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43 Pine Street, Weston
$9,500,000
6 Beds ⋅ 9 Baths ⋅ 73539148 MLS
One of South Side Weston’s most exceptional estate offerings, privately sited on 2.4 breathtaking resort-like acres. Meticulously maintained and masterfully renovated, this distinguished residence seamlessly blends timeless architecture with sophisticated modern luxury. Sun-drenched interiors and exquisite craftsmanship define every space, highlighted by a spectacular vaulted family room and chef’s kitchen overlooking magnificent grounds. The elegant fireplaced primary offers a serene private retreat. Exceptional quality extends throughout, with en suite bedrooms and generous guest quarters with separate entrance. Designed for grand-scale entertaining and effortless everyday living with a custom pool, spa, expansive patio, and beautifully renovated barn with loft, stalls, and half-court basketball court. A remarkable walk-out lower level presents endless possibilities for recreation, wellness, sports, or a significant car collection. A legacy property just minutes to Boston and Logan.

43 Pine Street, Weston

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: eXp Realty LLC - Corporate Office.
50 Laurel Rd., Weston
$7,295,000
5 Beds ⋅ 7 Baths ⋅ 73521260 MLS
Exceptional new home in one of Weston's most coveted neighborhoods. Spectacular naturally screened & private fully level lot with sports court and options for pool & accessory pool house with two car garage. The main house features 8889 sq ft with 5-6 bedrooms & en-suite bathrooms, and was thoughtfully designed by acclaimed architect Greg Legault featuring an open floor plan with an abundance of oversized windows flooding the home with natural light. An impressive kitchen with custom designer cabinetry and integrated high-end appliances flows to a vaulted 2 story family room. The primary suite includes large his and her closets & a stunning bathroom. The outstanding lower level features a guest bedroom, exercise room, oversized open area designed for billiards/card games/lounge with surround sound AV, & a room that has been prepped for a golf similar or home theater. Control 4 home automation system controls lighting, AV, security, and heating and cooling. Prepped for elevator.

50 Laurel Rd., Weston

Listing courtesy of Listing Agent: P. Matthew Harkins from Listing Office: Walden Realty Group LLC.
231 Westerly Road, Weston
$6,995,000
6 Beds ⋅ 9 Baths ⋅ 73486112 MLS
Beautifully conceived and architecturally inspired contemporary NY barn-style home with endless upgrade options that range from golf simulator to sauna/ pool/ cabana/ heated driveway list goes on. In one of Weston’s most exclusive neighborhoods. Boasting 7500 +/- sf, 6-7 bedrooms and 7 full baths and 2 half baths this home was meticulously designed with an open floor plan, soaring walls of windows, 9.5-inch flooring, 2 story foyer with glass railings, and lower-level wellness/rec wing. The kitchen is elegantly appointed with custom cabinetry, full butler panty and integrated high-end appliances. The private adult suite provides a quiet sanctuary bathed in natural light, separate dressing room and a spa-like bathroom. A thoughtful arrangement of indoor and outdoor spaces creates a symbiotic relationship between interior and exterior, offering unlimited opportunities for both formal and casual entertaining in a neighborhood setting.

231 Westerly Road, Weston

Listing courtesy of Listing Agent: Alexander Benson from Listing Office: Keller Williams Realty Boston South West.
10 Chandler Circle, Weston
$4,995,000
5 Beds ⋅ 6 Baths ⋅ 73535557 MLS
Beautiful custom built Modern Classic home sited in a premier estate location on the south side of Weston. Designed by acclaimed architect Marcus Gleysteen and built by luxury home builder Wellen Construction this property has an absolutely enchanting setting adjacent to 30 acres of conservation land and trails. Reminiscent of a country estate in Vermont it evokes relaxed comfort with finely crafted wood details, fireplaces, a screened porch and an oversized chef's kitchen. Walls of glass showcase views of this lushly landscaped 1.4 acre ultra private lot and french doors lead to a bluestone terrace perfect for outdoor living and entertaining. Highlights include four floors of finished space, a dramatic primary suite with vaulted ceilings and a fireplace, a gym, home office and finished lower level. Nestled on a quiet cul de sac near Chestnut Street, yet offering fast access to commuting routes, top ranked public and private schools and Boston. A rare blend of prime location and charm.

10 Chandler Circle, Weston

Listing courtesy of Listing Agent: Rosemary McCready from Listing Office: Compass.
9 Skating Pond Road, Weston
$4,995,000
5 Beds ⋅ 8 Baths ⋅ 73503213 MLS
Reimagined & redesigned stunning custom home on over 1 acre in Weston's prestigious Golf Club neighborhood. New layout, new floors, new custom built-ins, new kitchen, new butler pantry, new bathrooms, new moudings, white oak door trim, new furnaces, new AC condensers, new Marvin windows, new stone walls & landscaping...... Kitchen family room w/ breakfast nook opens to large family room w/ fireplace. Spacious living room/dining room ideal for entertaining. Private office off of grand foyer. Bedroom & en suite bath on first floor. Main bedroom w/ large custom closet & gorgeous spa-like bath. 3 additional bedrooms all w/ large closets & en suite baths. Front & back staircase. 2 mudrooms. Lower level w/ full bath, playroom, media room plus exercise. This home has huge Marvin windows creating a sunfilled home. Overlooking majestic Skating Pond & its rustic lodge designed by Fredrick Law Olmstead in 1909. Close distance to Weston Town Center and routes to Boston. A must see!

9 Skating Pond Road, Weston

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
21 Bemis Street, Weston
$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 Graystone Ln, Weston
$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.
95 Sylvan Ln, Weston
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 73583759 MLS
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

Listing courtesy of Listing Agent: Jonathan Caldwell from Listing Office: ACRE Property Advisors LLC.
4 Cherry Brook Road, Weston
$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.
44 Old Rd, Weston
$1,795,000
3 Beds ⋅ 3 Baths ⋅ 73543866 MLS
Enjoy the best of Weston living in this beautifully renovated 3 bedroom Cape, privately set on a landscaped one-acre lot just minutes from the town center. Designed for both everyday comfort and effortless entertaining, the home offers inviting spaces that flow from a beautifully appointed kitchen with high-end appliances and custom cabinetry to a fireplaced family room opening onto a spacious deck overlooking the peaceful grounds. Gather in the elegant fireplaced living room, host memorable dinners in the formal dining room and enjoy the flexibility of a first-floor bedroom for guests, a den, or home office. Upstairs, the spacious primary suite provides a private retreat with an adjoining office, two walk-in closets, and a balcony overlooking the gardens. Meticulously maintained, this exceptional home offers a wonderful blend of privacy, comfort, and convenience in one of Weston's premier locations.

44 Old Rd, Weston

Listing courtesy of Listing Agent: Karen Kirk from Listing Office: Engel & Volkers Wellesley.
30 Warren Ave, Weston
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 73485056 MLS
Welcome to 30 Warren Avenue, a beautifully maintained single-family home in a quiet and desirable Weston neighborhood. This spacious residence offers 4 bedrooms and 3 full bathrooms with a bright layout designed for comfortable living. The main level features a sun-filled living room with hardwood floors, a formal dining area, and a renovated kitchen with modern appliances. Recent upgrades include a finished basement, renovated kitchen and bathrooms, renovated attic, new windows, new gas furnace, new wall and attic insulation, and a tankless water heater. Enjoy outdoor living in the private backyard with a new patio and deck, perfect for relaxing or entertaining. Located in the top-rated Weston school district with convenient access to highways, shopping, dining, parks, and nearby walking trails, this home offers an ideal blend of privacy, comfort, and everyday convenience.

30 Warren Ave, Weston

Listing courtesy of Listing Agent: Yang Liu from Listing Office: Weston Realty LLC.
10 Bakers Hill, Weston
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 73528181 MLS
Nestled in one of Weston’s sought-after Northside neighborhoods, this classic center-entrance Colonial offers timeless charm and generous living spaces.The sun-filled front-to-back living room features gleaming hardwood floors and a beautiful fireplace. The kitchen includes an eat-in area that leads to a family room with sliders opening to a serene, private patio and backyard. A formal dining room, powder room, and welcoming foyer complete the first floor. Upstairs, the primary suite includes an updated ensuite bath and double closets. Three generous bedrooms with hardwood floors and a full bathroom are down the hallway. The exceptional finished lower level offers additional living space with a playroom, game room, laundry room and bathroom. Enjoy sidewalks to Weston town center, nearby bike paths and trails, and access to Weston’s top-rated schools all from this wonderful Colonial home located in a prime neighborhood setting.

10 Bakers Hill, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
118 - 120 Summer Street, Weston
$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.
120 Summer St, Weston
$1,350,000
3 Beds ⋅ 4 Baths ⋅ 73565840 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.

120 Summer St, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
28 River Road, Weston
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 73579333 MLS
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

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
94 Sunset Road, Weston
$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.
223 Boston Post Rd, Weston
$1,049,000
3 Beds ⋅ 2 Baths ⋅ 73563830 MLS
This Modern style home is simply spectacular with mid-century inspired architecture! Set back from the road, this home sits proudly on a gently sloped 1.1 acre lot. You'll find large windows creating sun-drenched spaces, rich wood-beamed ceilings and an exterior balcony off the primary bedroom. As you come up the paved driveway, you'll be greeted by a two-car garage with workspace and storage. Walk up the exterior stairway from the driveway and you'll enter the home to find a large kitchen with room for a dinette. It has wood cabinets, exterior-venting range hood and other appliances for entertaining and meal preparation. From the kitchen you'll find an open first floor plan with dining room, perfect for fine dining or casual mornings with coffee. The awe-inspiring two story living room has dramatic floor to ceiling picture windows, filling the space with sunlight. There's a central fireplace, exterior entry to the rear yard, coat closet and spiral staircase to the second floor. Also on the first floor is a guest bedroom and full bathroom. The second floor has a primary suite with walk-in closet, plus both interior and exterior balconies. There's a second bedroom and full bathroom with shower and linen closet. Throughout the house is electric baseboard heat that can be individually controlled in each room for ideal seasonal comfort. Easy to show by appointment. Use caution at the primary bedroom's interior balcony by keeping the privacy bifold doors closed for safety.

223 Boston Post Rd, Weston

Listing courtesy of Listing Agent: Robert Simone from Listing Office: Better Living Real Estate, LLC.
131 Wellesley Street, Weston
$850,000
4 Beds ⋅ 2 Baths ⋅ 73483468 MLS
Looking for a project? Welcome to the Rand House set on 1.38 acres of land. This iconic Antique Colonial circa 1790 is part of the land known as the Case Estates that the Town of Weston purchased from Harvard in 2016. The property must be restored in accordance with the deed restriction from the Historic Commission. There is an expansion area to the existing footprint if an addition is desired. Be a part of the next chapter. Bring your creativity and ideas to this sunny property in the semi rural part of Weston's center or get inspired with conceptual plans by Patrick Ahearn Architect.. Minutes to schools, library, pool and Lands Sake. Soils can accommodate a 5 bedroom septic system with garbage disposal. Buyer to design and install septic system. Can be purchased individually or together with 133 & 135 Wellesley St. Top rated public schools.

131 Wellesley Street, Weston

Listing courtesy of Listing Agent: Chaplin Partners from Listing Office: Compass.
135 Wellesley Street, Weston
$850,000
1 Baths ⋅ 73483470 MLS
Imagine the possibilities in repurposing Hillcrest Stables, the jewel of the Case Estates. Built in 1927, this gorgeous brick barn is built to last, with concrete and large timber providing many options for the next owner. West-facing walkout concrete and fieldstone lower level with three barn doors providing access for up to 6 cars. This site was previously owned by Harvard University’s Arnold Arboretum and is currently located on .69 acres of land backing up to 100s of ocres of conservation trails. There is 3614 sqft of space on three levels with many original architectural details still intact. The property is zoned Single Family Residential and must be restored in accordance with the deed restriction from the Historic Commission. Soils can accommodate a 5-bedroom septic system with garbage disposal. Buyers to design and install septic system. Can be purchased individually or together with 131 & 133 Wellesley St. Conceptual plans by Patrick Ahearn Architect. Top rated public schools

135 Wellesley Street, Weston

Listing courtesy of Listing Agent: Chaplin Partners from Listing Office: Compass.
133 Wellesley Street, Weston
$699,000
2 Beds ⋅ 1 Baths ⋅ 73483469 MLS
Imagine restoring an iconic school house built in 1910! Set on .68 acres of upland meadow on land known as the Case Estates that the Town of Weston purchased from Harvard in 2016. This little gem located between the Barn and Rand House is awaiting its next chapter. Bring your creativity and ideas to this sunny property in the semi rural part of Weston's center, or get inspired with conceptual plans by Patrick Ahearn Architect. The School House is zoned Single Family Residential and must be restored in accordance with the deed restriction from the Historic Commission. There is an expansion area to the existing footprint if an addition is desired. Land can accommodate a 5 bedroom septic system with garbage disposal. Buyer to design and install their own septic system. Sidewalks. Minutes from schools, library, pool and the Lands Sake. Top rated Weston Public Schools. Can be purchased individually or together with 131 & 135 Wellesley St.

133 Wellesley Street, Weston

Listing courtesy of Listing Agent: Chaplin Partners from Listing Office: Compass.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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