Bolton Real Estate

Welcome to Bolton, Massachusetts – a hidden gem nestled in Worcester County that perfectly blends small-town charm with modern conveniences. With its picturesque landscapes, rich history, and vibrant community spirit, Bolton offers an idyllic setting for families, professionals, and retirees alike.

Bolton is renowned for its stunning natural beauty, featuring rolling hills, lush forests, and serene ponds. Outdoor enthusiasts will appreciate the abundance of recreational opportunities, including hiking trails, parks, and nearby conservation areas. Whether you're exploring the scenic trails of the Bolton Conservation Trust or enjoying a leisurely afternoon at the picturesque Bolton Town Common, there’s always something to inspire your sense of adventure.

The town boasts a strong sense of community, with a variety of local events and festivals that bring residents together throughout the year. From the annual Bolton Fair to seasonal farmers' markets, there's always a chance to connect with neighbors and celebrate the town's vibrant culture.

Education is a cornerstone of Bolton, with highly-rated schools that cater to students of all ages. Families can take pride in the exceptional educational opportunities available, ensuring a bright future for their children.

Conveniently located just a short drive from major highways, Bolton offers easy access to nearby cities like Worcester and Boston, making it an ideal location for commuters. With a blend of historic charm and modern amenities, Bolton is a place where you can truly feel at home. Discover the warmth and welcoming spirit of Bolton today – your perfect community awaits!

Newest Listings in Bolton

$675,000

3 Beds ⋅ 2 Baths ⋅ 73568344 MLS

Brand new septic system, brand new kitchen, and brand new bathrooms! Welcome to 249 Green Road, a 3-bedroom, 2-bathroom home offering approximately 2,456 total square feet in a great Bolton location.The home has been thoughtfully updated, with some of the highlights including a brand new kitchen and bathrooms. One of the bathrooms also features a heated towel rack for an added touch of comfort. These updates give the home a fresh, modern feel while maintaining the character and functionality of the property.Outside, enjoy your own private pool, perfect for relaxing and entertaining during the warmer months. The 4-car garage is another major highlight, offering plenty of room for vehicles, storage, recreational equipment, a workshop, or whatever else you may need.The property is located in Bolton, a community known for its peaceful setting, open space, farms, and outdoor recreation, while still being convenient to shopping, restaurants, and surrounding towns. Whether you're enjoying the pool, taking advantage of the garage space, or exploring everything the area has to offer, this property gives you plenty of options.New septic, new kitchen, new bathrooms, a private pool, and a 4-car garage make 249 Green Road a unique opportunity to own a beautiful home in Bolton.

249 Green Rd, Bolton

Listing courtesy of Listing Agent: Chelen Smith from Listing Office: Serhant.

$1,650,000

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.

$1,350,000

4 Beds ⋅ 3 Baths ⋅ 73565775 MLS

This renovated Colonial offers an exceptional blend of timeless New England charm, sophisticated design & modern luxury. Set upon a gentle knoll in a desirable cul-de-sac neighborhood , this custom-crafted home has been impeccably maintained & thoughtfully updated throughout. The interior of this stunning home is brimming w/custom millwork & impressive architectural details. The custom chef's kitchen is a show stopper featuring expansive island, coffee center, & notable appliances including La Cornue CornuFé 110 Range, Sub-Zero Wine Refrigerator & Sub Zero French Door Refrigerator and opens seamlessly into the elegant dining room & cozy gas fireplaced living room w/a wall of built-in bookcases. The 2nd floor features a luxurious primary suite with walk-in closets, spa-like bath w/ dual vanities, jetted tub & shower, laundry room & 3 additional spacious bedrooms. A 2nd staircase leads to the expansive & versatile family room. Outside, a sprawling patio overlooks the private grounds featuring stone walls, fully fenced back/side yard, lush lawn & surrounding woodlands, creating a serene & private setting for entertaining or quiet relaxation. Enjoy wide-pine floors, energy efficient Buderus furnace, 1 new AC unit, newer roof & numerous upgrades reflecting the exceptional care given to this property. Ideally located near conservation land & trails, farm stands, orchards & winery, Bolton’s top-rated schools, & the vibrant shops, restaurants & amenities of downtown Hudson. This property is a true gem!!

24 Rocky Dundee Road, Bolton

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

$724,900

4 Beds ⋅ 3 Baths ⋅ 73563053 MLS

Classic Colonial in desirable South Bolton, privately situated on approximately 1.5 acres at the end of an unpaved shared driveway. Conveniently located near Nashoba Regional schools, conservation land, local farms and markets, recreation and I-495. Offering approximately 2,568 square feet of living space, this 4-bedroom home features a traditional floor plan with spacious living and dining rooms, a full basement and 2-car garage. Recent improvements include fresh interior and exterior paint, updated bathrooms and new hardwood flooring, providing a solid foundation for the next owner. The kitchen remains ready for modernization, while the older screened porch and rear deck offer an opportunity to create inviting outdoor living spaces overlooking the private property.With its classic architecture, generous room sizes and established setting, this home offers an excellent opportunity for buyers seeking to personalize a property and build equity over time. Enjoy nearby Nashoba Regional High School, Florence Sawyer School, conservation trails and open space, Bolton's resident Little Pond Town Beach, local farms and markets, and convenient access to Route 117 and I-495. Home is being sold AS-IS. Seller has not lived in the home and makes no representations regarding its condition or history. Buyers and their agents are encouraged to conduct their own due diligence and inspections.

1157 Main St, Bolton

Listing courtesy of Listing Agent: Patricia Sutherland from Listing Office: Keller Williams Realty Boston Northwest.

$774,900

3 Beds ⋅ 2 Baths ⋅ 73561339 MLS

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.

$589,000

2 Beds ⋅ 3 Baths ⋅ 73560020 MLS ⋅ ['Regency At Bolton'] BLDG.

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.

$1,998,000

5 Beds ⋅ 7 Baths ⋅ 73558929 MLS

Romantic French Country Estate in prestigious neighborhood! 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 primary suite w/dual vanities, tile shower, & 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. An elegant, curved staircase leads to Billiards & Media rooms opening to NEW salt h20 pool & outdoor entertaining area. A 2-story 56 X 26 carriage house completes this enchanting 1-of-a-kind home! Top rated “Brand New Nashoba Highschool 2027”& Master’s Academy

97 Fox Run, Bolton

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

$1,150,000

5 Beds ⋅ 4 Baths ⋅ 73557391 MLS

This grand Colonial built with the highest quality is available now in the amazing town of Bolton. As you enter your inviting front porch, you'll take notice of the newer Pella windows and tall ceilings. The open chef's kitchen has tall cabinets complete with stainless steel appliances and stone countertops. Enjoy your double sided wood burning fireplace by your informal and formal living areas. Or sit back in your screened in porch and relax looking out to your tranquil 4.5 acres. The outdoor space continues with a nice deck for grilling that leads down to a stone patio with outdoor fire pit. 4 large bedrooms upstairs with a primary suite as well as an additional 5th bedroom in the fully finished basement with full spa like bath, perfect for an in-law suite. New HVAC 2025, top of the line Buderus furnace, 50yr architectural shingles, Pella windows 2018, new well pump and whole house filter system 2017, professional exterior paint 2017 and new garage door.

68 Vaughn Hill Rd, Bolton

Listing courtesy of Listing Agent: Jeffrey Incutto from Listing Office: BA Property & Lifestyle Advisors.

$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.

$199,900

73555279 MLS

Bring your vision to life on this beautiful 2-acre parcel set along one of Bolton's most scenic country roads. Whether you're planning a custom home, or your next investment project, this property offers an outstanding opportunity in a desirable location. Enjoy a peaceful setting with the convenience of nearby commuter routes, top-rated schools, conservation land, local farms, orchards, equestrian facilities, and the shops and restaurants of vibrant downtown Hudson. Don't miss the chance to secure a prime piece of land and start building your future!

Long Hill Rd, Bolton

Listing courtesy of Listing Agent: Jim Black Group from Listing Office: Real Broker MA, LLC.

$850,000

2 Beds ⋅ 2 Baths ⋅ 73554754 MLS

Luxury single-level living at an exceptional value in Bolton's newest active adult community. Last remaining unit left and it has a large exclusive use area with true single-family living feel without the maintenance. This elegant new construction home offers over 2,000 square feet of thoughtfully designed living space featuring a great room, gourmet kitchen, oversized center island, private office, and attached two-car garage. The spacious primary suite includes a spa-inspired bath and a generous walk-in closet. Enjoy maintenance-free living, quality craftsmanship, and the opportunity to personalize finishes while construction is underway. Conveniently located near Rt. 495, golf courses, restaurants, shopping, and all that Bolton and the Nashoba Valley area have to offer.

1 Mallard Ln Unit 1, Bolton

Listing courtesy of Listing Agent: Derek Greene from Listing Office: The Greene Realty Group.

$899,900

4 Beds ⋅ 3 Baths ⋅ 73541906 MLS

Welcome to this stunning, beautifully refreshed Colonial set on a private 2.5-acre lot in sought-after Bolton. From the moment you enter, you’re greeted by sun-drenched spaces, gleaming hardwood floors, and a seamless layout designed for both everyday living and elevated entertaining. The show-stopping kitchen features upgraded cabinetry, a dramatic center island, stone countertops, stainless steel double ovens, and a wine chiller, all opening to a vaulted dining area with sliders to a spacious deck. The expansive second-floor primary suite is a true retreat, offering exceptional space, a custom walk-in closet, and a luxurious spa-like marble bath with double vanity. A first-floor bedroom adds incredible flexibility for guests or a home office. With a warm and inviting fireplaced living room, beautifully updated baths, and high-end finishes throughout, this home perfectly blends comfort, style, and privacy all in a prime location with easy access to major routes.

99 Corn Rd, Bolton

Listing courtesy of Listing Agent: William Thompson from Listing Office: Keller Williams Elite.

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