Browse All Weston MA Properties with Pool for Sale

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.

$16,900,000

6 Beds ⋅ 10 Baths ⋅ 73550581 MLS

A true showcase luxury gated estate, 50 Winsor Way is situated on over 2 acres of elevated and private land located off the Weston Golf Club. The estate features truly picturesque professionally landscaped grounds, expansive terraces and patios with views for entertaining, and a large showpiece swimming pool and patio with elegant fountains. 50 Winsor boasts more than 6 bedrooms including the luxurious main level master suite, 7 full bathrooms, 3 half bathrooms, and an expansive 4-car garage. Designed by Thoughtforms, this home boasts an expansive open floor plan and luxurious craftmanship and attention to detail throughout. The fully finished lower level is equipped with a recreation room, wine cellar, full theater room, wet bar, steam room, and sauna. On the second floor, four bedrooms offer private en suite bathrooms. This exceptional home is a unique grand colonial estate for the discerning buyer set in one of the most highly desired locations in all of Weston

50 Winsor Way, Weston

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.

$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.

$6,750,000

5 Beds ⋅ 9 Baths ⋅ 73533214 MLS

Introducing a timeless European inspired mansion with a private gate and elegant marble fountain. This custom estate is situated on 3 acres. A spectacular pool and spa complemented by a fully equipped pool house with a kitchen adorn the grounds. A beautiful wrought iron fence embraces the entire estate which includes stone patios and tennis court. The grand entry and living and dining rooms boast beautiful granite floors for fine entertaining. Additionally, rich oak wood floors are throughout the house. Three custom marble fireplaces grace the sitting areas. A first floor primary suite, private office and sunroom complete the main level. Upstairs has 4 large bedroom suites while the finished 3rd floor is ideal for a dual in-home office or guest bedroom. The tremendous lower level features a sauna, steam and home theater. This exceptional home embodies an elevated blend of refined and recreational living. This location provides excellent proximity to Boston and top-ranked schools.

15 Brown Street, Weston

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

$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.

$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.

$5,750,000

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.

$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.

$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.

$4,388,000

5 Beds ⋅ 7 Baths ⋅ 73475892 MLS

Elegant Custom Estate on 1.8 Acres in Weston! This stunning 8,000+ sq ft Colonial sits on a beautifully landscaped, level 1.8-acre lot with a private drive and circular entry. Inside, a grand foyer with a sweeping staircase opens to formal living and dining rooms with soaring ceilings, crown moldings, and French doors. The gourmet kitchen with marble countertops, super high-end & branded appliances flows into a spacious family room and sunroom, both with fireplaces. A luxurious first-floor primary suite offers a spa-like bath, dual walk-in closets, private office, and gym. Residents and guests can unwind in the spacious private theater, perfect for an immersive entertainment experience. The expansive finished basement offers an additional comfortable living area, ideal for recreation, relaxation, or extended guest stays.Outdoors, enjoy a bluestone patio with built-in grill and fire pit, plus a resort-style pool with waterfall spa, surrounded by elegant stonework. Very near to schools.

568 Wellesley St, Weston

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.

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Weston Homes with Pool

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