Weston Homes for Sale

Welcome to Weston, Massachusetts—a picturesque town nestled in Middlesex County that beautifully blends suburban tranquility with a vibrant community spirit. Known for its exceptional quality of life, Weston boasts an array of stunning natural landscapes, top-tier schools, and a rich history, making it a coveted destination for families and professionals alike.

Weston is renowned for its expansive green spaces, including the scenic Weston Town Center and the lush trails of the nearby Weston Reservoir. The town’s commitment to preserving its natural beauty is evident in its well-maintained parks and conservation areas, providing residents with ample opportunities for outdoor activities such as hiking, biking, and picnicking. With a charming downtown featuring boutique shops, delightful cafes, and local dining options, Weston offers a delightful small-town atmosphere while remaining conveniently close to the bustling cities of Boston and Cambridge.

For those considering a move to this enchanting town, there are a variety of homes for sale that cater to diverse lifestyles and preferences. From elegant colonial estates to modern family homes, Weston’s real estate market showcases properties that reflect both luxury and comfort. Many homes are situated on spacious lots, offering privacy and beautiful views of the surrounding landscape. With a strong sense of community and a commitment to excellence, Weston is not just a place to live; it’s a place to thrive.

Explore the homes for sale in Weston today and discover the perfect abode in this charming town where every day feels like a retreat!

Newest Weston Homes for Sale

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 73575873 MLS

OPEN HOUSE: Saturday 12 -1:30 and Sunday 12 - 1:30. House is being sold "as is". Opportunity to rehab and expand this 3-bedroom cape on .95-acre lot on a quiet street close to walking trails and bike path. Vaulted ceiling living room with fireplace and wood paneling, vaulted ceiling dining room with wood paneling. Additionally On the 1 st floor is the primary bedroom with vaulted ceiling and fireplace, 2 bedrooms and 2 baths, sunroom and direct access to a two-car garage. Home Office on the second floor. Backyard has a lovely stonewall with steps to a flat level area. Finished space in lower level. OFFERS DUE TUESDAY AT 12 PM; PLEASE ALLOW 24 HOURS TO REVIEW OFFER AS THIS IS AN ESTATE SALE.

94 Sunset Road, Weston

Listing courtesy of Listing Agent: Paige Yates from Listing Office: Coldwell Banker Realty - Weston.

$1,695,000

3 Beds ⋅ 2 Baths ⋅ 73575598 MLS

The one you’ve been waiting for—Nantucket charm in the heart of Weston. This quintessential shingle-style Cape offers timeless character, abundant natural light and a wonderfully inviting setting. The spacious living room features a fireplace, while the dining room showcases charming built-ins. An eat-in kitchen, three comfortable bedrooms, 1.5 baths and generous storage provide easy everyday living. Beautiful hardwood floors and classic architectural details add warmth throughout. A garage provides added convenience. Outside, enjoy a level backyard surrounded by beautiful gardens, creating a private and picturesque retreat abutting the prestigious Weston Golf Club. Renovate, expand, build new or move right in—the possibilities are exceptional. Easy access to Routes 128 and the Mass Pike, with a convenient location close to elementary schools, the library, soccer fields, Land’s Sake Farm, Memorial Pool and Weston Town Center. A rare opportunity to create your own vision in one of Weston’s most coveted settings.

60 Wellesley Street, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

$4,585,000

6 Beds ⋅ 7 Baths ⋅ 73575514 MLS

Introducing an elegant shingle and stone residence prominently situated in the prestigious Weston Estates neighborhood. This custom home is masterfully constructed with fine attention to detail by an acclaimed builder. A striking stone fireplace graces the family room and complements the open concept design. The classic floor plan features a grand two story foyer, charming sun room and fabulous finished lower level. The 6th bedroom suite located on the 3rd floor can be used as an in-home office or as a special getaway for guests. The exceptional grounds are architecturally enhanced with a decorative gazebo with a built-in kitchen. The exquisite backyard has a sprawling stone patio adorned with beautiful perennial gardens and manicured grounds. This unique home has all the desired amenities and gravitas for the most discerning buyer.

21 Westerly, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.

$2,075,000

4 Beds ⋅ 3 Baths ⋅ 73575393 MLS

Move-in ready Colonial in one of Weston’s most sought-after cul-de-sac neighborhoods, with sidewalks to Weston Center and the commuter rail. Set on a flat, private 1.39-acre lot near the Cherry Brook ball field, this exceptional home blends timeless architectural character with thoughtful modern updates and a welcoming community known for its block parties. Designed for gracious living and effortless entertaining, the main level features beautiful hardwood floors, an expansive front-to-back living room with fireplace and picture window, private den/office with fireplace, formal dining room with custom built-in, and an updated eat-in kitchen flowing seamlessly into the family room with picture window and fireplace. The light-filled sunroom overlooks a bluestone patio and vast, fenced backyard—perfect for play, gardening, pets, and summer gatherings. Upstairs, the primary suite offers a peaceful retreat with renovated en-suite bath featuring heated floors, hardwood floors, fireplace, and three closets, along with three additional bedrooms and an updated family bath also with heated floors. The finished lower level provides flexible space for a playroom, home gym, media room, or office. Central air, attached two-car garage, abundant natural light, and excellent storage complete the home. Moments to top-ranked Weston schools, boutique shopping and dining, commuter rail, and miles of conservation trails. A rare opportunity to enjoy privacy, community, and convenience in a coveted Weston setting.

4 Cherry Brook Road, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

$4,288,000

4 Beds ⋅ 4 Baths ⋅ 73574433 MLS

4 BEDROOMS, 3 FULL BATHS, 6442 SQUARE FEET.Situated on 2 acres of land with room to develop up to 6,000 more square feet onto the existing property, this is an unbelievable opportunity to be in the best location in Weston with the ability to expand — just a 15-minute commute to Boston. This renovated ranch-style estate is set in Weston's coveted South Side Golf Club neighborhood, bordering conservation land and scenic walking trails. Inside, the home offers light-filled, open living areas, dramatic high ceilings, and expansive windows throughout. A chef-caliber kitchen anchors the home with Wolf and Sub-Zero appliances, quartz counters, and custom cabinetry. The main level features a luxurious primary suite alongside two additional bedrooms, while the finished walkout lower level adds a guest/au pair suite, kitchenette, media room, and additional flexible living space.

80 Doublet Hill Rd, Weston

Listing courtesy of Listing Agent: William Montero from Listing Office: Gibson Sotheby's International Realty.

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 73574322 MLS

Nestled on one of Weston's most picturesque roads, this young Colonial completed in 2008 is a masterclass in timeless design and quality construction. Every detail has been thoughtfully considered, from the sun-drenched interiors to the refined finishes that flow effortlessly from room to room, striking a beautiful balance between elegant and inviting. Spacious gathering areas make entertaining a pleasure, while private retreats throughout the home offer quiet comfort at the end of the day. Meticulously maintained and truly move-in ready, this home reflects pride of ownership in every corner. The location is as exceptional as the home itself just minutes to Weston Center, award-winning schools, scenic conservation trails, shopping, dining, and easy access to major commuting routes. Rarely does a home offer this level of craftsmanship paired with such an unbeatable setting in one of MetroWest's most desirable communities.

703 Boston Post Rd, Weston

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.

$3,695,000

4 Beds ⋅ 6 Baths ⋅ 73574034 MLS

Architecturally designed, this 2024 modern farmhouse is beautifully sited on a level lot in the coveted south side of Weston. This thoughtfully 4 bed/5.5 bath Single Family is crafted with custom finishes across three levels, the sun-drenched open floor plan features 9' ceilings, crown moldings, and seamless flow. The chef’s kitchen offers custom cabinetry, Quartz “Blue Savoi” countertops, and a breakfast area with patio access, opening to a spacious family room with a stone fireplace. Once you enter the garage you are greeted with a large mudroom, half bath and laundry room. Also featured is a walk in pantry. Upstairs features four ensuite bedrooms, including a luxurious primary suite with fireplace, Carrera marble bath, and double walk-in closets. The finished lower level includes a gym/media room, custom wet bar, and full bath. Expansive backyard with room for a pool or sport court. Close to top schools, major routes, and Wellesley.

55 Oakdale Ave, Weston

Listing courtesy of Listing Agent: Christman Johnsson Group from Listing Office: Hammond Residential Real Estate.

$3,850,000

5 Beds ⋅ 6 Baths ⋅ 73573357 MLS

Incredible combination of stunning home with incredible land. Custom 5 bedroom home with over 6700 sq of living space with 12 ft ceilings! Designer kitchen with exposed beams create a unique and warm feeling. Open concept kitchen family room is filled with sunlight. Huge walk-in pantry. Large living room and dining room perfect for entertaining. Incredible cypress wood home office with floor to ceiling bookshelves. Main bedroom suite on the first floor with two full baths connected by a steam shower plus 2 walk-in closets. First floor also includes a 2nd kitchen and bedroom perfect for a guest suite or catering kitchen. Large mudroom. 2nd floor with 3 bedrooms all similar in size plus huge bonus/playroom. Lower level with 10' ceilings and 3000 sq ft currently set up with exercise area is perfect for future expansion. Over 1 acre of yard close to conservation. Great commute to Boston, close to Burchard Park with pickleball and enjoy top rated Weston Schools!

21 Bemis Street, Weston

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.

$1,250,000

3 Beds ⋅ 3 Baths ⋅ 73573157 MLS

Set in a coveted Weston location directly abutting town conservation land, this contemporary home offers an exceptional blend of modern style, comfortable living and everyday convenience. The open-concept floor plan features expansive windows, abundant natural light and a spacious sunroom opening directly to the back deck—perfect for relaxing or entertaining. The versatile layout includes 3–4 bedrooms, 2.5 baths, an inviting eat-in kitchen with ample counter space and pantry, living and dining rooms with built-in shelving, a private home office and a spacious primary suite with en-suite bath. Abundant storage throughout adds to the home's functionality. Enjoy direct access to Weston’s conservation trails, top-ranked schools and a prime location just down the street from the commuter rail, shops and restaurants. A rare opportunity to enjoy the very best of Weston living in an exceptional setting.

287 Glen Rd, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

$6,680,000

5 Beds ⋅ 9 Baths ⋅ 73573009 MLS

Privately sited on a cul-de-sac in Weston’s coveted South Side, this custom-built residence offers beautifully appointed living space across three finished levels, set on 1.38 acres. Designed by award-winning architect Bart O’Brien and built by Whitman Homes, the home brings together architectural distinction, exceptional craftsmanship, and professionally reimagined grounds to create a setting of impressive scale, privacy, and livability. A dramatic two-story foyer introduces formal living and dining rooms with custom millwork, hardwood floors, and multiple fireplaces. At the heart of the home, a light-filled family room with soaring ceilings and a commanding wall of windows opens seamlessly to a chef's kitchen with professional-grade appliances, center island, and two butler's pantries. A richly appointed library/home office and covered porch and bluestone patio complete a main level built for entertaining and everyday living. Five en-suite bedrooms include a luxurious primary suite with fireplace, custom walk-in closets, and beautifully appointed baths. The expansive walkout lower level extends directly to the backyard and features a great room with wet bar, media room, exercise room, and wine cellar. An attached three-car garage completes the residence. The grounds have undergone a significant professionally engineered, town-approved transformation — replacing formerly rocky terrain with an expansive, level, grassed backyard framed by mature trees and refreshed landscaping. The result is a rare combination of usable, private outdoor space for recreation, entertaining, and daily life, seldom found on estate lots of this scale. Ideally set on Weston's South Side bordering Wellesley — moments from Weston and Wellesley town centers, conservation trails, and the Weston public school district, with convenient commuter access to Boston. A distinguished offering in Weston, MA 02493 — where architecture, craftsmanship, and beautifully reimagined grounds come together.

25 Holly Cir, Weston

Listing courtesy of Listing Agent: Team Coyle from Listing Office: Compass.

$6,695,000

6 Beds ⋅ 8 Baths ⋅ 73572991 MLS

Enter through a long tree lined driveway and arrive at this extraordinary Shingle Style Estate on a sprawling 2.58 acre lot in one of Weston's most desirable Southside neighborhoods.This turn key Modern Classic residence offers over 9000sf of sun-filled interior space, 6 en suite bedrooms, a 4 car garage, an oversized chef's kitchen open to a fireplaced family room with french doors leading to stone terraces and a lushly landscaped backyard perfect for entertaining. Bordering conservation land and offering total privacy, this beautiful Nantucket style home built in 2016 offers magnificent level acreage and has potential for a pool and sports court. A lavish lower level features high ceilings, with an entertainment lounge, a glass walled wine cellar, a spectacular gym, full bath and flex space for a media room. The luxurious primary suite has vaulted ceilings, a fireplace, a balcony overlooking the breathtaking grounds and a spa like bathroom with steam shower. This home offers a rare combination of land, location and flawless move in condition. Enjoy fast access to Weston's top ranked public and private schools, all commuter routes and an amazing lifestyle in one of Greater Boston's premier communities.

250 Country Drive, Weston

Listing courtesy of Listing Agent: Rosemary McCready from Listing Office: Compass.

$5,395,000

6 Beds ⋅ 8 Baths ⋅ 73572478 MLS

Set on a private road at the end of a quiet cul de sac, 50 Willard offers exceptional privacy on 1.3 acres in one of Weston’s most desirable settings. This newly constructed 8,300+ sq ft home was designed for modern family living, with a light filled open floor plan, elegant family room, chef’s kitchen with oversized quartz waterfall island, breakfast area, butler’s pantry and wet bar. Four ensuite bedrooms upstairs include a serene primary suite with spa inspired bath and expansive walk in closet. The finished lower level features a gym, sauna, wine room, wet bar, theater and au pair suite. Beautifully landscaped grounds, generous patios and a three car garage create the perfect setting for entertaining, relaxing and family life. Just moments from Weston’s highly regarded schools, golf courses and walking trails, this 6 bed, 6.5 bath home combines new construction luxury with estate like privacy and easy access to Boston.

50 Willard, Weston

Listing courtesy of Listing Agent: Yassien Youssef from Listing Office: Compass.

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