Thoughtfully designed and truly unique, this custom 3 bedroom, 3 full bath Cape is set in a desirable Holliston neighborhood and offers a seamless blend of comfort and flexibility. Sunlight fills the first floor, where a fireplaced family room and dining area are framed by walls of windows overlooking the backyard. The bright, spacious kitchen features an eat-in breakfast nook surrounded by windows + flows effortlessly to an expansive deck-perfect for morning coffee + easy outdoor entertaining. A separate platform deck complete with string lights sets tone for summer evenings. Rare and highly sought-after, a first-floor primary suite provides a private retreat w/walk-in closet and full bath. Additional first floor spaces include a home office, den or sitting room, full bath, and first floor laundry. Upstairs offers two generous bedrooms w/Jack and Jill bath + an additional large bonus room. The unfinished basement with workshop offers future potential. Septic approved for 4 bedroom
A very special home with charm of an 1890's antique and a spectacular 2009 addition including ADU/in-law suite. The gourmet kitchen was expertly designed with a chef quality 6-burner Blue Star gas range flanked by Boos Block countertops with a generous dining area opening onto the stone patio.The mudroom entrance is perfect for a busy household and a private first floor apartment provides space for an in law area or ADU. The living room, family room, & renovated full bath round out the 1st floor. The master suite has a cathedral ceiling bedroom, designer bath, new closet by design shelving for the walk-in, and separate media room with skylights. Three additional bedrooms, hang out space, and laundry are on the second floor. Wide pine floors, recessed lighting, newer HVAC systems, new water heater, & numerous updates! Lovely spacious backyard with fruit trees, enclosed porch perfect for summer nights or morning coffee, circular driveway and 3 car garage. Near commuter rail & rail trail.
Original owner is offering this stunning end unit townhome with an idyllic setting. Wonderful open floor plan consists of chef's kitchen, a home office with built-ins, large primary bedroom with lovely views, first floor laundry and a dining area large enough for most get-togethers. Gleaming hardwoods throughout the main living area, lots of recessed lights, gas fireplace for those chilly evenings and plenty of storage. On the second floor there is a great room perfect for lounging, reading, or enjoying a separate peaceful place to escape. Good sized second bedroom and bath and a small room seller is using as a sewing room. Private outside deck and a two car attached garage add to the allure of this picture perfect property. Very rare offering in Holliston Woods.
Effortless living in this like-new 3BR 2.5BA townhouse-style condo set on a picturesque, level lot. Open-concept main level offers abundant natural light and a warm, inviting flow ideal for everyday living and entertaining. The kitchen features white cabinetry, center island, and granite countertops, opening to spacious living and dining areas. Upstairs includes three large bedrooms, two full baths, and a convenient laundry room. The primary suite offers a walk-in closet and bath with double vanity and tiled shower. Flexible layout allows one bedroom to serve as a home office or guest space. Additional highlights include a 2-car attached garage with EV charging, energy-efficient Pella windows, and an air purification system. Full basement provides excellent expansion potential and is already roughed for a bathroom. Enjoy no condo fees and a prime location near downtown Holliston and Stoddard Park, blending luxury, comfort and convenience. Do not miss this great condo!
Truly in a class all its own, this gracious home completely renovated and expanded upon by its former owner and premier builder as his own residence, is crafted with fine detailing and finishes. Stunning kitchen features a 6 burner Thermador range w/steam & convection, Thermador fridge & dishwasher; lovely dining & living rooms with built in cabinetry, pellet stove and access to the dreamy screened porch; dramatic, airy family room w/built ins , custom windows and French door to outside; fabulous home office with heated floor and separate entrance; large entry, back mudroom and full bath complete the main level. Upstairs are two primary suites/bedrooms, plus two other generously sized bedrooms with large closets; 2nd floor laundry; two dens/sitting rooms and an elevator to the handicapped accessible part of the second floor. Lower level with a media room with coffered ceiling, a game/rec room and a wine cellar. Gorgeous patio with hot tub; large backyard, mature trees & plantings.
Set on a registered scenic road in desirable Holliston, this spacious 4–5 BR home sits on 3+ private acres & offers great flexibility for today’s lifestyle. Owned solar panels provide excellent efficiency, covering all electrical needs incl. EV charging & central air, w/ seasonal credit banking. Inside features hardwood, laminate & carpet flooring, plus a welcoming family room w/ high-efficiency Lopi wood stove insert. The kitchen offers granite counters, black cabinetry & a slider to the deck for easy indoor/outdoor living. Versatile layout includes 2 potential primary en-suites—ideal for multigenerational living. First-floor primary has cathedral ceiling, walk-in closet/office & private bath. Extras: Ethernet, W/D, 2-car garage, 200-amp, roof (2017), new stair carpet & fresh paint. Includes seasoned firewood & Wyze system w/ cameras & Bluetooth garage. Competitively priced with consideration for future improvements—great value & chance to build equity!
Tucked away in one of Holliston’s most idyllic neighborhoods, this contemporary colonial offers a rare opportunity to create your dream home. This hidden gem has been lovingly maintained by one owner. Featuring 4 bedrooms and 3 full bathrooms, including a 1st-floor home office/den, the home offers a flexible and spacious layout filled with natural light. Oversized windows throughout invite the outdoors in, showcasing beautiful views of the surrounding property. The family room leads to an expansive deck, perfect for entertaining or enjoying peaceful mornings. A standout feature is the detached two-story garage with additional rooms and a unique tunnel connection to the main house—ideal for a workshop or studio. The interior has been freshly painted throughout. Features a new hot water heater (2025) and central A/C. Set on a combined 1.83 acres, including additional land at 0 Orchard Lane, the property offers both privacy and opportunity. A bit of cosmetic updating and welcome home!
Enjoy the peaceful serenity in this 4 bdrm, 1.5 bthrm home on a private corner lot in this sought after Brentwood neighborhood! As you enter, the mudroom allows you to kick off your shoes and head to the newer renovated kitchen with LVT flooring, updated cabinets, granite countertops, SS appliances and a pantry closet, plus freshly painted walls. There's a half bthrm off the kitchen, leading into the dining room. Hardwood floors throughout. A good sized LR w/wood fireplace and huge picture window for lots of light during the day. There's 2 closets in the front hallway for storage. Upstairs has 4 good sized bdrms w/closets, and the full bathroom. Head to the basement to enjoy the partially finished game/exercise room with a unique decorative fieldstone structure, and unfinished room for more storage and laundry. Great open backyard w/electrified 2-story barn w/work benches and loft for storage. Good commuting location w/minutes to routes 16 & 495 and close to restaurants and shopping!
Stately 4-bedroom, 2.5-bath Colonial set on nearly 3 acres in sought-after Holliston. A grand foyer welcomes you with a beautiful staircase and sets the tone for this impressive home. The stunning chef’s kitchen features an island, granite countertops, stainless steel appliances, pantry, and recessed lighting, with a slider leading to a covered screened porch overlooking the expansive grounds and natural surroundings. The family room showcases a soaring cathedral ceiling and wood fireplace, while gleaming hardwood floors flow throughout the main living areas. A dedicated home office offers ideal work-from-home space. Upstairs, the spacious primary suite includes a spa-like bath with soaking tub, separate shower, and custom walk-in closet, complemented by generously sized bedrooms and a full bath with dual vanity. Additional highlights include an attached two-car garage and a full walkout basement—offering space, comfort, and style in a beautiful setting.
Why rent when you can own?!?!?Welcome to Crestview Condominiums, where easy one-floor living meets comfort and convenience*This spacious 1-bedroom unit features a beautifully open, free-flowing layout that feels unexpectedly expansive*Two ductless mini-splits provide effecient year-round heating and cooling*The generous dining area easily accomodates a large table for everyday meals or festive gatherings*The bedroom is impressively sized with a fantastic walk-in closet, and the oversized bathroom adds to the home's appeal*Crestview is a well-managed community in desirable Holliston and the complex is undergoing a thoughtful transformation with new siding and windows being installed now and should be ready for you very soon*Upcoming driveway and laundry upgrades are also being planned*A sparkling inground pool adds summer enjoyment*With strong rental potential and a community on the rise, this is a wonderful opportunity for investors seeking a turnkey property in a high demand town*WOW!
** UNDER CONSTRUCTION ** NEARING COMPLETION ** Stunning Modern Farmhouse Colonial at Prestigious "The Homes at Pond View" 5 BEDROOMS ~ 4 1/2 BATHROOMS ~ 3 CARS GARAGES ~ PRIVATE 3.62 BREATHTAKING ACRES w/ NO CONSERVATION LAND ~ NATURAL GAS HEATING & COOKING ~ TOWN WATER ~ Custom White & Glass Cabinetry ~ En Suite 1st Floor Bedroom w/ Full Bathroom ~ Hardwoods Thru Out ~ Coffered & Tray & Cathedral Ceilings ~ Walk Up Attic ~ Dual Staircases ~ Quartz Countertops Thru Out ~ Custom Stamped Concrete Patio & Walkway ~ Thermador Appliances ~ 2nd Floor Bonus Room ~ Jack n Jill Bedrooms w/ Full Bathroom ~ Butler's Walk In Pantry ~ Polished Marble Bathrooms ~ Powder Room ~ Matte Black Metal Wraparound Porch ~ Kohler Plumbing ~ Spray Foam Insulation ~ Pool & Sports Court Capability ~ Family Neighborhood ~ Board & Batten Facade ~ Access to RTE: 16 & 495 ~ Hardie Arctic White Siding ~ His & Her Closets ~ 2nd Floor Laundry ~ Excellent Schools ** CALL OFFICE FOR PRIVATE SHOWINGS & FINAL SELECTIONS
Welcome to 14 Fiske Pond Road! A dream home built w/the most unparalleled attention to detail, millwork & craftsmanship. The 5BR, 5BA house will appeal to today's modern families, multi-generational families, down sizers, & empty-nesters w/1st & 2nd floor primary options. The 1st floor open concept is the heart of the home w/soaring ceilings & natural light pouring in.The kitchen has SS high end appliances, walk-in custom pantry, 92 bottle wine chiller, 6 burner range, wall oven, center island & leads to LR w/gas FP, and DR. The primary BR is its own oasis w/luxurious spa BA & custom walk-in closet. 2nd BR/office & full BA also on 1st .The mudroom & laundry are have radiant floors & lead to 3 car garage. The 2nd floor is a surprise! 3 BR's (two ensuite), a 2nd FR w/gas FP, wet bar & vaulted ceilings + generous bonus room. 9ft ceilings. All BA's have radiant heat, speakers in most of house, fire pit. Conveniently located <10 miles many town centers: Sherborn, Dover, Natick, Wellesley.

Holliston is located in Massachusetts. Holliston, Massachusetts has a population of 14,891. Holliston 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 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 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.