Holliston MA Real Estate, Homes, Condos for Sale

Unlock the potential of this hidden gem in Holliston! Tucked away and privately set back from the road, this home offers a rare opportunity to create your dream sanctuary on a spectacular 2.73-acre lot. Nature lovers will appreciate the tranquility of this location, which borders expansive conservation land, providing ultimate privacy and a peaceful backdrop. The property features a large, flat yard perfect for outdoor activities, gardens, or recreation. Inside, the home provides a versatile floor plan with 3 bedrooms and 2 full bathrooms. The first floor layout includes 2 bedrooms, a full bath and a large fireplaced living room. The second floor features the primary bedroom, a second full bath and a spacious second living room that offers excellent flexibility for a home office, media room, or guest retreat. A new septic system is being installed, the roof, heating system and hot water heater have all been updated in recent years and the large full basement provides ample storage and is already partially finished. This home is ready for a modern transformation and your personal touch, the expansive lot, and the coveted, secluded location make this a truly unique find. Bring your vision to reimagine this property and make it your own.

741 Winter St., Holliston

$300,000

73593884 MLS

Land Opportunity In Holliston, 11.27acres. Abuts the Mellen St conservation, and Winter Street. Buyers and Buyers agents to do their own due diligence. best to use mapping, town hall, and engineer to discuss all the possibilities. Likely use would be a single lot.

Winter St, 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

$899,000

5 Beds ⋅ 3 Baths ⋅ 73593644 MLS

Welcome to 1419 Washington Street in Holliston! This well-maintained three-family Colonial presents a fantastic opportunity for investors and owner-occupants alike. The property features two spacious 2-bedroom units and one lofted 1-bedroom apartment, each complete with its own private deck, in-unit washer and dryer, and dishwasher. Separately metered utilities offer added convenience, while a large driveway provides ample parking. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other two, this property offers excellent flexibility. With one unit expected to be delivered vacant at closing, the property is particularly appealing to owner-occupants. Conveniently located near downtown Holliston, local shops, restaurants, and major routes. Don't miss this opportunity to own a versatile multifamily property in Holliston! OPEN HOUSE SUNDAY, 10/25, FROM 12–2 PM! ALL OFFERS DUE TUESDAY, 10/27, BY 12 PM.

1419 Washington St, 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

$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

$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

$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

$500,000

73592610 MLS

A rare opportunity in Holliston: a 2+ acre estate homesite at the end of a brand-new cul-de-sac, offering the privacy and quiet of a wooded setting, with room for the kind of home and yard that are hard to find in town. The lot is for sale, and the seller will build your home as well: choose from our collection of custom floor plans, designed for luxury living and entertaining, or bring your own plans and we’ll bring them to life. Our in-house designer is there to help guide you through layouts, finishes, and details, taking you from first sketch to final walkthrough. Contact the listing agent for plans, pricing, and timeline.

000 Undisclosed, 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

$314,900

2 Beds ⋅ 1 Baths ⋅ 73590913 MLS

Welcome to this beautiful unit at Regency Park Condominium. Very well-maintained two bedrooms townhouse, both on the second floor. Hardwood flooring throughout the living room and bedrooms. Finished basement with extra room for work or entertainment and laundry. Washer and dryer will stay. Backyard for a fresh air and relaxing. Great location unit! Minutes from the downtown where you will find coffee shops, pharmacy and stores. Lake Winthrop and the walk trail are right there for spring and summer days. Don't miss the opportunity to see this unit, it won't last. Schedule a visit now, easy to show! Open house Saturday October 17th from 11:30am to 1pm.

43 Regency Dr Unit 43, 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

$1,799,000

4 Beds ⋅ 5 Baths ⋅ 73590622 MLS

Experience the art of exceptional living at 30 Mill Street, where timeless elegance, modern sophistication, and thoughtful design come together in this stunning 2026 luxury Colonial. Beautifully situated on nearly an acre along the Holliston–Hopkinton line, this remarkable residence offers approximately 4,587 sq. ft. of refined living space. An exquisite chef’s kitchen with a dramatic quartz waterfall island flows effortlessly into elegant entertaining areas, complemented by rich hardwood floors, architectural detailing, and three fireplaces. Four beautifully appointed en-suite bedrooms include a magnificent primary sanctuary featuring a fireplace, spa-inspired bath, and spacious dressing room. A private library, inviting second-floor lounge, and expansive finished lower level provide exceptional flexibility. Outdoors, a spectacular stone patio with a built-in kitchen creates the perfect setting for unforgettable gatherings. Complete with a three-car garage and proximity to golf, this is luxury living at its finest.

30 Mill St, Holliston

$400,000

73590343 MLS

This four acre parcel on a beautiful country road could be your next address. Approved and stamped mylar ANR plan in hand. See attached conceptual drawing with a five bedroom house, a swimming pool and a one bedroom auxiliary dwelling. Use this idea or bring your own. Current plan has a short cul-de-sac, but owner will go for a variance to change to driveway, which the town has sounded open to. Cost is buyers, but homeowner is willing to be involved with the town. Beautiful parcel. Sliver of land owned by another goes along Alpine Road, so no access/driveway to Alpine without purchasing from them. Unknown as to price for said piece, nor willingness to sell. As it stands now, it is one legal lot. Paperwork with attorney who is registering land at the registry, but it's not yet done. Please do not walk without permission as there are dogs on adjacent property who also walk on this land.

76B Hanlon Road, 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

$799,000

4 Beds ⋅ 3 Baths ⋅ 73588728 MLS

Welcome to 85 Alden Road, where modern updates, thoughtful design, and comfortable living come together. Beautifully renovated throughout, this 4-bedroom, 2.5-bath home offers an inviting open-concept layout that seamlessly connects the kitchen, dining, and living areas, creating the perfect setting for both everyday living and entertaining. The beautifully redesigned kitchen is the heart of the home, featuring quartz countertops, stylish new cabinetry, and a generous center island ideal for gathering with family and friends. New hardwood floors bring warmth and character to the main level, while new windows throughout fill the home with natural light. The finished lower level offers even more flexibility, featuring a fourth bedroom, half bath, and additional living space that can easily adapt to your needs. Step outside to enjoy the renovated deck and backyard, perfect for relaxing, entertaining, or simply enjoying the outdoors. Beyond the beautiful finishes, major improvements include a new roof, new septic system, and new furnace with central air conditioning, offering comfort and peace of mind for years to come. Enjoy convenient access to the Upper Charles Rail Trail, Lake Winthrop, and major commuter routes. With so many updates already completed, all that’s left to do is move in and make it your own!

85 Alden Rd, 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. 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

$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

$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

$699,900

2 Beds ⋅ 3 Baths ⋅ 73584532 MLS

Welcome to this stunning, like-new 2020 townhome that lives like a single-family home, set far back from the road on @ 1 acre in total, in a serene, wooded setting with a fully fenced-in, private yard. High ceilings and an open-concept design create a bright, spacious feel throughout. Wood flooring enhances the main living areas, while the finished walkout lower level, completed in 2022, adds two versatile rooms and approximately 700 SF of additional living space, all with high ceilings. The main bedroom features a spacious ensuite bath with a double vanity, a custom-tiled shower, and a large walk-in closet with a custom closet system. Convenient second-floor laundry is located near the bedrooms. Enjoy low-maintenance outdoor living with a composite front porch and rear deck overlooking the large, private fenced backyard. Additional highlights include a 2-car garage with an EV charger. 2 unit HOA $325/month covers exterior maintenance, landscaping, and snow removal. A beautifully maintained, like-new home offering comfort, flexibility, privacy, and modern convenience! See townhouse listing at MLS#73584502

1093 Washington St Unit 1093, Holliston

$699,900

2 Beds ⋅ 3 Baths ⋅ 73584502 MLS

Welcome to this stunning, like-new 2020 townhome that lives like a single-family home, set far back from the road on @ 1 acre in total in a serene, wooded setting with a fully fenced-in, private yard. High ceilings and an open-concept design create a bright, spacious feel throughout. Wood flooring enhances the main living areas, while the finished walkout lower level, completed in 2022, adds two versatile rooms and approximately 700 SF of additional living space, all with high ceilings. The main bedroom features a spacious ensuite bath with a double vanity, a custom-tiled shower, and a large walk-in closet with a custom closet system. Convenient second-floor laundry is located near the bedrooms. Enjoy low-maintenance outdoor living with a composite front porch and rear deck overlooking the large, private fenced backyard. Additional highlights include a 2-car garage with an EV charger and a low $325/month HOA covering exterior maintenance, landscaping, and snow removal. A beautifully maintained, like-new home offering comfort, flexibility, privacy, and modern convenience! Also listed as single-family MLS 73584532.

1093 Washington St Unit 1093, Holliston

$495,000

3 Beds ⋅ 2 Baths ⋅ 73582102 MLS

This bright & sunny home is situated on a 1/2 acre lot located in a popular Holliston neighborhood, close to shops, commuter rail and major routes. You will find and appreciate that this home was designed for easy and comfortable living. Featuring 3 bedrooms and 2 full baths, fireplace & slider to deck with wonderful elevated views of the back yard, one car garage and a circular driveway for easy entry and exit. You will love time spending in the kitchen with its many features including a skylight, granite countertop, recessed lighting, and stainless appliances. Much of the home offers gleaming hardwood floors. Top ranked schools. Only a few miles to Ashland or Framingham Train Stations.

2 Ashland Street, Holliston

$650,000

4 Beds ⋅ 2 Baths ⋅ 73581958 MLS

Welcome to 468 Underwood Street, a 4-bedroom, 1.5-bath Colonial in Holliston's desirable Brentwood neighborhood. Nestled on a nearly half-acre lot, this home has been extensively updated over the past five years, blending classic colonial character with modern, move in ready appeal. Accentuated by brand new granite stairs and a stunning paver entrance, this property offers exceptional curb appeal. Upon entering you are invited into the kitchen where sunlight streams in highlighting a perfect balance of contemporary style and bright, airy design. Crisp, porcelain floors serves a brilliant foundation, effortlessly reflecting light across the room. At the center of it all is a stunning new kitchen island, providing a focal point and a welcoming gathering spot. Topped with pristine quartz countertops, every surface gleams with a polished luster that maximizes brightness from day to night. Ensuring year round comfort, the entire open area is efficiently cooled by a sleek, modern mini-split system (2024). The second floor features a seamless layout with four well lit bedrooms, all boasting hardwood flooring and a renovated full bath (2021). Enjoy the beauty of every season from the comfort of a brand new 4-season porch with plenty of light to enjoy whether entertaining family and friends or just cozying up with a good book. Step directly from the sun filled 4 season porch into a charming new back patio (2024) offering an intimate, low maintenance outdoor nook perfect for your morning coffee. Many major essentials have been updated recently as well: a 1500-gallon, 4-bedroom septic system (2021), highly durable Hardie board siding (2024), fascia, and gutters (2024), double pane windows (2023), an asphalt driveway with an installed EV charger (2024) and a brand new hot water heater (2026). The entire property has been elevated by extensive landscape improvements framing the house in beautiful greenery with crisp and clean stonework (2022-2026). This delightful home sits in a highly desirable location just moments away from Holliston's famous Out Post Farm and beautiful Pinecrest Golf Club, bringing premier farm to table treats and weekend tee times right to your door steps.

468 Underwood St, 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

$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

$625,000

3 Beds ⋅ 2 Baths ⋅ 73579102 MLS

NEW PRICE! HOLLISTON's Favorite BRENTWOOD NEIGHBORHOOD! Lovingly maintained Raised Ranch built in 1964 with 1933 SF of living space. Foyer recently painted also has a Ceiling Fan, Sunny Formal Dining Room with Hardwood Floors, leads to an amazing Kitchen with wood floors, Maple Cabinets, Dual Fuel Double Oven, Ceramic Tile Back Splash, Skylight, 5 Burner Cook Top, Quartize Countertops which were done in 2024, Kitchen Appliances will stay new in 2020, Wall to Wall Carpet in Spacious Family Room, Three Bedrooms all with Hardwood Floors, One Car Garage, Screened Porch, Shed, Back Yard Play Area (w Rubber Mulch) 2021, plus many Recent Updates including Interior Painting 2025, 2026, C/A added 2022, Leaf Filter Gutters 2023, 2 furnaces, one new in 2024 and located in the garage, new Harvey Windows 2013, Exterior painted 2025, deck painted 2026, 200 AMP Board 2022, Water heater approx. 2 years old, Septic System 2023, Pentair Whole House Water Filter System 2023, Primary Bathroom Hardware (Sinks, Showers & Tub) 2024 This home is ready for immediate occupancy. WELCOME HOME!!

35 Jerrold Street, Holliston

$700,000

4 Beds ⋅ 2 Baths ⋅ 73579097 MLS

Simply delightful, this inviting Cape style home in beloved downtown Holliston is a true treasure. Walk to town, the Upper Charles Rail Trail, Lake Winthrop, schools and cafes, offering a close-to-everything location, while being off the beaten path. This home is bathed in natural light, with bright open spaces, and plenty of room to spread out. At the heart of this home is the kitchen, with its white cabinetry, gas cooking, center island and stainless appliances. The kitchen flows nicely to the sunny dining/eating area, as well as to the inviting family room with its vaulted ceiling, skylight and French door to the composite deck. Generously sized living room with fireplace and hardwood floors; great first floor bedroom/home office with a closet and built-ins. Upstairs you'll find the primary bedroom with hardwood floors, plus two additional bedrooms (currently partially opened up to create one larger space) with hardwood floors and closet. Full basement offers expansion possibilities; one car attached garage; maintenance free exterior; brand new four bedroom system currently being installed; new roof and skylights (2020); new ductless mini split systems (2020); replacement windows (2004 & 2008). Be a part of the lovely Holliston community, with its great schools and quality of life.

80 Pearl Street, Holliston

$799,900

4 Beds ⋅ 2 Baths ⋅ 73578467 MLS

Step right into this spacious, bright and airy home, located on the upper end of Chamberlain Street in the ever popular Brentwood neighborhood, and be prepared to be wowed! Completely updated and designed for easy modern living, this home is showcased by its jaw dropping kitchen featuring hardwood flooring, custom cabinetry, quartz countertops, stainless appliances, gas cooking, large L-shaped island, dining/eating area and vaulted ceiling. The kitchen flows seamlessly into the living room, highlighted by the beautiful fireplace with its granite surround. Fabulous sunroom with walls of windows and access to the new composite deck and inviting backyard, which invites a pool or sport court. Three generously sized bedrooms on the main level, all with hardwood floors and good closets. The main level bath is a stunner, with custom tiled tub/shower, double vanity with marble countertops, and tiled flooring. Second full bath with gorgeous tiled shower, heated floors and granite countertop. Lower level offers full sized windows, a very large family/game room, an additional bedroom, laundry area with a laundry sink, and lots of storage. Fantastic, 2 story two car garage ideal for New England life and chilly winters. Practical updates include a brand new 4 bedroom septic system; sunroom (2026); mini splits (2025); kitchen and living room renovation (2020); roof (2019). Additional features include dimmable anti-fog mirrors in both bathrooms; smart lighting; smart thermostat; front door access with either thumbprint or key; 200 amp electrical service; Pex plumbing pipes (more resistant to freezing). Easy access close by to acres of trails (located at the end of Chamberlain and Gorwin). The choice is an easy one ~ move right in and you can make this your home for the holidays!

426 Chamberlain St., Holliston

$219,900

1 Beds ⋅ 1 Baths ⋅ 73578152 MLS ⋅ ['Crestview Condominiums'] BLDG.

Discover refined condominium living at 152 Turner Rd U:57, Holliston, MA. Constructed in 1967, this 705 square foot residence offers a sophisticated urban retreat. This third-floor condominium, situated within a three-story building, provides an elevated perspective. The residence thoughtfully includes one bedroom, designed to offer a private and comfortable space. Complementing this, one full bathroom provides essential convenience and functionality. This property presents a compelling opportunity for discerning buyers seeking a well-appointed home. Just across the way is a freshing a fabulous inground pool. call broker to show, Don't miss out

152 Turner Rd Unit 57, Holliston

$769,900

4 Beds ⋅ 2 Baths ⋅ 73576934 MLS

Welcome home to this charming 4-bedroom Cape, nestled in one of Holliston’s most desirable neighborhoods with a fabulous walk-to-town location. Enjoy easy access to the Charles River Rail Trail, local eateries, in-town brewery, library, Goodwill Park and all that this vibrant community has to offer.At the heart of the home is the gorgeous 2019 renovated kitchen featuring beautiful stone countertops, stainless steel appliances and gas cooking. The sun-drenched cathedral family room is a favorite gathering space with beautiful hardwood floors and a cozy wood-burning stove, opening directly to an entertainment-sized crushed stone patio with a handsome cobblestone border. Imagine summer barbecues, fall evenings around the fire pit and nights spent under the stars!The inviting living room offers warm hardwood flooring, a bay window and fireplace—perfect for making memories around the holidays—while the breezeway adds a charming nook for morning coffee. Four bedrooms feature pretty hardwood flooring, including a conveniently located first-floor bedroom adjacent to a full bath, offering wonderful flexibility for guests or first-floor living. Two full tile baths include recent updates and a new vanity in the main bath.The finished lower level provides even more living space with room for a family room, home office, exercise area or playroom. Outside, the fabulous backyard offers plenty of space for four-legged friends, family gatherings and summer entertaining.Thoughtful improvements include a brand-new 4-bedroom septic system (2026), 3-year-old 4-zone forced hot water heating system with domestic hot water, replacement windows from 2019 through 2026, hardwood floors and a whole-house fan. Washer, dryer, refrigerator and basement refrigerator are included.A wonderful opportunity to enjoy timeless Cape character, thoughtful updates and a true neighborhood lifestyle in the heart of Holliston.

185 Marked Tree Rd, Holliston

$924,999

5 Beds ⋅ 4 Baths ⋅ 73576195 MLS

Set at the end of a long driveway and surrounded by 13 acres, this 3,368-square-foot, five-bedroom home offers a truly distinctive living experience. Built in 1985, the octagonal design gives the property an architectural character that is rarely found in today's homes.The first floor features all five bedrooms, creating a dedicated and comfortable private space for family and guests. The second floor serves as the main gathering level, with the kitchen and living area arranged around the home's unique shape and design.A finished walkout basement adds another level of usable space with direct access to the outdoors, providing plenty of opportunity for recreation, hobbies, entertaining, or additional living needs.Beyond the home, the expansive acreage offers a rare sense of space and seclusion, with a long driveway providing a private approach to the property. The combination of substantial acreage, five bedrooms, multiple levels of living space, and unconventional architecture makes this a property with a character all its own. Open house rescheduled to September 14th 5-7pm.

243 Oak St, Holliston

$299,000

2 Beds ⋅ 1 Baths ⋅ 73576026 MLS ⋅ ['Oakridge'] BLDG.

Welcome to Oakridge Condominiums! This spacious top-floor 2-bedroom unit an open floor plan and a gorgeous view in a peaceful setting at the end of a wooded cul-de-sac. Located in a garden-style building, this home offers comfortable, low-maintenance living. The building features on-site laundry, secure storage assigned to each unit, one assigned parking space, and ample guest parking. Enjoy a prime location just minutes from the commuter rail, grocery stores, shopping, parks, and the Charles River Rail Trail. For those seeking convenient, low-maintenance living, this condo is a great choice. With limited options at this price point, it is an excellent opportunity for a homeowner or investor.

49 Windsor Dr Unit 301, 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

$625,000

3 Beds ⋅ 2 Baths ⋅ 73575265 MLS

Charming antique Colonial in Holliston’s desirable Mudville neighborhood, filled with warmth, character, and classic New England appeal. Wide-plank pine floors run throughout the home, adding to its timeless charm. The bright and spacious eat-in kitchen features abundant natural light, cherry cabinetry, granite countertops, stainless steel appliances, and recessed lighting, with convenient access to the rear deck, perfect for relaxing or outdoor dining. The first floor also offers a comfortable living room, bedroom, and full bath, providing flexible living options. Upstairs are two additional bedrooms and a second full bath. Outside, enjoy a long, level yard with plenty of room for gardening, play, or entertaining. Enjoy the neighborhood lifestyle with a rail trail walking path just nearby, along with residential access to Lake Winthrop, where the beach, boat access, and playground offer another great spot to enjoy the outdoors. Ideally situated close to downtown Holliston’s shops, restaurants, and local amenities, this character-filled home offers a wonderful combination of antique charm, outdoor space, and a convenient location.

44 Exchange 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

$975,000

4 Beds ⋅ 3 Baths ⋅ 73574969 MLS

Imagine coming home to a backyard that feels more like Vermont than MetroWest. Set on nearly four acres and abutting conservation land, 330 Marshall Street offers a wonderful connection to nature, yet remains close to everything that makes Holliston so desirable. This beautifully cared-for Colonial has a timeless quality, with warm wood floors, detailed trim and an inviting floor plan that works equally well for everyday life or a house full of family and friends. The kitchen, with granite counters and new tile floors, opens easily to the surrounding rooms, while French doors add character and allow spaces to be connected or separate when desired. Spend winter evenings by the fireplace and warmer days on the screened porch or deck, overlooking a yard that truly feels like a retreat. Beyond the lawn, the woods invite morning walks, hikes or snowshoeing after a fresh snowfall. Toward the back of the property, a small pond offers the possibility of ice skating when winter conditions allow—followed by hot chocolate and s’mores around the outdoor fire pit. Upstairs are four nicely sized bedrooms, including a generous primary suite with vaulted ceiling, walk-in closet and beautifully updated shower. It's a perfect place for quiet and a good book at the end of a long day. The walkout lower level offers finished living area along with plenty of additional room for a gym, media room, workshop or future expansion. An attached 2-car garage with new doors, excellent storage, central air and leased solar panels add to the home’s appeal. It’s a setting that feels wonderfully removed from it all, yet everyday conveniences are surprisingly close. Holliston High School—ranked #30 on Boston Magazine’s 2026 list of Greater Boston’s Top Public High Schools—Out Post Farm and Pinecrest Golf Club are all just minutes away, while I-495 and Milford’s wide selection of shopping and restaurants are within easy reach. For those who value a little more land, a little more nature and a little more room to breathe, this is a special place to call home.

330 Marshall Street, Holliston

$799,900

3 Beds ⋅ 2 Baths ⋅ 73574220 MLS

SUNDAY OPEN HOUSE CANCELLED. ACCEPTED OFFER. Welcome to 47 Jarr Brook Rd, a beautifully remodeled cape style home offering timeless character, modern updates, and exceptional indoor-outdoor living in desirable Holliston. The heart of the home is the fully remodeled kitchen, completed in 2020, featuring an open-concept design that seamlessly connects to the living room and eat in breakfast nook. Thoughtfully appointed with stainless steel appliances, quartz counter tops, built-in microwave, center island, and wine cooler, this inviting space is perfectly suited for both everyday living and entertaining. The living room offers a warm and welcoming atmosphere centered around a classic fireplace and custom built ins. The home features three well-appointed bedrooms and two updated full bathrooms, providing comfortable and versatile living space. Step outside and discover a truly special private retreat. The professionally landscaped grounds feature beautiful patio hardscaping, creating an ideal setting for outdoor dining, entertaining, and relaxing. A new deck and screened-in porch provide additional spaces to enjoy the outdoors throughout the seasons, while the private pool area offers the perfect escape for summer days. A dedicated fire pit adds another gathering space for those cool summar and fall evenings. An attached one-car garage adds convenience and additional storage. Ideally located on a quiet cul-de-sac, this home is a must see. Showings start Friday.

47 Jarr Brook Rd, Holliston

$599,900

3 Beds ⋅ 1 Baths ⋅ 73572997 MLS

Consider this your invitation to fall a little bit in love with Holliston! This beautifully maintained gem proves that 1,356 sq. ft. can live remarkably large. Step inside to a bright, inviting main level where gleaming hardwood floors create an effortless flow from the spacious living area into a cozy dining space. The charming kitchen brings plenty of personality with beautiful natural wood cabinetry, granite countertops, and a skylight that pours in natural light. Three comfortable bedrooms and a full bath round out the main level, while the delightful sunroom is ready for everything from morning coffee to quiet afternoons. Head downstairs to discover a versatile family room offering even more room to spread out, work from home, host guests, or create your favorite hangout space. Outside, the charm continues with a lovely white garden arbor, storage shed, and inviting yard space to enjoy in the warmer months. Recent improvements offer wonderful peace of mind, including a 2024 roof and newer heating and water heater systems, while fresh 2025 paint and 2026 washer and dryer add to the move-in-ready appeal. Enjoy all that Holliston has to offer, with Holliston High School, local shops and restaurants, parks, walking trails, and easy access to commuter routes all close by. Warm, welcoming, and wonderfully cared for, this is a home that makes everyday living feel easy!

93 Jerrold St, Holliston

$2,250,000

5 Beds ⋅ 5 Baths ⋅ 73570164 MLS

Welcome to 14 Fiske Pond Road! A dream home built w/the most unparalleled attention to detail, millwork & craftsmanship. The 5BR, 5BA house will appeal to today's modern families, multi-generational families, down sizers, & empty-nesters w/1st & 2nd floor primary options. The 1st floor open concept is the heart of the home w/soaring ceilings & natural light pouring in.The kitchen has SS high end appliances, walk-in custom pantry, 92 bottle wine chiller, 6 burner range, wall oven, center island & leads to LR w/gas FP, and DR. The primary BR is its own oasis w/luxurious spa BA & custom walk-in closet. 2nd BR/office & full BA also on 1st .The mudroom & laundry are have radiant floors & lead to 3 car garage. The 2nd floor is a surprise! 3 BR's (two ensuite), a 2nd FR w/gas FP, wet bar & vaulted ceilings + generous bonus room. 9ft ceilings. All BA's have radiant heat, speakers in most of house, fire pit. Conveniently located <10 miles many town centers: Sherborn, Dover, Natick, Wellesley.

14 Fiske Pond Road, Holliston

$669,900

3 Beds ⋅ 1 Baths ⋅ 73569184 MLS

Privacy, acreage, and an incredible workshop—all in desirable Holliston! Set on 4.4 acres abutting town and conservation land, this well-maintained home offers a private, estate-like setting with space inside and out. Private 800+ foot driveway to the property. The home features a bright and comfortable layout, generous finished living space, a finished lower level, and covered decks perfect for enjoying the peaceful surroundings. The true showstopper is the massive multi-bay outbuilding with space for up to 6 vehicles—ideal for car enthusiasts, contractors, tradespeople, hobbyists, or anyone looking for a serious workshop right at home. With 4.4 acres, protected land along the property, abundant garage and workspace, and a convenient Holliston location, this is a unique property that’s increasingly difficult to find. Also conveniently located less than a half a mile from Holliston High school and Pinecrest Golf Club, and just 15 min to I-495.Newly installed septic, Title V Certificate of Compliance

636 Highland St, Holliston

$1,475,000

12 Beds ⋅ 6 Baths ⋅ 73568963 MLS

263 South St contains five townhouse units, comprised of one (1) 3-Bedroom/2-Bathroom unit, one (1) 3-Bedroom/1-Bathroom unit, and three (3) 2-Bedroom/1-Bathroom units with 6,582 square feet of gross living area in 9,615 square feet of gross area. The Property is currently situated on 4.07 acres. Parking is readily available with nine (9) garage spaces, as well as ample surface parking spaces. With its bucolic nature surrounded by 25 acres of Conservation land and excellent tenant history, 263 South Street is truly a unique, one-of-a-kind investment property. 263 South Street features an attractive mix of spacious townhouse-style residences designed to appeal to today's renters. Units 1–4 offer desirable three-level layouts consisting of a full basement, main living level, and second floor, with sliding door access to a large, shared backyard with lush grounds. Unit 5 is a well-appointed single-level apartment situated above the Property's garage bays. Each residence is equipped with in-unit laundry, providing added convenience for tenants. Interior finishes include Formica countertops in Units 1, 2, 3, and 5, while Unit 4 features granite countertops. All apartments are separately metered, with tenants responsible for heat, hot water, central air conditioning, and electric service. 263 South Street presents the incoming investor ample opportunity toincrease the rental rates by programmatically renovating the remaining four units. In addition, the property is improved by a detached, two-story structure which features a Six-car garage parking as well as finished space above the garage. The potential exists to create an additional apartment at the site. Units 3 & 5 have received new heat pump systems over the last 2 years while all units have received new A/C systems over the last 10 years. Numerous appliances and water heaters have been replaced since current ownership took over, as well as an upgraded leeching field over the last 2 years. The opportunity exists for new ownership to separate out water utilities and put this onto tenants, as there are currently 5 water meters.

263 South St, Holliston

$799,000

3 Beds ⋅ 3 Baths ⋅ 73568151 MLS

Far from your typical ranch! Gutted to the studs and completely reimagined in 2023, this home offers the look and feel of new construction with thoughtful design and high-end finishes throughout. The show stopping kitchen features vaulted ceilings, an oversized island, custom cabinetry, and quartzite countertops, opening seamlessly to the dining and living areas with custom built-ins. The primary bedroom offers a spacious walk-in closet, while the heated sunroom adds year-round living space. Extensive updates include a new roof, windows, whole-house spray foam insulation, prefinished hardwood floors, all-new electrical and panel, new plumbing throughout the home, HVAC, and water heater. A new driveway and back patio complete the improvements. Located in a desirable neighborhood close to shopping, parks, and trails, this move-in-ready home combines style, comfort, and the ease of single-level living.

74 Westfield Dr, Holliston

$599,900

3 Beds ⋅ 1 Baths ⋅ 73567586 MLS

CHERISHED FAMILY HOME IN BRENTWOOD! Lovingly held by the same family since 1965, this classic Holliston property on Chamberlain Street offers a rare combination of long-held heritage, privacy and an extraordinary list of major brand-new improvements. Set in one of the town's most established neighborhoods, this home is ready for its next chapter to be written. At its heart is a bright kitchen featuring a convenient breakfast bar, dedicated eat-in dining area and ample counter space. Updates include the skylights with remote-controlled blinds (2026), dishwasher and oven (2025). The formal dining room and sprawling living room offer the ideal footprint to host holiday celebrations with NEW carpet (2026) while the finished lower level provides excellent, flexible bonus space. Upstairs, beautiful hardwood floors carry through all three bedrooms. A full bathroom has built-in storage that showcases the home’s authentic character. True peace of mind comes from the extensive list of big-ticket capital improvements completed by the sellers. ***Recent upgrades include a NEW roof, NEW septic system, NEW driveway, NEW 200-amp electrical panel, NEW wall-to-wall carpeting, NEW skylights, and FRESH interior paint — all completed in 2026 – with a NEW hot water tank (2024) and REBUILT AC condenser and furnace (2025).*** Exterior painted in 2022. Outside enjoy half an acre of land with plenty of room for outdoor play, gardening, or weekend entertaining. Move right in, relax, and start making your own memories from day one!

210 Chamberlain St, Holliston

$674,900

4 Beds ⋅ 3 Baths ⋅ 73567627 MLS

Nestled in a desirable Holliston neighborhood, this spacious raised ranch is set on a private lot abutting conservation land. The bright and welcoming main level features cathedral ceilings, abundant natural light, hardwood floors, and a wood-burning fireplace. The sunny, white-cabinet kitchen offers direct access to a large deck overlooking the private backyard, built-in pool, and beautiful patio—ideal for relaxing and entertaining. The main level also includes a tiled full bath, a primary bedroom with a private half bath, and two additional generously sized bedrooms. The finished lower level offers an open-concept family room with a second wood-burning fireplace, a versatile bonus room suitable for use as a fourth bedroom or home office, a well-appointed laundry room, and an additional half bath. Warm and inviting, this home offers abundant living space, privacy, numerous updates, and a newer septic system.

68 Gregory Rd, Holliston

$685,000

3 Beds ⋅ 2 Baths ⋅ 73566661 MLS

A touch of modern city but in the quiet suburbs. This 3-bedroom, 2 bath raised ranch offers both. Property is over 2 acres of privacy and quiet, with modern updates in the kitchen and baths. Upper level offers an open living room with fireplace, that leads into the dining area and kitchen. Take a moment sitting in the sun either on your deck off the kitchen or sunroom with skylights off the dining area. Move down the hall and you will find closet space, three bedrooms, and a full jack-and-jill bath attached to the main bedroom. Proceed to the lower level and you will find a fire placed family room, bonus room, full bath, storage, and access to the 2-car garage. As a surprise there is a finished space as well as storage in the pull-down attic. Some other bonuses include a covered patio on the lower level in the back, newer oil tank, storage shed, and small little pond.

64 Marshall St, Holliston

$475,000

3 Beds ⋅ 1 Baths ⋅ 73566520 MLS

Welcome to 131 Goulding Street, a three-bedroom ranch offering the ease and convenience of one-level living on a level .48-acre lot. The home features a spacious living area, three bedrooms, and a full bath, along with a kitchen offering granite countertops and a gas stove. Additional features include replacement windows, vinyl siding, town water, and a one-car garage. The level lot provides plenty of outdoor space and offers the opportunity to create your own backyard setting. Conveniently located in Holliston, this property is a great opportunity for buyers looking for a ranch-style home with a practical layout and the potential to update and personalize the space to suit their needs.

131 Goulding Street, 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

$680,000

3 Beds ⋅ 2 Baths ⋅ 73562307 MLS

Welcome home to 203 Turner Road — a beautifully maintained split-level tucked on a quiet, tree-lined street in one of Holliston's most desirable neighborhoods, prized for top-rated schools, New England charm, and easy access to Rte 495 and the Mass Pike. Enjoy nearby Lake Winthrop for swimming, boating, and lakeside strolls, plus Ashland State Park just minutes away for hiking, trails, and outdoor recreation. All 3 bedrooms are situated on the main level, along with a full bath and a vaulted, beamed-ceiling living room centered on a brick fireplace and sunny bay window. Downstairs, the finished lower level adds incredible bonus space including a den or guest room, home office, separate workshop, second full bath, and laundry & pantry, perfect for remote work, hobbies, or guests. Step outside to a fully fenced, private 0.74-acre yard framed by mature trees, plus an incredible wraparound deck built for entertaining. An EV charging station is already installed, and with over $120,000 in work by the current owners: roof, furnace, septic, rebuilt chimney and more, this move-in-ready gem is not to be missed!

203 Turner Road, Holliston

$499,900

3 Beds ⋅ 2 Baths ⋅ 73562180 MLS

Opportunity knocks in this desirable neighborhood surrounded by higher-priced homes. This affordable three-bedroom ranch offers a smart layout with a fireplace living room, dining area, and an eat-in kitchen, plus three bedrooms and a full bath on the main level. The walk-out lower level expands your living space with a generous recreation room, workshop, and a half-bath/laundry area. Recent updates include newer gas heat, hot water (approx. one year old), and newer windows. With an expansive rear yard and solid bones, this original-owner home is a prime chance to build equity and customize to your vision. Act now.

187 Turner 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

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