Browse All Holliston MA Properties with Pool for Sale

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

$549,900

3 Beds ⋅ 1 Baths ⋅ 73593307 MLS

ATTENTION INVESTORS, FIRST TIME BUYERS & THOSE LOOKING TO DOWNSIZE!! This charming ranch is move-in ready, while offering an excellent opportunity to add your own personal touches and cosmetic updates to make it truly your own. 36 Regal offers comfortable single-level living in a desirable Holliston neighborhood, just moments from the Rail Trail. The bright and inviting living room features beautiful hardwood floors and a large bay window. The spacious kitchen offers ample cabinetry, counter space, and stainless steel appliances, with a versatile bonus space perfect for a home office, dining area, playroom, or flex space.Three bedrooms and a full bath complete the main level. But the real showstopper may be outside! Set on a large, level lot, the private backyard is made for summer entertaining, complete with a spacious deck and above-ground pool. A storage shed provides additional space for gardening equipment and outdoor essentials. Central air, natural gas heating, and a fantastic location close to schools, shopping, the Rail Trail, Route 16, Route 109, and major commuter routes add to the appeal. Homes like this don't come around often, move-in ready and perfectly positioned for enjoying everything this wonderful community has to offer, this is one you won't want to miss!

36 Regal Street, Holliston

$725,000

4 Beds ⋅ 2 Baths ⋅ 73590909 MLS

Welcome to 16 Roy Ave, a fully renovated 4-bedroom, 2-full-bath raised ranch on nearly half an acre with an in-ground pool located in a quaint setting. The bright, open main level features engineered hardwood floors, a sun-filled living room with a painted-brick fireplace flowing into the dining area, and a brand-new kitchen with a quartz waterfall island, two-tone cabinetry, tile backsplash and stainless steel appliances. The main level also offers a renovated full bath and three of the home's four bedrooms. The finished lower level adds a spacious bedroom with a slat accent wall and built-in brick shelving, a new tiled full bath and a two-car drive-under garage. Updates include a new roof, new septic system, new electric, new plumbing, a new gas boiler with hot water baseboard heat and a new water heater. The home also has central AC. Outside, enjoy a large yard with an in-ground pool, a storage shed and parking for eight. Close to Rt 126, downtown Holliston and the rail trail. Move right in!

16 Roy Ave, Holliston

$649,900

3 Beds ⋅ 3 Baths ⋅ 73588024 MLS

Welcome to 72 Alden Rd, a classic split level on a stunning half-acre lot located in a quiet, closed-loop neighborhood. In Law Potential! 3 bedrooms, 2 1/2 baths, & a flowing floor plan that makes everyday living effortless. Generous, light-filled rooms move naturally from one to the next, with three spacious bedrooms on the main level & a flexible living area on the lower level with it's own full bath and entry point- perfect for an in-law suite. Hardwood floors & a wood-burning fireplace bring warmth to every gathering. The dining room opens directly to the brand new wood deck & fenced-in backyard for seamless indoor-outdoor flow. The refreshed basement adds versatile bonus space - perfect as a playroom, home office, or full in law suite. Outside, the brand new deck anchors a stunning fenced-in backyard with a full in ground pool -made for outdoor living at its best. This backyard oasis invites you to linger long after the sun goes down. Easy access to Rt 16 or Rt 27, parks & trails completes this special home.

72 Alden Road, 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

$1,250,000

4 Beds ⋅ 5 Baths ⋅ 73580243 MLS

More than a home—this private retreat offers exceptional space for living, working and entertaining! Sited down a long private drive off a cul-de-sac neighborhood, this spacious 4-bedroom Colonial enjoys a wonderfully private setting while remaining convenient to Holliston Town Center and major commuting routes. The home features updated kitchen and baths, 4 full baths, gas heat and central air. A large, thoughtfully designed laundry room features custom built-ins and convenient access from both the mudroom and the outside deck—an especially practical feature for everyday living and summer days by the pool. The finished lower level provides terrific versatility with a kitchen area and flexible living space currently used for extended-family living, along with plenty of additional storage. Outdoor living is a highlight of this special property. A lovely, sun porch provides the perfect spot for relaxing, while overlooking the private grounds. Step outside and enjoy your own backyard oasis complete with an expansive deck and in-ground Gunite pool, creating your own backyard retreat for summer gatherings. A full bath conveniently located just off the deck provides easy access from the pool area. The attached 3-car garage features exceptionally high ceilings, easily accommodating larger SUVs and trucks, while one heated and air-conditioned bay offers the perfect space for a home gym, workshop or hobby area. The detached barn is an incredible bonus, offering finished, heated and air-conditioned space ideal for a private home office, yoga or fitness studio, art/craft space or other creative pursuits. Below, car enthusiasts will love the additional 2-bay garage featuring soaring ceilings along with heat and air conditioning—ideal for a car collection, workshop or additional recreational storage. With five garage bays, multiple flexible-use spaces, a pool and a wonderfully private setting, this is a truly unique property offering room to live, work, entertain and pursue your passions—all just minutes from the heart of Holliston.

57 Carl Road, Holliston

$799,900

3 Beds ⋅ 3 Baths ⋅ 73558504 MLS

Discover the single-family home at 621 Marshall Street, offering the perfect blend of comfort, space, and privacy. This spacious 2,077-square-foot home sits on an expansive 80,150-square-foot lot, creating your own private retreat. Enjoy summer days by the inground pool, unwind in the hot tub, or relax in the peaceful outdoor setting. This home provides three bedrooms, two full bathrooms and an additional half bathroom, a beautifully updated kitchen, and more. Additional highlights include a three-car garage, providing abundant space for vehicles, storage, or hobbies. Conveniently located in desirable Holliston, this exceptional property offers the tranquility of a large lot while remaining close to shopping, dining, schools, and commuter routes. Don't miss the opportunity to add your personal touches and make this remarkable home your own! Home being sold as is.

621 Marshall St, Holliston

$1,249,000

5 Beds ⋅ 4 Baths ⋅ 73554074 MLS

Grand and glorious, this stately home is located in a double cul-de-sac neighborhood of refined homes, in a prime location on the Hopkinton line, close to Pinecrest golf course, Holliston High School, the Waseeka Wildlife Sanctuary (Audubon) and the commuter rail. Beautiful private setting abuts protected open space, with a gorgeous heated inground saltwater pool, cabana, large composite deck and spacious, flat backyard lawn area. Wonderful interior floor plan with front and back staircases is ideal for multi-generational living - finished 3rd floor with living area, bedroom and full bath. Main level features a large home office w/French doors and built-ins; sunny kitchen with white cabinetry and brand new stainless appliances; dramatic vaulted ceiling family room with floor-to-ceiling gas stone fireplace; fireplaced game/living room with custom molding and access to dreamy screened porch; dining room with crown molding; powder room with laundry and large mudroom. Second level features four bedrooms, showcased by the lovely, fireplaced primary with its spa bathroom and walk-in closet; oversized bedrooms offer lots of closet space. The walkup third level provides a multitude of possibilities for in-law living, work from home or teen hangout space; walkout lower level with home gym/exercise room. This home has plenty of room for all, while offering warm, cozy and inviting spaces, both inside and out. Be part of the lovely community of Holliston, which offers both Montessori and French Immersion programs as part of their exceptional school system.

25 Erin Way, Holliston

$1,795,000

5 Beds ⋅ 6 Baths ⋅ 73538100 MLS

Nestled in sought-after Cedarbrook, this exceptional 5-bed Colonial offers many updates including exterior painting, composite deck, new carpeting on upper and lower levels, and five new A/C condensers, offering exceptional living indoors and out. A two-story foyer with mahogany inlaid flooring sets the tone as you enter. Main level features elegant living and dining rooms, a great room with stone fireplace and custom built-ins, plus private home office with gas fireplace. Chef’s kitchen features Wolf gas range, double ovens, warming drawer, beverage fridge and butler’s pantry with sink and second dishwasher. Second floor offers five bedrooms including primary suite w/ a sitting room, three full baths, and convenient second-floor laundry. The finished walkout lower level with 8’ ceilings and full bath adds flexible living space. Outdoor living includes new deck overlooking saltwater pool, large front yard and farmer's porch. A truly remarkable home for everyday living and entertaining!

16 Kingsbury Dr, Holliston

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Browse All Holliston MA Properties with Pool for Sale

Holliston Homes with Pool

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