16

Winchester, MA Houses for Sale

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  • /42

    $1,999,000 Open Sat 1:30PM - 2:30PM

    • 4 Beds
    • 2 Baths
    • 3,509 Sq Ft

    35 Glen Green, Winchester, MA 01890

    Welcome to this beautifully maintained Colonial in a highly desirable family neighborhood directly across from a scenic conservation area. The main level offers a bright, seamless flow with a living room, dining room, updated kitchen, full bath, family room, and a sunroom opening to the backyard. Upstairs features three comfortable bedrooms and a full bath, while the third-floor bonus room offers

    Andersen Group Realty Keller Williams Realty Boston Northwest

    35 Glen Green, Winchester, MA 01890
  • /31

    $1,999,000

    • 4 Beds
    • 3.5 Baths
    • 3,475 Sq Ft

    46 Church St, Winchester, MA 01890

    Welcome to 46 Church Street. This spacious, beautifully maintained, Paul Whitney built home is just outside the heart of Winchester center with easy access to the commuter rail, schools, restaurants, and shopping. Offering flexible living areas and abundant room throughout, the residence features four bedrooms, three and a half bathrooms, two dedicated home offices, and a generously sized bonus

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

    46 Church St, Winchester, MA 01890
  • /42

    $1,399,000

    • 4 Beds
    • 3.5 Baths
    • 2,490 Sq Ft

    95 Irving St, Winchester, MA 01890

    Beautiful newer-construction home in a wonderful Muraco school location! This meticulous 4-bed, 3.5-bath property offers modern living with an inviting open-concept layout & high ceilings spanning across 4 finished levels with attached garage! The stunning chef’s kitchen features high-end appliances, large island & abundant storage, flowing seamlessly into the dining area & living room with a gas

    Kim Covino Compass

    95 Irving St, Winchester, MA 01890
  • /37

    $2,299,000 Pre-Foreclosure

    • 7 Beds
    • 5.5 Baths
    • 4,929 Sq Ft

    89 Wildwood St, Winchester, MA 01890

    Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    89 Wildwood St, Winchester, MA 01890
  • /42

    $2,100,000

    • 6 Beds
    • 3.5 Baths
    • 4,122 Sq Ft

    77A Brooks St, Winchester, MA 01890

    This stately Victorian offers an exceptional blend of preserved character and modern functionality across its generous, well-appointed layout. Sunlit rooms highlight hardwood floors, detailed millwork, bay windows, and a graceful fireplace, creating a warm and elegant flow throughout the main level. The expansive kitchen features stone counters, a central island, French doors, and direct access

    Anne Spry Barrett Sotheby's International Realty

    77A Brooks St, Winchester, MA 01890
  • /35

    $1,995,000

    • 5 Beds
    • 4 Baths
    • 4,334 Sq Ft

    237 Swanton St, Winchester, MA 01890

    NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas

    Kim Covino Compass

    237 Swanton St, Winchester, MA 01890
  • /42

    $2,999,000

    • 5 Beds
    • 5.5 Baths
    • 5,257 Sq Ft

    19 Town Way, Winchester, MA 01890

    Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive

    Philip Vita Compass

    19 Town Way, Winchester, MA 01890
  • /36

    $3,600,000

    • 6 Beds
    • 7 Baths
    • 8,866 Sq Ft

    20 Amberwood Dr, Winchester, MA 01890

    Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

    Wei Wang WW Real Estate LLC

    20 Amberwood Dr, Winchester, MA 01890
  • /41

    $1,460,000

    • 3 Beds
    • 2.5 Baths
    • 2,316 Sq Ft

    26 Berkshire Dr, Winchester, MA 01890

    Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

    DANIEL BEIRNE OpenDoor Brokerage LLC

    26 Berkshire Dr, Winchester, MA 01890
  • /42

    $3,299,000

    • 5 Beds
    • 7 Baths
    • 7,101 Sq Ft

    257 High St, Winchester, MA 01890

    Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

    Kim Covino Compass

    257 High St, Winchester, MA 01890
  • /24

    $969,000

    • 3 Beds
    • 1.5 Baths
    • 1,302 Sq Ft

    139 High St, Winchester, MA 01890

    This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

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

    139 High St, Winchester, MA 01890
  • /25

    $949,000

    • 4 Beds
    • 1.5 Baths
    • 2,162 Sq Ft

    41 Squire Rd, Winchester, MA 01890

    Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest

    William Cordts Charlesgate Realty Group, llc

    41 Squire Rd, Winchester, MA 01890
  • /40

    $1,869,000 Open Sat 12PM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 3,294 Sq Ft

    20 Grove Place, Winchester, MA 01890

    From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

    Andersen Group Realty Keller Williams Realty Boston Northwest

    20 Grove Place, Winchester, MA 01890
  • /42

    $1,699,000

    • 4 Beds
    • 4 Baths
    • 3,343 Sq Ft

    263 Highland Ave, Winchester, MA 01890

    Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home

    Seeme Moreira Coldwell Banker Realty - Lexington

    263 Highland Ave, Winchester, MA 01890
  • /38

    $2,299,000

    • 5 Beds
    • 3.5 Baths
    • 5,006 Sq Ft

    276 High St, Winchester, MA 01890

    Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

    Kim Covino Compass

    276 High St, Winchester, MA 01890
  • /40

    $2,250,000

    • 6 Beds
    • 5 Baths
    • 3,728 Sq Ft

    6 Ivy Cir, Winchester, MA 01890

    Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large

    Rose Hall Blue Ocean Realty, LLC

    6 Ivy Cir, Winchester, MA 01890

Why Live in Winchester

Winchester, MA, a peaceful Greater Boston suburb, has evolved from a rural farming community to a primarily residential town with a population of nearly 23,000. Located 8 miles north of Boston, Winchester is known for its grand New England homes, ranging from historic Colonial Revivals to modern Cape Cods and ranch styles. The town boasts one of the best school districts in the state, with Winchester Public Schools serving over 4,300 students and receiving high ratings. The private Acera School also offers quality education. Outdoor enthusiasts can enjoy Mystic Lakes State Park, Middlesex Fells Reservation, and the Tri-Community Greenway, which connects Winchester with Woburn and Stoneham. The town's downtown area, bordered by Wedge and Mill Ponds, features a variety of markets, restaurants, boutiques, and service shops. Community events such as Winchester Town Day, PRIDEFest, and summer concerts at Town Common foster a strong sense of community. Wright-Locke Farm, a 383-year-old sustainable conservancy, provides fresh organic produce and nature-based activities. Winchester is accessible via U.S. Route 3 and Interstates 93 and 95, with public transit options including the MBTA bus and commuter rail. Logan International Airport is about 11 miles away. The town has a lower crime risk compared to the national average, with recent data indicating a decrease in violent crimes.

Home Trends in Winchester, MA

Housing Trends

Median Sale Price
$1,650,000
Median Single Family Sale Price
$1,822,500
Median Townhouse Sale Price
$1,424,500
Median 2 Bedroom Sale Price
$940,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$563
Number of Homes for Sale
16
Last 12 months Home Sales
168
Months of Supply
1.10
Median List Price
$1,699,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
6%
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