Holliston Real Estate

Welcome to Holliston, Massachusetts—a charming town nestled in the heart of Middlesex County, where small-town charm meets modern convenience. With its picturesque landscapes, rich history, and vibrant community spirit, Holliston offers an idyllic setting for families, professionals, and retirees alike.

Founded in 1724, Holliston boasts a captivating history that is reflected in its well-preserved architecture and quaint downtown area. As you stroll through the tree-lined streets, you'll find a delightful mix of historic homes and contemporary residences, each telling its own story. The town is renowned for its beautiful parks, including the scenic Holliston State Forest and the serene Ashland Reservoir, providing ample opportunities for outdoor enthusiasts to hike, bike, and enjoy nature.

Holliston's community spirit shines through its annual events, such as the popular Holliston Day and the summer concert series, fostering connections among residents and creating a vibrant social atmosphere. The town is served by excellent schools, making it a desirable location for families seeking quality education for their children.

Conveniently located just 20 miles from Boston, Holliston offers easy access to major highways, ensuring that commuting to the city is a breeze. With its blend of tranquility and accessibility, Holliston is perfect for those who want to escape the hustle and bustle of urban life while still being close to all the amenities of a major metropolitan area.

Whether you’re looking to buy your first home, downsize, or invest in a rental property, Holliston is a hidden gem waiting to be discovered. Come explore all that this delightful town has to offer!

Newest Listings in Holliston

$765,000

3 Beds ⋅ 3 Baths ⋅ 73598620 MLS

Beautifully blending the charm and character of an antique Colonial with the comfort and convenience of modern living, this extensively renovated home offers a truly special opportunity. Ideally situated on a corner lot in a convenient in town location, the property is adjacent to the Upper Charles Rail Trail and just two short blocks from Main Street's popular cafes, restaurants, and shops.The thoughtfully designed interior features a spacious, front-to-back open-concept main living area, creating an inviting setting for everyday living and entertaining. The well-appointed kitchen serves as the heart of the home, featuring an impressive seven-foot island, industrial-style sink, and walk-in pantry. A beautiful cedar shiplap mudroom and convenient half bath complete the first floor.Upstairs, you'll find three generously sized bedrooms with ample closet space, a dedicated home office, second-floor laundry, and two beautifully finished full bathrooms. A walk-up attic and full basement provide additional storage and future possibilities.The extensive renovation included all major systems and infrastructure, including updated electrical, plumbing, HVAC with two-zone central heating and air conditioning. Septic System is 2 years old. Improvements were also completed with energy efficiency in mind, offering the benefits of modern construction standards while preserving the timeless appeal of an antique Colonial.A rare combination of historic charm, modern amenities, generous living space, and an outstanding walkable location makes this home an exceptional place to call home.

33 Norfolk, Holliston

Listing courtesy of Listing Agent: Dennis Folan from Listing Office: Coldwell Banker Realty - Westwood.

$299,900

2 Beds ⋅ 1 Baths ⋅ 73598547 MLS

Be the first to see this newly renovated unit at Regency Park! Brand new kitchen with quartz counters and all new appliances, newly refinished wood floors throughout, bathroom updated and the entire unit freshly painted. Nice dining area open to living area perfect for entertaining. Back door off dining/kitchen area so you can step outside and grill or just enjoy back yard! Upstairs has 2 good sized bedrooms and a full bath. If you need extra space there's a front to back basement waiting to be finished. Flooring and washer and dryer already in place in the basement! All within a close distance to downtown and parks. Reasonable condo fee make this even more affordable. Vacant and priced to sell. More photos to be added after finishing touches and cleaning. No showings until Sunday November 8th please.

25 Regency Dr Unit 25, Holliston

Listing courtesy of Listing Agent: Maria Mainini from Listing Office: JDS Realty Group.

$215,000

1 Beds ⋅ 1 Baths ⋅ 73598127 MLS ⋅ ['Crestview Condominiums'] BLDG.

**** OPEN HOUSE SUN. 1 to 3pm **** Crestview Condominiums - a hidden jewel in a quiet residential setting! All updated and ready to move right in! White bright cabinet kitchen, updated, easy care hardwood look laminate flooring throughout. Updated thermo - insulated windows. Spacious open floor plan! Wonderful sunlight pours in the unit all afternoon. Updated sliders in the living room open to a nice balcony overlooking the landscaped front yard. The master bedroom has a huge walk in closets. Updated full bath with large linen closet and ceramic tile floor. Updated 100 amp. electric panel & circuit breakers. The entire complex is receiving a fresh new look: vinyl siding, new balcony railings, updated landscaping and soon to be re-paved walk ways and parking lots. Bright open secured/locked foyer has secure indoor mail boxes and package delivery boxes. Plus there are credit card operated laundry facilities on every level! Relax and enjoy lunch at the beautiful inground pool! Come see this gem and watch your equity grow!

147 Turner Rd Unit 81, Holliston

Listing courtesy of Listing Agent: Jerry Bluhm from Listing Office: REMAX Executive Realty.

$729,900

2 Beds ⋅ 3 Baths ⋅ 73596436 MLS ⋅ ['The Orchards At Holliston Condominium'] BLDG.

Welcome to 29 Garett Way, a Parkland end-unit townhouse at The Orchards with two bedrooms, two and a half baths, and flexible living spaces across three levels. A backyard abutting conservation land provides privacy and a natural backdrop to the home. Enjoy morning coffee, outdoor dining, or time to unwind on the sun deck overlooking the adjoining conservation land. Inside, the living room opens beneath an 18-foot cathedral ceiling, with two skylights bringing in natural light and a gas fireplace creating a focal point. Sliding doors connect the living room to the deck, extending the gathering space outdoors. Hardwood floors connect the main living areas, while nine-foot ceilings add to the open feel. The kitchen combines granite countertops, stainless steel appliances, a center island, and a breakfast area. A separate dining room provides space for everyday meals and larger gatherings. The first-floor primary suite offers the convenience of main-level living, with a walk-in closet and a private bath with granite finishes. Upstairs, an additional bedroom, an open loft suited to office space, and a separate bonus room can serve as a third bedroom, hobby room, or workspace. Modular California Closets, along with eave storage, provide practical organization and storage options. The finished lower level offers generous room for entertaining, from movie nights to gatherings with friends. Alongside the family room, a separate enclosed room provides flexibility as an office, game room, gym, or media room, with potential for a guest bedroom. Separate spaces allow room for recreation and focused activities without taking over the main living areas. EV charger in the garage and new water heater being installed. From the open living room and first-floor primary suite to the versatile finished lower level, this home balances gathering spaces with places to retreat. The end-unit setting, private rear outdoor space, and adjoining conservation land complete the setting at The Orchards.

29 Garett Way Unit 29, Holliston

Listing courtesy of Listing Agent: Ann Marie Silva from Listing Office: Redfin Corp..

$1,499,900

4 Beds ⋅ 4 Baths ⋅ 73595472 MLS

Luxury curated for the way you live!! A thoughtfully designed home with all the bells and whistles! Top brands like Subzero, Wolf, are a dream for a chef inspired kitchen with beautiful quartz countertops and backsplashes. Skylights let the sunshine pour in while your studio McGee Audrine sink helps with clean up. The dining area leads to an outside oversized blue stone patio which invites you to enjoy nature and migrate dinners from the table to meaningful patio conversations. High end plumbing fixtures such as Waterworks, Kohler, Toto, Signature, and Brizo kitchen faucets are featured throughout the home. Relax in your sun-drenched family room that features built in cabinetry with a gas fireplace. This home also has a lower-level room with a full bath and full walk-out for anyone seeking accommodations for an in-law, or home office, or secondary family room. Drive up your driveway with stone walls to come home to your personal oasis. Finally, after a long day, retreat to your primary bedroom with your private spa like bath featuring a soaking tub and tiled shower to unwind from life's demands. This environment is created to calm the mind and restore the spirit. This parcel abuts 2 large tracts of restricted conservation land assuring you that you will always hear the birds singing.

10 Laurel Glen Ct, Holliston

Listing courtesy of Listing Agent: Sherry Widak from Listing Office: Sherry Widak Real Estate.

$2,500,000

73595425 MLS

Northeast Private Client Group is pleased to present 459-465Washington St, a six-suite retail plaza on 1.53 acres in Holliston,Massachusetts, in the MetroWest region. The 1967 plaza holds 7,063rentable square feet along Washington Street.Five suites are home to everyday businesses: Subway, Kings Pizza,Jings Garden, a liquor store and a jewelry store, in suites from 563 to1,900 square feet. Three food operators and a package store give theplaza reasons for repeat, daily visits from the surroundingneighborhood.The value-add starts with one 1,600 SF suite. A new owner can choosethe tenant that best rounds out the mix and strengthens the plaza'sdraw. The plaza's next chapter is shaped by one leasing decision.The plaza's buildings, dating to 1967, cover roughly 11% of the 1.53-acresite, which gives a hands-on owner room to reposition the propertyover time.

459-465 Washington St, Holliston

Listing courtesy of Listing Agent: Tom Egbers from Listing Office: Northeast Private Client Group.

$650,000

3 Beds ⋅ 2 Baths ⋅ 73594125 MLS

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

741 Winter St., Holliston

Listing courtesy of Listing Agent: Jamie Keefe from Listing Office: Coldwell Banker Realty - Framingham.

$300,000

73593884 MLS

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

Winter St, Holliston

Listing courtesy of Listing Agent: Nicole Esposito from Listing Office: Keller Williams Boston MetroWest.

$899,000

5 Beds ⋅ 3 Baths ⋅ 73593644 MLS

Welcome to 1419 Washington Street in Holliston! This well-maintained three-family Colonial presents a fantastic opportunity for investors and owner-occupants alike. The property features two spacious 2-bedroom units and one lofted 1-bedroom apartment, each complete with its own private deck, in-unit washer and dryer, and dishwasher. Separately metered utilities offer added convenience, while a large driveway provides ample parking. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other two, this property offers excellent flexibility. One unit will 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!

1419 Washington St, Holliston

Listing courtesy of Listing Agent: Elizabeth Mason from Listing Office: Longwood Residential, LLC.

$1,025,000

4 Beds ⋅ 3 Baths ⋅ 73593616 MLS

Welcome to this beautifully maintained Colonial, ideally situated on a lovely 1+ acre lot in a wonderful neighborhood on a quiet cul-de-sac! An inviting farmer’s porch, lush lawn and lovely plantings create exceptional curb appeal. Inside, a tiger maple hardwood entry leads to a living room with hardwood flooring and an elegant dining room featuring random width wide pine floors installed with historical cut nails and crown molding. The spacious eat-in kitchen offers quartz countertops, center island, stainless steel appliances, refinished hardwood floors, recessed lighting, tile backsplash and pantry. Relax in the inviting family room with wood-burning fireplace, skylight, ceiling fan and French doors leading to a low-maintenance Trex deck overlooking the private, gorgeous backyard, complete with irrigation, vegetable garden and storage shed. A convenient mudroom and half bath complete the first floor. Upstairs, the primary suite features a cathedral ceiling, walk-in closet and private bath with stone-topped double vanity and custom double shower. Three additional bedrooms, a full bath and convenient laundry area complete the second floor. Walk-up access to the unfinished attic provides additional storage space. The finished lower level offers fantastic flexibility with brand-new luxury vinyl flooring, recessed lighting, bonus room and private home office with separate heating zone and double-hung windows for maximum natural light. Recent 2026 improvements include new carpeting on the stairs, hallway and primary bedroom, beautifully refinished hardwood floors in the entryway and kitchen, and fresh interior paint in many rooms. Additional updates include new microwave, refrigerator & dryer 2026, vinyl windows 2022, heat pump for AC 2024, roof 2013 and boiler/hot water heater 2014. Complete with an attached two-car garage and security system, this exceptionally cared-for home offers comfort, charm and room to spread out inside and out! Enjoy all that Holliston has to offer, from its charming downtown shops and restaurants to Lake Winthrop, the Upper Charles Rail Trail and a vibrant community atmosphere.

6 Beaver Brook Dr, Holliston

Listing courtesy of Listing Agent: Vesta Group from Listing Office: Vesta Real Estate Group, Inc..

$650,000

3 Beds ⋅ 3 Baths ⋅ 73593545 MLS

Tucked away in a much-desired Holliston neighborhood, while offering convenient access to local amenities, you’ll find an impressive split-level home w an abundance of space. Beginning in the living room on the main level where a large picture window fills the space w natural light, you’ll find beautiful hardwood floors that go throughout most of the main level. The living room & dining room are open concept just off the kitchen. Past the kitchen, prepare to be wowed by the expansive great room, complete w beamed vaulted ceilings, skylights, a pellet stove, & sliding-doors to an oversized deck, perfect for outdoor entertaining. Also on the main level you’ll find 3BRs w 2 full BAs which includes the primary suite, w a walk-in closet & private BA. The lower level delivers even more flexibility w a home office, large recreation room featuring a fireplace & built in, as well as an additional space that would make a great meditation room, playroom or craft room. An additional half bathroom & laundry area round out the lower level. This home’s flexible and versatile floor plan make this a wonderful home for extended guest visits w excellent space for entertaining, work, or everyday living. Outside, the fenced yard provides a private setting playing fetch with the dog or just relaxing. Notable improvements include mini-splits installed in 2021, as well as double-pane windows & new skylights installed in 2022. This spacious & versatile Holliston home is one you won’t want to miss!

105 Dodd Drive, Holliston

Listing courtesy of Listing Agent: Colleen Crowley from Listing Office: Lamacchia Realty, Inc..

$799,900

4 Beds ⋅ 3 Baths ⋅ 73593357 MLS

Room for everyone at 631 Central Street! Set on three-quarters of an acre, this home offers a true in-law setup with a heated in-ground pool, making it ideal for multi-generational living or anyone who wants space to spread out. The main house features hardwood floors, an open living and dining area with a brick fireplace and rustic wood mantel, and an updated kitchen with white cabinetry, granite counters, stainless appliances, and a planked wood ceiling. Three bedrooms and a full bath on the main level, plus a lower-level family room, additional bedroom, half bath, laundry room, and garage, give you plenty of flexibility. The in-law suite has its own private entrance and features a stunning vaulted kitchen with rich wood cabinetry, granite, a large center island, opening to a bright living and dining area. It also includes a bedroom, a full bath with a tiled walk-in shower, in-unit laundry, and a lower-level den with generous storage. Step outside to enjoy summers by the heated pool, surrounded by a paver patio, pool house, and vinyl privacy fencing with a peaceful wooded backdrop. Solar panels, two driveways, and ample parking add to the appeal. Conveniently located near downtown Holliston, the rail trail, shopping, restaurants, and Routes 16 and 495, this is a rare opportunity to own a versatile home with space, privacy, and room to grow. First Showing Open House Saturday October, from 11AM to 12:30PM

631 Central St, Holliston

Listing courtesy of Listing Agent: Michael Vaz from Listing Office: Century 21 Signature Properties.

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Holliston Real Estate

Newest Listings in Holliston

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