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Why Buy a Home in Holliston, MA?

Holliston is a town that perfectly captures the spirit of a classic New England community while offering some of the most unique local features in the MetroWest area. Known for its picturesque "Main Street" lined with historic homes and local shops, Holliston is a destination for buyers who want a town with a soul. It is a community where the Upper Charles Rail Trail runs right through the heart of town, providing miles of paved pathways for biking, walking, and enjoying the outdoors—a major draw for active families and nature lovers.

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For those balancing work and lifestyle, Holliston offers a convenient "middle ground" location. It sits comfortably between I-495 and Route 126, providing easy access to the tech corridors of Framingham and Natick, as well as the 495 belt. While Holliston is peacefully residential, residents have the luxury of choosing between the Holliston or Ashland MBTA stations for their commute into Boston, making it one of the more flexible towns for rail travelers in the region.

Education and community engagement are the pillars of life here. Holliston is famous for its French Immersion program within the public school system, which is a significant attraction for families seeking a global perspective for their children. The town also boasts beautiful recreational spots like Lake Winthrop for swimming and boating, and the scenic Pinecrest Golf Club. If you are looking for a town that values its history, invests in its schools, and offers a true sense of belonging, Holliston is an outstanding choice.

The Holliston housing market is diverse, offering everything from meticulously preserved 18th-century homes to modern subdivisions. Because of the town's high ranking for safety and school quality, properties here are considered excellent long-term investments.

Contact the realinsyghts group today at (508) 686-0940.

Find a home in Holliston, MA

97 Old Cart Path, Holliston
$1,525,000
4 Beds ⋅ 5 Baths ⋅ 73575584 MLS
Wow! Spectacular sweeping East-facing views and exceptional craftsmanship define this one-of-a-kind custom home in the coveted Highlands at Holliston. Beautifully sited on over an acre above Old Cart Path, this stunning residence offers three levels of luxurious living and extraordinary spaces for both everyday living and entertaining. A welcoming farmer’s porch opens to a grand two-story foyer with brilliant hardwood floors and custom millwork. The expansive main level features a dramatic two-story family room with coffered ceiling, an enormous gourmet kitchen with custom cabinetry, center island and walk-in pantry, plus an exceptional media room with movie screen and projector. A gracious living room, formal dining room, oversized home office, and full bath complete the level. Upstairs, you'll find an expanded balcony, luxurious primary suite with grand bath, two walk-in closets, and sitting area, complemented by a princess suite, two additional bedrooms, full bath, and laundry. The finished lower level is an entertainer’s dream with full bar, game and bonus rooms, and full bath. Outside, enjoy manicured grounds, an expansive composite deck and oversized patio while taking in the amazing views. Ideally located in one of Holliston’s most desirable neighborhoods with access to the Charles River Rail Trail. A truly extraordinary offering where breathtaking views, exceptional finishes, remarkable scale, and sophisticated amenities create an exceptional luxury lifestyle. Seller Owned Solar transfers to Buyers.

97 Old Cart Path, Holliston

Listing courtesy of Listing Agent: Tara D'Amato from Listing Office: Engel & Volkers Wellesley.

457 Hanlon Rd, Holliston
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 73590193 MLS
Discover a distinguished single-family country estate, meticulously crafted in 1975, offering 4834 square feet of refined living space. This property stands as a testament to enduring design & thoughtful construction, providing a harmonious blend of comfort and functionality. The residence features 2 well-proportioned primary suites, each designed to offer privacy & tranquility. One suite is located in a newer home addition & is handicap accessible by way of an interior elevator & ramp, a curbless oversize shower & barrier-free roll under sink. In addition this space offers a large custom closet and sitting room, the perfect respite for those requiring these enhancements as well as discerning buyers that appreciate large, gracious spaces. The second primary suite features a very comfortable bedroom & sitting room, lots of closet space & a gorgeous designer en suite perfect for teens wanting "their own space" or live- in help Complementing these sleeping quarters are two additional bedrooms, one with a customized walk-in closet, providing ample convenience & personal space for residents & guests alike. Further enhancing the property's appeal is a chef's kitchen featuring stainless steel Thermador appliances, granite tops, peninsula seating space & a butlers pantry with an abundance of storage. The adjoining dining room/living room features an open floor plan, custom built-in cabinetry, a Harman Frost Enamel pellet stove & access to a beautiful screen porch. The great room is a show piece of its own - soaring ceiling, hardwood floor with inlay border & custom rug, built-in cabinetry, large Palladium window with custom motorized shades & access to the outer deck. The lower level features a large game room with natural brick flooring & a coffered ceiling, a pellet stove, an adjoining wine cellar & space for a dedicated gym/art studio/craft room. Another bonus in this home is a beautiful & bright home office with Palladium window, motorized shades, radiant heat & a separate entrance. A spacious 3-car garage offers significant utility for vehicle storage & additional organizational needs. This home is conveniently located at the Hopkinton line, with easy access to Routes 85, 126 and 495. The expansive lot provides a generous outdoor environment, ideal for various recreational pursuits or simply enjoying the natural surroundings. To truly appreciate the sophisticated design & unique scale of this property, we invite your private viewing.

457 Hanlon Rd, Holliston

Listing courtesy of Listing Agent: Roberta Waters from Listing Office: Realty Executives Boston West.

35 Johnson Drive, Holliston
$1,175,000
4 Beds ⋅ 3 Baths ⋅ 73592000 MLS
Welcome home to this beautiful Colonial, set on a private 3-acre lot in Holliston's sought-after Cedarbrook neighborhood. With plenty of room to gather with friends and family or find a quiet place to unwind, this home offers a wonderful balance of comfortable living spaces and thoughtful design. The spacious kitchen features granite countertops, a large center island, double wall ovens and a sunny dining area for morning coffee or casual meals. Just beyond, the inviting family room features a cathedral ceiling, gas fireplace and a stunning wall of glass sliders that fills the room with natural light and brings the beauty of the outdoors right into your living space. Imagine curling up by the fire on a chilly New England evening, surrounded by views of the changing seasons. Step outside to the expansive deck with a covered seating area, perfect for summer dinners, entertaining friends or simply enjoying the peaceful wooded surroundings. A fenced yard offers comfort that little ones or furry friends won't wander. Back inside, the adjoining game room with wet bar and wine refrigerator makes entertaining easy while the formal dining room is ready for holidays and special occasions. A separate living room/office offers a comfortable space to relax or work from home. Surround sound speakers throughout downstairs and all season speakers on deck are all ready for you to connect a surround system to! Upstairs, the generous primary suite with new carpet includes two walk-in closets, a private office area and a spacious bath with soaking tub, tiled shower and double vanity. There are three additional bedrooms, a full bath and separate laundry room. A charming loft with built-in shelving and window seat is a lovely spot to read or enjoy a little quiet time. The large unfinished basement offers possibilities for future living space, while the three-car garage, walk-up attic and updated heating and cooling systems add everyday convenience. It's rare to find a home with this much privacy in such a wonderful neighborhood, with shopping, schools and major routes nearby!

35 Johnson Drive, Holliston

Listing courtesy of Listing Agent: Katie McBride from Listing Office: REMAX Executive Realty.

6 Beaver Brook Dr, Holliston
$1,025,000
4 Beds ⋅ 3 Baths ⋅ 73593616 MLS
Welcome to this beautifully maintained Colonial, ideally situated on a lovely 1+ acre lot in a wonderful neighborhood on a quiet cul-de-sac! An inviting farmer’s porch, lush lawn and lovely plantings create exceptional curb appeal. Inside, a tiger maple hardwood entry leads to a living room with hardwood flooring and an elegant dining room featuring random width wide pine floors installed with historical cut nails and crown molding. The spacious eat-in kitchen offers quartz countertops, center island, stainless steel appliances, refinished hardwood floors, recessed lighting, tile backsplash and pantry. Relax in the inviting family room with wood-burning fireplace, skylight, ceiling fan and French doors leading to a low-maintenance Trex deck overlooking the private, gorgeous backyard, complete with irrigation, vegetable garden and storage shed. A convenient mudroom and half bath complete the first floor. Upstairs, the primary suite features a cathedral ceiling, walk-in closet and private bath with stone-topped double vanity and custom double shower. Three additional bedrooms, a full bath and convenient laundry area complete the second floor. Walk-up access to the unfinished attic provides additional storage space. The finished lower level offers fantastic flexibility with brand-new luxury vinyl flooring, recessed lighting, bonus room and private home office with separate heating zone and double-hung windows for maximum natural light. Recent 2026 improvements include new carpeting on the stairs, hallway and primary bedroom, beautifully refinished hardwood floors in the entryway and kitchen, and fresh interior paint in many rooms. Additional updates include new microwave, refrigerator & dryer 2026, vinyl windows 2022, heat pump for AC 2024, roof 2013 and boiler/hot water heater 2014. Complete with an attached two-car garage and security system, this exceptionally cared-for home offers comfort, charm and room to spread out inside and out! Enjoy all that Holliston has to offer, from its charming downtown shops and restaurants to Lake Winthrop, the Upper Charles Rail Trail and a vibrant community atmosphere.

6 Beaver Brook Dr, Holliston

Listing courtesy of Listing Agent: Vesta Group from Listing Office: Vesta Real Estate Group, Inc..

272 Mill St, Holliston
$970,272
4 Beds ⋅ 4 Baths ⋅ 73585683 MLS
Imagine coming home to a place where there is room for everyone, space for everything, and something special around every corner. Welcome to 272 Mill St in Holliston, a home made for living, gathering, creating, and making memories. Set on a beautiful, level one-acre lot, this spacious 4-bedroom, 4-bath home offers over 2,000 square feet of living space, but it’s everything beyond the numbers that makes this home so special. Picture summer days spent around the gorgeous in-ground pool, friends and family gathered in the backyard, and quiet mornings or relaxing evenings in the oversized sunroom overlooking it all. Beyond the pool, the expansive yard offers room for backyard games, summer cookouts, gardening, entertaining, or simply spreading out and enjoying the outdoors. Have cars, projects, hobbies, or simply wish you had more space? The incredible attached 4-car garage is a car enthusiast’s, mechanic’s, or hobbyist’s dream, while the workshop and abundant storage offer even more room to create, work, and organize. Downstairs, discover an entirely different level of possibilities with its own living room, kitchenette, bedroom, and full bath. It’s an ideal setup for extended family, guests, a private retreat, or potential future ADU use, subject to town approval. There’s room here for everyone to have a space of their own and plenty of places to come together. Located near Pinecrest Golf Club with convenient access for commuters, 272 Mill St offers a rare combination of space, versatility, privacy, and outdoor living. This isn’t simply a house with great features. It’s the kind of place where summers are spent by the pool, projects come to life in the workshop, family and friends always have a place to stay, and home becomes the place everyone wants to be.

272 Mill St, Holliston

Listing courtesy of Listing Agent: Jennifer DeLuca from Listing Office: Berkshire Hathaway Home Services Commonwealth Real Estate.

543 Central Street, Holliston
$849,999
4 Beds ⋅ 4 Baths ⋅ 73593792 MLS
Welcome to 543 Central Street, a beautifully updated 4-bedroom home that proves you don’t have to choose between charm, spacious rooms, and eco-friendly efficiency. Tucked away on a private lot that backs directly to conservation land, this property feels like a hidden retreat while remaining just moments from the heart of Holliston. Inside, the home is bathed in natural light, featuring a versatile layout with generously sized rooms that easily adapt to your lifestyle, whether you need a quiet home office or space to spread out. The renovated kitchen flows right into a stunning great room, where cathedral ceilings, exposed beams, and a massive picture window frame the greenery outside. The sustainability features here are a total game-changer. With owned solar panels and a high-efficiency heat pump installed in 2022, the home’s energy system is so effective that the current owners actually generate more electricity than they consume. Imagine a home that handles all your heating and cooling and still sends you a check at the end of the month.The second floor offers four spacious bedrooms, while the lower level adds even more flexibility with a bonus room and a full bathroom. Outside, the property is a true oasis. With over three acres of land, direct trail access, and an updated gunite pool, it’s a dream setting for hosting summer gatherings or enjoying a quiet morning coffee on the deck. Recent capital improvements, including a newer roof, windows, siding, and insulation, mean you can move in with total peace of mind. Whether you’re drawn to the privacy, the trail-side location near Lake Winthrop, or the incredible energy savings, 543 Central Street is a rare find in the wonderful town of Holliston. Come see it for yourself!

543 Central Street, Holliston

Listing courtesy of Listing Agent: The Powissett Group from Listing Office: Compass.

631 Central St, Holliston
$799,900
4 Beds ⋅ 3 Baths ⋅ 73593357 MLS
Room for everyone at 631 Central Street! Set on three-quarters of an acre, this home offers a true in-law setup with a heated in-ground pool, making it ideal for multi-generational living or anyone who wants space to spread out. The main house features hardwood floors, an open living and dining area with a brick fireplace and rustic wood mantel, and an updated kitchen with white cabinetry, granite counters, stainless appliances, and a planked wood ceiling. Three bedrooms and a full bath on the main level, plus a lower-level family room, additional bedroom, half bath, laundry room, and garage, give you plenty of flexibility. The in-law suite has its own private entrance and features a stunning vaulted kitchen with rich wood cabinetry, granite, a large center island, opening to a bright living and dining area. It also includes a bedroom, a full bath with a tiled walk-in shower, in-unit laundry, and a lower-level den with generous storage. Step outside to enjoy summers by the heated pool, surrounded by a paver patio, pool house, and vinyl privacy fencing with a peaceful wooded backdrop. Solar panels, two driveways, and ample parking add to the appeal. Conveniently located near downtown Holliston, the rail trail, shopping, restaurants, and Routes 16 and 495, this is a rare opportunity to own a versatile home with space, privacy, and room to grow. First Showing Open House Saturday October, from 11AM to 12:30PM

631 Central St, Holliston

Listing courtesy of Listing Agent: Michael Vaz from Listing Office: Century 21 Signature Properties.

33 Cheryl Ln, Holliston
$799,900
3 Beds ⋅ 2 Baths ⋅ 73580836 MLS
INTEREST RATE BUY DOWNS AVAILABLE! Welcome home to this exceptional fully renovated residence, ideally situated in one of Holliston's most desirable neighborhoods. Every inch of this home has been thoughtfully transformed from top to bottom, offering the rare combination of a turn-key home within a warm, established community.This gut renovation leaves nothing to chance — a new roof, new windows, all-new mechanical systems, and a new septic system provide complete peace of mind for years to come. No detail was overlooked, ensuring worry-free ownership from day one.Step inside to discover a bright, sun-filled interior with a spacious, open feel throughout. The brand-new kitchen is a true showstopper, featuring gorgeous solid quartz countertops, high-end fixtures, and premium finishes that blend timeless style with everyday function — perfect for cooking, entertaining, and gathering.The beautifully renovated bathrooms continue the home's elevated aesthetic, showcasing elegant tile showers and designer fixtures that create a spa-like retreat right at home.With its generous layout, abundant natural light, and meticulous attention to detail, this home offers move-in-ready luxury in a location that's second to none. Enjoy the charm and convenience of one of Holliston's premier neighborhoods, close to top-rated schools, scenic parks, and easy commuter access.This is a rare opportunity to own a completely renovated home where every system, surface, and finish is brand new — combining modern luxury with an unbeatable location. Don't miss your chance to make this exceptional property your own!

33 Cheryl Ln, Holliston

Listing courtesy of Listing Agent: Jonathan Carlson from Listing Office: Carlson & Company, LLC.

65 Brooksmont Dr Unit 15, Holliston
$769,000
2 Beds ⋅ 3 Baths ⋅ 73566269 MLS ⋅ ['Brooksmont Condominium'] BLDG.
A bright, showroom condition home in a community that is 8 years young and has matured into a beautiful location. In the immediate vicinity are two grocery stores, pharmacies, full service banks and a quintessential New England village downtown. The association has turned over to owner control meaning the priorities of the community are set by the residents while being young enough to be assessment free! This condominium, constructed in 2018, presents an immaculate property with two bedroom suites, one on the main level and a second in the upper level. A perfect condition home, offering a total of 2360 square feet of sophisticated living space. On the upper level one thousand square feet make up a suite of 3 areas and a full bath. A bedroom with walk-in closet, bonus room and loft connecting the two. The first floor consists of nearly fourteen hundred square feet is dedicated to a convenient easy floor plan to lead a single level lifestyle. This residence is thoughtfully designed for discerning individuals seeking a refined lifestyle within a private setting. The kitchen serves as the heart of this home, featuring an open-plan design that seamlessly integrates with the dining and living room. It is equipped with stainless steel appliances and a central island, with sink and dishwasher, providing both functional workspace and a focal point for social gatherings. The living room, adjacent to the kitchen/dining, is enhanced by a fireplace, offering an inviting atmosphere for relaxation and entertaining. An additional feature that enhances practical daily living, is the main level laundry room. Expanded living is available through the living room sliding door leading out to the deck with woodland views. The main bathroom is appointed with a double vanity and a walk-in shower, designed for both convenience and a touch of luxury. Additional amenities include a full basement, providing ample storage or potential for further customization. The property also benefits from an attached garage with space for two vehicles. Discover the exceptional living experience offered by this distinguished Holliston condominium. Quick closing possible.

65 Brooksmont Dr Unit 15, Holliston

Listing courtesy of Listing Agent: John Vaillancourt from Listing Office: MA Homes, LLC.

105 Dodd Drive, Holliston
$695,000
3 Beds ⋅ 3 Baths ⋅ 73593545 MLS
Tucked away in a much-desired Holliston neighborhood, while offering convenient access to local amenities, you’ll find an impressive split-level home w an abundance of space. Beginning in the living room on the main level where a large picture window fills the space w natural light, you’ll find beautiful hardwood floors that go throughout most of the main level. The living room & dining room are open concept just off the kitchen. Past the kitchen, prepare to be wowed by the expansive great room, complete w beamed vaulted ceilings, skylights, a pellet stove, & sliding-doors to an oversized deck, perfect for outdoor entertaining. Also on the main level you’ll find 3BRs w 2 full BAs which includes the primary suite, w a walk-in closet & private BA. The lower level delivers even more flexibility w a home office, large recreation room featuring a fireplace & built in, as well as an additional space that would make a great meditation room, playroom or craft room. An additional half bathroom & laundry area round out the lower level. This home’s flexible and versatile floor plan make this a wonderful home for extended guest visits w excellent space for entertaining, work, or everyday living. Outside, the fenced yard provides a private setting playing fetch with the dog or just relaxing. Notable improvements include mini-splits installed in 2021, as well as double-pane windows & new skylights installed in 2022. This spacious & versatile Holliston home is one you won’t want to miss!

105 Dodd Drive, Holliston

Listing courtesy of Listing Agent: Colleen Crowley from Listing Office: Lamacchia Realty, Inc..

423 South St, Holliston
$685,000
3 Beds ⋅ 2 Baths ⋅ 73587965 MLS
This distinguished home offers a unique blend of historical charm and contemporary appointments, setting the stage for refined living. The kitchen is thoughtfully designed for both culinary pursuits and social gatherings, featuring stainless steel appliances, stone counters, an island, and a peninsula, providing an ideal space for meal preparation and informal dining. The living room serves as a central gathering point, enhanced by a fireplace that offers warmth and ambiance, complemented by elegant wide pine flooring that extends throughout the first floor. The large primary bedroom with its oversized walk in closet, offers a balcony overlooking your expansive backyards adds seamless connection to the outdoors, while another bedroom is distinguished by built-in shelves, adding both character and practical storage solutions. The property further benefits from a private yard, offering a tranquil retreat, and a brick patio, perfect for outdoor entertaining or quiet relaxation. A large carriage house provides additional storage and the potential for expanding with either a home office/craft room/or ADU on the second floor. We invite you to discover the distinctive appeal of this exceptional Holliston residence. Brand New Septic system just installed! Other updates are attached to the listing. Showings start Friday morning.

423 South St, Holliston

Listing courtesy of Listing Agent: Ritucci & Swift - Your Home Team from Listing Office: Realty Executives Boston West.

801 Winter St, Holliston
$665,000
3 Beds ⋅ 3 Baths ⋅ 73575142 MLS
Unique residence offering space, character, and tremendous potential! Set on 5 acres with a large, private back yard surrounded by mature woods. This 3-bedroom, 2.5-bath home offers approximately 2,192 sqft of living space along with a 40x40 barn, 2-car garage, and a brand-new 3-bedroom septic system being installed prior to closing. The main level offers an open dining and kitchen area with island, range, black appliances, Woodmode dark walnut cabinetry, and imported Italian tile flooring. A spacious living room with laminate flooring, full bath, and screened porch with wood flooring. The primary bedroom includes a built-in AC unit and private half bath, with two additional bedrooms offering comfortable living space. The walk-out lower level adds 696 sqft including recessed lighting, laminate flooring, and a carpeted room that could serve as an office or studio. A full bath with tile flooring and tile shower completes the level. Oil-fired heat, 200-amp electrical service, and a 2017 water heater round out the mechanicals. The 40x40 barn is a standout feature, offering excellent potential for storage, workshop, hobbies, agricultural use, or other possibilities, subject to zoning and approvals. Part of the barn roof has been replaced. This home offers an excellent opportunity for buyers seeking fantastic land, substantial space, and the potential to make it their own — set in desirable Holliston, with a welcoming community, excellent schools, scenic conservation areas, and convenient access to major routes. A must see!

801 Winter St, Holliston

Listing courtesy of Listing Agent: Vesta Group from Listing Office: Vesta Real Estate Group, Inc..

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