Holliston MA Real Estate, Homes, Condos for Sale

Don't miss the final opportunity to build your dream home in this exclusive Nantucket-style enclave on the Holliston/Sherborn town line. Restrictive covenants preserve the timeless character of this private community for generations to come. Enjoy over 25 acres of shared open space featuring scenic meadows, walking trails, and a peaceful pond. Bring your own architect and builder, or work with the seller to create your custom home. Seller has approved house plans and will provide septic designs, making it even easier to bring your vision to life.

15 Fiske Pond Rd, Holliston

$1,300,000

5 Beds ⋅ 4 Baths ⋅ 73554074 MLS

Grand and glorious, this stately home is located in a double cul-de-sac neighborhood of refined homes, in a prime location on the Hopkinton line, close to Pinecrest golf course, Holliston High School, the Waseeka Wildlife Sanctuary (Audubon) and the commuter rail. Beautiful private setting abuts protected open space, with a gorgeous heated inground saltwater pool, cabana, large composite deck and spacious, flat backyard lawn area. Wonderful interior floor plan with front and back staircases is ideal for multi-generational living - finished 3rd floor with living area, bedroom and full bath. Main level features a large home office w/French doors and built-ins; sunny kitchen with white cabinetry and brand new stainless appliances; dramatic vaulted ceiling family room with floor-to-ceiling gas stone fireplace; fireplaced game/living room with custom molding and access to dreamy screened porch; dining room with crown molding; powder room with laundry and large mudroom. Second level features four bedrooms, showcased by the lovely, fireplaced primary with its spa bathroom and walk-in closet; oversized bedrooms offer lots of closet space. The walkup third level provides a multitude of possibilities for in-law living, work from home or teen hangout space; walkout lower level with home gym/exercise room. This home has plenty of room for all, while offering warm, cozy and inviting spaces, both inside and out. Be part of the lovely community of Holliston, which offers both Montessori and French Immersion programs as part of their exceptional school system.

25 Erin Way, Holliston

$785,000

4 Beds ⋅ 2 Baths ⋅ 73553937 MLS

Welcome to 47 Westfield Dr, a delightful single-family home that seamlessly blends comfort and functionality. Spanning 2,075 square feet, this residence offers 4 well-proportioned bedrooms, 2 bathrooms, and a versatile open floor plan designed to suit your lifestyle. Step inside to discover a bright and updated kitchen that boasts an eat-in kitchen with island perfect for cooking and entertaining opening to a family room. Adjacent, a formal dining room sets the stage for memorable gatherings. A large living room overlooks the front yard with an oversized window. The outdoor amenities invite you to relax and unwind. Enjoy grilling in the newly added covered barbecue area, hosting on the deck, or lounging on the patio. A fenced-in yard adds privacy and creates a welcoming atmosphere for outdoor activities. Recent updates include adding mini-splits, creating an open kitchen/dining flow, first floor bath including adding shower, adding an incredible pantry room as well as a multi-functional mudroom/laundry room and storage. Brand new paved driveway! See agent for additional updates and features. 47 Westfield Dr presents an outstanding opportunity to enjoy the best of both indoor and outdoor living in a beloved Holliston neighborhood!

47 Westfield Dr, Holliston

$990,000

5 Beds ⋅ 4 Baths ⋅ 73553201 MLS

You won't see another home like it. Nestled on 13 private acres with frontage on two roads, this extraordinary 3,600 square foot geodesic dome offers a truly rare opportunity to own one of the area’s most distinctive homes. Surrounded by nature and set far back from the road, the property provides exceptional privacy and a peaceful setting while still offering convenient access to nearby amenities. The unique architectural design creates an unforgettable living experience with expansive interior spaces, soaring ceilings, and endless potential to customize and make it your own. Whether you are a homeowner seeking a one-of-a-kind retreat, an investor looking for a compelling income-producing opportunity, or a developer exploring the possibilities of the expansive land and dual road frontage, this property is packed with potential. A rare chance to unlock the value of a truly unique estate.

243 Oak St, Holliston

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 73552868 MLS

Equestrian/Farm & Residential..Own a Piece of History!This historic landmark, once known as Kampersal Dairy Farm, is currently a working animal and produce farm where the charm of the old blends seamlessly with today's modern conveniences.The main house recently underwent a 1,000+ sq. ft. addition featuring an oversized 2 car garage w/ hydraulic lift. Kitchen, Bathrooms, MF 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, with easy access to Rts. 495, 109 &16

85 Fisher Street, Holliston

$769,000

4 Beds ⋅ 2 Baths ⋅ 73552598 MLS

Welcome to 54 Jarr Brook Rd, a beautifully updated and thoughtfully designed 4-bedroom, 2-bath Cape ideally situated at the end of a cul-de-sac. With its inviting interiors, the home offers a wonderful blend of style and comfort. The main level features a renovated kitchen with an island, pantry, dining area and multiple windows overlooking the expansive backyard. The adjacent sun-filled family room includes a fireplace with custom built-ins and flows seamlessly into the living room, creating an ideal space for entertaining. A bedroom and full bath complete the first floor. Upstairs are 3 additional bedrooms and a second full bath. The partially finished lower level provides flexible space for a playroom, gym or home office. Outside, the backyard and deck create an inviting setting for outdoor dining, entertaining and gardening. Enjoy a desirable neighborhood location with convenient access to the town center, schools, major routes and commuter rails. A true gem of a home!

54 Jarr Brook Rd, Holliston

$679,900

3 Beds ⋅ 2 Baths ⋅ 73550973 MLS

Welcome to 100 Marylyn Street, a beautifully maintained home offering 4 bedrooms, 2 full bathrooms, and 1,773 square feet of comfortable living space. Thoughtfully designed with a functional layout, this home provides the perfect balance of everyday living and entertaining.The spacious interior features generous living areas filled with natural light, a well-appointed kitchen, and flexible spaces to accommodate a variety of lifestyles. Four bedrooms provide plenty of room for family, guests, or a home office, while two full baths add convenience.Outside, enjoy a private yard with space for outdoor entertaining, gardening, or simply relaxing. Situated in a desirable Holliston neighborhood, this home offers easy access to top-rated schools, parks, shopping, dining, and major commuter routes while maintaining the charm and character that make Holliston such a sought-after community.Don't miss this opportunity to own a wonderful home in one of Holliston's most desirable neighborhoods

100 Marilyn, Holliston

$275,000

2 Beds ⋅ 1 Baths ⋅ 73550283 MLS

Attention CASH BUYERS, CONTRACTORS, INVESTORS, BUILDERS, FLIPPERS, or ambitious owner-occupants looking for their next opportunity! This property needs work but offers incredible potential in an outstanding Holliston location. Situated just off Lake Winthrop and around the corner from Stoddard Park and the public beach, the setting is hard to beat. Property includes MULTIPLE LOTS with frontage/access on two streets, creating exciting potential possibilities for expansion, redesign, or future use. Buyers are responsible for performing their own due diligence with the Town of Holliston regarding any potential building, expansion, or development opportunities. Whether renovating, rebuilding, or creating your dream home, the finished product will be located in one of Holliston’s most desirable areas. The property is being sold as-is and will not qualify for traditional financing. Don’t miss this rare chance to create instant equity in a well-established community!

42 Cottage Dr, Holliston

$699,900

3 Beds ⋅ 3 Baths ⋅ 73549747 MLS

Open houses CANCELLED!! Renovated in 2021, this stunning 3-bedroom, 3-bath home is the perfect combination of timeless charm and modern convenience, ideally situated on a picturesque tree-lined street in one of Holliston's most sought-after neighborhoods. Designed with today's lifestyle in mind, this move-in-ready home features a beautifully updated kitchen with granite countertops, SS appliances, and custom cabinetry that opens effortlessly to the main living spaces. A cozy fireplace anchors the bright & inviting living room, while central air conditioning ensures year-round comfort. The fully finished lower level adds exceptional versatility with a spacious family room, full bath, and the potential for a fourth bedroom, guest suite, home office, or in-law living area. Set on a corner lot in an established Holliston neighborhood, this home is just minutes from Holliston Center, Goodwill Park, Lake Winthrop, the Upper Charles Rail Trail, local restaurants, shopping,

129 Marked Tree Road, Holliston

$950,000

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

$1,649,900

4 Beds ⋅ 4 Baths ⋅ 73547142 MLS

MOVE-IN READY! Close before the school year starts! Welcome to the 2nd release on Holliston’s newest 3-home cul-de-sac. Occupying the cul-de-sac's most expansive lot, this 4-bed, 3.5-bath estate is rooted in Organic Modern design, pairing wide-plank European Oak with West Elm lighting. The main level features an executive office with custom built-ins, formal dining, and a chef’s kitchen boasting a white oak island, premium quartz & GE Café appliances. The culinary center flows into a casual eating area and a grand family room anchored by a statement architectural fireplace wall. Upstairs, a luxurious primary suite offers a spa en-suite and massive walk-in closet. Engineered with zero fossil fuels: high-efficiency insulation, Bosch heat pumps & an EV-ready 3-car garage. Downstairs, a sun-drenched, unfinished full walk-out lower level offers up to ~1,300 sq ft for future expansion. Backed by Holliston’s top schools, don't miss this opportunity!

105 Bonney Drive, Holliston

$660,000

3 Beds ⋅ 2 Baths ⋅ 73546744 MLS

Welcome to this charming 3-bedroom, 2-bath Cape nestled on a beautiful 0.74-acre lot bordering the Rail Trail and just minutes from town. Filled with warmth and character, this inviting home features an eat-in kitchen that flows seamlessly into a cozy living room with fireplace, plus a dining room perfect for entertaining. A first-floor bedroom with custom built-ins and a full bath provides exceptional flexibility for guests, a home office, or convenient one-level living. Upstairs, the spacious primary bedroom offers double closets, complemented by an additional bedroom and full bath with a walk-in glass-enclosed shower. Hardwood floors add timeless appeal throughout most of the home. The walk-out basement opens to a large backyard with endless possibilities, while the oversized garage with loft storage offers versatile space for hobbies, a studio, workspace, or future expansion. With its thoughtful layout, abundant storage, and exceptional setting, this home offers a rare opportunity

73 Water St, Holliston

$650,000

3 Beds ⋅ 2 Baths ⋅ 73546582 MLS

*OPEN HOUSES CANCELED - OFFER ACCEPTED* The best of all worlds, offering the character and charm of an antique with the updates for today's modern lifestyle; all in the highly coveted and beloved Mudville neighborhood, walking distance to shops, Upper Charles Rail Trail, schools, playground, lake and cafes. Stunning kitchen features custom cabinetry, hardwood flooring, gas cooking, double oven, island, built-ins and eating area; the family room addition is open to the kitchen, with built-ins, lots of windows and a French door to the gorgeous patio and fenced backyard; 1st floor laundry; mudroom/back hallway, powder room and inviting living room complete the main level. Period staircase brings you upstairs to three bedrooms, all with hardwood flooring. Magazine worthy bathroom with radiant heated floors, soapstone countertops/custom vanity & stunning, tiled bathtub/shower. Updates: driveway, front steps (2025); roof (2014); Veismann heating system (2011); Pella windows (2011 & 2006).

79 Union Street, Holliston

$839,900

4 Beds ⋅ 4 Baths ⋅ 73544214 MLS

Slow down, breathe deep, and come home to 3.5 private acres on a scenic country road where gardens bloom, trails invite exploration, and evenings end around the fire pit beneath the stars. This 4–5 bedroom Colonial offers the perfect balance of peaceful living and everyday convenience. Inside, a flexible layout includes two potential primary suites, including a first-floor retreat with cathedral ceilings, walk-in closet/office, and private bath. Hardwood floors, granite countertops, updated cabinetry, and a welcoming family room with a high-efficiency Lopi wood insert create warmth and comfort, while the deck extends your living space outdoors. Owned solar panels produce nearly all the home's electricity, including EV charging, and agricultural zoning offers endless possibilities for gardening, hobby farming, or simply enjoying wide-open space. Competitively priced, this home is ready for your personal style to make it uniquely yours.

15 Bullard St, Holliston

$649,000

3 Beds ⋅ 2 Baths ⋅ 73541116 MLS

Discover a refined lifestyle at 58 Wedgewood, a thoughtfully designed single-family residence in Holliston, MA.on a cul de sac and a great location to garden. This home offers a harmonious blend of classic charm and comfortable living, set within an expansive 19602 square foot lot. The three bedrooms provide versatile spaces for rest and personal retreat. The primary bedroom has an ensuite bathroom and another full bathroom.Convenience and comfort are well-addressed for daily routines. You can access the Charles River Rail Trail through a private gate. Embrace the opportunity to experience this distinguished property firsthand with a tour. Close proximity to the Boston Honey Company, convenient to the highway and shopping.

58 Wedgewood Dr, Holliston

$350,000

3 Beds ⋅ 2 Baths ⋅ 73540309 MLS

***Now RANGE PRICED $350,000-375,000 - seller will consider offers in this range. Investors, Contractors & Visionaries – Don't Miss This Opportunity! Bring your imagination to this 3-bedroom, 2-full-bath home situated on a large, level lot with endless potential. This property requires a complete renovation and is the perfect project for a rehab loan or cash buyer looking to build equity. The property also features two sheds, including one with electricity, offering excellent storage, workshop, or hobby space possibilities. If you're looking for your next flip, investment property, or renovation project, this could be the opportunity you've been waiting for!

40 Maple St, Holliston

$950,000

3 Beds ⋅ 3 Baths ⋅ 73540173 MLS

New Construction! Perfectly sized single-family home completed in 2026, offering 1813 square feet of meticulously designed living space, gleaming hardwood floors throughout. Upon entrance you will be greeted with an open floor of spacious luxury living room, cozy electric fireplace that flows into an open quartz filled kitchen, waterfall island, convenient pantry, spacious dining area, half bath and an easily accessible laundry room.Through the sliders onto the beautifully paved outdoor patio,its private, peaceful and great for entertaining.The residence features three thoughtfully appointed bedrooms, providing private retreats for all occupants, the primary suite offers a large custom closet, fireplace and modern full bath. Complementing other bedrooms an additional full bath. This exceptional property is poised to provide a refined living experience. We invite you to schedule a private showing to fully appreciate its distinctive qualities of this beautiful home.

53 Louis St, Holliston

$560,000

2 Beds ⋅ 2 Baths ⋅ 73539958 MLS

Nice home in a nice neighborhood at a great price. This inviting residence offers an updated living room, comfortable bedrooms, and a layout designed for easy living. Whether you’re enjoying quiet mornings or hosting friends and family, this home adapts beautifully to your lifestyle. This used to be a 3 bedroom, but was changed to a 2 bedroom to expand the size of the primary bedroom. A room on the lower level (Den) has heat and a half bath and can easily be used as the third bedroom. Newer roof and Leaf Guard gutters, new 3 bedroom Title 5 system 6/26, exterior painted 2024 and new chimney cap 5/26. Nestled in a desirable neighborhood on one half acre with a large yard with an above ground pool, close to everyday conveniences, it’s the perfect setting to live in Holliston at a great price!

54 Shaw Farm Road, Holliston

$219,900

1 Beds ⋅ 1 Baths ⋅ 73539584 MLS ⋅ ['Crestview Condominiums'] BLDG.

Don't miss this opportunity to own this move-in ready condo in desirable Crestview Condominiums. Offering an open floor plan with a renovated kitchen, vinyl flooring throughout the main living area, newer windows, and updated appliances all less than five years old, this home has been thoughtfully maintained and improved. A recently installed heat pump system in the bedroom provides efficient year-round comfort. Step outside through the living room slider to enjoy your private balcony, the perfect spot to relax or enjoy your morning coffee. Residents enjoy access to the community swimming pool and a location that offers the perfect balance of convenience and recreation, with nearby walking and biking trails, local ponds, and Lake Winthrop. Ideally situated with easy access to major highways and commuter routes, this home also includes one off-street parking space and offers low-maintenance living in a convenient Holliston location. Schedule your showing today!

152 Turner Road Unit 38, Holliston

$959,000

4 Beds ⋅ 3 Baths ⋅ 73538157 MLS

Discover an exceptional lifestyle opportunity at 65 Woods Xing, a distinguished single-family residence that offers both the privacy of a wooded sanctuary and the desirable location of one of Holliston's most popular neighborhoods. This expansive 2898 square foot home features four well-proportioned 2nd floor bedrooms, providing ample personal space; including a master bedroom suite with two walk in closets, and large private bath. The first floor living space is a perfect blend of convenience with the open kitchen integrated with the fireplaced family room with sliders to a newly expanded deck. There is also a formal dining room and front facing living room with french doors, separate laundry utility room, and direct access to the two-car garage. The basement offers an additional 600 sq. ft. of multipurpose finished space along with a very large utility storage area. New Central AC system installed in 2024.

65 Woods Xing, Holliston

$1,875,000

5 Beds ⋅ 6 Baths ⋅ 73538100 MLS

Nestled in sought-after Cedarbrook, this exceptional 5-bed Colonial offers many updates including exterior painting, composite deck, new carpeting on upper and lower levels, and five new A/C condensers, offering exceptional living indoors and out. A two-story foyer with mahogany inlaid flooring sets the tone as you enter. Main level features elegant living and dining rooms, a great room with stone fireplace and custom built-ins, plus private home office with gas fireplace. Chef’s kitchen features Wolf gas range, double ovens, warming drawer, beverage fridge and butler’s pantry with sink and second dishwasher. Second floor offers five bedrooms including primary suite w/ a sitting room, three full baths, and convenient second-floor laundry. The finished walkout lower level with 8’ ceilings and full bath adds flexible living space. Outdoor living includes new deck overlooking saltwater pool, large front yard and farmer's porch. A truly remarkable home for everyday living and entertaining!

16 Kingsbury Dr, Holliston

$650,000

3 Beds ⋅ 2 Baths ⋅ 73537973 MLS

OFFERS DUE 6/22 @3pm. This inviting 3-bedroom, 1.5-bath split-entry home is set on a generous, nearly half-acre fenced lot, offering privacy and abundant outdoor space. The sun-filled main level features a bright living room centered around a cozy wood-burning fireplace and enhanced by a large bay window that fills the space with natural light. The formal dining area flows into the updated kitchen with direct access to a screened porch—perfect for outdoor dining, entertaining, or relaxing. The lower level offers valuable additional living space with a spacious family room, half bath, utility/laundry area, and direct access to the attached 2-car garage. Thoughtfully designed for comfortable everyday living and effortless entertaining, this home delivers a versatile layout and exceptional indoor-outdoor appeal. Updates include 2025 HVAC, 2026 Dishwasher, 2020 Tankless Water Heater among other improvements throughout the house. Don't miss this gem in a sought-after neighborhood!

31 Robert Rd, Holliston

$1,399,000

4 Beds ⋅ 5 Baths ⋅ 73537793 MLS

Elegance, sophistication and modernity have a specific address. This beautiful property is ready to move in. Open-concept main level offers abundant natural light. The kitchen features white cabinetry, double edge island, and quartz countertops, opening to spacious living and dining area. The slider door goes to a deck and a private patio for gathering and barbecue. Second level has a large master bedroom with a walk-in closet, beautiful bath with a bathtub and balcony overlooking the calm backyard and where you can enjoy the sunset. Two great sizes bedrooms with Jack and Jill bath. Convenient laundry room with sink and cabinets. House offers two fireplaces. There is one bedroom with a full bath on the first floor to serve as a home office or guest space. A 2-car attached garage with EV charging. Finished basement with a full bathroom offers a great potential for a games room, TV and entertainment. Come to check it out. Open House July 11 from 11am to 12:30pm.

1172 Washington St, Holliston

$1,325,000

4 Beds ⋅ 4 Baths ⋅ 73537764 MLS

Nestled on a cul-de sac in one of Holliston's most sought-after neighborhoods, this beautiful Colonial offers an exceptional blend of elegance, comfort, and everyday livability. The spacious kitchen is the heart of the home and serves as a natural gathering place, featuring freshly painted cabinetry, premium appliances, wine cooler, center island, and dining area which flows seamlessly into the inviting step-down family room + oversized three-season porch, creating the perfect setting for entertaining or relaxing while overlooking the private backyard. Newly installed and refinished hardwood floors add warmth and sophistication throughout. A dedicated first-floor office and additional living room. Upstairs, the spacious primary suite features an updated spa-inspired bath and 2 walk in closets, complemented by three additional bedrooms and second-floor laundry. Finished lower level offers exceptional flexibility with space for a media room, game room, exercise area, or hobbies.

45 Johnson Dr, Holliston

$1,389,000

4 Beds ⋅ 3 Baths ⋅ 73537618 MLS

This exceptional brick-front colonial's true distinction begins with its perfect positioning on one of the finest lots in this premiere Holliston neighborhood. An immediate impression of quality and care is felt as you enter this meticulously maintained and thoughtfully updated home offering a seamless blend of refined finishes + inviting living spaces. The floor plan flows effortlessly to outstanding outdoor living, with a new 3 season porch overlooking an oversized patio + heated, saltwater inground pool w/private backyard-ideal for summer gatherings or quiet evenings. Gourmet kitchen with commercial-grade appliances and sun-filled, step-down family room anchored by a center fireplace. Dedicated first-floor office provides an ideal work-from-home space. Convenient first-floor laundry and mudroom. Upstairs a luxurious primary suite is a private retreat w/a beautifully remodeled spa-inspired bath + impressive walk-in dressing room. Finished lower level for more flexible living space.

15 Saddle Ridge Rd., Holliston

$799,900

4 Beds ⋅ 3 Baths ⋅ 73537058 MLS

Fall in love with this meticulously enhanced 4-bed, 2.5-bath Colonial nestled in a Holliston neighborhood, showcasing extensive upgrades and inviting living spaces. Nearly every major feature has been improved: 2024 roof, gutter guards & A/C; 2023 hardwoods, stairs, front steps, septic; 2022 primary bath; 2021 half bath; 2018 full bath + siding; 2017 windows—too many updates to list; see attached update sheet for the full list. The oversized granite eat-in kitchen opens to a spacious family room with gas stove, creating the perfect hub for daily living. A dining room with French doors leads to a screened porch overlooking perennial gardens. A front-to-back living room with brick fireplace offers another inviting gathering space. Upstairs, the refreshed primary suite features a custom tiled shower, plus three additional bedrooms and an updated full bath. Full basement for future expansion. Two-car garage with newer automatic doors. Minutes to 495. Nothing to do but move in. Welcome Home

23 Bonney Drive, Holliston

$1,399,000

4 Beds ⋅ 4 Baths ⋅ 73532141 MLS

Step into 120 Mohawk Path in Holliston, a charming and versatile home in a peaceful, highly desirable neighborhood offering comfort, privacy, and convenience. This inviting residence features a bright, functional layout with spacious living areas designed for everyday living and entertaining. The kitchen offers ample cabinetry and workspace, opening to comfortable dining and living areas filled with natural light. The fully finished basement is a standout feature, adding exceptional living space with a family room, home gym, bar area, and a dedicated project/work space—perfect for entertaining, hobbies, or relaxing. Bedrooms are well-sized with generous closets, and bathrooms are thoughtfully designed for everyday ease. Outside, enjoy a private setting with space for outdoor enjoyment, gardening, or future enhancements. Conveniently located near top-rated schools, shopping, dining, parks, and commuter routes, this home offers the perfect blend of small-town charm and modern convenience

120 Mohawk Path, Holliston

$1,185,000

4 Beds ⋅ 4 Baths ⋅ 73530442 MLS

Enjoy country club living from the comfort of home in this stately 4-bedroom Colonial ideally situated on a quiet cul-de-sac. The beautifully landscaped grounds feature a level yard, resort-style pool area, spacious deck, and screened porch, creating the perfect setting for outdoor entertaining and relaxation. Inside, you'll find classic architecture. Highlights include: a spacious foyer, home office w/ French doors, fireplace & built-ins; formal living room w/ fireplace; elegant DR w/ fireplace & sliders leading to the screened porch.The beautifully updated kitchen showcases a large center island with quartz waterfall countertop, high-end appliances, and plenty of cabinetry. A large family room with wood-burning stove offers comfortable everyday living. 4 generously sized bedrooms occupy the 2nd floor. Lower level features TV room/ playroom, extensive unfinished space & oversized 2 car garage. Whole house generator provides peace of mind. Close town trails. An exceptional offering!

10 Winston Rd., Holliston

$619,900

3 Beds ⋅ 2 Baths ⋅ 73525575 MLS

Stunning Georgian split entry home. Inside you're greeted with bright HW floors and an open concept LR/DR to Kitchen. Kitchen has been tastefully remodeled w/white cabinetry,tiled floor,sink,New appliances and corian countertops. Off the kitchen is the Oversized deck, great for weekend get togethers or evening dinners. Back in and down the hall there is a coat closet/utility storage and 3 generously sized bedrooms. A fully remodeled bathroom with marble floor, new vanity, toilet and tiled shower. All upper floor windows have been replaced. Down to the lower level, featuring a tiled family room with wood stove, a laundry in half bath, and a freshly carpeted office/walk in closet bonus space. This level has access to your two car garage with work bench and extra storage. Exit door to the covered patio and fenced in yard with beautiful flowering gardens. Quiet lot, Great Commuter location,easy access to Upper Charles bike path and minutes to rts 495,109,16 and 85.

1 Fisher Street, Holliston

$950,000

4 Beds ⋅ 3 Baths ⋅ 73524755 MLS

This beautifully refreshed 4-bedroom, 2.5-bath Colonial blends timeless charm with tasteful modern updates throughout. Fresh interior paint enhances the bright and welcoming atmosphere, while the sun-filled first floor showcases gleaming hardwood flooring and durable tile in the kitchen for both style and easy maintenance. Spacious living and dining areas create an ideal flow for comfortable everyday living and effortless entertaining. Upstairs, you’ll find four generously sized bedrooms, including a serene primary suite featuring a tiled en suite shower. The basement provides valuable bonus space perfect for a home gym, playroom, media room, or additional storage. Step outside to your private backyard retreat complete with an inviting in-ground pool featuring a brand new liner, motor, and valve, perfect for relaxing and summer gatherings. Located in an established neighborhood this home offers access to a lake area and basketball court. Close to area amenities and highway access.

157 Rolling Meadow Dr, Holliston

$1,795,000

5 Beds ⋅ 5 Baths ⋅ 73518090 MLS

Set within one of Holliston’s most desirable neighborhoods, this exceptional custom Colonial offers 4,760 sq ft of upscale design & architectural detail throughout. Sun filled white kitchen w/ quartz countertops, oversized island, pantry & spacious dining area w/ sliders leading to deck overlooking the private backyard. Stunning LR w/ coffered ceiling, fireplace & dramatic wall of windows. Glass panel doors lead to a private sitting room. Mudroom w/ custom cubbies & half bath off the 3 car garage. The 2nd level showcases a luxurious primary retreat w/ tray ceiling, sitting area, dual walk in closets including oversized dressing room & spa inspired bath w/ soaking tub. A second private ensuite bdrm plus two additional bedrooms connected by Jack & Jill bath. Convenient 2nd floor laundry. Finished 3rd floor w/ full bath offers ideal space for guest suite or fitness room. Walkout lower level ready for future expansion. Patio w/ fire pit & outdoor setting complete this stunning residence.

39 Summit Pointe Drive, Holliston

$729,900

4 Beds ⋅ 2 Baths ⋅ 73521079 MLS

Welcome to this well-maintained and updated Colonial in one of Holliston’s most popular neighborhoods. The main level offers a gracious foyer with an imported sandstone floor and contemporary European-style propane fireplace for a warm welcome. The spacious formal dining room serves the new kitchen featuring radiant heat flooring, beautiful cabinetry, stainless appliances, granite countertops and an eat in area. The comfortable family room adjacent opens to a patio piped for a gas grill and large landscaped backyard. Pantry, laundry and a half bath round out this main floor. Step up into the large sun filled living room with a beautiful array of built-ins, then up to 4 generously sized bedrooms - the primary with double closets and a full bath with on demand heat off the hallway. Behind the scenes is updated 200 amp service and owned solar panels. Privately located deep in this pretty neighborhood, with a choice of T stations, shopping, restaurants and great schools.

57 Wingate Rd, Holliston

$1,250,000

4 Beds ⋅ 5 Baths ⋅ 73519732 MLS

Sited at the end of a lovely cul-de-sac, enveloped by nature and conservation, offering complete privacy, this gracious home is tucked into a private neighborhood of exclusive homes. Sunny, two-story foyer with marble flooring; 10' ceilings on 1st floor; lovely living room with HW floors; dramatic two story family room with a floor to ceiling fireplace, custom built-ins and back staircase; skylit kitchen w/Thermador double oven, gas cooktop, granite counters and sunny eating area; butler's pantry w/custom cabinetry plus a 2nd pantry; spacious home office with French doors and custom cabinetry; stunning dining room w/tray ceiling, crown molding and beautiful windows; mudroom and two powder rooms complete the main level. Second level features a lovely primary suite with a vaulted ceiling, two walk-in closets, spa bathroom w/double vanity, jacuzzi & large shower; three additional bedrooms (one ensuite) are spacious and offer generous closet space. Walkout basement ideal for finishing.

10 Timber Ledge Drive, Holliston

$215,000

1 Beds ⋅ 1 Baths ⋅ 73519536 MLS ⋅ ['Crestview Condominiums'] BLDG.

Welcome to this surprisingly spacious one-bedroom condo in Crestview Condominiums! This sunny first-floor unit features a generous living/dining area, a kitchen with ample cabinetry and counter space, plus coat and utility closets. Two heat/AC pumps provide year-round comfort. The large bedroom offers a walk-in closet and sits next to a large bathroom with a linen closet. Enjoy abundant parking, a swimming pool, and nearby recreation including Lake Winthrop and Ashland State Park. Conveniently located near shopping, Routes 126 and 16, and the Framingham commuter rail, all within a quiet Holliston neighborhood known for top-rated schools. Ideally located near the parking lot and side entrance, this home is perfect for first-time buyers, downsizers, or investors. Laundry and mail rooms are just down the hall!

147 Turner Rd Unit 73, Holliston

$675,000

3 Beds ⋅ 2 Baths ⋅ 73518705 MLS

Feel instantly at home in this charming Storybook-style 3-bedroom, 2 full bath Cape, where thoughtful updates come together beautifully. Nestled on a picturesque lot surrounded by lush perennial gardens, the property offers an escape into nature. Inside, the heart of the home is the stunning kitchen, featuring stylish finishes, and opens seamlessly into the spacious dining room. The fireside living room is filled with natural light from a beautiful picture window, a flexible first-floor bedroom, ideal as a guest room, home office, or den, sits adjacent to an updated full bath, all completing the main level. Upstairs, you’ll find two generous front-to-back bedrooms with charming Cape-style character, along with a second updated full bath. Gleaming wood flooring extends throughout both levels. Additional highlights include a welcoming screened-in porch, an expanded deck for easy entertaining, ample storage in the unfinished basement and easy access to the 1-car garage. Come see!

135 Locust St, Holliston

$849,900

3 Beds ⋅ 2 Baths ⋅ 73518536 MLS

This stunning contemporary home at 65 Briarcliff Lane offers the perfect blend of style, comfort, and flow. Featuring 3 spacious bedrooms and 2 renovated full bathrooms, this beautifully maintained property showcases gleaming hardwood floors throughout and an inviting open concept designed for modern living. The updated kitchen is a true centerpiece, offering beautiful finishes, custom cabinetry, and great functionality for both everyday living and entertaining. The sun-filled living areas flow seamlessly, creating a warm and welcoming space. Downstairs, the finished basement includes a dedicated office space perfect for remote work, a home gym, or additional living area. Set on a picturesque lot in a wonderful neighborhood this home combines contemporary charm with everyday convenience. **NEW ROOF July 2026** Don't miss this turnkey opportunity!

65 Briarcliff Ln, Holliston

$249,900

73517865 MLS

Hard to find 8+Acre Lot with approved septic design and order of conditions.

Parcel D Prentice Street, Holliston

$725,000

3 Beds ⋅ 3 Baths ⋅ 73517320 MLS

Effortless living in this like-new 3BR 2.5BA, attached single family, 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, but very young home! Prime location near downtown Holliston & Stoddard Park, blending luxury, comfort & convenience. Do not miss this great home!

228 Norfolk St Unit 228, Holliston

$850,000

3 Beds ⋅ 4 Baths ⋅ 73517201 MLS

Welcome to your completely furnished brand new home, just one short year from new and endless upgrades make this a home not to be missed with no condo fees or HOAs !! The moment you walk into the open living room and dining area with a truly gourmet kitchen and upgraded stainless steel appliances you will realize you are home. The second floor features three bedrooms each with a private or adjoining bath, A spacious primary suite awaits with a large walk in closet ,spacious bath room with double sinks, tiled shower and soaking tub . Basement is fully finished for playroom , gym or additional office. Private backyard and deck add exterior value to this timeless home. Recent build to the latest energy code offers you energy efficiencies not found in todays market.

615 Norfolk St, Holliston

$950,000

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

$725,000

3 Beds ⋅ 3 Baths ⋅ 73510333 MLS ⋅ ['228-230 Norfolk Street Holliston Condo'] BLDG.

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!

228 Norfolk St Unit 228, Holliston

$2,375,000

5 Beds ⋅ 5 Baths ⋅ 73484458 MLS

** 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 ~ 10 Feet Iron Grey Island ~ 5 Inches Oak Hardwoods ~ Coffered & Tray & Cathedral Ceilings ~ Walk Up Attic ~ Dual Staircases ~ Quartz Countertops ~ 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

Lot 8 Pond View, Holliston

$1,600,000

4 Beds ⋅ 5 Baths ⋅ 73483639 MLS

LUXE New Construction! Exceptional 4BR, 5BA custom home offering 4,600+ SF of STUNNING living space on a private wooded lot just under 2 acres. Gorgeously designed w/three finished levels, including a walk-up 3rd floor w/additional family room & flexible living space. Gather your family around the Incredible chef's kitchen with Custom Espresso Cabinetry & 8' Center Isle, gas cooktop, Wall oven & Quartz counters! Step outside thru your french door to a 20 x 20 Paver patio Luxurious primary suite with soaring ceilings, custom walk-in closet, & spa-like bath with soaking tub, glass-enclosed tile shower, Dual vanity w/quartz, & private water closet. Guest bedrooms offer private en suite bathes. First-floor home office with full bath plus second floor office option or exercise room. Hardwood floors, coffered ceiling crown molding, 9’ ceilings, & 2nd floor laundry. Walk-out basement, 3-car garage, welcoming front porch, & 20x20 stone patio & you will love to call this home!

615 Mayflower Landing, Holliston

$2,350,000

5 Beds ⋅ 5 Baths ⋅ 73480548 MLS

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.

14 Fiske Pond Road, Holliston

$875,000

73477032 MLS

A rare opportunity to build your dream home on a picturesque one-acre lot, already featuring a recently constructed 1,675 sq. ft. two-car garage with a spacious loft and a heated half bath. Enjoy serene views of a neighboring pond and a beautiful pastoral landscape, offering both privacy and charm. This scenic setting is perfectly balanced with convenience, located close to town and near the Hopkinton line. Less than a mile from the Mass Audubon Wildlife Sanctuary, Pinecrest Golf Club, and local farm markets, and just over a mile from the highly rated Holliston High School, this exceptional property offers the best of country living with easy access to amenities. Plot being sold is Lot One as shown on Plan of Land recorded with the Middlesex South Registry of Deeds as Plan No. 538 of 2022 which lot contains 43,650 square feet of land as shown on said Plan.

147 N Mill Street, Holliston

$1,075,000

4 Beds ⋅ 3 Baths ⋅ 73456867 MLS

Immaculately cared for in every way, this gracious home sited on a lovely private lot makes it an easy choice. From the moment you step in to the two-story foyer, the high ceilings throughout and the open floor plan welcome you home. Stunning kitchen with solid cherry cabinetry, stone countertops, gas cooktop, large center island; dramatic family room w/gas fireplace and soaring ceiling; lovely dining and living rooms w/crown molding; home office w/French doors & access to a full bathroom; hardwood flooring throughout the first floor. Primary bedroom with tray ceiling and updated bathroom; 3 more generously sized bedrooms, laundry room and guest bath with double vanity complete the second level. Finished lower level with rec room and exercise areas. The grounds include a bluestone patio w/stone fireplace, custom designed inground pool, koi pond, privacy fencing and a putting green! Updates include carpeting, HVAC systems, irrigation, large screened room, Pella windows, roof and more.

140 Goulding St., Holliston

$429,900

73450133 MLS

Beautiful 5.76-acre parcel located in a scenic setting directly adjacent to the Holliston Rail Trail and Wenakeening Woods comprising 40 acres of conservation land with trails and a lake. A building permit is in hand for a 3,000+/- sq ft home with 5 bedrooms, plus an approved septic plan. Significant site improvements include clearing and rough grading for the house location area, plus access to the lot from the street. The land being conveyed consists of two parcels described as Parcel 1 (Lot 1A) which contains 3.76 +/- acres and Parcel 2 containing 2 +/- acres. Enjoy a convenient location near shopping, major routes and Holliston's picturesque town center. This is a great opportunity for anyone looking to build their dream home on a beautiful private lot.

1366 Washington Street, Holliston

$350,000

73444417 MLS

9+ Acre Parcel in Holliston, MA – Endless Possibilities.Discover the perfect opportunity to own over 9 acres of beautiful, versatile land in the highly sought-after town of Holliston. Nestled in a quiet, scenic setting with mature trees and natural landscapes, this expansive parcel offers the ideal canvas for your vision—whether it's a private estate, equestrian retreat, or potential development (buyer to perform due diligence). This rare offering combines privacy and convenience, located just minutes from top-rated schools, charming downtown shops, dining, and major commuting routes. Enjoy the peace of the countryside with easy access to everything Holliston and the greater MetroWest area have to offer. Zoned for residential use with ample frontage and flexible site options, this property presents a unique investment in both lifestyle and value. Don’t miss your chance to create something truly special in one of Massachusetts’ most desirable communities.

Hill St, Holliston

$400,000

73431673 MLS

This four acre parcel on a beautiful country road could be your next address. Approved and stamped mylar ANR plan in hand. See attached conceptual drawing with a five bedroom house, a swimming pool and a one bedroom auxiliary dwelling. Use this idea or bring your own. Current plan has a short cul-de-sac, but owner will go for a variance to change to driveway, which the town has sounded open to. Beautiful parcel. Sliver of land owned by another goes along Alpine Road, so no access/driveway there without purchasing from them Unknown as to price for said piece, nor willingness to sell. As it stands now, it is one legal lot. Paperwork with attorney who is registering land at the registry, but it's not yet done. We expect the lot to be flagged in September. Please do not walk without permission as their are dogs on adjacent property who also walk on this land.

Lot 2 Hanlon Road, 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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