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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.

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..

50 Nashaway Road, Bolton
$850,000
3 Beds ⋅ 3 Baths ⋅ 73581428 MLS
This picturesque property nestled in one of Bolton’s most coveted neighborhoods captures the best of the Bolton lifestyle where children can safely play & neighbors become friends. This captivating Colonial has been thoughtfully enhanced by its current owners w/numerous updates & improvements including renovated kitchen & baths, refinished hardwood floors, & freshly painted interior, creating a turnkey residence that balances timeless architecture with sophisticated, modern comfort. The heart of the home is the beautifully updated kitchen, featuring gleaming white cabinetry, stone countertops, stainless steel appliances, soapstone sink, and an inviting dining area overlooking the tranquil koi pond and surrounding woodlands. The adjoining fireplaced family room with vaulted beamed ceiling, creates a warm and welcoming space to gather w/family and friends. A lofted bonus room above adds flexible space for a playroom, craft studio, homework area, or 2nd home office. Upstairs, the serene primary suite features a spa-inspired bath & walk-in closet while 2 additional generously sized bedrooms, & full bath completes the 2nd level. A partially finished lower level offers additional versatile living space. Outside, the expansive yard & abutting woodlands create an idyllic backdrop for play, outdoor entertaining, gardening, and a connection to nature. Enjoy a convenient location near orchards, winery, conservation trails, farm stands, commuter routes & top rated schools.

50 Nashaway Road, Bolton

Listing courtesy of Listing Agent: Amy Balewicz Homes 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.

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