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185 Kettle Hole Rd, Bolton
$800,000
4 Beds ⋅ 4 Baths ⋅ 73594605 MLS
Discover an extraordinary setting in Bolton’s coveted Kettle Hole neighborhood, where this classic Colonial is beautifully nestled on 2.51 acres overlooking a rare glacial landform that lends the neighborhood its name & distinctive character. Surrounded by tranquil woodlands, this inviting home offers exceptional privacy, generous living spaces & a wonderful connection to nature. At its heart, a spectacular sun-filled family room boasts a soaring vaulted ceiling, cozy fireplace & distinctive round window framing picturesque treetop views. A gracious fireplaced living room, formal dining room & versatile 1st-floor office provide wonderful spaces for gathering, entertaining & working from home. The center island kitchen with pantry opens to a delightful 3-season porch & two composite decks, inviting you to unwind amid the beauty of nature & soothing sounds of a nearby babbling brook. Upstairs, discover four generously sized bedrooms, including a primary suite with soaking tub & separate shower. The finished walk-out lower level adds a playroom, exercise area, flexible guest room/office and bathroom with shower. Enjoy peace of mind with a 50-year roof with transferable warranty (2020), water heater (2025), whole-house ERV system (2020), humidifier (2021), generator, irrigation & gutter guards. Enjoy an enviable location near conservation trails, farm stands, shopping, Bolton’s new high school opening in 2027 & commuter routes. Brimming with potential, this cherished home invites you to bring your personal vision to life in a setting that simply cannot be replicated!

185 Kettle Hole Rd, Bolton

Listing courtesy of Listing Agent: Kotlarz Group from Listing Office: Keller Williams Realty Boston Northwest.

72 Golden Run Rd, Bolton
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 73589315 MLS
An extraordinary private estate where architectural distinction, refined luxury, and resort-style living converge. Set majestically on 4.5 acres in coveted Bolton, this exceptional 4-bedroom, 3.5-bath residence offers almost 5,000 square feet of exquisitely designed living space, surrounded by unparalleled privacy and natural beauty. From its striking architecture to its sophisticated interiors and upscale finishes, every element has been thoughtfully curated to create an elevated living experience. Spectacular three-season sunroom with walls of glass, providing an airy retreat and captivating views in every season. Gourmet Chef's kitchen with high end appliances and expansive center island, perfect for entertaining! Separate office space with beautiful wet bar. Gorgeous primary suite with additional sitting room & en suite bathroom flooded with natural light. 3 additional large bedrooms once including a private loft. Great room with vaulted ceilings and The expansive, fully finished walk-out lower level extends the home’s versatility, offering exceptional space for entertaining, recreation, relaxation, or a private retreat.Beyond the interiors, the property transforms into a spectacular private resort. A magnificent gunite pool and Jacuzzi take center stage, complemented by a beautifully appointed pool house that creates the ultimate destination for summer entertaining, intimate gatherings, and leisurely afternoons. Lush grounds and complete privacy provide a serene backdrop rarely found in a property of this caliber.A remarkable five-car garage adds an extraordinary level of convenience and flexibility for car enthusiasts, recreational vehicles, collections, or additional storage. Every detail—from the grand scale of the residence to the exceptional outdoor amenities—reflects a commitment to quality, comfort, and sophisticated living.A truly exceptional offering for the discerning buyer seeking an extraordinary estate where privacy, architecture, luxury, and resort-style amenities come together seamlessly. No detail overlooked .

72 Golden Run Rd, Bolton

Listing courtesy of Listing Agent: Andrea Beth Castinetti from Listing Office: Castinetti Realty Group.

296 Berlin Road, Bolton
$824,900
4 Beds ⋅ 3 Baths ⋅ 73587427 MLS
Some homes simply have a feeling—and this Bolton retreat is one of them. Tucked into just under TEN acres of lawn and woodland, this special 4 bedroom home pairs incredible New England character with the comforts of everyday living. Inside, warm pine floors, dramatic exposed beams and wood-plank ceilings immediately set it apart, creating a main level that feels both distinctive and wonderfully inviting. The heart of the home is an expansive kitchen with quartz counters, oversized island, stainless appliances, abundant cabinetry, wine storage and chiller, opening easily to the dining and living spaces. A terrific mudroom keeps real life organized, while the whole house water filtration system lends peace of mind. Upstairs, the spacious primary suite offers architectural ceiling lines, generous closets and a private bath with soaking tub and separate glass shower. 3 additional bedrooms, a double-vanity family bath and second-floor laundry offer plenty of room to spread out. An enormous basement with large windows offers exciting potential for future finished space, while substantial storage above the oversized 2-car garage creates another opportunity for expansion. Outside, a covered front porch, brand-new multi-level Trex deck overlooks the beautifully private backyard complete with gardens and sweeping lawn surrounded by acres of wooded privacy. All of this in picturesque Bolton—beloved for its highly regarded schools, quintessential New England charm and apple-country landscape, yet wonderfully convenient to everyday amenities and commuter routes. A home with soul, space and a setting that is increasingly hard to find.

296 Berlin Road, Bolton

Listing courtesy of Listing Agent: Team Darlene & Company from Listing Office: Lamacchia Realty, Inc..

281 Main Street, Bolton
$1,400,000
4 Beds ⋅ 5 Baths ⋅ 73584784 MLS
This stately Contemporary Queen Anne tucked away in the private community of Great Brook Estates is a truly rare offering rich in character and timeless appeal. Enjoy the peace & serenity of this spectacular property set on 5+ breathtaking park-like acres of lush lawns, enchanted woodlands, mature gardens, and classic stone walls. Imagine entertaining as guests mingle on the spacious deck, play games on the sprawling lawn, or stroll the tranquil grounds bursting with vibrant seasonal color. Step inside to discover an inviting interior distinguished by custom millwork, impressive architectural details, and expansive windows that bathe the home in natural light. A custom chef's kitchen features expansive stone counters, walk in pantry w/wet bar, dining area, & notable appliances flowing seamlessly into the striking fieldstone-fireplaced living room and cheerful light-filled sunroom with walls of windows framing year-round panoramic views of the private grounds. A well-appointed home office with custom cabinetry and an ensuite guest bedroom complete the 1st level. Retreat to the inviting primary suite, featuring a sitting area, custom walk-in closets, and an indulgent spa bath. An enchanting finished 3rd level offers endless possibilities for a playroom, artist’s loft, or creative retreat. The finished walkout lower level, complete with bonus room and full bath, provides additional versatile living space to accommodate changing needs. Enjoy a coveted east Bolton location abutting conservation land & trails, orchards, major commuter routes & top rated schools. This property is a true gem waiting to be discovered!

281 Main Street, Bolton

Listing courtesy of Listing Agent: Amy Balewicz Homes from Listing Office: Keller Williams Realty Boston Northwest.

106 Green Road, Bolton
$1,029,000
4 Beds ⋅ 3 Baths ⋅ 73584736 MLS
Stately columns frame the covered front porch, creating a distinctive first impression for this Bolton Colonial. Inside you will find a graceful dining room accented by chair rail, a nearby office with custom built-ins offering a polished setting for work or study, a spacious living room centered around a brick fireplace and a sunroom, where wood-paneled cathedral ceilings and walls of windows create a memorable place to relax. Continue into the kitchen, designed with a dining area, generous island, tile backsplash, granite counters, recessed lighting, and stainless steel appliances. A separate laundry room keeps everyday tasks neatly organized. Upstairs, the main bedroom makes a striking retreat with its own fireplace, cathedral ceiling, walk-in closet, and en suite bath featuring a double vanity, tiled shower, and soaking tub. The partially finished lower level offers flexible bonus space along with unfinished utility and storage areas. Central air provides added comfort throughout the warmer months. Updates include a new water filtration system ($11,000) and an ADT alarm system ($10,000) transferrable to new owners! Outdoors, a large brick patio extends the living area for meals and gatherings, complemented by a storage shed and fenced yard. An attached garage and plenty of off-street parking add practical convenience. Set on a wooded corner lot along a dead-end road, the property is just minutes from Nashoba Regional High School, with nearby trails enhancing the location.

106 Green Road, Bolton

Listing courtesy of Listing Agent: Genevieve Botelho from Listing Office: Lamacchia Realty, Inc..

78 Frye, Bolton
$1,029,000
4 Beds ⋅ 3 Baths ⋅ 73581367 MLS
Set along a picturesque country road, this beautifully appointed Colonial offers an exceptional blend of timeless charm, thoughtful updates, and inviting indoor-outdoor living. Surrounded by meticulously landscaped grounds, the property provides a private and serene setting while offering an array of desirable amenities.The gracious interior features a stunning cathedral-ceiling living room, creating an impressive sense of volume and natural light. The updated kitchen is both stylish and functional, with gorgeous granite and farm sink. The spacious primary suite is complemented by an updated private bath. An additional updated guest bath and a third full bath provide exceptional convenience for family and guests.A generous laundry room adds practicality, while the finished lower level offers even more flexibility. An expanded finished basement addition features a large French door opening directly to the outdoors, creating an ideal setting for a home office, fitness studio, media/recreation room, or private guest space. Numerous important updates enhance the home's comfort and peace of mind, including a newer roof, furnace, central air conditioning system, and gutters. Outside, the beautifully curated grounds are truly an extension of the home, with established gardens, a relaxing hot tub, and a storage shed. Whether enjoying quiet mornings surrounded by nature or entertaining guests in the thoughtfully designed outdoor spaces, this distinctive property offers a wonderful combination of comfort, character, and country-road tranquility.

78 Frye, Bolton

Listing courtesy of Listing Agent: Mary O'Hagan from Listing Office: Barrett Sotheby's International Realty.

51 Danforth Ln, Bolton
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 73576895 MLS
Exclusively positioned at 51 Danforth Ln in Bolton, MA, this distinguished 2005 colonial single-family residence offers 3,303 square feet of refined living space in great condition. The gourmet kitchen is beautifully appointed with brand-new stainless-steel appliances, stone countertops, and a central island with an integrated sink. The impressive vaulted foyer leads to the elegant formal living room and dining room. There is a tranquil first floor office.The expansive family room features a soaring vaulted cathedral ceiling and a striking fireplace, providing an elegant and comfortable setting for relaxation and gatherings. The thoughtfully designed primary bedroom includes a jetted bathtub and double vanity, creating a spa-like retreat within the home. There are 3 other spacious bedrooms sharing a bath with the second floor foyer leading to the walk up attic. The finished walk-out basement provides valuable additional living space and opens directly to the outdoors, offering a spacious game room and large play room with the pool table area. Outside, the private fenced in backyard offers an exceptional setting for entertaining and unwinding, with a patio, fire pit, and private outdoor hot tub and deck with screened in porch. The two-car garage adds further convenience and functionality. Combining classic colonial architecture with modern amenities, versatile finished living space, and inviting indoor and outdoor areas, this residence offers a distinctive opportunity for comfortable, sophisticated living in Bolton.

51 Danforth Ln, Bolton

Listing courtesy of Listing Agent: Erik Osachuk from Listing Office: Keller Williams Realty North Central.

149 Nourse Rd, Bolton
$950,000
4 Beds ⋅ 3 Baths ⋅ 73579005 MLS
Captivating architecture, abundant natural light & an exceptional setting define this distinctive Contemporary, beautifully set back on 4.5 acres along one of Bolton’s prettiest country roads amid extraordinary perennial gardens & mature landscaping. Dramatic windows frame the surrounding landscape throughout, creating a wonderful connection between indoors & out. At the heart of the home, the cabinet-packed kitchen offers granite counters, a 6' center island, dual pantries & incredible storage and workspace, opening seamlessly to the spectacular living room with vaulted ceilings & windows on three sides. An impressive dining room with a wall of windows framing breathtaking views provides an enviable space for gathering & entertaining. Awaken to seasonal mountain views in the peaceful primary suite featuring a walk-in closet & spa-like bath with dual vanity, jetted tub & glass/marble shower. A versatile 1st-floor office with separate entry & adjoining half bath offers excellent work-from-home or guest potential. The finished lower level adds a spacious family room & convenient mudroom, while hardwood floors, Andersen windows & doors add to the home's appeal. Brimming with updates that enhance livability & offer peace of mind, including a new roof with 50-year transferable warranty (2022), exterior paint, oil tank & dishwasher (2025), water softener (2020), Level 2 EV charger & 30-amp generator transfer switch (2024) and microwave (2026). Outside, spectacular perennial-filled gardens create an ever-changing display of color, complementing the picturesque natural backdrop through every New England season. Ideally located between Bolton's K-8 school & NEW high school in '27, with conservation trails, orchards, farmstands, golf, eateries & commuter routes nearby.

149 Nourse Rd, Bolton

Listing courtesy of Listing Agent: Kotlarz Group from Listing Office: Keller Williams Realty Boston Northwest.

33 Wheeler Rd, Bolton
$900,000
4 Beds ⋅ 3 Baths ⋅ 73578702 MLS
Full of character, unexpected spaces & thoughtful details, this expanded Cape is anything but ordinary. Privately set back on 5+ acres on a dead-end street, a welcoming farmer’s porch invites you to slow down and enjoy the extraordinary perennial-filled gardens & visiting wildlife. Inside, spaces unfold with wonderful versatility. Host memorable dinner parties in the spacious dining room or curl up beside the living room pellet stove and watch the snow fall outside. The showpiece is the enormous 31'x25' family room addition, where soaring ceilings, walls of windows, warm Brazilian hardwood floors, a dramatic fieldstone fireplace & Mt. Vernon pellet stove create an unforgettable gathering space. Open to the well-appointed kitchen with granite counters, this incredible space easily accommodates a crowd. Outdoor entertaining is just as impressive, with a remarkable 36' three-season sunroom opening to multi-tiered composite decks, while the bocce court & fire pit beckon friends and family to gather, play & linger a little longer—all surrounded by the private backyard & woodlands. An organic raised-bed garden adds to the outdoor appeal, with fencing that can also serve as a generous dog enclosure. A flexible 1st-floor office/bedroom with adjacent full bath adapts beautifully as needs change. Upstairs, even the hallway has personality—an extra-wide design and charming dormer outside two bedrooms create a delightful reading nook. Radiant heated floors in the family room, dining room, kitchen, foyer, laundry & 2nd-floor baths add another layer of comfort. The expansive finished lower level offers a playroom, plentiful storage & large game room leading to the oversized 3-car garage, adding even more versatility. Brimming with thoughtful improvements including a Generac whole-house generator, Buderus boiler, LeafGuard gutters, hot water tank ('25) & Roth double-walled oil tank ('26). A distinctive home where there is room to gather, retreat, play & enjoy the outdoors—yet Highland Commons, vibrant downtown Hudson & major commuter routes are conveniently nearby.

33 Wheeler Rd, Bolton

Listing courtesy of Listing Agent: Kotlarz Group from Listing Office: Keller Williams Realty Boston Northwest.

39 Sanders Lane, Bolton
$1,745,000
4 Beds ⋅ 5 Baths ⋅ 73556563 MLS
Welcome to Bolton Hill Estates, where modern luxury meets timeless farmhouse charm. Ideally situated in Bolton, just minutes from the historic Bolton Center and the vibrant downtown of Hudson, this exceptional new construction home offers 4,010 square feet of thoughtfully designed living space with four bedrooms, four-and-a-half baths, and a three-car garage on a private homesite. A dramatic two-story foyer welcomes you into an open and inviting floor plan designed for today's lifestyle. The stunning family room features a soaring vaulted ceiling and flows seamlessly into the gourmet kitchen and sun-filled breakfast area. The kitchen is beautifully appointed with Decor appliances and a sophisticated blend of white and natural wood cabinetry, quartz countertops, premium finishes, a spacious pantry, and an adjacent mudroom for everyday convenience. A formal dining room and private study provide elegant spaces for entertaining, working from home, or quiet relaxation. Step outside to the first-floor deck, offering the perfect setting for outdoor dining, morning coffee, or simply enjoying the peaceful surroundings. Upstairs, the luxurious primary suite offers a private retreat with a spa-inspired bath featuring a double vanity, soaking tub, oversized shower, and expansive custom designed walk-in closet. Three additional ensuite bedrooms provide exceptional comfort and privacy for family and guests. Hardwood flooring, designer finishes, and thoughtfully curated details enhance every space throughout the home. Experience refined New England living in one of Bolton's newest and most desirable neighborhoods. Move-in anticipated early 2027.

39 Sanders Lane, Bolton

Listing courtesy of Listing Agent: Janice Dumont from Listing Office: JD Advisors, Inc.

26 Corn Road, Bolton
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 73518033 MLS
Beyond the stately stone entrance, a winding drive reveals one of Bolton's most thoughtfully crafted private estates—a residence where timeless New England architecture, exceptional craftsmanship, and extraordinary natural beauty exist in perfect harmony. Privately sited on 6.53 acres surrounded by mature woodlands, curated gardens, tranquil water features, and conservation trails, this custom-built Craftsman Colonial offers over 5,100 square feet of impeccably designed living space. Designed as a forever home, every detail reflects an uncompromising commitment to quality. Rich architectural millwork, soaring ceilings, three fireplaces, and walls of windows create warm, inviting interiors filled with natural light. The elegant living room showcases a hand-applied silver-leaf-conferred ceiling, while the chef's kitchen is appointed with custom maple and cherry cabinetry, a 48" Wolf gas range with dual ovens, griddle and indoor grill, a 48" Sub-Zero refrigerator, ideal for everyday living and entertaining. The luxurious primary suite offers a private retreat, while the finished walk-out lower level provides exceptional flexibility with a lounge, media room, fitness space, guest accommodations, and direct access to the beautifully landscaped grounds. Outdoors, bluestone patios and walkways, a mahogany deck, mature gardens, and an extensive irrigation system create an idyllic setting for enjoying every season. Built with longevity and efficiency in mind, the home features an Energy Kinetics high-efficiency boiler, three-zone central air with five comfort zones, whole-home audio, central vacuum, smart home lighting, automatic standby generator, oversized three-car garage, Andersen windows, copper gutters, and a Rhino Shield exterior coating with transferable warranty. Perhaps the home's greatest luxury is its remarkable level of stewardship. Custom designed in collaboration with the original owners and meticulously maintained for more than two decades, every finish, system, and detail has been thoughtfully preserved through proactive care. From the pristine condition of the cabinetry and flooring to the mechanical systems, the pride of ownership is immediately evident. A truly exceptional offering where timeless design, enduring craftsmanship, and unmatched privacy come together to create one of Bolton's finest residences.

26 Corn Road, Bolton

Listing courtesy of Listing Agent: Suzanne Dutkewych from Listing Office: Hazel & Company.

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