Winchester Real Estate

Winchester Real Estate

Nestled in the heart of Middlesex County, Winchester, Massachusetts, is a charming suburban town that perfectly blends small-town charm with modern conveniences. Known for its picturesque landscapes and vibrant community, Winchester offers a welcoming atmosphere that appeals to families, professionals, and retirees alike.

Founded in 1850, Winchester boasts a rich history reflected in its beautifully preserved architecture and quaint downtown area. The town is home to an array of local shops, cafes, and restaurants, making it a delightful spot to explore on foot. Residents enjoy a strong sense of community, with numerous events and activities throughout the year, from farmers' markets to seasonal festivals.

Education is a cornerstone of Winchester, with its highly-rated public schools and proximity to esteemed institutions such as Winchester High School and several private schools. The town’s commitment to education ensures that families have access to quality learning environments, making it an attractive option for those with children.

Nature enthusiasts will appreciate the town's abundant green spaces, including the scenic Horn Pond and the picturesque Fells Reservation, perfect for hiking, biking, and picnicking. With easy access to major highways and public transportation options, commuting to Boston and surrounding areas is a breeze, allowing residents to enjoy the best of both suburban tranquility and urban excitement.

In Winchester, you’ll find a community that values history, education, and connection. Whether you’re looking for a cozy home, a vibrant lifestyle, or a place to plant your roots, Winchester, MA, is a gem waiting to be discovered.

Newest Listings in Winchester

$1,125,000
5 Beds ⋅ 3 Baths ⋅ 73555245 MLS
Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

8-10 Oak St, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
$2,225,000
4 Beds ⋅ 4 Baths ⋅ 73554545 MLS
Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail, Lincoln Elementary School and the Middlesex Fells Reservation with miles of trails, hiking, running and The Sheepfold dog park. The traditional yet open layout features an updated kitchen, spacious living and dining areas, refreshed baths, fresh paint and updated mechanical systems. A versatile bonus room with a private staircase offers endless possibilities as a home office, media room, guest space, playroom or fitness area. The finished lower level with half bath adds valuable living space. Enjoy outdoor living on the wraparound deck overlooking a private backyard with mature landscaping.

6 Davey Ln, Winchester

Listing courtesy of Listing Agent: Gretchen Papineau from Listing Office: Coldwell Banker Realty - Andovers/Readings Regional.
$1,150,000
4 Beds ⋅ 3 Baths ⋅ 73554139 MLS
Classic center-entrance Colonial set on a cul-de-sac with a wonderful sense of flow and everyday function. The main level offers formal living and dining rooms, a spacious front-to-back fireplaced family room with first-floor laundry and half bath, plus a bright kitchen with island, dining area, and direct access to the deck. Upstairs, the primary suite includes a walk-in closet and private bath, complemented by three additional bedrooms and a full bath. A two-car under garage connects to the unfinished basement, offering excellent storage and future possibilities. Central air, gas heat, hardwood floors, and a level lot complete this inviting home.

11 Williams Cir, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 73554036 MLS
New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new deck railings, a freshly painted finished lower level with brand-new carpeting, and the seller will replace the second-floor HVAC system, providing valuable peace of mind for the next owner. Inside, you'll find sun-filled living spaces, an updated kitchen, generously sized bedrooms, and a versatile finished lower level ideal for a family room, home office, gym, or playroom. The true showstopper is the spectacular backyard retreat. Designed for entertaining and everyday enjoyment, the private outdoor oasis features a heated saltwater pool with a beautiful waterfall, an expansive patio, mature landscaping, and an outdoor entertaining area rough-plumbed for a future outdoor kitchen—making it easy to create the backyard you've always envisioned. Ideally located just minutes from Winchester Center, top-rated schools, shopping, dining, parks, and commuter routes, this is a rare opportunity to own a turnkey home with outstanding updates, exceptional outdoor amenities, and an unbeatable Winchester location.

241 Ridge St, Winchester

Listing courtesy of Listing Agent: Team Lillian Montalto from Listing Office: Lillian Montalto Signature Properties.
$849,000
3 Beds ⋅ 2 Baths ⋅ 73553626 MLS
Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and effortless entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or a dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester Center commuter rail, and major routes, this home embodies the very best of Winchester living. No HOA fee.

15 Clark St Unit 15, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.
$700,000
2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.
Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new chandelier. Spacious primary bedroom has LARGE WALK-IN CLOSET plus a sink and linen closet before the entry to the water closet where you'll find a large tub. Second bedroom/office has double closet and is across hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR and find NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (all recently done in 2026), NEW WASHER AND DRYER 2025 and NEW HOT WATER HEATER (2024). Love the COVERED PARKING in the garage below the building, association POOL, two ELEVATORS plus the convenience of being only one flight of stairs up from the street level. Location near town center, TRAIN, shopping, restaurants, schools and library is superb.

666 Main Unit 211, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,099,000
5 Beds ⋅ 3 Baths ⋅ 73553083 MLS
Exceptional two-family opportunity with incredible potential to renovate/expand! Situated on a large, level corner lot with frontage on both Cross Street and Verplast Avenue, this property offers endless possibilities for investors, builders, or owner-occupants. The first-floor unit features a fireplaced living room, an updated kitchen, three bedrooms, 1.5 baths and sunroom overlooking the expansive backyard. The second unit offers a spacious and flexible layout with a living room, kitchen, 2 bedrooms, laundry room and full bath. The generous lot, separate entrances, and existing footprint create an ideal opportunity to modernize the current two-family, expand the living space, or explore redevelopment possibilities. Whether you're looking for a strong income property or your next renovation project, this property is full of potential and ready for its next chapter!

257 Cross St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 73551306 MLS ⋅ ['Graystone At Winchester'] BLDG.
OFFER ACCEPTED-OH CANCELLED!Discover luxury & convenience in this impeccably maintained 2-3 bed, 2.5-baths unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering a 1st floor primary suite! The gourmet kitchen showcases custom cabinetry, granite countertops, top-of-the-line stainless appliances w/new gas stove. The open-concept living & dining area w/ a gas fireplace, gleaming hardwood floors & soaring cathedral ceilings w/ skylights, leading to a private, deck & yard—perfect for outdoor relaxation. The spacious first-floor primary suite offers a marble bathroom w/ a custom walk-in shower & generous closet space. Upstairs, the spacious second bedroom, full bath plus an oversized loft family room area w/ potential to wall off a portion for 3rd bedroom, & a cozy a den/ office The walkout LL has high ceilings & offers opportunity to finish 1440SF for gym/rec room, media room, storage or anything you desire!

18 Graystone Circle Unit 18, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$950,000
3 Beds ⋅ 1 Baths ⋅ 73549935 MLS
Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

47 Water Street, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.
$729,000
3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ['Winchester Green'] BLDG.
Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The finished lower level offers a family room, half bath, oversized closets, and an in-unit laundry area with additional storage. Enjoy easy access to the 2,600-acre Middlesex Fells Reservation, offering miles of scenic walking, running, and biking trails.

247 Washington St Unit 11, Winchester

Listing courtesy of Listing Agent: Heejeong Joo from Listing Office: Coldwell Banker Realty - Lexington.
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 73549484 MLS
Completely renovated in 2021, this stunning 3-bedroom, 2.5-bath townhouse offers the comfort and feel of a single-family home with three levels of beautifully finished living space. The open and inviting floor plan features hardwood floors throughout, modern finishes, and abundant natural light. The spacious third-floor primary suite provides a private retreat with spacious walk in closet and its own full bath. Second floor features 2 ample sized bedrooms, full bath and laundry. Step outside through the sliding glass doors to a newly installed stone patio and backyard—perfect for relaxing, entertaining, or outdoor dining. Additional highlights include two off-street parking spaces and thoughtful updates throughout. Ideally located just moments from the Winchester Center commuter rail station, vibrant downtown shops and restaurants, Winchester High School, and the brand-new Lynch Elementary School, this move-in ready home offers the perfect combination of style, space, and convenience.

52 Salem Street Unit 52, Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,699,000
3 Beds ⋅ 4 Baths ⋅ 73549106 MLS
Beautifully updated & impeccably maintained 3 BR, 3.5 bath home on a sought-after cul-de-sac w/lovely front & side yards, abutting conservation land for exceptional privacy. The main level features a spacious living room, updated sunroom, granite kitchen w/newer SS appliances, abundant cabinetry, peninsula seating, & dining room w/ access to an inviting deck. Two 1st floor bedrooms & two full baths, including an en-suite, offer exceptional flexibility. The 2nd floor primary suite is a private retreat w/ a vaulted ceiling, oversized walk-in closet, spacious bath w/ double vanity. This level offers an additional storage closet & unfinished room w/expansion potential. En-suite bedrooms on both the 1st & 2nd floors provide a versatile floor plan. The bright walk-out lower level includes a large family room w/ access to an expansive deck, mudroom, laundry room, half bath, & bonus room ideal for overnight guests. Replacement windows & beautiful storage shed complete this move in ready home.

2 Olde Lyme Road, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
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