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8 Rolling Hills Trl, Bolton
$509,900
4 Beds ⋅ 3 Baths ⋅ 24215987 MLS
Looking for a home where space, privacy, and a great location come together? Nestled in the sought-after Birch Mountain neighborhood on 1.6 acres, this beautifully cared-for home offers over 2,200 square feet of bright, inviting living space with 4 spacious bedrooms and 2.5 baths. From the moment you step inside, you'll feel the warmth of a home that has been meticulously maintained and truly loved. Sun-filled living spaces, generously sized rooms, and a layout made for everyday living and entertaining give you plenty of room to make it your own. This home offers the peaceful setting you've been looking for without sacrificing space or convenience. Move-in ready and waiting for its next chapter!

8 Rolling Hills Trl, Bolton
18 Lucks Way, Bolton
$589,900
3 Beds ⋅ 3 Baths ⋅ 24215567 MLS
ESCAPE THE ORDINARY AT 18 LUCKS WAY! A PRIVATE 4-ACRE COUNTRY RETREAT! Enjoy a blend of privacy, beauty, & timeless charm in this Custom-Built, Original-Owner Home nestled in the picturesque countryside! A winding private driveway welcomes you to 4 serene acres with mature trees, stone walls, colorful perennial gardens, and views of a neighboring horse. Relax on the wraparound porch and enjoy peaceful mornings, spectacular fall foliage, and the tranquility of nature! Step inside to an impressive open-concept design featuring soaring vaulted ceilings, sun-filled living spaces, and a dramatic second-floor balcony overlooking the main living area and 2 story foyer. An inviting floor to ceiling fieldstone Fireplace with stove insert creates the perfect gathering place, the inviting Kitchen offers granite countertops, solid maple cabinetry, SS appliances, and generous workspace along with large eat-in space surrounded by bright windows. Enjoy a formal Dining room for holiday dinners and a wonderful mudroom with large pantry and convenient first-floor Laundry, and an attached 2-Car Garage with unfinished, prewired space above-ideal for a future Bonus Room or 4th Bedroom. UNIQUE 1st FL SUITE w/Full Bath, Soaking tub and His & Her Closets. The expansive 9-foot walkout Basement with double-wide exterior doors offers more possibilities for workshop or storage! Quality 2x6 construction, 200-amp, generator hookup, Forced Hot Air & C/Air, and fully owned, paid-off solar panels add Value!

18 Lucks Way, Bolton
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
2 Old Harvard Rd, Bolton
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73594117 MLS
Tucked along a peaceful, scenic side road with direct access to 600+ acres of conservation land & nearly 17 miles of trails, this exceptional Colonial offers an elevated lifestyle connected to nature. The open floor plan unfolds with ease—anchored by a chef-inspired kitchen with generous center island, pantry & sunlit dining area flowing effortlessly into a spacious family room with cozy gas fireplace, perfect for everyday moments & memorable gatherings. At day’s end, unwind in the serene primary suite featuring an expansive walk-in closet & a luxurious bath w/ soaking tub & walk-in tiled shower. A versatile 1st floor office or guest room & a well-designed mud room enhance function & flexibility, while the unfinished walk-out lower level presents an exciting opportunity to create the space you’ve always envisioned. Bring your vision to life in a truly special setting—where nature, privacy & possibility come together.

2 Old Harvard Rd, Bolton
6 Nourse Road, Bolton
$650,000
3 Beds ⋅ 2 Baths ⋅ 73594063 MLS
Nestled on an expansive corner lot along one of Bolton's most scenic roads, this charming Ranch offers the ease of one-floor living, modern comfort, & timeless character. The heart of the home is an updated kitchen featuring a center island, stone counters, and stainless appliances, opening to a cheerful dining area — perfect for everyday living and entertaining. The spacious family room adorned w/exposed beams, an impressive stone fireplace & wall of windows flooding the room w/natural light creates a warm & inviting gathering space. Unwind in the dreamy primary bedroom w/custom built-ins. A front living room offering additional flex space, 2 additional bedrooms, 2 full bathrooms, mudroom, & laundry room are all thoughtfully arranged on the main level. A finished walk out lower level provides versatile living spaces to meet evolving needs for a home office, playroom, or guest room. Step outside to a stone patio & lush expansive fenced yard offering endless possibilities for gardening, play, or relaxation. Enjoy energy efficient solar panels, Buderus furnace, handsome hardwood floors, freshly painted exterior, and a desirable location near Bolton town center, NEW high school & elementary school, commuter routes, conservation trails, golf course & more!

6 Nourse Road, Bolton
00 Long Hill Road, Bolton
$169,900
73593345 MLS
Every great home starts with the right piece of land. Set along one of Bolton’s scenic country roads, this 2.06-acre wooded parcel offers an opportunity for builders, investors, and prospective homeowners to explore the possibilities of a property in a desirable Central Massachusetts location! Zoned R1, with a perc test on file and water, gas, and electricity at the street, this lot is worth a closer look for those considering their next project. Enjoy the charm of Bolton’s countryside while remaining close to local favorites, including Bolton Orchards, Bolton Spring Farm, scenic conservation areas and walking trails, and Nashoba Valley Winery. Nearby downtown Hudson offers a variety of restaurants, cafés, shops, and everyday conveniences. The property also offers access to the Florence Sawyer School and Nashoba Regional School District, along with convenient connections to major commuter routes. Ready to explore the possibilities? Take a closer look at this Bolton property and start planning what comes next!

00 Long Hill Road, Bolton
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
52 Country Club Rd, Bolton
$899,900
4 Beds ⋅ 5 Baths ⋅ 24214232 MLS
Prepare to be captivated by this stunning, stately brick Colonial, perfectly situated on a beautifully landscaped lot surrounded by mature trees and natural beauty. This exceptional residence offers 5 bedrooms and 4.5 bathrooms, blending timeless elegance with everyday comfort and privacy. Each spacious bedroom features its own ensuite bathroom, providing the ultimate convenience for family and guests alike. The versatile fifth room can easily serve as a private home office, guest suite, or an additional oversized bedroom to fit your lifestyle. From its classic curb appeal to its thoughtfully designed interior, this home is truly one of a kind. Step outside to your own private backyard, where a beautifully finished stone patio and spacious deck create the perfect setting for relaxing or entertaining. Surrounded by mature trees, the expansive yard offers exceptional privacy and plenty of room to add the pool of your dreams, making this outdoor space full of endless possibilities.

52 Country Club Rd, Bolton
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
42 Castlerock Ln, Bolton
$899,999
4 Beds ⋅ 4 Baths ⋅ 24212552 MLS
Meticulously maintained Colonial located on a cul-de-sac in Bolton, built in 2007, offering 4 bedrooms, 3.5 bathrooms and 3,664 square feet on 1.09 acres. Hardwood floors, crown molding and wainscoting complement the interior. A front entry with sidelights welcomes you into a spacious, bright foyer. The kitchen features cherry cabinetry, stainless steel appliances and hardwood flooring, and opens to a generous family room with a stone fireplace. Two staircases provide access to the second floor, where the primary suite includes two spacious closets and a bathroom with a whirlpool tub, separate shower, cherry vanity cabinetry and double sinks. Three additional bedrooms, a Jack-and-Jill bathroom, a convenient second-floor laundry room and a separate nook offering library or storage space complete the second floor. The finished third floor provides approximately 600 additional square feet for recreation, a home office or other flexible use. This space is not included in the stated 3,664 square feet. Outside, a spacious, low-maintenance Trex deck overlooks the expansive, private, park-like yard with an irrigation system. An oversized 5-car garage provides ample room for vehicles, storage and hobbies.

42 Castlerock Ln, Bolton
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
385 Green Road, Bolton
$1,850,000
5 Beds ⋅ 4 Baths ⋅ 73585881 MLS
Introducing a rare opportunity to experience elevated luxury living in a quintessential New England setting. 3 privately positioned homesites ranging from 4-5 picturesque acres, offer the space, seclusion, and natural beauty that are increasingly rare to find. Each lot is thoughtfully positioned to maximize privacy yet part of an intimate enclave of 5 homes, offering the best of both worlds: the seclusion of a private estate and the warmth of a community. Direct access to conservation land and scenic walking trails offers a daily connection to nature right outside your door. Buyers can choose the path that suits them best. Select one of our professionally designed plans, such as our signature Farmhouse Colonial, showcasing thoughtful architectural details, timeless charm, distinctive custom millwork, and high-efficiency construction. Or bring your own plans and partner with our distinguished builder, a respected craftsman known for meticulous attention to detail, superior quality, and an unwavering commitment to excellence. Either way, you'll have the opportunity to collaborate on design elements and finishes so your home is tailored to your individual style and lifestyle. 3 Exclusive Lots Available Starting @$1,850,000

385 Green Road, Bolton
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
24 Sanders Lane, Bolton
$1,660,000
4 Beds ⋅ 4 Baths ⋅ 73579137 MLS
Welcome to Bolton Hill Estates, a new neighborhood of custom homes set in scenic Bolton. With construction underway, there is still time to personalize your home with your choice of finishes and selections. Blending timeless farmhouse architecture with modern luxury, this thoughtfully designed home offers an elegant balance of comfort, style, and functionality. The open-concept main living area features a gourmet kitchen with premium finishes, a sun-filled dining area, and a spacious family room anchored by a cozy fireplace, an inviting setting for both everyday living and entertaining. The home offers four bedrooms and three-and-a-half bathrooms, including an ensuite guest bedroom conveniently located on the first floor. Wooded views provide a peaceful backdrop, complementing the home’s New England setting. Every detail reflects quality craftsmanship and thoughtful design, from the architectural character to the carefully considered floor plan. Bolton Hill Estates offers the opportunity to enjoy refined New England living in a private, thoughtfully designed neighborhood surrounded by natural beauty.

24 Sanders Lane, Bolton
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
14 Annie Moore Road, Bolton
$1,025,000
4 Beds ⋅ 4 Baths ⋅ 73578942 MLS
This picturesque property on one of Bolton’s most scenic private roads provides a rare opportunity to live in a truly special setting, surrounded by conservation land bestowing peace, privacy, & a daily connection to nature. A welcoming foyer opens into the heart of the home a well-appointed kitchen w/generous island, stainless appliances, dual ovens & stone counters flowing effortlessly into the sun-filled family room w/soaring ceilings, fireplace & oversized windows framing views of the surrounding landscape. A formal dining room sets the stage for memorable gatherings, while a 1st-floor office offers flexibility for remote work. Retreat to the 2nd floor primary suite w/double walk in closets, sitting area & spa-like bath. The finished walk out lower level extends the living spaces further, featuring a spacious bonus room w/bar and private guest suite w/full bath. Step outside to the expansive deck overlooking the lush lawns, mature plantings, & and shaded woodlands. Enjoy distinctive millwork, recent updates including roof, appliances, & freshly painted exterior and an unbeatable location near commuter routes, farm stands, conservation trails & vibrant downtown Hudson!

14 Annie Moore Road, Bolton
68 Quaker Lane, Bolton
$950,000
4 Beds ⋅ 3 Baths ⋅ 73578922 MLS
Enjoy peace, serenity, & an abundance of privacy at this meticulously maintained Colonial nestled on 4.5 acres brimming w/custom architectural details exuding classic & timeless elegance. Enter into a gracious foyer leading to the heart of this beautiful home, a cabinet-packed kitchen w/spacious island, induction cooktop, dual ovens, & stone counters flowing seamlessly into the striking fireplaced family room w/wood stove, soaring ceiling, & a wall of windows flooding the room w/natural light. A formal dining room offers an elegant setting for special gatherings, while the 1st-floor office w/French doors provides a convenient work from home space. Step outside to the expansive deck offering views of the tranquil backyard & abutting woodlands or gather around the backyard fire pit, the perfect spot for toasting marshmallows on those cozy fall evenings. Unwind in the dreamy primary bedroom suite w/sitting area, generous walk-in closet & indulgent spa bath. A finished LL offers additional space for a 2nd home office, playroom, or home gym. Enjoy distinctive millwork, recent updates including a new roof, hw heater, carpet & newer appliances, complemented by a freshly painted interior & exterior and an unbeatable location near major routes, top rated schools, farm stands, & vibrant downtown Hudson!

68 Quaker Lane, Bolton
14 Dean Dr, Bolton
$475,000
3 Beds ⋅ 2 Baths ⋅ 24205465 MLS
Move in ready and energy efficient! New central heating and cooling system, oil tank, well pump, hot water heater, water softener, water filtration system, garage door opener, roof 10 years old. Fenced in yard for kids or pets. Hardwood floors, crown molding, and fresh interior paint. The kitchen features custom cabinetry, granite counters, marble backsplash, and ceramic tile flooring. A formal dining room and a spacious living room with a fireplace add charm. The finished lower level provides extra living space for gym, family room or office. With a plumbed in half bath and finished laundry room. Level lot great for entertaining. A large 2 car garage. Easy commute to 84. 91 and less than 10 minutes to Manchester center. A stones throw to local farms, parks, and bike trails, giving the area a true vacation like feel. This turnkey home is a gem. Seller is actively looking for a home!

14 Dean Dr, Bolton
15 Converse Rd, Bolton
$389,900
3 Beds ⋅ 2 Baths ⋅ 24203711 MLS
Charming 3-bedroom 2-Bath home nestled in a peaceful, wooded setting, offering privacy and a warm, inviting atmosphere. The spacious interior features beautiful hardwood floors and a comfortable living area filled with natural light. The kitchen offers ample cabinetry, granite countertops, and a convenient layout that opens to the dining area. A striking brick fireplace creates a wonderful focal point and adds character and warmth to the main living space. Outside, enjoy a generous lawn surrounded by mature trees and established landscaping, creating a tranquil setting for relaxing or entertaining. A wonderful opportunity to own a home with classic charm, privacy, and plenty of potential.

15 Converse Rd, Bolton
56 West St, Bolton
$469,900
4 Beds ⋅ 2 Baths ⋅ 24203929 MLS
Set on a scenic two-acre lot in desirable Bolton, this beautifully renovated Colonial offers an exceptional blend of classic charm, expansive land, and modern turnkey upgrades. The sun-filled interior welcomes you with a bright, open layout highlighted by refreshed flooring and tasteful finishes throughout. At the heart of the home, the stunning updated kitchen showcases sleek quartz countertops, a stylish tile backsplash, refreshed cabinetry, and new appliances. Upgraded bathrooms accompany four spacious bedrooms, while a side sunroom atrium and an enclosed all-season front porch offer versatile options for a home office, quiet lounge, or bonus entertaining space. Outside, a private rear deck overlooks the sprawling, peaceful backyard, framed by new siding and gutters. Complete with an attached garage and private driveway, this move-in-ready property provides countryside serenity just minutes from Bolton Center, local parks, walking trails, top schools, and quick commuting access via I-384.

56 West St, Bolton
51 Watrous Rd, Bolton
$384,000
3 Beds ⋅ 2 Baths ⋅ 24195758 MLS
Welcome home to this charming, meticulously maintained contemporary nestled on 2.83 beautiful acres in a very private, rural setting in desirable Bolton, CT. Offering 3 bedrooms and 1.5 baths, this inviting home blends comfort, character, and thoughtful updates. The spacious primary bedroom is a true retreat, featuring gorgeous custom hardwood floors and a cozy propane fireplace. Hardwood flooring continues throughout the upper level. Downstairs, abundant natural light highlights earthy slate flooring and a wood-burning fireplace, creating a warm space to relax or gather with loved ones. Updates within the past three years include mini-split heating and cooling systems, new windows, new gutters, and a new water softener. Enjoy peaceful mornings on the Trex front deck, surrounded by nature and privacy. The oversized, heated and cooled two-car garage offers exceptional space for vehicles, hobbies, and projects, while a separate storage shed provides additional room. DON'T MISS THIS OPPORTUNITY! A $5,000 BUYER CREDIT IS OFFERED! Enjoy the privacy, character, and peaceful rural setting this special Bolton home has to offer. Schedule your showing today and imagine making it your own!

51 Watrous Rd, Bolton
921 Main Street, Bolton
$950,000
4 Beds ⋅ 2 Baths ⋅ 73573131 MLS
Move with confidence while keeping the comfort and luxury you deserve. Whether you’re downsizing or rightsizing, this elegant single-story home offers open concept, single-level living in an exceptionally private 5-acre setting. Step outside into your own secluded backyard sanctuary surrounded by natural green borders and mature woodlands. Designed with an emphasis on light and flow, the home delivers a rare architectural experience defined by dramatic 18-foot ceilings and sophisticated passive solar design—keeping the interior naturally warm in winter and comfortably cool in summer. This one-level sanctuary includes a spacious primary suite, three additional bedrooms, a dedicated home office, and a flexible playroom. Outside, discover an inviting oasis designed for relaxation, featuring elegant patios and a beautiful, flowering pergola. Explore the possibility of a custom Accessory Dwelling Unit (ADU) with an effortless, quick access to Route 495.

921 Main Street, Bolton
32 Notch Rd, Bolton
$435,000
3 Beds ⋅ 3 Baths ⋅ 24203757 MLS
BEAUTIFUL HOME WITH A BACKYARD OASIS! A major renovation was done in 2014 adding the second floor which consists of 2 bedrooms, a full bathroom (shower with tub,) laundry room and a den area with built-in book shelves & cabinets and window seat. The main level has a renovated kitchen featuring an island with breakfast bar seating, stainless steel appliances, tile backsplash and charm to spare! The large dining room is open to the kitchen and is perfect for entertaining. The living room draws you in with garden views! FIRST FLOOR PRIMARY BEDROOM SUITE with walk-in closet & full bathroom with walk-in shower! As a part of the 2014 project, the siding, roof, all the windows (minus the living room,) plumbing and electrical were all done, essentially leaving little of the 1951 home left. The half bathroom was also updated in 2014. A rear mudroom seamlessly connects the garage to the home with extra closet space. Did I mention the PARK-like yard with huge blueberry bushes, 2 sheds, 2 stone patio areas, and a deck for enjoying the view?! The basement shows the STEEL I-BEAM construction and offers plenty of storage & workshop space. Close to everything with nearby highway access, hiking trails at Bolton Notch State Park, Hop River State Trail, ice cream at Fish Family Farm, chocolate at Munson's, 20 minutes to Hartford & UCONN's Storrs campus, yummy restaurants, farmers markets, etc! *Price went up due to sellers being willing to give a large credit for a future septic replacement*

32 Notch Rd, Bolton
14 Houghton Farm Ln, Bolton
$1,125,000
5 Beds ⋅ 3 Baths ⋅ 73568995 MLS
Surrounded by conservation land and peaceful woodland views, this exceptional and beautifully maintained 5-bedroom Colonial offers a rare opportunity to enjoy nature, privacy, and community in one of Bolton's premier neighborhoods. Built in 2019, this thoughtfully designed home features rich hardwood flooring, elegant millwork, a private first-floor office, and a stunning two-story family room with a vaulted ceiling, walls of windows, and marble fireplace. Elegantly appointed kitchen opens seamlessly to the main living spaces, creating an inviting flow for comfortable living. Upstairs, the luxurious primary suite serves as a private retreat with a sitting area, custom walk-in closet, and spa-inspired bath. Three additional bedrooms and a finished walk-up third floor provide exceptional flexibility for guests, recreation, or work-from-home needs. Outside, a spacious stone patio overlooks the private backyard, offering the perfect setting for outdoor entertaining. Cherish the quiet, secluded setting but just minutes to I-495 and downtown Hudson. Offering a rare blend of natural beauty, serenity, and convenience, this spectacular property embodies the very best of New England living.

14 Houghton Farm Ln, Bolton
114 Fox Run Rd, Bolton
$1,499,000
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
18 Shoddy Mill Rd, Bolton
$459,900
4 Beds ⋅ 4 Baths ⋅ 24201099 MLS
Welcome home to your own quiet and tranquil retreat tucked away in a wonderfully private setting. An inviting front porch sets the tone, offering the perfect spot to relax and enjoy the peaceful surroundings, inside, this welcoming home features 4 bedrooms one being over the garage, with separate staircase, providing plenty of flexibility for today's lifestyle. With its separate feel and generous space, this room offers wonderful potential for in-law suite, guest quarters, home office, or private retreat. If you're looking for privacy, versatility and a place that truly feels like an escape from everyday, this is one you won't want to miss.

18 Shoddy Mill Rd, Bolton
3 Sargent Rd, Bolton
$689,900
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
5 Llynwood Dr, Bolton
$389,900
2 Beds ⋅ 2 Baths ⋅ 24197756 MLS
Colonial on private level lot across the street from Bolton Lake, and steps from the walking path to Indian Notch Park. This home features 2 full baths, one on each level. Currently 2 bedrooms but could easily be converted to 3 or 4 bedroom with the unfinished room over garage, or make it a family room. Huge Master suite with soaking tub, and sitting room. Private beach association rights. Whole house Kohler generator. This home is being sold As Is.

5 Llynwood Dr, Bolton
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
10 Laurwood Dr, Bolton
$400,000
4 Beds ⋅ 3 Baths ⋅ 24196819 MLS
A classic Colonial with a floor plan that simply works. The bright living room features a large front-facing picture window and hardwood floors, flows seamlessly into the formal dining room. The family room opens to the kitchen, creating the true heart of the home, with direct access to the wraparound deck overlooking the private backyard. Upstairs has four bedrooms and two full bathrooms, with hardwood floors throughout. The multi-level deck steps down to a wide, level yard bordered by mature woods, providing exceptional privacy and a wonderful setting for relaxing or entertaining. A walkout lower level offers convenient access to the backyard and additional possibilities for future living space. While the interior finishes are ready for cosmetic updates, the home's excellent layout, generous space, and beautiful setting are hard to beat. This is a fantastic opportunity to build equity and make the home your own. Recent mechanical updates include an oil-fired boiler and a 200-amp electrical panel with a generator interlock already installed. Continent location, close to highway and shopping centers. Sold AS-IS.

10 Laurwood Dr, Bolton

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