Holliston, MA Houses for Sale

Exceptional two-level home with two remarkable expansions, designed for entertaining and everyday living. The main level, the social hub, features formal dining and living rooms with fireplace, flowing into a carefully crafted eat-in kitchen with granite, abundant storage, and breakfast bar. The cathedral family room stuns with soaring wood-planked vaulted ceilings, dramatic floor-to-ceiling

Ann Atamian Gibson Sotheby's International Realty

This spacious home in a highly coveted Holliston neighborhood offers a wonderfully flexible floor plan, with plenty of room for all. Brand new 5 bedroom septic system; 3 full baths, 2 fireplaces, updates galore and a gorgeous, private, flat backyard. Entertain with ease and style in the huge, magazine worthy kitchen, featuring hardwood floors, custom cabinetry, lots of counter space, oversized

Kathy Chisholm Realty Executives Boston West

Attractive, well maintained 4 bedroom, 2 1⁄2 bath home located in a private setting at the end of a small cul-de-sac. Large living and dining rooms offer multiple configurations for entertainment and family gatherings. Wired ethernet installed for fast home networking. Heated sunroom overlooks a fenced in backyard great for kids and pets. Upstairs includes 4 bedrooms and a recently upgraded

Greg Richard Realty Executives Boston West

Set on over 3 acres at the end of a cul-de-sac, this beautiful 4-bedroom Garrison Colonial offers both privacy and charm in the desirable town of Holliston. Meticulously maintained, the home features many recent updates including a new high-efficiency heating system (2023), roof (2017), fresh interior paint (2025), and brand-new bedroom carpets (2025). A spacious family room addition creates an

Campos Homes RE/MAX Real Estate Center

Elegant brick-front Colonial in one of Holliston’s premier Toll Brothers neighborhoods—originally the model home with every upgrade. Set on a cul-de-sac across from hiking trails and walkable to Pinecrest Golf Club. Over 3,900sqft includes a vaulted family room with fireplace, formal living and dining rooms, and a granite kitchen with hardwoods and built-ins. The expansive primary suite offers a

Joshua Shalin ERA Key Realty Services-Bay State Group

Set at the end of winding Mitchell Road, with views behind of vast farmland, this grand three-story home has had vast improvements added both inside and out since its original construction. An oversized family room with vaulted ceiling, stone chimney and fireplace, and large picture windows overlooking the back yard is the centerpiece of the first floor's open-concept design. The grand kitchen is

Richard Wilcox Distinctly New England

Fabulous four bedroom colonial in one of Holliston's most sought after neighborhoods, close to shopping, commuter rail and major routes. Sited on a private corner lot, on a cul-de-sac, this home has been meticulously updated and maintained. Stunning kitchen with granite counters, custom cabinetry, built-in window seat, brand new double oven, Fisher Paykel dishwasher, walk-in pantry and crown

Kathy Chisholm Realty Executives Boston West

Attention Contractors! Charming Multi-Level Home in a Desirable Neighborhood – Great Potential!! Discover the possibilities with this spacious 4-bedroom, 1.5-bath home located in one of the area's most sought-after neighborhoods. With multiple levels of living space, this property offers both functionality and flexibility for a variety of lifestyles. Step outside and enjoy the large backyard

Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

Welcome to Holliston! This charming Antique Colonial is the perfect opportunity to make your mark in the heart of Mudville. Ideally located just a short walk to downtown Holliston, Lake Winthrop, and local schools, this home blends classic character with modern updates.Enjoy the open-concept family and dining room addition (2005), a fully remodeled kitchen and bath (2008), updated electrical, and

Street Property Team Keller Williams Realty Boston Northwest

Welcome to this charming Cape-style 4-bedroom/2 bath home with a 1-car garage. This property, w/over a half-acre of amazing outdoor space including newly planted gardens, features a 1st floor living room & fireplace that flows perfectly into the eat in kitchen with stainless steel appliances. The 1st floor is rounded out with a full bathroom & 2 bedrooms. Off the kitchen area, step into to the

Amy Uliss MDM Realty, Inc

Meticulous craftsmanship defines this exceptional home in the coveted Deer Creek community. Built as the builder’s own residence, every detail reflects superior design and quality. A dramatic entry sets the tone with elegant millwork, gleaming hardwood floors, and abundant natural light. The main level offers a dining room, private office, family & living room, both w/ fireplace & custom built-in

Kathleen McBride RE/MAX Executive Realty

Opportunity knocks in one of Holliston’s most sought-after neighborhoods! This classic ranch offers single-level living with solid bones and many important updates already done, including vinyl siding, a newer hot water heater, central A/C, a newer generator, and more. Bring your vision and creativity—cosmetic updates throughout will make this home shine! Set on a generous lot, this property

Team Rice RE/MAX Executive Realty

This charming 3-BR, 2.5-bath Cape-style home offers a perfect blend of comfort and space. Second-floor and back-of-house additions make this home much larger than it appears.The welcoming front LR features a large picture window filling the room w/natural light, and the DR is an ideal setting for special occasions while the eat-in kitchen is perfect for everyday meals. A cozy fireside FR

Lynn Rossini RE/MAX Executive Realty

Discover this this beautifully maintained Italianate Colonial, ideally located in the heart of Holliston. Light-filled with high ceilings and open concept, the first floor welcomes you with a large front entry.This legal two-family home offers the best of both worlds—functioning seamlessly as a spacious single-family residence with the added bonus of a flexible private exterior entry, lower-level

Stephanie Sugden Compass

Welcome to 9 Ruth Ellen Rd! This single-family residence in presents a remarkable opportunity to establish roots in a desirable neighborhood. This property offers a blend of classic charm and the potential for modern enhancements. The residence features four bedrooms and two full bathrooms, along with a conveniently located half bathroom, providing ample space for comfortable living. With 2118

Gustavo Villatoro Coldwell Banker Realty - Framingham

**Back on the market to due Buyer Cold Feet** Charming antique Colonial on a sunny corner lot in Holliston’s beloved Mudville! This 3-bedroom home blends historic character with thoughtful updates—featuring wide-plank hardwood floors, a light-filled layout, and a versatile bonus room ideal for a home office, studio, or playroom. The warm, inviting kitchen flows into spacious dining and living

Janine Wuschke Keller Williams Realty

You must see this gorgeously updated raised-ranch in the coveted Brentwood neighborhood. Lovely brand new kitchen - cabinets, ss appliances, quartz counters & oversized island open to fireplace living rm & dining rm. Sparkling hdwd floors throughout the main level. Three of the four bedrms & fabulous main bathroom w/ tile shower/bath, tile flr & solid surface vanity. Phenomenal added space in the

Vesta Real Estate Group Vesta Real Estate Group, Inc.

Located in a cozy cul-de-sac with an awesome yard and gorgeous views of the woods with walking trails! This home has 4610 sqft of living space NOT including a walk-up 3rd level ready to be finished. The 1st floor has 9' ceilings and a wide open floor plan with lots of natural light. Family room with fireplace, large dining room, separate office or reading room, mudroom, and your dream kitchen

Craig Morrison Realty Executives Boston West

Incredible Opportunity on 6 Private Acres in Holliston!Builders and investors take note — this is a rare chance to own a stunning 6-acre wooded lot perched on Jasper Hill, offering sweeping views of Holliston’s town center. The property features a single-family home in need of extensive renovation or tear-down, making it an ideal site for new construction.Imagine building a custom dream home or

Enis Shehu Cameron Real Estate Group - Framingham

NEW PRICE!!! Nestled amidst 32 breathtaking acres of serene beauty, this exquisite custom shingle home built in 2006, epitomizes luxury living! Spanning over 5700 SF of living space, every element of this 5 bedrm | 4.5 bath masterpiece is designed w/the utmost attention to detail & quality craftsmanship. The first floor offers a luxurious primary suite w/an en-suite bathroom featuring a walk-in

Kimberly Collins Berkshire Hathaway HomeServices Robert Paul Properties

Welcome to The Homes on Bonney Drive – a private three-home cul-de-sac in Holliston! 110 Bonney Drive offers ~3,500 sq. ft. of beautifully designed living space on over an acre. This 4-bedroom, 3.5-bath home blends modern luxury with energy-efficient living: all-electric, solar-ready, and roughed for EV charging. Open-concept layout features a gourmet kitchen, spacious family room, home office,

Stephen O'leary O'Leary Homes

** UNDER CONSTRUCTION ** TIME TO CUSTOMIZE YOUR PERSONAL TOUCH ~ CALL OFFICE FOR INFO & WALK THRU ** MODERN FARMHOUSE COLONIAL @ STUNNING "The Homes at Pond View" 5 Bedrooms ~ 4 1/2 Bathrooms ~ 3 Cars Garages ~ Town Water ~ Natural Gas Heating & Cooking ~ GORGEOUS TALL PINES ESTATE HOMESITE w/ 3.62 ACRES w/ NO CONSERVATION WETLANDS ~ Family Neighborhood ~ Excellent Schools ~ SPORTS COURT & POOL

Francis Vazza Four Season Homes, Llc

Welcome to this beautifully maintained center entrance colonial, perfect blend of classic charm and modern finishes. This 4 bedroom, 2.5 bath home is truly in a nature lover's paradise. Very close distance you will find Ashland Woods,120 acres of natural beauty, an ideal place to hike and enjoy nature. Less than 2 minutes away is the Ashland Reservoir where you can kayak, swim and fish, and hike

John Szolomayer RE/MAX Executive Realty

Discover elegance and comfort at 8 Raymond Way, Ashland, MA — a beautifully maintained 4-bedroom, 3-bathroom home that blends style, space, and functionality in one of Ashland’s most coveted neighborhoods. With light-filled, inviting living areas, an open layout ideal for entertaining, and quality finishes throughout, this property offers both immediate move-in appeal and long-term value. The

John Grande Media Realty Group Inc.