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$689,000
3 Beds 3 Baths 73575142 MLS
Unique residence offering space, character, and tremendous potential! Set on 4.4 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
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

$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

$795,000
3 Beds 3 Baths 73568274 MLS
From the moment you arrive, it is clear that this custom 3-bedroom, 3-full-bath Cape has been lovingly and meticulously maintained, inside and out. Thoughtfully designed for both everyday living and entertaining, this home offers inviting spaces, wonderful flexibility, and a backyard connection to nature that is truly special.Step inside through the convenient mudroom entrance, where there is room to leave the day behind before entering the bright dining area. French doors draw you outside to the deck, creating an easy flow for summer dinners, morning coffee, or simply relaxing while overlooking the private backyard. At the heart of the home, the spacious kitchen offers plenty of room to gather, while the center fireplace living room provides a warm and welcoming place to unwind. A large family room complete with custom built-ins gives everyone space to spread out, and a first-floor office offers the flexibility so many buyers are looking for today.Upstairs, the oversized primary suite feels like a private retreat, complete with a spa-like full bath and two walk-in closets. Two additional bedrooms and a third full bath provide comfortable accommodations for family and guests.The finished lower level extends the living space even further, with a large great room or flexible space ready for movie nights, games, exercise, hobbies, or whatever suits your lifestyle. A spacious workshop is an added bonus for projects, storage, or creating a space of your own.Outside is where this property becomes even more special. Enjoy the privacy of the backyard, shoot hoops on your own basketball court, or follow the path that leads directly to the Upper Charles Rail Trail. Imagine stepping out your back door for a walk or bike ride, or enjoying cross-country skiing and snowshoeing when winter arrives. This wonderful trail connection brings year-round recreation right to your doorstep. Beautifully cared for and thoughtfully designed, this is more than a house—it is a home that offers space to gather, room to grow, and a lifestyle to enjoy in every season.

1804 Washington St, 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

$785,000
2 Beds 3 Baths 73566269 MLS ['Brooksmont Condominium'] BLDG.
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 over one thousand square feet make up a suite of 3 rooms, on the first floor there are nearly fourteen hundred square feet dedicated to a convenient easy place to create your home. This residence is thoughtfully designed for discerning individuals seeking a refined single level 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, complete with a 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 wooded 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

$1,174,900
4 Beds 4 Baths 73559699 MLS
Open House: Saturday & Sunday from 11 to 12:30 - Tucked at the end of a peaceful cul-de-sac on nearly an acre of beautifully wooded, professionally landscaped grounds, this immaculate Colonial Garrison is the definition of move-in-ready perfection. From the moment you arrive via the paver lined driveway, it's clear this home has been meticulously maintained and thoughtfully updated with a high level of quality craftsmanship throughout. Step inside to find gleaming hardwood floors flowing seamlessly across nearly every room. The heart of the house is a chef's dream kitchen, featuring custom in-lay cabinetry, a large center island with honed marble counters, and a suite of high-end appliances including a Sub-Zero refrigerator, Viking gas cooktop, and Wolf double ovens. Also found in this expansive Kitchen is a wet bar, beadboard and a wine rack. A built-in wet bar makes entertaining effortless, and the open flow into the sun-drenched, cathedral-ceilinged family room — complete with fireplace and skylights — creates the perfect gathering space for family and friends. Also downstairs you will find a large Dining Room and a Study with built ins that are perfect for an upscale home office. Upstairs, the primary suite is a private retreat with a walk-in closet and a spa-worthy en-suite bath boasting a freestanding soaking tub, glass-enclosed tile shower, and double vanity. Three additional bedrooms and another stunningly renovated full bath complete the second floor. The finished lower level adds even more living space with a wine cellar, home gym, versatile bonus room and full bath. The options are endless with this expansive space. A perfect space for a home office, media room, additional bedroom and/or a home gym. Outside, the show-stopping deck overlooks a private, park-like backyard — the perfect setting for morning coffee, weekend barbecues, or simply soaking in the serenity of your professionally landscaped surroundings. A two-car garage, mudroom with custom built-ins, arched doorways, a custom wood finish package that includes wainscoating, shiplap, crown moldings make this is a rare opportunity to own a truly turnkey home in one of Holliston's most desirable neighborhoods.

21 Foxwood Cove, Holliston

$1,899,000
4 Beds 5 Baths 73557149 MLS
NEW CONSTRUCTION. Comfortable sophistication best describes this newly constructed home, located on a country road and situated on almost an acre of land. The open-concept first floor is ideal for family gatherings and entertaining, featuring an impressive kitchen with a large center island,  with a quartz waterfall countertop, a wine cooler, and stainless steel appliances. The kitchen and dining area flow seamlessly into the living room, which is accented by a gas fireplace. Additionally, a dedicated library/office provides a wonderful space for working from home or quiet reading. Upstairs, a central sitting area with a second fireplace connects four bedrooms, each featuring hardwood floors, ribbon lighting, and its own private bath. The primary suite is a retreat in its self, offering a third fireplace that provides the sleeping area with a warm glow. The primary bath includes a soaking tub, an oversize tile shower, and a double vanity, while the dressing room provides ample space for clothing and accessories; it's nothing less than a dream. A convenient second-floor laundry room is also located just off the sitting area. If the above-ground living space is not enough, the full, finished basement is the perfect spot for play or hosting a game-viewing party. The living space continues outside to a stone patio complete with an outdoor kitchen. Three car garage with high ceilings provides space for larger vehicles or multilevel storage . Plus, the property is close enough to the golf course that you can drive your cart home to drop off your clubs. Don't miss the opportunity to see this stunning home. ANY OFFERS PRESENTED BETWEEN 8/28-9/5 - PLEASE ALLOW 48 HOUR RESPONSE TIME

30 Mill 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

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