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$680,000
3 Beds 2 Baths 73575571 MLS
Welcome to this charming split-level/ranch-style home set on a spacious, beautifully landscaped lot surrounded by mature trees. A gently sloping front lawn, generous paved driveway, and attached garage create an inviting first impression. Inside, the bright main level features gleaming hardwood floors, large windows, and a warm fireplaced living room. The spacious dining area flows naturally into the kitchen, which offers white cabinetry, ample storage, generous workspace, and stainless appliances, with large windows overlooking the surrounding greenery. Hardwood flooring continues through much of the main living area and bedrooms, including a bright primary bedroom with generous closet space and peaceful yard views. Flexible additional bedroom/office space offers versatility for today's needs. The finished lower level provides excellent additional living space for a family room, playroom, home office, or recreation area, along with laundry, utility, storage, and workspace. A basement entrance/exit provides convenient access to the yard. Major systems have been updated, including a newer roof, heating system, and windows, offering added peace of mind. Step outside to enjoy the screened porch overlooking the private, fenced backyard, ideal for relaxing, dining, or entertaining. The expansive yard offers room for recreation and gardening, with a dedicated basketball area adding to the outdoor appeal. A peaceful setting, flexible living spaces, updated major systems, and inviting indoor-outdoor spaces make this a wonderful place to call home.

35 Donna Rd, Holliston

$689,000
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

$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

$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

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