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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.

97 Fox Run Road, Bolton
$1,799,800
5 Beds ⋅ 7 Baths ⋅ 73591402 MLS
Take advantage of Fall Market Savings. Seller has relocated presenting next owner over a 1/2 million dollars in SAVINGS! The hard work is done for you....NEW POOL, patios, putting green, kids play area, entertainment room, basketball practice area, outside stone hearth. BONUS 2 story carriage house! This Romantic French Country Estate is located in Bolton's prestigious "FOX RUN" neighborhood! Hate cookie cutter homes? This home and neighborhood are for you. Sweeping treelined driveway guides to expansive lawns, trellis gardens, pergolas, stonewalls, patios, outdoor gas hearth, putting green & play area. Breathtaking great room w/ European details of exposed timer beams, floor 2 ceiling windows, 2-story fireplace, Parisian moldings & trims. Stone island & Wolf /Subzero, copper sink & banquette seating. Formal dining enclave, oenophilia, music or library nook. French doors open to balcony overlooking pool area & gardens. Luxurious 1st Floor primary suite w/dual vanities, 2 Custom closets, tile shower, WC & spa tub w/ picture window to soak in the picturesque grounds. 3 more bedrooms w/ ensuite baths - one that is handicap friendly all on the main level. Artisan crafted wood & iron banisters lead to Au Pair/Guest suite w/ private Bedroom/Office & Full Bath. An elegant, curved staircase leads to Billiards & Media rooms opening to NEW salt h20 pool & outdoor entertaining area. A detached 2-story 56 X 26 carriage house (perfect for car collection, hobby space or golf simulator) Enchanting 1-of-a-kind home! Top rated “Brand New Nashoba Highschool 2027” & Elite Master’s Academy. A fairy tale setting at a magical price. Home is Move in Ready .....Quick Closing possible.

97 Fox Run Road, Bolton

Listing courtesy of Listing Agent: Jacky Ann Foster from Listing Office: MJT Realty Group.

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.

55 Coventry Wood Road, Bolton
$775,000
3 Beds ⋅ 3 Baths ⋅ 73588218 MLS
This captivating Contemporary in a desirable East Bolton neighborhood is a truly distinctive retreat, thoughtfully designed to embrace its natural surroundings while offering an inviting blend of vintage character and modern updates. Dramatic vaulted ceilings and expansive windows fill the open-concept interiors with natural light bringing the beauty of the surrounding woodlands indoors. The cabinet-rich chef’s kitchen features a center island, stainless steel appliances, and gas cooking, flows effortlessly into an expansive family room - an ideal setting for everyday living and gathering. The intimate dining room, warmed by a cozy fireplace, sets the stage for memorable dinner parties. An expansive composite deck overlooking tranquil woodlands extends the living experience outdoors creating a peaceful, private backdrop for enjoying the seasonal babbling brook and changing colors of the seasons. Relax & unwind in the luxurious primary bedroom suite w/generous dual closets & updated full bath. The finished walk-out lower level w/updated 1/2 bath offers exceptional versatility for a home gym, play room, home office, or in home business. Ideally situated near commuting routes, conservation trails, farm stands, and local dining, this special property offers something increasingly rare: distinctive contemporary architecture paired with a deep connection to nature.

55 Coventry Wood Road, Bolton

Listing courtesy of Listing Agent: Amy Balewicz Homes 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..

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..

422 Still River Road, Bolton
$799,000
3 Beds ⋅ 3 Baths ⋅ 73581444 MLS
Fully renovated and beautifully appointed, this exceptional ranch offers an elevated take on single-level living set against a picturesque backdrop of sprawling lawn, mature landscaping, and private woodlands. Thoughtfully designed for both everyday comfort and effortless entertaining, the home pairs sophisticated finishes with inviting spaces for both quiet moments and unforgettable gatherings. The gleaming white kitchen is both timeless and contemporary, with crisp white cabinetry, quartz countertops, stainless appliances and connects effortlessly to the bright and open-concept living spaces, creating an atmosphere that is bright, sophisticated open concept living spaces. The spectacular primary suite is a private retreat, distinguished by its vaulted ceiling, walk-in closet w/custom shelving system, and spa inspired bath - a space designed to make every day feel a little more indulgent. Step outside to the cheerful screened porch overlooking the private backyard, an idyllic setting for morning coffee, al fresco dining, or evenings spent lingering long after sunset. The finished walk-out lower level is a destination of its own with a stylish wet bar, inviting lounge, exposed brick accents, cozy pellet stove, & full bath. Whether hosting game nights, relaxing by the fire, or settling in for a movie, this versatile space offers an entirely separate space for gathering and making memorable moments. With its beautifully curated interiors, seamless indoor-outdoor connection, and exceptional versatility, this is more than a renovated ranch. It is a home designed around the way you want to live.

422 Still River Road, Bolton

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

35 Bare Hill Road, Bolton
$750,000
3 Beds ⋅ 2 Baths ⋅ 73581442 MLS
Welcome to this captivating bow house Cape nestled on a picturesque lot on one of Bolton’s most scenic roads providing a rare opportunity to live in a truly special storybook setting bestowing peace, privacy, & a daily connection to nature. The stylishly renovated kitchen w/soap stone countertops, upscale appliances, spacious island, & wood stove flows seamlessly into the vaulted ceiling family room w/exposed beams & Rumford fireplace ideal for gathering w/friends & family. Savor your morning coffee in the cheery 3 season sunroom or step outside to the expansive Azek composite deck w/lighted posts offering tranquil views of the sprawling backyard & abutting woodlands creating a serene backdrop for outdoor living. Enjoy the convenience & comfort of a 1st floor primary bedroom & full bath. Upstairs you’ll find 2 generous bedrooms & a freshly updated bath. The beautifully finished walk-out lower level offers an inviting retreat w/warm hardwood floors, cozy cast iron stove, and abundant space designed for both relaxation and entertaining. Filled w/character & natural light and direct access to the outdoors, this versatile level adds an exceptional layer of living space to the home. Enjoy refinished wide pine floors, extensive millwork, & an excellent location near Vaughn Hill conservation land & trails, winery, orchards, commuter routes & top rated schools. This is a must see property for the discerning buyer seeking style and soul.

35 Bare Hill Road, Bolton

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

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.

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.

114 Fox Run Rd, Bolton
$1,550,000
5 Beds ⋅ 5 Baths ⋅ 73567553 MLS
Welcome to 114 Fox Run Road, an impressive Bolton residence offering nearly 5,900 square feet of beautifully appointed living space on approximately 1.66 acres. With five bedrooms, generous entertaining spaces and a three-car garage, this exceptional property combines timeless New England appeal with the peace of mind of significant recent improvements.Since 2025, the home has undergone an extensive refresh, including a brand-new roof, new boiler and water heater, new garage doors, freshly painted exterior and a completely repainted interior—major investments that allow the next owner to move in and enjoy the home from day one.Inside, spacious, light-filled rooms provide an ideal balance of comfortable everyday living and sophisticated entertaining. The expansive floor plan offers wonderful flexibility for gatherings, working from home and hosting overnight guests.The outdoor living spaces are equally impressive. Set on beautifully landscaped grounds, the property features an outdoor kitchen and patio, fireplace, and gazebo, creating a private setting for summer entertaining, crisp fall evenings and year-round enjoyment.Located in one of Bolton’s desirable residential settings, 114 Fox Run Road offers the rare combination of space, privacy, substantial recent upgrades and exceptional indoor-outdoor living.Beautifully refreshed, thoughtfully updated and truly move-in ready—this is a home where the major work has already been done.

114 Fox Run Rd, Bolton

Listing courtesy of Listing Agent: Heather Burke from Listing Office: Kinlin Grover Compass.

3 Sargent Rd, Bolton
$699,900
3 Beds ⋅ 2 Baths ⋅ 73561339 MLS
**WANT TO LOWER YOUR MORTGAGE PAYMENT? Yes, please! Ask us about the lender-sponsored rate buydown program. Buyer must qualify through the participating lender; terms and conditions apply.** *SIGNIFICANT PRICE REDUCTION. MOTIVATED SELLER!* Tucked away at the end of a private dead-end road, this contemporary Cape offers a lifestyle defined by privacy, tranquility, beautiful natural surroundings and flexible living spaces. Freshly painted throughout in a designer-selected color palette complemented by handsome hardwood floors, this home is polished, inviting and move-in ready. The dramatic, skylit living room features a soaring cathedral ceiling and stunning floor-to-ceiling brick fireplace, creating an impressive gathering space filled with abundant natural light. The open-concept flow into the dining area and kitchen—featuring white cabinetry, granite counters and stainless steel appliances—makes entertaining effortless, while a slider opens to an expansive deck overlooking your own wooded oasis and extends everyday living outdoors. With two bedrooms, a full bathroom and laundry on the main level, this home provides a rare opportunity for single level living without sacrificing space—ideal for guests, multigenerational living or buyers planning ahead. Upstairs, the primary suite offers unparalleled privacy, with an exterior balcony nestled among the treetops, while the versatile loft overlooks the great room below—together creating a distinctive owner’s retreat. Need additional space? The finished lower level offers endless possibilities—from movie nights and game days to a home office, fitness studio or guest space—you decide! An attached two-car garage provides convenience, while the dedicated outside kennel area is a welcome bonus for dog lovers. Whether you’re enjoying quiet mornings on the deck, afternoons exploring your five wooded acres and nearby conservation trails, or peaceful evenings relaxing after a long day, this is a home that lets you slow down and truly enjoy where you live. Located within the top-rated Nashoba Regional School District and just minutes from 495, Route 117, and local restaurants and amenities, this home offers the perfect balance of convenience and quiet. If you’ve been searching for a sense of escape, a connection to nature, and room to breathe without sacrificing accessibility, welcome home!

3 Sargent Rd, Bolton

Listing courtesy of Listing Agent: Emma Weisman from Listing Office: Keller Williams Realty North Central.

55 Pondside Dr Unit 55, Bolton
$589,000
2 Beds ⋅ 3 Baths ⋅ 73560020 MLS ⋅ ['Regency At Bolton'] BLDG.
SELLER WILL CREDIT $5,000 AT CLOSING TOWARDS SIX MONTHS OF HOA FEES! Welcome to Regency at Bolton, a 55+ active adult community. 55 Pondside Dr is a bright and open unit with soaring ceilings, cathedral style large windows. First floor has a master suite, full bath, large walk in closet and laundry for easy access. The upstairs area has a bedroom, full bathroom, a large loft area, perfect for relaxation. The bonus room offers flexibility as an office, crafts or a storage room. A nice deck that overlooks a wooded area. Unfinished basement is very spacious.The Regency offers a perfect blend of comfort, connection and peaceful living. Enjoy the charm of a friendly neighborhood where people know and interact with each other. You will love the group activities and social gatherings. The community feels genuine, surrounded by a quiet country feel, with convenient access to local amenities. This home is ideal for those looking to simplify without sacrificing lifestyle. Whether you’re enjoying morning walks through the community, relaxing outdoors, or entertaining friends and family, this home offers an easy living setting. The clubhouse has a view of the pond with a water fountain and is perfect for working out or private larger gatherings with your family and friends. Close proximity to Rt 495, Rt 2 and Masspike. Priced to sell and Easy to show!

55 Pondside Dr Unit 55, Bolton

Listing courtesy of Listing Agent: Maria Koral from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

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.

90 Corn Rd, Bolton
$379,000
73507290 MLS
Opportunities like this are becoming increasingly rare. Set on 4.13 in the desirable town of Bolton, this exceptional homesite is surrounded by prestigious residences and protected conservation land, offering the perfect balance of privacy, natural beauty, and everyday convenience.With a fully approved 7-bedroom septic design and permit already in hand, this property offers remarkable flexibility to create a truly extraordinary estate. Design the custom home you've always envisioned while taking full advantage of Massachusetts' Accessory Dwelling Unit (ADU) regulations. Whether you envision a detached carriage house for guests, a private in-law residence, an au pair suite, a dedicated home office, an apartment above your garage, or an income-producing rental, the approved septic capacity opens the door to endless possibilities that are seldom available in this area. Create a multigenerational compound, generate supplemental rental income, or simply enjoy the flexibility to adapt your property as your family's needs evolve.Boasting approximately 775 feet of road frontage, the parcel may also offer future subdivision potential (subject to town approvals), providing additional long-term investment value.Ideally located just minutes from Bolton's highly regarded schools, local orchards and farms, conservation trails, and major commuter routes including I-495 and Routes 2, 117, and 290, this is an exceptional opportunity to build not just a home, but a legacy property designed around your lifestyle for generations to come. contractors, builders, developers, investors, approved septic design, permits, buildable, development opportunity, site plan

90 Corn Rd, Bolton

Listing courtesy of Listing Agent: Christopher Mackin from Listing Office: Hazel & Company.

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Bolton Real Estate

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