Rare opportunity in South Sudbury's coveted Cutler Farm cul-de-sac neighborhood! This exceptional home blends neighborhood charm with private tranquility and offers both first- and second-floor primary bedroom options, providing flexibility to suit a variety of lifestyles. A welcoming two-story foyer opens to a living room with a gas fireplace and a spacious dining room with a butler's pantry. The open-concept custom kitchen with a large island, high-end appliances, and dining area flows seamlessly into an inviting family room with a beautiful stone fireplace-ideal for entertaining. An expansive screened-in porch extends the living space throughout the warmer months. The main-level primary suite is a true retreat with a spa bath and private deck with hot tub. Upstairs features four generous bedrooms (second primary, if desired) with en-suite and Jack-and-Jill baths, plus a home office loft. The walk-out lower level offers a play area, game room with bar, bonus room/home office, workout room, workshop, and ample storage. The beautiful grounds provide access to Sudbury Valley scenic trails and Loring Elementary School. This home is ideal for multigenerational living and entertaining. Located minutes to shopping, dining, and Routes 9, 30, 20, and the Mass Pike (90) making commuting to Boston and beyond effortless. This is a must see!

Dreams Do Come True! Elegance and craftsmanship abound! Set on a beautifully landscaped private lot, the home welcomes you with classic curb appeal and a gracious entry. Sunlight pours into the well appointed formal living and dining rms, creating comfortable spaces ideal for family living and entertaining.The thoughtful layout flows effortlessly into informal gathering areas, where a spacious family rm and casual dining nook overlook the serene grounds. A stylish kitchen anchors the home, designed for daily living and special occasions. Upstairs, generously sized bedrms provide comfort and privacy, while the primary suite offers a retreat-like atmosphere.Outdoor living is equally impressive with lush landscaping,mature plantings,and space to relax and entertain in style with stone bar area,hottub and pool.For the nature enthusiast, this property abuts Ford Folley, Tippling Rock, and Callahan State Park.Best of all is a four car garage for the car buff! Perfect location close to town.

Built just 10 yrs ago, this beautifully crafted home pairs classic New England architecture w/ exceptional craftsmanship & a floor plan designed for the way people live today. Natural light moves easily through the home, highlighting rich hardwood floors, substantial millwork, wainscoting, coffered ceilings & architectural details that give each room its own character. The gracious foyer & staircase establish an impressive sense of arrival, while the connection between the kitchen & living room allows the main gathering spaces to flow naturally together. The main level also offers a private office, gracious dining room & a 1st floor bedroom w/ adjacent full bath, ideal for guests, extended family or an au pair. Designed for those who genuinely enjoy cooking & gathering, the kitchen features custom cabinetry, quartz counters, premium appliances, marble herringbone backsplash, farmhouse sink, oversized island & an impressive walk in pantry. Connecting the kitchen & dining room, a wet bar w/ wine refrigerator & dedicated coffee station adds both function & a polished finishing touch. Sliders from the kitchen open to an oversized composite deck overlooking professionally landscaped grounds & a private wooded backdrop, while the adjoining fireplaced living room is framed by expansive windows capturing views of the backyard. A custom mudroom w/ built ins provides an organized transition from the garage. Upstairs, the generously proportioned primary suite offers space for a sitting area, dual walk in closets & a beautifully finished bath w/ soaking tub, glass enclosed shower & dual vanities. The secondary bedrooms are equally well proportioned, while a spacious sitting room creates a separate place to read, relax or gather away from the main living areas. 2nd floor laundry completes the level. Spanning the footprint of the home, the unfinished walkout lower level opens directly to a backyard patio & offers exceptional potential for future expansion, whether envisioned as a media lounge, fitness studio, wine cellar or recreation space. The expansive yard combines open lawn w/ mature landscaping & a wooded perimeter, while the deck & patio create two distinct levels of outdoor space. Meticulously maintained inside & out, this is a home whose quality extends well beyond first impressions, all located in a sought after, young Sudbury neighborhood.

Be prepared to step into your Dream Lake House. Newly constructed and ready for all the activities lake living has to offer in all four seasons. The home can be delivered fully furnished so that all you need to do is pack your bags and grab the keys to the pontoon boat. You will find a huge covered back porch spanning the entire length of the home for gazing and taking in the views. The main living area is open, with an eat-in kitchen, an island, and lots of open workspace. The top floor has two bedroom suites with full baths. The lower level is a walk-out and has additional rooms and a laundry room. Across the street is also a newly constructed oversized garage with space for cars and jet skis- you name it. You will enjoy your own stairs to a private dock, giving you direct lake access. Rarely do we find a new build on the lake! Make this one yours and schedule a showing.

Beautifully designed and professionally decorated center-entrance Colonial blending timeless elegance with modern luxury, nestled in one of Sudbury’s most convenient neighborhoods. Fully renovated in 2006 with the expertise of a renowned architect, interior designer, and landscape architect this home offers outstanding indoor and outdoor living. The interior features a spacious kitchen with a large center island, an impressive suite of high-end appliances including a warming oven and refrigerator and freezer drawers built into the island along with a generous dining area. A front-to-back living room with fireplace, dining room, and private office/den with a wet bar provide elegant spaces for entertaining and everyday living. The inviting family room, highlighted by a fireplace and charming window seats, flows seamlessly into an enclosed three-season porch, creating a warm and welcoming retreat for relaxing, gathering, and enjoying the changing seasons. Upstairs offers 5 spacious bedrooms, including an en-suite bedroom. The luxurious primary suite features a hallway, full bath, and custom built-ins. A mudroom and finished walkout lower level add everyday convenience and flexibility. Outside offers a farmer's porch, sports court, bluestone patio featuring a built-in grill and refrigerator, and an expansive deck. Impeccable landscaping with accent lighting completes the picture, delivering exceptional curb appeal. Located just minutes from top-rated schools, shopping, dining, the Rail Trail, and major commuting routes. Driveway is located on Hillside Place which is a private cul-de-sac.

An opportunity to own this sought-after home within the enclave of The Trails at Wayside. This property boasts clean lines, soaring ceilings, and an incredibly versatile open floor plan. Tucked away, it offers privacy and enchanting woodland views, bordered by a natural boundary. Step into the open kitchen, seamlessly connected to the spacious family room. A gas-burning fireplace and sliding doors lead to the backyard, creating an indoor-outdoor living experience. On the first floor, you’ll also find a separate dining room, family room, and office with glass pocket doors for privacy, a walk-in pantry, and a full bath. Ascend to the upper level, where four generously sized bedrooms await. The primary suite stands out with its private balcony. A separate wing offers a full bath, a laundry room, and a beautifully appointed bonus/flex room, perfect for guests, a playroom, or a home office. The third floor is framed and ready to be finished. The basement is a blank canvas

A premier property and location beautifully sited and perched above the road, and quite possibly the best location in the neighborhood. This home is designed for comfortable living with well-planned entertaining spaces. You will find a large, open eat-in kitchen that flows gracefully into the family and living room. There are sliders that open onto a beautiful brick-and-stone patio overlooking the private backyard and gardens. There's a three-season porch with both glass and screen windows. You can enjoy a formal dining room with pocket doors and an adjacent wetbar. The first level has a generously sized office or den with a pellet stove. On the upper level, there are four bedrooms and a bonus craft room. One of the additional bedrooms is an ensuite, separate from the primary, which lends itself well to a guest or extended-family space. This home was built with the capability to finish the third-floor walk-up, as seen in the pictures. An exceptional offering and much versatility.

Set amid park-like grounds with a private wooded backdrop, this expansive Upton home stands out for its generous living space, thoughtful updates and remarkable flexibility. Updated kitchens and baths throughout bring a fresh, polished feel to the home, while impressive architectural details begin in the soaring two-story foyer and continue into the dramatic family room, where a vaulted ceiling, fireplace and an extraordinary collection of windows fill the space with natural light and views of the surrounding landscape. At the center of the main level, the updated kitchen features quartz counters, extensive cabinetry, stainless appliances, gas/propane cooking and an oversized island. Its open connection to the breakfast area and family room creates an inviting gathering space, while the generous dining room provides plenty of room for larger occasions. A private office or library with built-in bookshelves offers a quiet, distinctive space away from the main gathering areas. The home's generous proportions continue upstairs, where the exceptionally spacious primary suite features two walk-in closets and a beautifully updated, spa-like private bath. Three additional bedrooms, another updated full bath and conveniently located laundry complete the bedroom level. One of the property's greatest advantages is the finished lower level. With its own updated kitchen, bedroom, full bath, living/guest space and recreation room, it offers an outstanding setup for multigenerational living or extended family, while also providing tremendous flexibility for recreation, guests, a home gym or additional living space. Outdoors, a heated inground pool with newer liner, expansive deck with pergola, raised garden beds, brick walkways, fire pit, flowering shrubs and perennials create a wonderful setting for summer gatherings and time at home. Tucked within mature landscaping and a wooded setting, the backyard feels like its own retreat while remaining convenient to Upton's town center, schools, recreation and major commuting routes. An oversized garage provides exceptional vehicle and storage space, while fully owned solar and a newer 5-bedroom septic system are significant improvements for the next owner. See for yourself at our open house on August 15th, 2026 from 12-1:30 PM.

Exceptional home in a premier cul de sac setting featuring a coveted first floor primary suite and a beautifully designed, light filled floor plan. At the heart of the home is a large showcase kitchen with abundant cabinetry, solid surface counters, and superb workspace, all connecting seamlessly to the home’s open central core—a bright, inviting layout ideal for everyday living and entertaining. A well placed first floor study/workspace offers comfort and privacy in an excellent location within the floor plan. Rich moldings, hardwood floors, and thoughtful architectural details enhance every room. A three- season porch and expansive rear deck provide effortless indoor- outdoor living with tranquil views of woods and open space. The second floor includes generous bedrooms, multiple baths, and excellent storage. A rare blend of comfort, style, and privacy at the beautiful end of the cul de sac with glorious privacy. SELLER financing available to qualified buyers!

PRICE REDUCED & ready for immediate occupancy. Well designed renovated/enlarged home has so much space & quality features to offer and enjoy. Brick & stone walkway welcomes you into LR/DR opening to the heart of the home--bright skylit Chef's.kit w dining area, lots of cabs, large ctr island w counter bar flowing directly into fabulous FR with tons of natural light. Perfect space for family gatherings or entertaining. .Vaulted ceilings, HW flrs. 3 good size BR's plus impressive MBR suite with alcove for office or quiet retreat. Large vanity w Dbl sinks, cabs, jetted tub & glass shower. LL has addl FP Fam rm plus another room for rec rm/aupair /inlaw./office, etc Laundry/mud rm has closet & cabs. 3 season porch w wall of windows opens to fabulous flat rear grounds. Beautiful perennial plantings all around. High end gas IBC furnace/hot water/cent air. 2 1/2 car gar (3 if tandem) . Sought-after central location near all that Sudbury has to offer-school system, rail trail, Swim & Tennis, Conservation, medical, shopping, etc EMPTY & ready for new owners to appreciate this home.