Browse All Sudbury MA Properties with Pool for Sale

UPDATED, SOPHISTICATED AND EXCEPTIONALLY DESIGNED! This remarkable Contemporary home has been completely curated and is truly dream-worthy. Tucked away on a CUL-DE-SAC OFFERING DIRECT ACCESS TO THE coveted 104 MILE MASS CENTRAL RAIL TRAIL, this home has been RENOVATED TO PERFECTION, delivering chic style and an incredible indoor-outdoor experience. Step inside and prepare to be wowed by an open-concept design, soaring vaulted ceilings, and an effortless floor plan! The kitchen with a large center island is without a doubt the heart of the home! THE SUNROOM IS A TRUE RETREAT and could become a four season room, with panoramic views and direct access to the back deck, perfect for morning coffee or an evening cocktail. The inviting living room features a fireplace with an exposed brick chimney for added character! The far end of the main level offers three bedrooms - including a proper primary with a gorgeous ensuite bath. THE LOWER LEVEL FEELS LIKE A TRUE EXTENSION OF THE FIRST FLOOR, complete with a spacious family room filled with natural light, an additional office space, and full bath, ideal for guests, work, or play! Outside is a private oasis - THE FULLY FENCED-IN YARD features an in-ground pool, back deck, and mature landscaping ready for ultimate enjoyment. The two car attached garage has additional room for storage! VACATION AT HOME and enjoy the Rail Trail and pool! Live the life you've dreamt of!

45 Whispering Pine Road, Sudbury

Listing courtesy of Listing Agent: The Zur Attias Team from Listing Office: The Attias Group, LLC.

$2,100,000

5 Beds ⋅ 5 Baths ⋅ 73574826 MLS

Escape to your own private oasis just 18 miles from downtown Boston. Set on 1.8 beautifully landscaped acres, this elegant farmhouse-style Colonial offers an exceptional blend of timeless architecture, refined interiors, and resort-like outdoor living. Surrounded by specimen trees and thoughtfully curated plantings, the property provides countless opportunities to relax, entertain, and enjoy the sights and sounds of nature. Dine alfresco, gather with friends, or spend summer days swimming and lounging poolside. The cabana features its own indoor kitchen and bath, while an outdoor jacuzzi offers another inviting place to unwind. Expansive grounds provide plenty of space for picnics and play. Inside, bright and airy rooms, high ceilings, and elegant millwork create an inviting backdrop for both grand gatherings and quiet moments. Four levels of living space offer exceptional flexibility, giving everyone room to pursue their interests. The lower level is designed for recreation and entertainment, with a media room, music/theatre space, billiards area, and additional versatile spaces. On the third level, discover a charming artist’s studio alongside a bonus room ideal for a tween hangout, second home office, guest suite, exercise area, or creative retreat. Conveniently located in South Sudbury and within the highly regarded Loring Elementary School district, the property is also within walking distance of ballfields, trails, shopping, and dining. With its distinctive character, extraordinary amenities, and enviable setting, this spectacular home offers a rare combination of elegance, comfort, recreation, and convenience. A truly special property that must be experienced in person to be fully appreciated.

12 Quaker Lady Ln, Sudbury

Listing courtesy of Listing Agent: Denise Garzone from Listing Office: William Raveis R.E. & Home Services.

$2,495,000

4 Beds ⋅ 4 Baths ⋅ 73571809 MLS

Once in a blue moon, an estate comes to market that is truly unlike anything else. Custom built and set amid magnificent gardens inspired by the landscapes of Europe, Japan, and Morocco, 82 Old Garrison Road in Sudbury is a remarkable expression of architecture, artistry, and nature. Reimagined and reconstructed in 2004, this architecturally distinctive contemporary estate offers four bedrooms, four baths, and more than 4,500 square feet of living space, privately set on approximately five beautifully cultivated acres. Designed to create a seamless connection between indoors and out, the home unfolds through light-filled living spaces, walls of glass, and unexpected architectural moments, each framing a different view of the surrounding landscape. At the heart of the property are gardens cultivated over many years as a true labor of love. Meandering paths lead through an ever-changing landscape of specimen plantings, perennial gardens, tranquil water features, intimate gathering spaces, a small orchard, and a greenhouse. Around each turn is something new to discover, creating an experience that feels worlds away while remaining in the heart of Sudbury. The grounds are equally suited to relaxation and entertaining, with an in-ground pool surrounded by lush plantings and multiple outdoor spaces that invite long afternoons, quiet mornings, and memorable gatherings beneath the open sky. Inside, the home is warm, sophisticated, and wonderfully individual. Expansive windows bring the gardens into nearly every room, while thoughtfully designed living and entertaining spaces reflect the same creativity found throughout the grounds. The flexible layout provides versatile accommodations for residents and guests, complemented by distinctive spaces for dining, gathering, working, and retreat. A three-car garage, whole-house generator, metal roof, warm cedar-shingle exterior, and expansive ipe decking add substance and practicality. Set within Sudbury’s storied Wayside Inn Historic District, the property feels remarkably removed while remaining connected to the heart of town. More than a home, 82 Old Garrison Road is a private world unto itself, shaped by imagination and an extraordinary appreciation for beauty. For the discerning buyer seeking privacy, originality, and a property that simply cannot be replicated, this is a rare opportunity to become the next steward of one of Sudbury’s most distinctive estates.

82 Old Garrison Rd, Sudbury

Listing courtesy of Listing Agent: Peace Nguyen from Listing Office: Engel & Volkers Wellesley.

$4,450,000

5 Beds ⋅ 8 Baths ⋅ 73558871 MLS

A one-of-a-kind European-inspired estate on 5.6 private wooded acres, featuring a private elevator, a 15-car garage compound, an indoor pool pavilion ready for completion, an immense customizable lower level, and exceptional craftsmanship. Some homes are built to satisfy the market. Others are created to fulfill a vision. La Farigoule belongs unmistakably to the latter. Inspired by the timeless country estates of France and Southern Europe, this extraordinary custom residence was conceived not as a speculative development, but as a lifelong private estate where architecture, craftsmanship, and imagination took precedence over convention. Every room, proportion, and crafted detail reflects a singular vision, giving the home remarkable character and unmistakable personality. Set amid secluded woodlands, La Farigoule reveals itself through remarkable spaces and unexpected discoveries. A private elevator serves every level, from the expansive lower level to the attic, combining elegance with convenience. The spectacular 15-car garage compound offers an extraordinary setting for automobile collectors, while a rare underground passage discreetly connects it to the residence- an architectural feature almost never found in a private home. A magnificent indoor swimming pool pavilion awaits completion as a year-round wellness retreat. Beneath the residence, an immense lower level can become a private cinema, wine cellar, fitness center, spa, golf simulator, guest residence, or exceptional entertainment venue. These spaces invite the next owner to shape the estate around a personal lifestyle. Even the smallest details express the home's European spirit. A traditional wood-fired pizza oven evokes Tuscany and Provence, where family and friends gather around simple pleasures, fine food, and memorable evenings. Handcrafted millwork, custom stonework, soaring spaces, and bespoke details create warmth, authenticity, and timeless elegance rarely found in contemporary construction. La Farigoule is more than a luxury residence- it is a home with a soul. Created not simply to impress, but to endure, it is complete in its architectural vision while offering opportunities for personalization without compromising its identity. Only minutes from Boston, yet surrounded by privacy, La Farigoule is for those who seek originality over convention, craftsmanship over fashion, and character over excess. Some houses are admired. Some houses are envied. La Farigoule is remembered.

145 Dutton Road, Sudbury

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

$1,850,000

5 Beds ⋅ 4 Baths ⋅ 73556293 MLS

A private two-acre escape where everyday living feels like a vacation. Blending timeless New England character with modern updates and extraordinary outdoor amenities, this special property offers the perfect balance of comfort, recreation, and relaxation. The main level features a renovated kitchen with new countertops and appliances that opens to a spacious family room with a gas fireplace and a beautiful screened-in porch, creating the perfect space to enjoy the peaceful surroundings in every season. A formal dining room, private office, mudroom, and versatile flex space ideal for a second office, home classroom, or creative retreat complete this level. Upstairs, the primary suite offers a peaceful escape with a sitting room, walk-in closet, and ensuite bath with soaking tub and separate shower. Three additional bedrooms and a second-floor laundry room complete this level, while the finished third floor provides endless possibilities as a playroom, media room, or bonus living space. A separate fifth bedroom with a full bath is perfect for guests, extended family, or an au pair.Designed for entertaining and creating lasting memories, the outdoor living spaces are truly exceptional. During their ownership, the sellers thoughtfully transformed the backyard into a private retreat featuring a heated saltwater pool with an automatic cover,pool house, professionally designed multi-sport court for basketball, tennis, and pickleball, expansive patios and hardscaping, a fire pit with landscape lighting, irrigation system,and beautifully landscaped grounds with fruit trees, flowering cherry trees, spring bulbs, and a charming chicken coop/greenhouse. The extensive list of seller improvements continues throughout the home and includes fresh interior paint, updated bathrooms, a remodeled garage, a dedicated art studio, new A/C condenser, water filtration system, radon mitigation system, an added electrical panel, and a seller-owned Tesla solar system w/3 Telsa Powerwalls, providing added efficiency and long-term value. A rare opportunity to own a turnkey property where luxury, recreation, and everyday living come together in one remarkable home!

12 Trillium Way, Sudbury

Listing courtesy of Listing Agent: Kathryn Lee from Listing Office: Gibson Sotheby's International Realty.

$1,319,000

4 Beds ⋅ 4 Baths ⋅ 73541221 MLS

Come see this beautiful freshly painted colonial! Set on over an acre, with mature gardens, a heated, gunite pool, screened gazebo and fully fenced backyard, this home offers an outdoor oasis for any season. Enter from the stately front steps to a welcoming and elegant foyer. On either side are the formal dining room and the bright and open living room leading to the library with views of the glorious backyard. The main level finishes with the heart of the home. There is a glorious newer kitchen with two wall ovens and a large center island. The kitchen opens into the large family room, with a gas fireplace and soaring ceilings. The four bedrooms are upstairs, each with lovely views of nature. The finished lower level has it’s own full bathroom and walkout access to the fully fenced backyard and pool area. Ideally located close to the Concord border, this distinguished home is near shopping, recreation, and top schools, offering a chance to enjoy historic Sudbury in style.

821 Concord Road, Sudbury

Listing courtesy of Listing Agent: Kimberly Anderson from Listing Office: Coldwell Banker Realty - Sudbury.

$1,849,000

4 Beds ⋅ 3 Baths ⋅ 73510795 MLS

Have you ever dreamed you were living in a fairytale? W/ a majestic & strong stone front accent exterior, meticulously maintained, diverse landscape, & a winding grand staircase w/ soaring ceiling height & marble floor foyer. The perfect place to live like you are true royalty! The main floor features 2 oversized living rooms, a study (channel your inner "Belle" & make it a library, or if you are more of a "Beast" than perhaps a private "West Wing"), an amazing pantry room with shelving to store all of your culinary equipment (including Mrs. Potts and Chip) & ingredients you do not wish to store in the spacious, double oven, & 6 burner stovetop kitchen. A convenient 1/2 bath, DR, ample 3 closets for coats and storage complete this part of the "castle". As we continue up the ceremonious staircase you will find 3 bedrooms, superb laundry space, & full bath. The real reward is the primary suite! & when festivities are to be outside, the expansive pool is the perfect place to reign from.

7 Saddle Ridge Road, Sudbury

Listing courtesy of Listing Agent: Jessica Cavallaro from Listing Office: Keller Williams Realty North Central.

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Sudbury Homes with Pool

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Browse All Sudbury MA Properties with Pool for Sale

Sudbury Homes with Pool

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