bathroom end unit lives and feels like a single home with windows on all three sides. The kitchen offers a

    Kim Covino Compass

    22 Grove Place Unit 4, Winchester, MA 01890
  • 25 Wedgemere Ave, Winchester, MA 01890
    25 Wedgemere Ave, Winchester, MA 01890
    25 Wedgemere Ave, Winchester, MA 01890
    /42

    $3,745,000 Sold Aug 08, 2025

    • 7,587 Sq Ft
    • $494/SF
    • 44 Days On Market
    • 7 Beds
    • 8 Baths
    • Built 2010

    25 Wedgemere Ave, Winchester, MA 01890

    Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7

    Prestige Homes Realty Team Prestige Homes Real Estate, LLC

    25 Wedgemere Ave, Winchester, MA 01890
  • 26 Olive St, Winchester, MA 01890
    26 Olive St, Winchester, MA 01890
    26 Olive St, Winchester, MA 01890
    /37

    $1,000,000 Sold Aug 01, 2025

    • 1,977 Sq Ft
    • $506/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    26 Olive St, Winchester, MA 01890

    Don't miss this rare opportunity to own a charming home with an expansive yard on a quiet cul-de-sac street! This lovely 3-bedroom ranch is meticulously maintained and situated in the sought-after Muraco school district. The main floor features an eat-in kitchen, formal dining room, and a sun-filled living room with a fireplace, perfect for relaxing or entertaining. Gleaming hardwood floors run

    Andersen Group Realty Keller Williams Realty Boston Northwest

    26 Olive St, Winchester, MA 01890
  • 32 Oneida Rd, Winchester, MA 01890
    32 Oneida Rd, Winchester, MA 01890
    32 Oneida Rd, Winchester, MA 01890
    /38

    $1,627,000 Sold Jul 31, 2025

    • 2,853 Sq Ft
    • $570/SF
    • 7 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1930

    32 Oneida Rd, Winchester, MA 01890

    Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

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

    32 Oneida Rd, Winchester, MA 01890
  • 15 Churchill Rd, Winchester, MA 01890
    15 Churchill Rd, Winchester, MA 01890
    15 Churchill Rd, Winchester, MA 01890
    /41

    $2,425,000 Sold Jul 31, 2025

    • 5,501 Sq Ft
    • $441/SF
    • 61 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2025

    15 Churchill Rd, Winchester, MA 01890

    Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor

    Kim Covino Compass

    15 Churchill Rd, Winchester, MA 01890
  • 83 Canal St Unit 85, Winchester, MA 01890
    83 Canal St Unit 85, Winchester, MA 01890
    83 Canal St Unit 85, Winchester, MA 01890
    /39

    $1,149,000 Sold Jul 31, 2025

    • 2,300 Sq Ft
    • $500/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2017

    83 Canal St Unit 85, Winchester, MA 01890

    This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary

    Mary O'Hagan Barrett Sotheby's International Realty

    83 Canal St Unit 85, Winchester, MA 01890
  • 8 Chestnut St, Winchester, MA 01890
    8 Chestnut St, Winchester, MA 01890
    8 Chestnut St, Winchester, MA 01890
    /42

    $2,635,000 Sold Jul 31, 2025

    • 5,354 Sq Ft
    • $492/SF
    • 117 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1850

    8 Chestnut St, Winchester, MA 01890

    Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and

    The McLaren D'Agostino Team Compass

    8 Chestnut St, Winchester, MA 01890
  • 49 Lincoln St, Winchester, MA 01890
    49 Lincoln St, Winchester, MA 01890
    49 Lincoln St, Winchester, MA 01890
    /29

    $1,300,000 Sold Jul 30, 2025

    • 2,238 Sq Ft
    • $581/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1905

    49 Lincoln St, Winchester, MA 01890

    Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking

    Vantage Point Team William Raveis R.E. & Home Services

    49 Lincoln St, Winchester, MA 01890
  • 50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, Winchester, MA 01890
    /42

    $1,650,000 Sold Jul 30, 2025

    • 2,646 Sq Ft
    • $624/SF
    • 18 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1957

    50 Johnson Rd, Winchester, MA 01890

    One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins.

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

    50 Johnson Rd, Winchester, MA 01890
  • 34 Swan Rd, Winchester, MA 01890
    34 Swan Rd, Winchester, MA 01890
    34 Swan Rd, Winchester, MA 01890
    /42

    $2,690,000 Sold Jul 30, 2025

    • 4,704 Sq Ft
    • $572/SF
    • 6 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1954

    34 Swan Rd, Winchester, MA 01890

    Situated in the prestigious Myopia Hill neighborhood, this exceptional sprawling ranch offers a rare combination of timeless elegance & modern comfort. Set on a lush, private acre, offering nearly 4,500 sq ft of beautifully maintained living space designed for both everyday living & grand-scale entertaining. Exquisite custom woodwork, built-ins & moldings lend sophistication throughout.

    Laurie Cappuccio Classified Realty Group

    34 Swan Rd, Winchester, MA 01890
  • 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

Showing Results 1 - 40, Page 1 of 8

Massachusetts Middlesex County 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 $1,962,827.
What is the average time to sell a house in Winchester, MA?
The houses for sale in Winchester, MA spend an average of 20 days on the market.
What is the number of active homes for sale in Winchester, MA?
There are 32 active homes for sale in Winchester, MA.
How many homes have sold over the last 12 months in Winchester, MA?
156 homes have sold in Winchester, MA over the last 12 months.

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 20 days on the market compared to the national average of 52 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,712,500, up 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,712,500
Median Single Family Sale Price
$1,924,000
Median Townhouse Sale Price
$1,499,000
Median 2 Bedroom Sale Price
$1,200,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$554
Number of Homes for Sale
32
Last 12 months Home Sales
156
Months of Supply
2.50
Median List Price
$1,775,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
18%
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