Weston Real Estate

Welcome to Weston, Massachusetts – a hidden gem nestled in the heart of Middlesex County. Known for its picturesque landscapes and rich history, Weston offers a unique blend of suburban tranquility and urban accessibility, making it a desirable destination for families, professionals, and retirees alike.

With its charming New England architecture and sprawling estates, Weston boasts an impressive array of homes that reflect both traditional and contemporary styles. The town is renowned for its exceptional public schools, which consistently rank among the best in the state, ensuring that families have access to top-notch education. Weston’s commitment to preserving its natural beauty is evident in its numerous parks, conservation areas, and scenic trails, perfect for outdoor enthusiasts and nature lovers.

Centrally located, Weston provides easy access to major highways and public transportation, allowing residents to commute to nearby Boston and surrounding areas with ease. The town's vibrant community is enriched by local shops, fine dining options, and cultural attractions, ensuring that there’s always something to do. Whether you're exploring the historic Weston Town Center, enjoying a leisurely afternoon at one of the town’s many parks, or participating in community events, you’ll find a welcoming atmosphere that fosters connection and belonging.

For those seeking a place where charm meets convenience, Weston is an ideal choice. Experience the best of suburban living while being just a stone's throw away from the excitement of city life. Discover your dream home in Weston, where every day feels like a retreat!

Newest Listings in 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.

$1,795,000

3 Beds ⋅ 3 Baths ⋅ 73572129 MLS

A rare opportunity to own a truly distinctive stone residence in Weston. Set on over an acre of beautifully landscaped grounds, this charming 3-bedroom, 3-bath home offers approximately 3,250 square feet of living space with timeless architectural character throughout. Spacious living and entertaining areas, abundant natural light, and unique architectural details create a warm and inviting atmosphere. The standout feature is the heated indoor swimming pool, offering a private year-round retreat for swimming, fitness, entertaining, and relaxation. The property also features mature landscaping, generous outdoor space, privacy, and a two-car attached garage. Conveniently located near Weston Center with easy access to major commuter routes, shopping, dining, and area amenities. A truly one-of-a-kind Weston residence combining character, privacy, space, and an indoor pool—an offering rarely available in this market.

120 Church St, Weston

Listing courtesy of Listing Agent: Alp Kantar from Listing Office: Boston Brokerage Group.

$10,850,000

7 Beds ⋅ 9 Baths ⋅ 73569449 MLS

Few properties offer the sense of privacy, space and comfort found at 15 Claridge Drive while remaining just minutes from Boston. Encompassing 3.75 acres of beautifully landscaped grounds in one of Weston’s most desirable settings, this thoughtfully designed estate offers a rare quality of life with the ease and amenities of a private retreat. Designed by architect Thomas Catalano with landscape design by Morgan Wheelock, the home was created for comfortable family living, entertaining and multigenerational use. Set on a gentle slope overlooking rolling lawns, the property feels peacefully set apart from the pace of everyday life. Mature landscaping, specimen plantings and open grounds create a bucolic and spacious setting where children can play, family and friends can gather, and there is room to simply enjoy being at home. The main home offers five spacious bedrooms, each with an ensuite bath. A private guest apartment includes two bedrooms and a full kitchen, offering flexibility for extended family and guests. The home features multiple rooms for gathering and entertaining, along with two private offices. A four-season conservatory, fully equipped gym, state-of-the-art media room, and wine cellar with tasting room provide spaces for work, wellness, entertainment and relaxation. An elevator provides access to all four floors of the home. Outdoors, the pool, tennis court, lawns and gardens create a private setting for recreation, summer gatherings and quiet afternoons at home. The finest materials were selected to create this exceptional estate. Exterior details include stucco, Dolomitic limestone and Chelmsford granite, a Vermont slate roof and custom mahogany windows by Tischler. Inside, thoughtful materials and meticulous craftsmanship continue throughout. A stone foyer, cantilevered limestone staircase and dramatic three-story rotunda add architectural character, while generous living spaces keep the home comfortable and welcoming. With its combination of privacy, quality, space and proximity to Boston, 15 Claridge Drive offers a rare opportunity to shape daily life around what matters most, a place for family to live, gather, play and grow together.

15 Claridge Drive, Weston

Listing courtesy of Listing Agent: Dean Poritzky from Listing Office: Engel & Volkers Wellesley.

$2,850,000

3 Beds ⋅ 5 Baths ⋅ 73569214 MLS

Completely renovated and expanded in 2023 this custom home offers an exceptional amount of flexible living space -- far beyond a traditional three-bedroom layout -- with multiple rooms across several levels offering endless possibilities for working, entertaining, exercising, relaxing, and pursuing hobbies at home. Abutting a picturesque seasonal brook, the home features large windows that fill the interior with natural light and capture beautiful views. Quality finishes, generous living areas, and a beautiful natural setting make this a truly special Weston home.

28 Bogle, Weston

Listing courtesy of Listing Agent: Valentina Ossikine from Listing Office: Blue Seagull Realty.

$1,350,000

3 Beds ⋅ 4 Baths ⋅ 73566247 MLS

Rarely does a property offer this combination of history, acreage, versatility and potential. Set on 1.38 picturesque acres, this exceptional antique property includes four separate structures—an expanded main residence, accessory dwelling, remarkable three-story barn, and oversized two-car garage—plus a storage shed and two greenhouses. Formerly used as a farm, the property offers a unique opportunity to create a private estate, homestead or multi-generational retreat.The main house is rich in historic character, featuring wide-plank wood floors, beamed ceilings, a welcoming living room, dining room and home office. The spacious primary suite is a true retreat with a vaulted, beamed ceiling, en suite bath and walk-in closet. Historic details blend beautifully with thoughtful updates, including a newer gas heating system and updated electrical.The accessory house features an eat-in kitchen with abundant cabinetry, comfortable family room, spacious bedroom and walk-in closet. Mini-splits provide efficient heating and cooling. The impressive three-story barn, complete with a full bath and potential bedroom, offers endless possibilities for studio, office, guest space, recreation or additional living space.Renovate, expand or move right in—this one-of-a-kind property invites you to imagine what’s possible. Ask about the $250,000 preservation fund available to buyer.

118 - 120 Summer Street, Weston

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

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