Escape the ordinary & step into something truly special! This expanded log home is a rare Holliston find—warm, inviting, & privately tucked away on a serene retreat lot while still being moments from everything. Just a short walk or bike ride brings you to downtown cafés, shops, & the Upper Charles Rail Trail. The open floor plan offers a front-to-back living room with a cozy fireplace, while the kitchen & dining area flow seamlessly into a spacious family room with gleaming hardwood floors. A full bath completes the 1st floor. Upstairs, the primary bedroom boasts two generous closets, and the beautifully renovated hall bath showcases a rustic-modern design. But the magic happens outdoors: your own private wilderness retreat. Enjoy a fenced backyard filled with birdsong—from bright cardinals to visiting orioles—while lounging by the gorgeous propane-heated Gunite pool. Unwind around the circular firepit as the sun sets & nature fills the air. A home that feels like you are on vacation
Truly an oasis, offering elegance and comfort in a lovely private setting, tucked into a quiet neighborhood. This sun filled home features a fabulous floor plan with 4/5 bedrooms (including one on the main level); 3 full baths; dramatic skylit family room with gas fireplace; gorgeous kitchen with gas cooking and custom cabinetry; open living and dining rooms; dreamy screened porch transitions to the beautiful backyard and magazine worthy inground pool. Upstairs are four very generously sized bedrooms, showcased by the primary bedroom with its tray ceiling, stunning bathroom and walk-in closet; 2nd floor laundry; updated hallway bath with double vanity. Lower level adds a game/recreation room, craft room/office and spacious exercise or play area. Numerous updates (see attachment) include roof, Pella windows, HVAC systems, carpeting & more. Beautiful grounds include a bluestone patio with stone fireplace, koi pond with waterfall, privacy fencing and even a putting green! A true gem!
Let your new story begin in The Highlands at Holliston! A sense of arrival is instant as you enter this impeccably maintained home, where timeless elegance meets luxurious comfort. A grand dual staircase with iron balusters makes a striking first impression. Enjoy mornings in a sunlit solarium overlooking an expansive yard with raised garden beds, evening conversations beneath coffered ceilings & oversized windows in the great room, or cooking in the gourmet kitchen. A serene sitting room with tray ceiling & French doors offers a quiet retreat; a first-floor office to work from home. Herringbone hardwoods & curated décor flow throughout. Upstairs are 4 spacious bedrooms, inc. a master suite w3 closets & an alcove for nursery, yoga, meditation, or reading. Two bedrooms share a Jack-and-Jill bath while another is en suite. This house is just brimming with upgrades! The walkout basement leads to a custom patio & offers future expansion options. Top schools & popular town!
Love to host the holidays? This multi-level home offers an inviting living space designed for hosting friends & family. The oversized kitchen with cathedral ceilings & large island with ample seating & dining area is the perfect place to gather & entertain. The kitchen opens up to the beautiful sunroom that overlooks your private 2.68-acre lot. As the weather cools down, spend your evenings cozied up with a book by the pellet stove in the living room. The lower-level spacious family room features a built-in wet bar, ideal for game nights or game days. With multiple levels of living, generous room sizes, & a great flow for entertaining, this home combines comfort, function, & style in a convenient setting. Less than a half mile from Lake Winthrop, allowing you to easily enjoy that lake life. Automatic house generator, Roof (2017), Work shed with electricity & two additional sheds. Amazing town with award winning schools & charming downtown. **BRAND NEW SEPTIC being installed*
Suburban Lifestyle:Nestled in a peaceful wooded setting, this 3-bedroom, 1.5-bath Saltbox Colonial combines classic charm with thoughtful updates. Built in 1989 with durable post & beam oak timber construction, the home features wide 12-inch pine floors and a warm, open layout. The updated kitchen offers quartz slab countertops, high-quality Shaker cabinets, and an under-counter microwave. The inviting main level includes upgraded lighting and opens to a brand new composite deck overlooking the trees—perfect for relaxing or entertaining. Upstairs are three comfortable bedrooms and a full bath. The lower level features a family room with new laminate flooring, built-in oak storage, and an office nook. Additional updates include a new walkway, Nest smart thermostats, Kwikset digital lock, professional radon remediation, and custom top-down/bottom-up window treatments. A perfect blend of privacy, character, and modern comfort in desirable Holliston.
This home blends modern comfort with future-ready features, making it a standout in Holliston’s competitive market. Modern elegance and value meet at 1014 Highland St. This brand-new 3 bed, 3.5 bath home sits on a private 1.3-acre lot in sought-after Holliston, just minutes from Pinecrest Golf Club. Enjoy a bright open-concept layout, designer kitchen with quartz counters, stainless appliances, and a spacious walk-in pantry—perfect for storing bulk purchases, freeing up countertop space, and keeping everything well organized. Two en-suites — including a luxurious primary suite with a spa-like bath and heated floors. Features include hardwood flooring, EV charger prep, solar-ready setup, and a 1-car garage. With excellent schools, commuter access, and lifestyle amenities nearby, this home delivers comfort, style, and value.
Situated at the end of a quiet cul-de-sac, this lovingly maintained house boosts 4 bedrooms upstairs and a recently upgraded owner’s bathroom. Flooded with natural light, it also includes newly renovated flooring and a bright and airy family room as well as a heated sun room, central air and a 2 car garage. The versatile layout, with French doors, is the perfect mix of open and private spaces. Cozy 2nd family room with working fireplace is excellent for movie nights. The basement is large and dry, great for storage or expansion. The yard includes a playset and a tree fort. Annually, turtles nest in the front yard. This move in ready Holliston house is a real find and open to all reasonable offers.
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, and a luxurious primary suite. Built by a trusted local builder, with select finishes still available to personalize your home. Enjoy top-rated schools, parks, and convenient access to major routes. Expected completion Winter 2026

Holliston is located in Massachusetts. Holliston, Massachusetts 01746has a population of 14,891. Holliston 01746 is more family-centric than the surrounding county with 38.06% of the households containing married families with children. The county average for households married with children is 35.9%.
The median household income in Holliston, Massachusetts 01746 is $142,348. The median household income for the surrounding county is $111,790 compared to the national median of $69,021. The median age of people living in Holliston 01746 is 44.2 years.
The average high temperature in July is 83 degrees, with an average low temperature in January of 16.2 degrees. The average rainfall is approximately 49.8 inches per year, with 43.6 inches of snow per year.