Holliston MA Historical Real Estate, Homes for Sale

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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$950,000

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

$634,000

3 Beds ⋅ 2 Baths ⋅ 73541116 MLS

Welcome to 58 Wedgewood Drive, a beautifully maintained Holliston home offering over 2000 square feet of comfortable, versatile living and direct access to the Upper Charles Rail Trail. The well-appointed kitchen features stone countertop, stainless steel appliances, a center island, and plenty of space for everyday meals and entertaining. Rich hardwood flooring adds warmth and character to the inviting living room while comfortable bedrooms and 2 full baths complete the main living areas. Downstairs the spacious lower level offers even more room to gather and unwind. With an open layout and a dry bar, it's fantastic space for entertaining, movie nights, game days or simply relaxing with family and friends. Outside, the private backyard provides a peaceful setting for outdoor dining, gardening, or enjoying warm summer evenings,, And with direct access to the Upper Charles Rail Trail, miles of scenic walking and biking trails are almost right outside you door. Move-in ready and wonderfully located, this is a home designed t be enjoyed both inside and out.

58 Wedgewood Dr, 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

$749,000

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

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