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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
$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
$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
$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
$739,000
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. 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 is just waiting on a well test, spoke with the town once they get the results they can issue certificate.

636 Highland 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
$499,000
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
$599,900
3 Beds ⋅ 1 Baths ⋅ 73564423 MLS
Welcome to 36 Regal Street! This charming ranch 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, your own backyard escape just in time to enjoy the last moments of summer! 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 St, 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
$403,800
3 Beds ⋅ 1 Baths ⋅ 73562233 MLS
This cottage-style home offers genuine potential in a desirable setting near Lake Winthrop, Stoddard Park Beach, Patoma Park and recreational amenities. The home features two bedrooms, one full bathroom and approximately 1,060 square feet of living area in a practical single-level layout. Bring your ideas and explore the opportunity to personalize and improve the property. This property has been placed in an upcoming event. All bids should be submitted at Xome.com void where prohibited. Please submit any pre-auction offer received through the property details page on Xome.com. Any post-auction offers will need to be submitted directly to the listing agent. Response within 3 business days. All properties are subject to a 5% buyer's premium pursuant to the Auction Participation Agreement and Terms & Conditions minimums will apply.

66 Lakeshore Dr, 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
$860,000
3 Beds ⋅ 3 Baths ⋅ 73558504 MLS
Discover the single-family home at 621 Marshall Street, offering the perfect blend of comfort, space, and privacy. Built in 1965, 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
$785,000
4 Beds ⋅ 2 Baths ⋅ 73553937 MLS
Welcome to 47 Westfield Dr, a delightful single-family home that seamlessly blends comfort and functionality. Spanning 2,075 square feet, this residence offers 4 well-proportioned bedrooms, 2 bathrooms, and a versatile open floor plan designed to suit your lifestyle. Step inside to discover a bright and updated kitchen that boasts an eat-in kitchen with island perfect for cooking and entertaining opening to a family room. Adjacent, a formal dining room sets the stage for memorable gatherings. A large living room overlooks the front yard with an oversized window. The outdoor amenities invite you to relax and unwind. Enjoy grilling in the newly added covered barbecue area, hosting on the deck, or lounging on the patio. A fenced-in yard adds privacy and creates a welcoming atmosphere for outdoor activities. Recent updates include adding mini-splits, creating an open kitchen/dining flow, first floor bath including adding shower, adding an incredible pantry room as well as a multi-functional mudroom/laundry room and storage. Brand new paved driveway! See agent for additional updates and features. 47 Westfield Dr presents an outstanding opportunity to enjoy the best of both indoor and outdoor living in a beloved Holliston neighborhood!

47 Westfield Dr, Holliston
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 73552868 MLS
Where timeless country living meets endless possibility- Once known as Kampersal Dairy Farm, this exceptional farm and home offer the space, charm and freedom you've been waiting for! The main house recently underwent a 1,000+ sq. ft. addition featuring an oversized 2 car garage w/ hydraulic lift. Kitchen, Bathrooms, Main Floor Primary Bedroom, Office, and Breezeways are all new. Renovations also include a full-length rear deck with sliders off the Kitchen and Primary BR. The wood stove efficiently heats the entire home, while portions of the original house have been preserved.Oversized three-story Barn recently received a board-and-batten facelift and offers abundant storage below. Set on just under 5 acres, Continue operating as a farm, Raise or board horses, Explore subdivision potential, or enjoy Country Living. Conveniently located near the Upper Charles Rail Trail, perfect for horse back riding and most outdoor activity, with easy access to Rts. 495, 109 &16

85 Fisher Street, Holliston
$899,900
6 Beds ⋅ 4 Baths ⋅ 73549299 MLS
Gracious and stately, this sunny center entrance colonial offers a lovely updated main house plus two income generating apartments, making this a wonderful opportunity and investment. Located in the charming village of downtown Holliston, this home offers a coveted lifestyle of walking to schools, shops, cafes, playground, library, Upper Charles Rail Trail and Lake Winthrop. Updated kitchen features white cabinetry, wood flooring, granite counters, stainless appliances and an exposed beam; living room with pine flooring, built-ins and working fireplace; family room with lots of windows, built-ins, working fireplace and pine flooring; spacious dining room with beautiful original mantle and detailing, plus built-ins. The new screened porch & half bath complete the main level. Upstairs bedrooms are spacious and inviting, including the primary bedroom which offers the potential of being two rooms. Walk up 3rd floor provides either another bedroom or a fabulous home office space. A gem!

865 Washington St., Holliston
$644,000
3 Beds ⋅ 2 Baths ⋅ 73541116 MLS
Price recently reduced Move-in ready ranch that encompasses 2089 square feet of well-maintained living space. This property offers a refined living experience, thoughtfully designed for both comfort and sophisticated entertaining. The kitchen is appointed with stainless steel appliances, new stove and dishwasher Dec of 25 and features a central island, providing an efficient and stylish space for culinary endeavors. The living room offers a welcoming atmosphere, ideal for relaxation and social gatherings and three bedrooms, This residence provides ample accommodation designed for privacy and convenience. Great open space to entertain in the lower level with a dry bar. The expansive 19602 square foot lot includes a private yard, offering a secluded outdoor environment for leisure and recreation.

58 Wedgewood Dr, Holliston
$209,900
1 Beds ⋅ 1 Baths ⋅ 73539584 MLS ⋅ ['Crestview Condominiums'] BLDG.
Don't miss this opportunity to own this move-in ready condo in desirable Crestview Condominiums. Offering an open floor plan with a renovated kitchen, vinyl flooring throughout the main living area, newer windows, and updated appliances all less than five years old, this home has been thoughtfully maintained and improved. A recently installed heat pump system in the bedroom provides efficient year-round comfort. Step outside through the living room slider to enjoy your private balcony, the perfect spot to relax or enjoy your morning coffee. Residents enjoy access to the community swimming pool and a location that offers the perfect balance of convenience and recreation, with nearby walking and biking trails, local ponds, and Lake Winthrop. Ideally situated with easy access to major highways and commuter routes, this home also includes one off-street parking space and offers low-maintenance living in a convenient Holliston location. Schedule your showing today!

152 Turner Road Unit 38, Holliston
$899,900
6 Beds ⋅ 4 Baths ⋅ 73514969 MLS
Gracious and stately, this sunny center entrance colonial offers a lovely updated main house plus 2 income generating apartments (with 2 driveways); a wonderful opportunity & investment. Located in the charming village of downtown Holliston, this home offers a coveted lifestyle of walking to schools, shops, cafes, playground, library, Upper Charles Rail Trail and Lake Winthrop. Updated kitchen features white cabinetry, wood flooring, granite counters, stainless appliances and an exposed beam; living room with pine flooring, built-ins and working fireplace; family room with lots of windows, built-ins, working fireplace and pine flooring; spacious dining room with beautiful original mantle and detailing, plus built-ins. The new screened porch & half bath complete the main level. Upstairs bedrooms are spacious and inviting, including the primary bedroom which offers the potential of being two rooms. Walk up 3rd floor provides either another bedroom or great home office space. A gem!

865 Washington Street, Holliston
$999,000
2 Baths ⋅ 73479044 MLS
Former bank. Two story 3,345 SF building with drive through located on Route 16 in Holliston.

818 Washington St, Holliston
$649,000
3 Beds ⋅ 2 Baths ⋅ 73328308 MLS
Escape to this beautifully maintained, sun-drenched 3-bed, 2-bath Raised Ranch on scenic 1/2-acre lot! The open-concept main level features gleaming hardwood floors, fireplaced living room, and a seamless flow to the dining area. Gourmet kitchen boasting granite countertops, tiled backsplash, stainless steel appliances with center island / breakfast bar. French doors off the kitchen lead to a screened-in porch overlooking the private, lush backyard. The lower level offers a spacious family room with fireplace, recessed lighting, full bath with laundry, and direct access to the attached garage. Recent updates include roof, windows, vinyl siding, electrical, heating, central A/C, kitchen, baths, septic system and more. Conveniently located near all that Holliston has to offer, this turn-key home is ready for you to move right in!

186 Locust St, Holliston