289

Recently Sold Winchester, MA Homes

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  • 155 Highland Ave, Winchester, MA 01890
    155 Highland Ave, Winchester, MA 01890
    155 Highland Ave, Winchester, MA 01890
    /41

    $1,510,000 Sold Sep 02, 2025

    • 1,965 Sq Ft
    • $768/SF
    • 8 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1900

    155 Highland Ave, Winchester, MA 01890

    Charming turn-of-the-century 5-bedroom Gambrel-style home in move-in condition, blending classic character with modern updates. This spacious residence features a beautifully updated interior with central air, a stunning primary suite with private bath, custom closet system, and generous living spaces throughout. The detached 2-car garage adds convenience, while the location offers unbeatable

    Pirani & Wile Group Advisors Living - Winchester

    155 Highland Ave, Winchester, MA 01890
  • 107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    /42

    $2,350,000 Sold Aug 29, 2025

    • 5,824 Sq Ft
    • $404/SF
    • 60 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 1911

    107 Cambridge St, Winchester, MA 01890

    Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz

    Stephen Stratford William Raveis R.E. & Home Services

    107 Cambridge St, Winchester, MA 01890
  • 17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    /42

    $2,218,500 Sold Aug 29, 2025

    • 3,940 Sq Ft
    • $563/SF
    • 74 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1983

    17 Wagon Wheel Rd, Winchester, MA 01890

    Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends

    Yifei Wang Dreamega International Realty LLC

    17 Wagon Wheel Rd, Winchester, MA 01890
  • 70 Woodside Rd, Winchester, MA 01890
    70 Woodside Rd, Winchester, MA 01890
    70 Woodside Rd, Winchester, MA 01890
    /40

    $1,200,000 Sold Aug 27, 2025

    • 2,566 Sq Ft
    • $468/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1930

    70 Woodside Rd, Winchester, MA 01890

    Have you ever dreamed of owning a house with a white picket fence? Here it is! Eight rooms, four bedrooms, 2.5 baths. Corner lot with backyard patio, shed and one car garage. The large living room with many windows and a fireplace opens to the dining room. French doors from the dining room lead to a room that can be used as a family room, play room for the kids, or another bedroom. The

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

    70 Woodside Rd, Winchester, MA 01890
  • 12 Olde Lyme Rd, Winchester, MA 01890
    12 Olde Lyme Rd, Winchester, MA 01890
    12 Olde Lyme Rd, Winchester, MA 01890
    /42

    $2,500,000 Sold Aug 27, 2025

    • 4,215 Sq Ft
    • $593/SF
    • 4 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1955

    12 Olde Lyme Rd, Winchester, MA 01890

    *** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates

    Mary Beth McGillicuddy Engel & Völkers , South Shore

    12 Olde Lyme Rd, Winchester, MA 01890
  • 29 Vine St Unit 7, Winchester, MA 01890
    29 Vine St Unit 7, Winchester, MA 01890
    29 Vine St Unit 7, Winchester, MA 01890
    /35

    $720,000 Sold Aug 26, 2025

    • 1,300 Sq Ft
    • $554/SF
    • 4 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1980

    29 Vine St Unit 7, Winchester, MA 01890

    Immerse yourself in the vibrant heart of Winchester Center with this exquisite 2-bedroom, 1.5-bathroom condominium! Step into the open-concept living and dining area, where a modern touch meets downtown flair. A rare freestanding wood-burning fireplace accentuates the space, offering warmth and a touch of classic charm. Delight in the recently renovated kitchen, designed for both style and

    Philip Vita Compass

    29 Vine St Unit 7, Winchester, MA 01890
  • 8 Garfield Ave, Winchester, MA 01890
    8 Garfield Ave, Winchester, MA 01890
    8 Garfield Ave, Winchester, MA 01890
    /38

    $1,062,350 Sold Aug 22, 2025

    • 1,536 Sq Ft
    • $692/SF
    • 42 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1940

    8 Garfield Ave, Winchester, MA 01890

    Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a custom built free standing office/cottage/gym/ movie house, blends timeless charm w/ modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace w/ built ins, the dining room is perfect

    Kim Covino Compass

    8 Garfield Ave, Winchester, MA 01890
  • 14 Hillside Ave, Winchester, MA 01890
    14 Hillside Ave, Winchester, MA 01890
    14 Hillside Ave, Winchester, MA 01890
    /42

    $1,330,000 Sold Aug 21, 2025

    • 2,605 Sq Ft
    • $511/SF
    • 73 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1870

    14 Hillside Ave, Winchester, MA 01890

    Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps from Town Center! This property has been lovingly owned & maintained by the same family for 70+ years and is now ready for new owners. Prepare to fall in love with the charm and period details of this circa 1870 historic home, the first house built on Hillside Ave. The 1st floor

    Seeme Moreira Coldwell Banker Realty - Lexington

    14 Hillside Ave, Winchester, MA 01890
  • 171 Swanton St Unit 12, Winchester, MA 01890
    171 Swanton St Unit 12, Winchester, MA 01890
    171 Swanton St Unit 12, Winchester, MA 01890
    /28

    $785,500 Sold Aug 20, 2025

    • 1,435 Sq Ft
    • $547/SF
    • 8 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1984

    171 Swanton St Unit 12, Winchester, MA 01890

    Welcome to The Village in Winchester! This picturesque 80-unit condominium community is set along conservation land and the Aberjona River. Unit 12 is a spacious, renovated 2-bedroom, 2.5-bath townhouse offering a bright living room with skylight and gas fireplace, updated kitchen, dining room, and private outdoor patio. The second floor features a large primary suite with ample closet space and

    John and Maria Reilly JMR Real Estate Group LLC

    171 Swanton St Unit 12, Winchester, MA 01890
  • 3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    /33

    $1,240,000 Sold Aug 20, 2025

    • 2,570 Sq Ft
    • $482/SF
    • 9 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1966

    3 Socrates Way, Winchester, MA 01890

    Unlock the potential of this tri-level home in one of Winchester’s sought-after neighborhoods! Set on a 20,000 sq ft lot, this 4 bed, 2.5 bath, 1966-built home offers 2,116 sf of living space, a 2 car garage, & endless possibilities for renovation or redevelopment. The main level features a formal living room, dining room, & kitchen leading to a deck overlooking the backyard. A cozy family room

    Pirani & Wile Group Advisors Living - Winchester

    3 Socrates Way, Winchester, MA 01890
  • 109 Thornberry Rd, Winchester, MA 01890
    109 Thornberry Rd, Winchester, MA 01890
    109 Thornberry Rd, Winchester, MA 01890
    /19

    $1,820,000 Sold Aug 19, 2025

    • 3,784 Sq Ft
    • $481/SF
    • 5 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1974

    109 Thornberry Rd, Winchester, MA 01890

    Ideally located in one of Winchester’s most desirable neighborhoods, this classic Colonial blends timeless design with thoughtful updates. At the heart of the home, the beautifully updated kitchen features a generous center island, opening to a spacious family room with a slider leading to a large deck overlooking the expansive, level backyard - perfect for summer entertaining. Just off the

    Andrew Martini Compass

    109 Thornberry Rd, Winchester, MA 01890
  • 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
  • 163 Main St, Winchester, MA 01890
    163 Main St, Winchester, MA 01890
    163 Main St, Winchester, MA 01890
    /36

    $1,175,000 Sold Aug 18, 2025

    • 2,335 Sq Ft
    • $503/SF
    • 8 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1961

    163 Main St, Winchester, MA 01890

    Charming multi-level home in close proximity to Winchester Center, public transit, Lincoln Elementary, and McCall. The main level offers an open floor plan with beautiful hardwood floors, bay windows, a skylit eat-in kitchen, and abundant natural light. Perfect for entertaining, the living and dining rooms flow seamlessly to a spacious yard, relaxing patio, and mature gardens. The top floor

    Andersen Group Realty Keller Williams Realty Boston Northwest

    163 Main St, 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
  • 9 Emerson Ct, Winchester, MA 01890
    9 Emerson Ct, Winchester, MA 01890
    9 Emerson Ct, Winchester, MA 01890
    /41

    $790,001 Sold Aug 15, 2025

    • 1,441 Sq Ft
    • $548/SF
    • 12 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1901

    9 Emerson Ct, Winchester, MA 01890

    Looking for the ideal first home or a peaceful place to settle into your next chapter? This charming 3-bedroom, 2-bath home, nestled at the end of a quiet dead-end street, was completely remodeled in 2009. Step inside to a warm and welcoming space with a practical layout—everything you need without the fuss. Whether you're just getting started or looking to simplify, this move-in-ready home is a

    Rodrigo Serrano Leading Edge Real Estate

    9 Emerson Ct, 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
  • 518 Washington St, Winchester, MA 01890
    518 Washington St, Winchester, MA 01890
    518 Washington St, Winchester, MA 01890
    /40

    $1,160,000 Sold Aug 14, 2025

    • 2,302 Sq Ft
    • $504/SF
    • 22 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1915

    518 Washington St, Winchester, MA 01890

    Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry.

    Rodrigo Serrano Leading Edge Real Estate

    518 Washington 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

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 $1,920,107.
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 22 active homes for sale in Winchester, MA.
How many homes have sold over the last 12 months in Winchester, MA?
160 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 $1,660,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,660,000
Median Single Family Sale Price
$1,900,000
Median Townhouse Sale Price
$1,542,500
Median 2 Bedroom Sale Price
$940,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$551
Number of Homes for Sale
22
Last 12 months Home Sales
160
Months of Supply
1.70
Median List Price
$1,699,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
13%
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