Waterfront homes for sale & real estate in Holliston, MA

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OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
More than a home—this private retreat offers exceptional space for living, working and entertaining! Sited down a long private drive off a cul-de-sac neighborhood, this spacious 4-bedroom Colonial enjoys a wonderfully private setting while remaining convenient to Holliston Town Center and major commuting routes. The home features updated kitchen and baths, 4 full baths, gas heat and central air. A large, thoughtfully designed laundry room features custom built-ins and convenient access from both the mudroom and the outside deck—an especially practical feature for everyday living and summer days by the pool. The finished lower level provides terrific versatility with a kitchen ar

$1,250,000

4 beds4.5 baths3,509 sq ft

57 Carl Rd, Holliston, MA 01746

Sun porch • Custom built-ins • Updated kitchen

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
This beautifully updated 4-bedroom, 3.5-bathroom home perfectly pairs eco-friendly efficiency with a bright, versatile architectural layout. Situated on a premier, private lot backing to conservation land, the property offers a peaceful retreat just moments from the heart of Holliston. The sun-drenched interior features generous proportions, providing flexible living spaces and dedicated home office options. A renovated kitchen flows seamlessly into a striking great room defined by cathedral ceilings, exposed beams, and an expansive picture window - an incredible layout built for entertaining. The lower level further enhances the home's versatility, introducing a bonus space and a full bath

$899,995

4 beds3.5 baths2,640 sq ft

543 Central St, Holliston, MA 01746

Private lot • Cathedral ceilings • Renovated kitchen

FLOOR PLAN

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
Wow! Spectacular sweeping East-facing views and exceptional craftsmanship define this one-of-a-kind custom home in the coveted Highlands at Holliston. Beautifully sited on over an acre above Old Cart Path, this stunning residence offers three levels of luxurious living and extraordinary spaces for both everyday living and entertaining. A welcoming farmer’s porch opens to a grand two-story foyer with brilliant hardwood floors and custom millwork. The expansive main level features a dramatic two-story family room with coffered ceiling, an enormous gourmet kitchen with custom cabinetry, center island and walk-in pantry, plus an exceptional media room with movie screen and projector. A gr

$1,575,000

4 beds5 baths5,997 sq ft

97 Old Cart Path, Holliston, MA 01746

Gourmet kitchen • Custom millwork • Farmer's porch

OPEN SUN, 11AM TO 1PMFLOOR PLAN

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
NEW PRICE! HOLLISTON's Favorite BRENTWOOD NEIGHBORHOOD! Lovingly maintained Raised Ranch built in 1964 with 1933 SF of living space. Foyer recently painted also has a Ceiling Fan, Sunny Formal Dining Room with Hardwood Floors, leads to an amazing Kitchen with wood floors, Maple Cabinets, Dual Fuel Double Oven, Ceramic Tile Back Splash, Skylight, 5 Burner Cook Top, Quartize Countertops which were done in 2024, Kitchen Appliances will stay new in 2020, Wall to Wall Carpet in Spacious Family Room, Three Bedrooms all with Hardwood Floors, One Car Garage, Screened Porch, Shed, Back Yard Play Area (w Rubber Mulch) 2021, plus many Recent Updates including Interior Painting 2025, 2026, C/A added

$639,000

3 beds1.5 baths1,933 sq ft

35 Jerrold St, Holliston, MA 01746

Ceiling fan • Formal dining room • Raised ranch

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
Discover refined condominium living at 152 Turner Rd U:57, Holliston, MA. Constructed in 1967, this 705 square foot residence offers a sophisticated urban retreat. This third-floor condominium, situated within a three-story building, provides an elevated perspective. The residence thoughtfully includes one bedroom, designed to offer a private and comfortable space. Complementing this, one full bathroom provides essential convenience and functionality. This property presents a compelling opportunity for discerning buyers seeking a well-appointed home. Just across the way is a freshing a fabulous inground pool. call broker to show, Don't miss out

$219,900

1 bed1 bath705 sq ft

152 Turner Rd #57, Holliston, MA 01746

Inground pool • $620 HOA • 2 parking spots

Property at 25 Erin Way, Holliston, MA 01746, 5 beds, 3.5 baths

$1,249,000

5 beds3.5 baths4,969 sq ft

25 Erin Way, Holliston, MA 01746

Property at 85 Fisher St, Holliston, MA 01746, 3 beds, 2.5 baths

$999,000

3 beds2.5 baths2,266 sq ft

85 Fisher St, Holliston, MA 01746

Property at 865 Washington St, Holliston, MA 01746, 6 beds, 3.5 baths

$899,900

6 beds3.5 baths3,466 sq ft

865 Washington St, Holliston, MA 01746

Property at 228 Norfolk St #228, Holliston, MA 01746, 3 beds, 2.5 baths

$700,000

3 beds2.5 baths1,936 sq ft

228 Norfolk St #228, Holliston, MA 01746

Property at 615 Norfolk St, Holliston, MA 01746, 3 beds, 3.5 baths

$825,000

3 beds3.5 baths2,600 sq ft

615 Norfolk St, Holliston, MA 01746

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OPEN SAT, 2PM TO 4PMVIDEO TOUR

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
Welcome home to effortless one-level living in one of Ashland’s most desirable 55+ locations. This pristine free-standing home offers 1690 SF and sits on a premium lot backing up to peaceful conservation land (Ashland State Park), offering the perfect blend of privacy and convenience. Located just minutes from the commuter rail, Reservoir Beach, and the community center, this turnkey property checks every single box. Step inside to a bright, airy floor plan highlighted by high ceilings, gorgeous palladian windows and beautiful hardwood floors. The heart of the home is an expansive 24x13 eat-in kitchen featuring durable Corian countertops, abundant cabinet space, updated appliances and

$669,000

2 beds2 baths1,690 sq ft

41 Haven Way #41, Ashland, MA 01721

Corian countertops • Eat in kitchen • Premium lot

OPEN SAT, 12:30PM TO 2:30PM

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
Fabulous opportunity in Ashland, MA! This home offers luxury finishes far beyond its price. Renovated gourmet kitchen features a chef’s dream: 48" Thermador dual-fuel range (gas cooktop/electric double ovens), paneled hood, quartz counters, and a massive 9ft+ island with seating & storage. Enjoy year-round comfort with updated HVAC (heating & cooling). The practical mudroom has built-ins and sliders leading to a private deck and an above-ground pool with solar cover and fenced backyard—perfect for entertaining! Main level boasts hardwood flooring in all three bedrooms, plus an upgraded full bathroom and stylish new interior doors. Lower level living shines with

$649,900

3 beds2 baths1,567 sq ft

29 Prospect St, Ashland, MA 01721

Private deck • Gourmet kitchen • Massive 9ft island

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
Beautiful end unit lovingly maintained by the original owner. Large airy rooms with an open floor plan. The kitchen features warm wooden cabinety and a Corian counter top with a space for casual dining. The dining room is perfect for entertaining and is open to the large living room with its vaulted ceilings, two skylights, a lighted fan and a slider to the private side yard. The large bedroom has a great walk-in closet with access to the attic, three windows and wall to wall carpeting. The full bath has tile flooring, an oversized shower and a double vanity with a Corian top. On the second level there is a large loft and a full bath. It would be perfect as a family room, office or a guest

$539,000

1 bed2.5 baths1,530 sq ft

1 Haven Way #1, Ashland, MA 01721

Double vanity • Open floor plan • Walk-in closet

OPEN SAT, 1PM TO 2PM

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
BUYERS TAKE NOTICE—5 South Main Street—a unique Sherborn property at an incredible price! Admired by all who pass by, this eye-catching, charming, expanded and renovated Cape with views of mature trees from every window also includes a 3-story antique BARN adding to it’s appeal. As part of Leland Farms, an ALL AGES townhouse development in the heart of downtown Sherborn, this turn-key property delivers all the convenience of MAINTENANCE FREE living while looking and feeling entirely like a standalone single-family home. Sun-filled and move-in ready, the home spans three levels with versatile, multi-functional spaces to suit a variety of lifestyle. Warm hardwood floors flow

$799,000

3 beds2.5 baths2,238 sq ft

5 South Main St #17, Sherborn, MA 01770

Central a c • 3 story antique barn • $809 HOA

OPEN SAT, 1PM TO 2PM

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
BUYERS TAKE NOTICE—5 South Main Street—a unique Sherborn property at an incredible price! Admired by all who pass by, this eye-catching, charming, expanded and renovated Cape with views of mature trees from every window also includes a 3-story antique BARN adding to it’s appeal. As part of Leland Farms, an ALL AGES townhouse development in the heart of downtown Sherborn, this turn-key property delivers all the convenience of MAINTENANCE FREE living while looking and feeling entirely like a standalone single-family home. Sun-filled and move-in ready, the home spans three levels with versatile, multi-functional spaces to suit a variety of lifestyle. Warm hardwood floors flow

$799,000

3 beds2.5 baths2,238 sq ft

5 South Main St, Sherborn, MA 01770

Central a c • 3 story antique barn • 6 parking spots

ABOUT THIS HOME
Waterfront Home for sale in Holliston, MA:
Dating to circa 1750, historic “Long Acres Farm” is one of Sherborn’s most distinctive antique residences, beautifully reimagined through extensive renovations and expansion. The home has evolved over nearly three centuries, blending its early New England character with a fresh, casual California-inspired aesthetic designed for modern living. A comprehensive renovation thoughtfully updated virtually every room while preserving the architectural details and sense of history that make the property so special. At the heart of the home is a dramatically expanded and completely redesigned kitchen featuring custom cabinetry, gas cooking, generous workspace and a full walk-in pan

$2,295,000

5 beds4 baths6,000 sq ft

6 Curve St, Sherborn, MA 01770

Full walk-in pantry • Renovated bathrooms • Outdoor deck

Property at 53 Green Ln, Sherborn, MA 01770, 4 beds, 3.5 baths

$1,700,000

4 beds3.5 baths4,650 sq ft

53 Green Ln, Sherborn, MA 01770

Property at 23 Oak St, Medway, MA 02053, 4 beds, 2.5 baths

$824,900

4 beds2.5 baths2,712 sq ft

23 Oak St, Medway, MA 02053

Property at Lot 8 Emerald Dr, Hopkinton, MA 01748, 5 beds, 5.5 baths

$2,100,000

5 beds5.5 baths5,248 sq ft

Lot 8 Emerald Dr, Hopkinton, MA 01748

Property at 10 Pond View Ln, Ashland, MA 01721, 6 beds, 5.5 baths

$1,495,000

6 beds5.5 baths4,924 sq ft

10 Pond View Ln, Ashland, MA 01721

Property at 145 Nason Hill Rd, Sherborn, MA 01770, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths3,605 sq ft

145 Nason Hill Rd, Sherborn, MA 01770

Property at 12 Walcott Valley Dr #12, Hopkinton, MA 01748, 2 beds, 1.5 baths

$439,900

2 beds1.5 baths1,600 sq ft

12 Walcott Valley Dr #12, Hopkinton, MA 01748

Property at 8 Washington St, Sherborn, MA 01770, 5 beds, 5 baths

$1,998,000

5 beds5 baths5,656 sq ft

8 Washington St, Sherborn, MA 01770

Property at 320 Western Ave, Sherborn, MA 01770, 4 beds, 2.5 baths

$1,395,000

4 beds2.5 baths3,076 sq ft

320 Western Ave, Sherborn, MA 01770

Property at 49 Walnut Way #49, Hopkinton, MA 01748, 3 beds, 2.5 baths

$825,000

3 beds2.5 baths1,812 sq ft

49 Walnut Way #49, Hopkinton, MA 01748

Property at 26 Southfield Ln #26, Sherborn, MA 01770, 2 beds, 2.5 baths

$859,000

2 beds2.5 baths2,410 sq ft

26 Southfield Ln #26, Sherborn, MA 01770

Property at 28 S Mill St, Hopkinton, MA 01748, 5 beds, 3 baths

$1,495,000

5 beds3 baths4,873 sq ft

28 S Mill St, Hopkinton, MA 01748

Property at 13 Davenport Ln #13, Hopkinton, MA 01748, 3 beds, 4 baths

$1,775,000

3 beds4 baths5,096 sq ft

13 Davenport Ln #13, Hopkinton, MA 01748

Property at 147 Washington Street Lot 2, Sherborn, MA 01770

$719,000

Land3.52 acres (lot)

147 Washington Street Lot 2, Sherborn, MA 01770

Property at 14 Sewall Brook Ln, Sherborn, MA 01770

$1,295,000

Land18.67 acres (lot)

14 Sewall Brook Ln, Sherborn, MA 01770

Waterfront Homes for Sale in Holliston

There are currently 10 waterfront homes for sale in Holliston at a median listing price of $800K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Holliston stay on the market for 32 days and receive 1 offers. This map is refreshed with the newest listings in Holliston every 15 minutes.

In the past month, 14 homes have been sold in Holliston. In addition to houses in Holliston, there was also 1 condo, 1 townhouse, and 1 multi-family unit for sale in Holliston last month. Find your dream home in Holliston using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Holliston are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Holliston. Our Holliston real estate stats and trends will give you more information about home buying and selling trends in Holliston. If you're looking to sell your home in the Holliston area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Holliston with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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