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25 Forest Ridge Road, Weston
$2,288,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73594503 MLS ⋅ 4,591 SqFt.
Gracious ranch-style home on 1.22 acres in a desirable Weston cul-de-sac setting, offering 4 bedrooms, 3 full baths and approx. 4,591 sq. ft. of versatile living space. Sun-filled interiors showcase hardwood floors, custom built-ins and expansive windows framing scenic views. A fireplaced living room flows into the dining room, while the inviting family room features a vaulted ceiling, fireplace and custom cabinetry. The newly renovated kitchen (2026) offers stainless steel appliances, a large island, skylights and generous storage. The spacious primary suite includes a walk-in closet, a luxurious bath and a sitting/office area. Two additional bedrooms and a full bath complete the main level. The finished walkout lower level provides a fourth bedroom with a renovated en-suite bath, a recreation room, private office, exercise room, laundry and cedar closet. Enjoy outdoor living on the patio, a sunlit yard and the convenience of an attached 2-car garage. Updates include a roof and kitchen skylights (2018), plus driveway, septic tank, oil burner and water heater (2021). Convenient to the commuter rail, bike path, Weston schools, shopping and dining, with easy access to I-95 and I-90.

25 Forest Ridge Road, Weston
6 Overlook Dr, Weston
$1,199,000
ACTIVE Status ⋅ 73594428 MLS
An exciting opportunity to build. Set on an expansive 40,000+ sq. ft. lot, this property offers potential for new construction in a highly desirable community known for its top-rated schools and convenient commuter access. Percolation testing has been completed to meet new construction standards, with results supporting the potential for more bedrooms than the existing septic system. With the water shut off, electric service removed, and heating removed, several initial site preparations are already in place to help get your project underway. Draft plans are available upon request. Whether you’re an end user looking to build your dream home or builder seeking your next project, this is a chance to do something special. Conveniently located near parks and major routes, this property is ready for your vision.

6 Overlook Dr, Weston
6 Overlook Dr, Weston
$1,199,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73594426 MLS ⋅ 1,390 SqFt.
An exciting opportunity to build. Set on an expansive 40,000+ sq. ft. lot, this property offers potential for new construction in a highly desirable community known for its top-rated schools and convenient commuter access. Percolation testing has been completed to meet new construction standards, with results supporting the potential for more bedrooms than the existing septic system. With the water shut off, electric service removed, and heating removed, several initial site preparations are already in place to help get your project underway. Draft plans are available upon request. Whether you’re an end user looking to build your dream home or builder seeking your next project, this is a chance to do something special. Conveniently located near parks and major routes, this property is ready for your vision.

6 Overlook Dr, Weston
451 Wellesley St, Weston
$4,800,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 73593840 MLS ⋅ 12,148 SqFt.
Set on 5.6 private acres on Weston’s highly desirable south side, this impressive estate offers exceptional privacy and timeless appeal. Tucked at the end of a long, winding driveway, this Federal Colonial blends classic architecture with comfortable living, featuring sun-filled interiors, a dramatic two-story family room with fireplace, a bright sunroom, and a stylish home office. The flexible layout includes a first-floor bedroom suite ideal for guests, while upstairs offers five bedrooms, including a spacious primary suite with fireplace, luxurious bath, dressing area, and multiple walk-in closets, along with four additional bedrooms and three full baths. The finished walk-out lower level with a separate entrance includes a kitchen, bedroom, full bath, exercise and media rooms—perfect for extended living or entertaining. Complete with a five-car garage and located just minutes from the state’s top public schools, with convenient access to Boston.

451 Wellesley St, Weston
50 Willard, Weston
$4,950,000
6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 73593022 MLS ⋅ 8,309 SqFt.
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
819 Boston Post Road, Weston
$1,350,000
CONTINGENT Status ⋅ 73593002 MLS
Open, level, and sunny 1.92-acre lot of developable upland meadow. The property abuts hundreds of acres of town conservation land with miles of connecting trails, and a sidewalk leads to Weston Town Center and the Wayland shops, including the Coach Grill restaurant. As the last undeveloped parcel on Boston Post Road, it offers top-rated schools and a convenient commuter location. Build your dream home today!

819 Boston Post Road, Weston
643 Boston Post Rd, Weston
$2,850,000
3 Beds ⋅ 5 Baths ⋅ CONTINGENT Status ⋅ 73592991 MLS ⋅ 3,504 SqFt.
SUNDAY OH CANCELED. Completed in 2023, this beautifully designed residence offers the rare combination of modern living in the heart of Weston Center and an expansive, level 1.36-acre setting. Exceptional craftsmanship and high-end finishes are evident throughout, with a sophisticated kitchen, beautifully appointed baths with radiant floor heat, and thoughtful architectural details elevating every space. The open, light-filled floor plan flows seamlessly between the kitchen, dining and living spaces and an inviting family room overlooking the backyard. A first-floor primary suite provides a private retreat, while the second level offers two additional en-suite bedrooms, a spacious bonus room, loft and laundry. The lower level extends the home’s versatility with a recreation and sitting area, dedicated gym and turfed activity space, bringing the home’s total usable space to approximately 4,303 SF. An expansive deck and exceptionally large, level backyard offer room to entertain, play and unwind—all in a convenient central Weston location. Seller is upgrading the septic to a five-bedroom system, creating possibilities for future expansion, such as an ADU. Move in and make it home for the holidays!

643 Boston Post Rd, Weston
5 Deer Path Lane, Weston
$6,495,000
6 Beds ⋅ 8 Baths ⋅ CONTINGENT Status ⋅ 73591991 MLS ⋅ 8,773 SqFt.
A true masterpiece awaits! This stunning, newly-constructed home 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, pool house and more. Conveniently located close to top-rated schools, Weston / Wellesley town centers, trails and commuting routes.

5 Deer Path Lane, Weston
445 Glen Rd, Weston
$1,790,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73591604 MLS ⋅ 2,420 SqFt.
A rare opportunity to own a single family in the highly desirable South Side of Weston, ideally situated on one of the town's most scenic roads! Set on 1.4 acres, this charming 4-bedroom 2.5 Bath New England home offers incredible potential to expand, or create your dream home. Enjoy the convenience of being just a short walk to Weston Middle and High Schools, with easy access to Wellesley, Route 9, major highways, and nearby conservation trails. The main level features an eat-in kitchen, dining and living rooms with built-ins, a fireplace, spacious sun-filled family room, full bath, office nook, and laundry. Upstairs offers 4 generously sized bedrooms and 1.5 baths. A detached garage/workshop, storage shed, stone walls, patio, and expansive backyard provide plenty of space and flexibility for outdoor enjoyment and entertainment. A fantastic opportunity to bring your vision to life in one of Weston's most sought-after locations!

445 Glen Rd, Weston
172 Country Drive, Weston
$3,295,000
6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73589867 MLS ⋅ 5,354 SqFt.
Set on 1.58 professionally landscaped acres in one of Weston’s most desirable neighborhoods, this brick Colonial has been extensively renovated and offers a spacious, highly functional floor plan. The updated kitchen features new appliances, a walk-in pantry, and breakfast area with wet bar, opening to a family room with fireplace. The main level is complete with a formal dining room, front-to-back living room with a second fireplace, and private first-floor office with custom built-in bookcases. Upstairs, all five bedrooms are conveniently located on one floor, including the primary suite with a newly renovated spa-like bath, large walk-in closet, and expansive sunroom ideal as a sitting area or private retreat. The finished lower level offers exceptional flexibility with a large recreation room, additional bedroom or bonus room, two full baths, kitchenette, exercise room, and exterior access to the backyard—ideal for extended family or guests. Surrounded by mature landscaping with private wooded views and paths, the property also includes a two-car garage, spacious mudroom, and two laundry areas. Move-in ready and filled with natural light, this exceptional Weston home offers generous living space in a beautiful setting with convenient access to schools, town center, and Boston.

172 Country Drive, Weston
306 Merriam Street, Weston
$1,599,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73589150 MLS ⋅ 2,964 SqFt.
Charming Cape on over 3 acres of luscious grounds,. This 4 bedroom home offers versatile/open floor plan with gorgeous hardwood floors and updated windows and elevated lighting plan including many lights on dimmers. Enchanting flat stone walkway meanders to front door. Gracious entry with coat closet for guests. Formal living room with classic fireplace and picture window. Home office with vaulted ceilings and french doors. Mudroom with exterior access and garage. Washer/dryer hook up on main level and in basement. First floor bedroom and full bath. Dining room connects to centrally located kitchen with granite countertops with seating, stainless steel appliances, and eat-in-kitchen area, large family room seamlessly connected. Huge deck with built in seating, overlooking private oasis. Second floor with sunny primary suite and ensuite bath, walk-in cedar closet and dressing area. Two additional bedrooms both with large walk-in closets. Bonus, flex room for upstairs office or exercise. Tasteful mature landscaping, stone walls, an outdoor fieldstone chimney for gathering and grilling. Large unfinished basement, with separate wine room potential. Sidewalk to town center. Close to sought after Silver Hill Neighborhood and commuter rail flag stop. Top rated Weston Schools.

306 Merriam Street, Weston
863 Boston Post Road, Weston
$3,495,000
6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73587759 MLS ⋅ 6,485 SqFt.
Privately set on 2.7 acre, this distinguished 16-room landmark residence embodies the timeless elegance and gracious scale of a classic New England estate, thoughtfully enhanced for modern living. A stately entry welcomes you to beautifully preserved architectural details, including dramatic ceilings and windows, exquisite millwork and hardwood floors throughout. Designed equally for grand entertaining and intimate gatherings, the formal living room is anchored by a handsome fireplace, while the richly appointed library, with its own fireplace and built-in bookcases, offers a warm and inviting retreat. A comfortable family room provides a relaxed setting for everyday living. At the heart of the home, the exceptional chef’s kitchen features a generous dining area and beautifully appointed butler’s pantry with direct service to the expansive formal dining room, where a fireplace creates an elegant backdrop for memorable occasions. A first-floor guest bedroom or dedicated home office provides exceptional flexibility. The second floor offers a private bedroom level with a spacious primary with full bath, three additional bedrooms and two more full baths. A separate staircase leads to a private accessory apartment with its own kitchen, sitting room, two bedrooms and full bath—ideal for extended family, guests or staff. Expansive covered porches overlook the heated pool and broad open lawns, creating a beautiful setting for summer entertaining and relaxed outdoor living. Rarely does a property combine such gracious proportions, historic character, versatility and convenience. The 2.7 acres include an approximately 1-acre buildable lot currently going through the town of Weston Flexible Development zoning and subdivision process. Ask listing agent for details.

863 Boston Post Road, Weston
1 Cabin Rd, Weston
$5,850,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73583804 MLS ⋅ 4,252 SqFt.
Set on 4.66 acres of beautiful, wooded land, 1 Cabin Rd presents a rare opportunity to create something truly special in Weston. Tucked into a private, natural setting, the property offers an exceptional sense of peace, seclusion, and connection to the surrounding landscape. Whether envisioned as the setting for a thoughtfully designed new home, a renovation or expansion, or another long-term vision, the property provides a unique canvas for a buyer looking to create something truly tailored to their needs. With its generous acreage, wooded setting, and privacy, 1 Cabin Rd is an opportunity to imagine what could be created here.

1 Cabin Rd, Weston
1 Cabin Rd, Weston
$5,850,000
ACTIVE Status ⋅ 73583805 MLS
Set on 4.66 acres of beautiful, wooded land, 1 Cabin Rd presents a rare opportunity to create something truly special in Weston. Tucked into a private, natural setting, the property offers an exceptional sense of peace, seclusion, and connection to the surrounding landscape. Whether envisioned as the setting for a thoughtfully designed new home, a renovation or expansion, or another long-term vision, the property provides a unique canvas for a buyer looking to create something truly tailored to their needs. With its generous acreage, wooded setting, and privacy, 1 Cabin Rd is an opportunity to imagine what could be created here.

1 Cabin Rd, Weston
95 Sylvan Ln, Weston
$2,650,000
4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73583759 MLS ⋅ 3,934 SqFt.
Make it home in time for the holidays! Bathed in beautiful natural light, this exquisitely updated 3,934-square-foot Garrison Colonial offers four bedrooms, four and a half baths, and an elegant open-concept layout designed for refined everyday living and effortless entertaining. Sophisticated finishes include a chef’s kitchen appointed with a premium Thermador appliance package. The luxurious primary suite features an expansive walk-in closet ready for the buyer to customize and a spa-like en suite bath with a deep soaking tub and generous walk-in shower. Upstairs, three additional bedrooms, two bathrooms, and a convenient laundry room provide comfort and ease. Ample office and bonus spaces, along with a walkout lower level, offer exceptional flexibility for work, guests, recreation, or wellness. Extensive updates—including brand-new electrical, plumbing, HVAC and roof—ensure peace of mind and turnkey living. Set on a gorgeous street on Weston’s coveted south side, the property is complemented by a level, beautiful yard and an abundance of sunlight throughout the day.

95 Sylvan Ln, Weston
111 Summer Street, Weston
$1,250,000
ACTIVE Status ⋅ 73583702 MLS
OPPORTUNITY TO BUILD YOUR DREAM HOUSE IN A+ SOUTH SIDE WESTON LOCATION. Beautiful, mature, 40k sq ft wooded lot with existing 4 bedroom cape home in a neighborhood replete with multi-million-dollar estate homes only 12 miles to Boston. Located with easy access to top ranked local and private schools, Weston Center, Wellesley Center, Newton, all major routes and commuter transit (1 mile to entrance ramp to Mass Pike & I-95/128), and close to Brandeis (North Station) AND Auburndale (South Station) Commuter Rail Stations, close to Riverside/Grove Street green line station, the Weston Golf Club and Leo J. Martin Memorial Golf Courses. Please make an appointment to walk the land. Passing title V.

111 Summer Street, Weston
448 Concord Road, Weston
$4,995,000
6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 73579890 MLS ⋅ 11,330 SqFt.
A rare and exceptional six bedroom estate with timeless architectural appeal, Designed by Jan Gleysteen Architects, this custom home showcases unsurpassed craftsmanship, meticulous attention to detail and curated finishes throughout. The first floor welcomes you with the grand foyer's dramatic staircase, a richly appointed mahogany-paneled library, and elegant formal living and dining rooms. The kitchen includes a large island, breakfast room that leads to the family room anchored by a beautiful limestone fireplace and screened in porch. Five en suite bedrooms are highlighted by the expansive primary suite complete with a spa-like bath and generous walk-in closets. The third floor has a sun-filled sitting room with a 6th bedroom. The lower level offers a bonus room with bar, golf simulator room and home gym. Set on one of Weston's most picturesque roads close to trails and major commuting routes to Boston and Cambridge.

448 Concord Road, Weston
28 River Road, Weston
$1,175,000
3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579333 MLS ⋅ 1,925 SqFt.
Beautifully renovated 8-room farmhouse blending timeless character with modern comfort and style. A welcoming front porch, composite back deck and lovely level lot create inviting spaces for outside relaxing and entertaining. The main level features a spacious open concept family room, dining room, and beautifully appointed kitchen with hardwood floors, top-of-the-line appliances, and gas cooking. Upstairs the primary suite offers an ensuite bath, expansive closet space, and skylights that fill the room with natural light plus two additional bedrooms, a private home office, and a full bath, all with hardwood floors. The unfinished lower level provides abundant storage and excellent potential for future living or recreation space. A one-car garage adds convenience. Close to shopping, the Weston Golf Club, top Weston schools! Commuters dream with easy access to the Massachusetts Turnpike, Route 95, and commuter rail trains to both North and South Station.

28 River Road, Weston
20 Blueberry Hill Road, Weston
$2,295,000
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579326 MLS ⋅ 5,450 SqFt.
Set in one of Weston’s idyllic and most beloved Southside neighborhoods, this extensively renovated home blends timeless comfort with modern living. Gleaming hardwood floors flow through the inviting living and dining rooms into the beautifully reimagined kitchen, featuring an oversized marble island, premium appliances, and a bright eat in area that opens to an expansive deck overlooking the serene grounds. The adjacent family room, complete with custom built-ins and a fireplace, offers the perfect setting for family gatherings and entertaining. A palatial primary suite with a private sunroom, dual walk in closets, and a stunning stained glass window provides a true retreat. Two additional bedrooms complete the main level. The lower level further expands the living space with a recreation/media room, yoga room, gym, additional bedroom suite, and versatile spaces for a home office, playroom, or guest space. Turnkey and beautifully updated, including a new roof in 2026 and 5 bedroom septic, this special home offers an easy commute to Boston all with Weston's with top-rated schools.

20 Blueberry Hill Road, Weston
130 Summer St, Weston
$2,475,000
4 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 73579146 MLS ⋅ 4,812 SqFt.
Welcome to Weston! This exceptional transitional Colonial makes a striking first impression, with a meandering tree-lined driveway leading to a private courtyard framed by mature hedging, a classic fountain, inviting patio, and elegant granite entry. Designed for both luxurious living and effortless entertaining, the home offers a first-floor living option with a beautiful fireplace, recently updated primary bath, and walk-in closet. The main living room is filled with natural light from oversized windows and anchored by a handsome stone fireplace, offering a bird’s-eye view of the backyard courtyard, complete with firepit and sport court for year-round enjoyment. The kitchen and dining areas flow seamlessly into the living space, highlighted by a built-in stone pizza oven. The beautifully appointed kitchen features custom cabinetry, dramatic counter-to-ceiling windows surrounding the large undermount sink, and a 48-inch WOLF range with direct-vent hood—truly a chef’s dream. The attached garage opens to a well-appointed mudroom with a second entrance, laundry, half bath, and abundant storage. Upstairs, a second primary suite offers a tile walk-in shower, custom walk-in closet, and its own washer and dryer, while two additional bedrooms each feature ensuite baths. The walkout lower level provides a spacious family room with fireplace, abundant windows, additional flexible rooms, and a full bath, with direct access to the expansive grounds. An exceptional Weston offering where privacy, elegance, and everyday comfort come together. Welcome Home!

130 Summer St, Weston
73 Chestnut Street, Weston
$9,450,000
7 Beds ⋅ 11 Baths ⋅ ACTIVE Status ⋅ 73577074 MLS ⋅ 12,461 SqFt.
Magnificent residence sited on 2.78 private and pristine acres in one of Weston’s most coveted locations. Completely renovated with the highest level of finishes offering every modern amenity. This exceptional home offers estate-like living designed equally for comfortable family life and sophisticated entertaining. The modern designer kitchen anchors the center of the home and flows seamlessly into the sumptuous fireplaced family room with access to private deck overlooking the pool and grounds and spacious screened porch, creating an inviting open floor plan. The formal dining room enhanced by a butler’s pantry is complemented by a well-proportioned formal living. Multiple home offices, a generous mudroom, dog-washing room and a large gym are just a few of the exceptional features this home offers. This home offers two luxurious primary suite options, one on each of first and seconds levels providing exceptional flexibility. All bedrooms are generously sized and feature ensuite baths. The lower level provides dedicated play, craft and billiard spaces along with ample storage. A sleek and private two-bedroom accessory dwelling with separate entrance and two-car garage offers additional accommodations. Resort-like grounds are enhanced with a beautiful pool, well equipped cabana, expansive patios, and private tennis court, creating an extraordinary setting for year-round living and entertaining. The incomparable residence provides the ultimate in private living while offering easy access to Boston and Weston’s renowned schools.

73 Chestnut Street, Weston
37 School Street, Weston
$1,575,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73576394 MLS ⋅ 2,840 SqFt.
Beautifully sited on over 2 private acres, this 8-room, 4-bed, 3-bath home offers comfort, charm, and room to grow. The spacious living room features a fireplace and hardwood floors, flowing into a formal dining room with two classic corner cabinets and a sun-filled kitchen with white cabinetry, stainless appliances, and center island. Two generous bedrooms and a full bath complete the first floor; Upstairs are two more spacious bedrooms including one with oversized closet and built ins and another full bath. The finished lower level includes a family and game room, kitchenette, laundry, full bath, and ample storage, a possible guest or au pair suite. Enjoy the huge, level, fenced-in yard. 2 car garage. Sidewalks to Weston’s top schools, library, vibrant town center, Memorial Pool, Weston Golf Club & Land’s Sake Farm. 15 miles to Boston and close to all major routes and the commuter rail. A rare opportunity in a premier location to renovate, expand or move right in!

37 School Street, Weston
94 Sunset Road, Weston
$1,100,000
3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73575873 MLS ⋅ 2,300 SqFt.
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
21 Westerly, Weston
$4,585,000
6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 73575514 MLS ⋅ 8,000 SqFt.
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
4 Cherry Brook Road, Weston
$2,075,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73575393 MLS ⋅ 3,340 SqFt.
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
703 Boston Post Rd, Weston
$2,495,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73574322 MLS ⋅ 5,446 SqFt.
Nestled on one of Weston's most picturesque roads, this young Colonial completed in 2008 offers something truly rare in Weston: a coveted in-town location. The Town Green, Weston Center, the library, the elementary schools, and Land's Sake Farm, with its seasonal harvests and pick-your-own fields, are all just moments from your front door. In a town known for sprawling estates and winding country roads, a home that pairs this level of craftsmanship with such close proximity to the heart of town is a special find. Inside, 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. Beyond the center, enjoy scenic conservation trails, nearby shopping and dining, and easy access to major commuting routes. Rarely does a home offer this blend of quality, character, and town center convenience in one of MetroWest's most desirable communities.

703 Boston Post Rd, Weston
55 Oakdale Ave, Weston
$3,595,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73574034 MLS ⋅ 5,126 SqFt.
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
21 Bemis Street, Weston
$3,850,000
5 Beds ⋅ 6 Baths ⋅ UNDER AGREEMENT Status ⋅ 73573357 MLS ⋅ 6,700 SqFt.
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
25 Holly Cir, Weston
$6,680,000
5 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 73573009 MLS ⋅ 7,766 SqFt.
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
250 Country Drive, Weston
$6,350,000
6 Beds ⋅ 8 Baths ⋅ PRICE CHANGED Status ⋅ 73572991 MLS ⋅ 9,500 SqFt.
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

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