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$2,795,000
4 Beds ⋅ 4 Baths ⋅ 73550628 MLS
Experience the perfect balance of luxury, privacy & effortless one-level living in this renovated contemporary, nestled on 1.64 acres in the coveted Webster Hill Estates neighborhood. Designed to embrace its natural surroundings, the sun-filled open floor plan was designed for gathering & enjoying every season. The airy kitchen with quartz countertops, premium appliances, pantry, opens to the dining area as well as the family room & flows seamlessly to the wraparound porch, creating exceptional indoor-outdoor living overlooking peaceful woodlands. A sprawling living room with handsome fireplace is the perfect place to unwind. A luxurious primary suite with luxurious master bath, while the finished walkout lower level provides flexible space with a recreation room, sitting room, two bedrooms and a full bath. Outside, enjoy exceptional privacy with expansive grounds & private walking trails, all while being just minutes from Weston Center, the Rail Trail & the commuter rail.

34 Hilltop Rd, Weston

Listing courtesy of Listing Agent: Arianna Brown from Listing Office: Compass.
$6,975,000
6 Beds ⋅ 8 Baths ⋅ 73546861 MLS
This newly-constructed, Contemporary offers the pinnacle of luxury living on Weston’s coveted Southside. The dramatic, 2-story foyer flows seamlessly into both formal and informal spaces. The dining / living room is optimal for family gatherings & entertaining, and the custom kitchen w/an exceptional quartz island, high-end appliances and wet bar adjoins a generous eat-in area and fireplaced family room overlooking the beautiful grounds. There is also an ensuite bedroom/office, large mud room, pantry and powder room on this floor. A stunning, white oak staircase with glass railings leads to the 2nd level featuring an elegant primary suite with a gorgeous, spa-like bath and grand, walk-in closet, three ensuite bedrooms and laundry. The lower level offers a bar area and recreation room, ensuite bedroom, media room with potential for a golf simulator, gym and full bath with sauna. The expansive outdoor space has a lovely patio with a fire pit and kitchen, and there is a potential for a pool. A true masterpiece close to top-rated schools and Weston / Wellesley town centers.

5 Deer Path Lane, Weston

Listing courtesy of Listing Agent: Beyond Boston Properties Group from Listing Office: Compass.
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 73526239 MLS
Set on a beautifully landscaped 1.43-acre lot, this contemporary Cape-style home blends spacious living with architectural character and resort-style amenities. Offering 3 bedrooms, including a private primary suite with en suite bath, the home is designed for both everyday comfort and effortless entertaining. The dramatic great room features soaring ceilings, skylights, fireplace, and wet bar, while a separate living room with fireplace and formal dining room provide inviting spaces to gather. The kitchen with stainless steel appliances and abundant cabinetry opens seamlessly to the main living areas and sunroom overlooking picturesque grounds, creating a peaceful year-round retreat. Additional highlights include a versatile loft, home office, finished lower-level playroom, and flexible space for work, guests, or recreation. Outside, enjoy a private backyard oasis with in-ground pool, expansive lawn, and mature landscaping. Exceptional South Side offering near top ranked schools!

242 Winter St, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
$5,995,000
5 Beds ⋅ 7 Baths ⋅ 73525277 MLS
New construction in one of Weston’s most exclusive neighborhoods, blending transitional design, exceptional craftsmanship, and state-of-the-art systems. This sun-filled home offers 5 bedrooms, 5 full and 2 half baths, 10’ ceilings, oversized windows, and curated finishes that offer scale and warmth. The chef’s kitchen features 36" refrigerator and a 36” freezer, double ovens, wine tower, and walk-in pantry, opening to an expansive family room with custom tray ceiling. The main level includes a private office, formal living and dining rooms, custom mudroom, and flexible first-floor primary or guest suite. Upstairs offers a second primary, three additional bedrooms, a lounge/game room, and laundry. The finished lower level with 11.5’ ceilings includes a second kitchen, theater, large entertaining space, and full bath. Set on 1.23 level acres with circular drive, patio, outdoor kitchen, pool potential, and 3-car garage, just minutes to town, top-ranked schools, and the commuter rail.

10 Hitching Post Lane, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
$2,499,900
4 Beds ⋅ 7 Baths ⋅ 73522675 MLS
Welcome to 130 Summer St. This spectacular approx 5181 sqft Contemporary masterpiece is set on 2.67 private acres featuring sprinkler system and backyard sports court. Built for entertaining, the chefs kitchen boasts a large center island, Wolf & Sub-Zero appliance, add'l refrigerator / ice maker built into bar, and a custom fireplace pizza oven. Sliders leading out front, with open flow leading into the fireplaced, cathedral ceiling, living room. All 4 bedrooms feature en-suite full baths, highlighted by two primary suites. the 1st floor suite includes a renovated full bath with jacuzzi tub, separate shower stall & walk in dressing room / closet. The oversized 2nd floor suite features a full bath, walk-in closet & private laundry. The fully finished basement adds a fireplaced den, full bath and private office. Completing this home is the heated 3 car garage spaces. This home offers unmatched luxury and convenience

130 Summer St, Weston

Listing courtesy of Listing Agent: The APEX Team from Listing Office: Results Realty.
$3,250,000
4 Beds ⋅ 6 Baths ⋅ 73513386 MLS
This sophisticated, contemporary Colonial, custom built in 1995, offers over 6,400 sq ft of beautifully updated living space with high-end finishes throughout. Ideally sited on a private Southside cul-de-sac, it’s surrounded by meticulously maintained, English garden–style grounds, creating a serene setting.Featuring 4 bedrooms, 5 full baths, and 1 half bath, the home blends timeless elegance with modern comfort. Sun-filled interiors and a flowing layout are ideal for everyday living and entertaining. The updated kitchen showcases honed white marble countertops, professional-grade appliances, and a wood-fired oven, opening to a stunning family room with vaulted ceilings and walls of windows.Additional highlights include a tiger cherry–paneled living room with coffered ceiling and stone fireplace, formal dining room, and sunroom. Upstairs, the primary suite offers a fireplace, sitting area, and spacious marble bath.

1 Graystone Ln, Weston

Listing courtesy of Listing Agent: Dean Poritzky from Listing Office: Engel & Volkers Wellesley.
$7,550,000
6 Beds ⋅ 9 Baths ⋅ 73511372 MLS
Designed for elevated everyday living and effortless entertaining, this exceptional residence at 132 Country Drive in Weston offers the perfect blend of luxury, comfort, and convenience. Set in one of Weston’s most desirable neighborhoods—known for its top-ranked schools and peaceful surroundings—the home is just minutes from Boston and major commuter routes. Inside, an oversized chef’s kitchen with a large center island and walk-in pantry anchors the open-concept layout. Expansive living and dining spaces are filled with natural light, creating an inviting atmosphere throughout. Upstairs, four spacious bedrooms each feature en-suite baths and custom closets, including a luxurious primary suite with a private deck, spa-like bath, and walk-in closet. The lower level is designed for entertaining and wellness, complete with a second living area, home theater, golf simulator, gym, sauna, and more. Outdoors, the walk-out backyard offers a fire pit, dining space, and room for a future pool.

132 Country Drive, Weston

Listing courtesy of Listing Agent: Simon Collaborative Group from Listing Office: Gibson Sotheby's International Realty.
$5,999,000
4 Beds ⋅ 7 Baths ⋅ 73511241 MLS
This California Contemporary defines sophisticated living at its finest. Majestically nestled on 2 private, stunning acres in the coveted Weston Country Club neighborhood.The terraced grounds are accented with stone patios, a salt water pool and cabana. Soaring ceilings and an abundance of sunlight flood the multiple levels of thoughtfully designed living spaces. A dramatic family room has sweeping views of the magnificent rolling grounds while overlooking the open floor plan of the main entertainment level The bright and spacious kitchen with a prep pantry and breakfast room lead to the outside patios. The primary suite is adorned with a beautiful wood beamed ceiling and brick fireplace. Dual spa-like bathrooms are complemented by dual walk in closets. 3 en-suite bedrooms are situated in their own private enclaves. The lower level features a fabulous playroom, traditional media room and a brick wine cellar. Stone walls, a receiving court and 4 car garage complete this special home

44 Meadowbrook Road, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 73506812 MLS
Introducing a sophisticated contemporary retreat offering exceptional privacy, tranquil surroundings, and a seamless connection to nature. The open, versatile layout blends indoor and outdoor living for an elevated entertaining experience.The well-appointed kitchen flows into a spacious dining area and multiple inviting sitting spaces. Three beautifully designed bedrooms, including a bright and airy primary suite, complete the main living level.The walk-out lower level opens to stunning stone patios and terraces, including a custom fire pit area surrounded by peaceful natural scenery. A separate retreat with soaring beamed ceilings and a cozy sitting area is ideal for a home office or studio. Enjoy fishing in Hobbs Brook, serene wooded views, and easy commuter rail access to Boston in this truly one-of-a-kind home.

40 Hobbs Brook Road, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
$2,480,000
4 Beds ⋅ 3 Baths ⋅ 73500883 MLS
Tucked into Weston’s sought-after Kings Grant neighborhood, this expanded and versatile home offers exceptional flexibility for today’s lifestyle needs. The dramatic living room features soaring ceilings, a wood-burning fireplace, and direct access to a bright sunroom, creating a warm and inviting setting for everyday living and entertaining.The kitchen flows seamlessly into the dining area, forming the heart of the home — an inviting gathering space for daily family life and casual entertaining. The first floor also includes a private primary suite and a dedicated study that can easily function as an additional bedroom, guest room, or home office.Upstairs offers three spacious bedrooms and a full bathroom, providing comfortable separation and flexibility for family or guests.A detached garage includes two parking bays plus a separate workshop.A separate access carriage house offers flexible bonus space for RV truck parking, workplace, and possible ADU conversion.

39 Kings Grant Rd, Weston

Listing courtesy of Listing Agent: Keystone Homes Group from Listing Office: Keller Williams Realty Boston Northwest.
$14,850,000
7 Beds ⋅ 12 Baths ⋅ 73493889 MLS
Timeless elegance meets modern luxury in this extraordinary Weston estate, situated on 5.3 stunning acres just minutes from Boston. Built by a renowned local builder and reimagined with Leslie Fine Interiors, this home blends superior craftsmanship, global influences and design. Bright, inviting spaces include a newly renovated kitchen, luxurious primary suite, soaring ceilings, and dramatic walls of glass. The property is a haven for entertaining, featuring a resort-style pool, pool house, orchard, indoor basketball court, private theater, and a space-themed arcade. Custom elements and unique spaces add sophistication, while a wine cellar, billiards/ping pong area, and expansive granite patios elevate the experience. Every inch of this masterpiece is crafted with exquisite attention to detail, offering a seamless fusion of elegance and comfortable living! A true destination home where art, design, and luxury converge to create an amazing property!

67 Byron Road, Weston

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$3,995,000
5 Beds ⋅ 7 Baths ⋅ 73486131 MLS
An award-winning architect brings sophisticated modern design to Weston at 11 Winthrop Circle. This extraordinary home offers 8,500 sq. ft. of sun-filled living space with an open floor plan, expansive windows, and beautiful contemporary mill work. The Poggenpohl kitchen flows seamlessly into a stunning family room with fireplace, perfect for everyday living and entertaining. Elegant living and dining rooms provide wonderful gathering spaces, while a first-floor office can also serve as a guest bedroom. The second floor features five bedrooms, including an exceptional primary suite w/ a European-inspired spa bath. The finished lower level offers flexible space for a media room, game room, gym, or playroom. Set on a private, beautifully sited lot, the home captures abundant natural light throughout the day. Conveniently located within walking distance to Cat Rock Park, with over 80 scenic acres and 5.5 miles of trails. A special home combining design, space, and an exceptional location.

11 Winthrop Circle, Weston

Listing courtesy of Listing Agent: Simon Collaborative Group from Listing Office: Gibson Sotheby's International Realty.
$3,245,000
5 Beds ⋅ 4 Baths ⋅ 73485263 MLS
Stunning 5-bedroom, 3.5-bath contemporary multi-level home, thoughtfully gut renovated and expanded in 2008, offering impressive space, craftsmanship, and design. The gourmet eat-in kitchen opens seamlessly to a generous family room with fireplace and custom built-ins, creating an ideal setting for everyday living. An elegant formal living room and dining room with fireplace and built-ins add charm and functionality for entertaining. The luxurious primary features two walk-in closets and a spa bath. Two dedicated home office areas provide flexibility for today’s lifestyle. The finished game room with wet bar and fireplace is perfect for recreation and gatherings. Enjoy outdoor living on the patio with a built-in grill and fire pit, or relax in the 3 season porch. Highlights include soaring 12’ ceilings, Murano light fixtures, custom built-ins, and high-end finishes throughout. A heated three-car garage with epoxy floors and an organized garage system completes this impressive home.

11 Hillcrest Road, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
$9,990,000
5 Beds ⋅ 10 Baths ⋅ 73475863 MLS
This peerless modern 2-acre estate is located in a highly desired private neighborhood in Weston. Exterior features a beautiful, flat landscaped yard, patio w/grill, and a full sports court. The luxurious 5 bed, 7f/3h bath interior features lofty 12’ high ceilings with walls and ceilings of glass, opening the space to the exterior and drenching this home in sunlight. Smart home features include Lutron shades to provide unmatched comfort. Unmatched detail throughout,with main level foyer, floating staircases, and an open flow to the main dining and living areas. Chef’s kitchen w/top of the line appliances & breakfast bar opens to the large family room with fireplace. Huge office, mudroom, and large 3car garage finish the main level. 2nd floor features an amazing master suite, w/2 large baths and dressing rooms. 4 additional bedroom suites and laundry finish the 2nd floor. The lower level features a large gym, pickleball/sportsroom, playroom/media room, cedar closet, and amazing storage.

70 Possum Rd, Weston

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.
$6,950,000
5 Beds ⋅ 7 Baths ⋅ 73463766 MLS
Architecturally striking Prairie-style contemporary custom built with a refined focus on nature, craftsmanship, and simplicity. South-facing open layout with walls of glass overlooking professionally designed grounds and serene private setting. Heated pool with automatic cover and integrated jacuzzi, with pool and landscape irrigation supplied by a private well. German-engineered windows offer exceptional thermal performance. Home features high-performance heat pump heating, 400-amp electrical service, and an automatic natural gas–powered generator. Motorized blinds throughout. Dramatic kitchen and great room with lacquered cabinetry, dual oversized islands, premium appliances, and gas fireplace. Spa-like primary baths with heated floors and rainfall showers. Finished lower level offers generous bedroom, fitness, and entertaining spaces. Heated three-car garage. Covered porch and 1.39-acre lot with overlook the Japanese inspired gardens and private grounds.

15 Myles Standish Rd, Weston

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

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