Luxury homes for sale & real estate in Holliston, MA

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ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
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 roo

$1,199,900

4 beds3 baths4,130 sq ft

140 Goulding St, Holliston, MA 01746

Game recreation room • Gorgeous kitchen • Inground pool

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
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 bedr

$1,565,000

4 beds3.5 baths4,643 sq ft

151 Mohawk Path, Holliston, MA 01746

Coffered ceilings • Sunlit solarium • Raised garden beds

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
Nestled in a serene country setting, this impeccably maintained detached home is located in the highly sought-after 55+ community of Hollis Hills Preserve. Designed for comfort and easy living, the home features a spacious open-concept layout combining the kitchen, dining, and living areas—ideal for both everyday living and entertaining. You'll find two generously sized bedrooms, 2.5 bathrooms, two dedicated home offices, and a cozy family room on the second floor, offering flexibility and ample space for work or guests. Enjoy the peace and privacy of this quiet location, all while being just minutes from the charm and convenience of Holliston Center.

$925,000

2 beds2.5 baths2,384 sq ft

43 Bittersweet Cir #43, Holliston, MA 01746

Quiet location • Open-concept layout • $588 HOA

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
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

$1,599,900

4 beds3.5 baths3,469 sq ft

110 Bonney Dr, Holliston, MA 01746

Gourmet kitchen • Private cul-de-sac • Spacious family room

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
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 steam shower, walk in closet, office & access to private azek deck, gorgeous chef's kitchen w/ 11.5 ft island for cooking & entertaining, formal dining room, living/music room, warm & inviting family room w/ stunning stone fireplace w/ French doors leading to patio, spacious

$2,075,000

5 beds4.5 baths5,737 sq ft

45 Wendy Ln, Holliston, MA 01746

Walk-in steam shower • Primary suite • Custom shingle home

Property at Lot 8 Pond Vw, Holliston, MA 01746, 5 beds, 4.5 baths

$2,250,000

5 beds4.5 baths4,959 sq ft

Lot 8 Pond Vw, Holliston, MA 01746

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NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
WELCOME HOME to EMERSON PLACE & The Stunning To-Be-Built Contemporary WILLOW MODEL. Designed for Modern Living, This Home Features a Desirable FIRST FLOOR PRIMARY SUITE with Private Bath, Double Vanity & Tiled Shower. Main Level Offers an Open Concept Floorplan with 9’ Ceilings, Spacious Kitchen with Custom Cabinetry, Quartz Countertops, and Center Island with Pendant Lighting, Opening into Large Family Room with Hardwood Floors & Custom Fireplace! Plus Added Convenience of First-Floor Laundry. Upstairs Includes Two Generously Sized Bedrooms with Ample Closet Space & Full Main Bath. Buyers Also Have The Option To Convert This Level Into a Second Primary Bedroom

$1,200,000

3 beds2.5 baths2,620 sq ft

10 April Way, Millis, MA 02054

Custom cabinetry • Quartz countertops • Spacious kitchen

OPEN DEC 6, 11AM TO 1PM

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
Nestled in a quiet, tranquil Medway neighborhood, this 4-year-old Colonial offers modern comfort and thoughtful design throughout. With approximately 2,950 sq. ft. of living space above/below ground, the home features soaring 9-ft ceilings, an attached 2-car garage, and a beautifully crafted private patio that opens to a new 10-person hot tub—perfect for relaxing or entertaining! Inside, enjoy cozy evenings by the charming gas fireplace and efficient propane heat, along with central air to keep summers cool. The stunning kitchen boasts a farmhouse sink, double oven, large island, and an open floor plan flowing seamlessly into the living room, making it an entertainer’s dream! So

$899,000

3 beds2.5 baths2,950 sq ft

78-A Fisher St, Medway, MA 02053

Gas fireplace • Private patio • Farmhouse sink

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
Quality Lobisser built new construction home on private, wooded 1.7 acre lot. A rare find in Hopkinton! The spectacular kitchen was designed for serious cooking and serious entertaining. The spacious kitchen, and family room ( with fireplace) includes a stunning glass surround dining area. There is a paneled first floor office with french doors PLUS a first floor guest bedroom with attached full bath. Large mudroom with many built in storage option leads to attached three car garage. Four additional bedrooms, three more full baths, plus a laundry room ( with utility sink) complete the second floor. The primary suite includes four closets, lavish bath, window seat, plus a sitting area. A l

$2,179,000

5 beds5 baths4,836 sq ft

11 N Mill St, Hopkinton, MA 01748

Spectacular kitchen • Large mudroom • Private wooded lot

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
WELCOME HOME TO EMERSON PLACE & This Beautiful Contemporary SPRINGVIEW Model - Already Up & Ready For a Quick Closing! First Floor Layout Features a Modern Open Floorplan with 9' Ft Ceilings - Spacious Kitchen with Custom Cabinetry, Quartz Countertops & Center Island with Pendant Lighting - Opening Into the Large Family Room with Inviting Custom Fireplace & Hardwood Floors, Plus Added Flex Space as Perfect Spot for Home Office or Playroom! Upstairs Includes 4 Spacious Bedrooms with Ample Closet Space, Full Main Bathroom & Convenient 2nd Floor Laundry. Primary Bedroom Suite Boasts a Private Bath with Double Vanity & Tiled Shower. Situated On a Lovely Lot a

$1,049,000

4 beds2.5 baths2,808 sq ft

6 April Way, Millis, MA 02054

Custom cabinetry • Quartz countertops • Custom fireplace

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
Welcome to 1 Emerald Drive, an exceptional new luxury home on Hopkinton’s premier cul-de-sac of eight custom residences. Thoughtfully designed and impeccably crafted, this home blends timeless elegance with modern functionality. The open, light-filled layout showcases white oak floors, exquisite millwork and designer lighting throughout. The gourmet kitchen impresses with Thermador appliances, granite counters, and a custom walnut wood-accent island that adds warmth and artisan appeal. A spacious family room features a stunning feature-wall fireplace. The first-floor guest suite provides flexibility, while the second-floor primary retreat offers spacious walk-in closet and a spa-like

$2,399,000

5 beds5.5 baths5,357 sq ft

1 Emerald Dr, Hopkinton, MA 01748

Walk-in closet • Gourmet kitchen • Thermador appliances

ABOUT THIS HOME
Luxury Home for sale in Holliston, MA:
Attention builders, developers, investors, and visionary homebuyers!Exceptional opportunity in a school district ranked among the top 1% in the nation. All groundwork and approvals are complete, foundation poured, 5-bedroom septic, storm drainage, irrigation, driveway, and landscaping in place. Includes the foundation for an oversized 3-car garage and approved plans for a stunning 8,848 sq ft custom home. The property currently includes a livable house, allowing flexibility while construction continues. Privately set on over 3 acres of scenic land surrounded by fine homes and located less than 20 miles from Boston. 3D renderings shown are for illustration purposes only, reflecting what the

$1,100,000

4 beds2.5 baths3,552 sq ft

21 Spywood Rd, Sherborn, MA 01770

Irrigation • Foundation poured • Driveway

Property at 2 Towne Lyne Rd, Sherborn, MA 01770, 4 beds, 2.5 baths

$1,150,000

4 beds2.5 baths2,739 sq ft

2 Towne Lyne Rd, Sherborn, MA 01770

Property at 3 Jameson Dr #3, Millis, MA 02054, 2 beds, 2.5 baths

$1,100,000

2 beds2.5 baths1,832 sq ft

3 Jameson Dr #3, Millis, MA 02054

Property at 30 Broken Tree Rd, Medway, MA 02053, 4 beds, 2.5 baths

$950,000

4 beds2.5 baths3,128 sq ft

30 Broken Tree Rd, Medway, MA 02053

Property at 18 Wildwood Dr, Sherborn, MA 01770, 4 beds, 2.5 baths

$1,079,000

4 beds2.5 baths2,342 sq ft

18 Wildwood Dr, Sherborn, MA 01770

Property at 19 Sycamore Way Unit L:40, Medway, MA 02053, 3 beds, 2.5 baths

$1,114,096

3 beds2.5 baths3,200 sq ft

19 Sycamore Way Unit L:40, Medway, MA 02053

Property at 6 Rivendell Ln, Millis, MA 02054, 4 beds, 3 baths

$1,485,000

4 beds3 baths3,400 sq ft

6 Rivendell Ln, Millis, MA 02054

Property at 6 Glen Ellen Blvd #6, Millis, MA 02054, 3 beds, 3 baths

$1,050,000

3 beds3 baths2,656 sq ft

6 Glen Ellen Blvd #6, Millis, MA 02054

Property at 56 Fisher St, Medway, MA 02053, 4 beds, 2.5 baths

$874,900

4 beds2.5 baths3,000 sq ft

56 Fisher St, Medway, MA 02053

Property at 6 Brook St, Sherborn, MA 01770, 3 beds, 2.5 baths

$1,150,000

3 beds2.5 baths2,859 sq ft

6 Brook St, Sherborn, MA 01770

Property at 101 Olive St, Ashland, MA 01721, 5 beds, 4.5 baths

$999,900

5 beds4.5 baths3,614 sq ft

101 Olive St, Ashland, MA 01721

Property at 22 May Rd, Millis, MA 02054, 4 beds, 2.5 baths

$1,075,000

4 beds2.5 baths2,515 sq ft

22 May Rd, Millis, MA 02054

Property at 6 Freedom Trl, Medway, MA 02053, 4 beds, 3 baths

$1,125,000

4 beds3 baths3,629 sq ft

6 Freedom Trl, Medway, MA 02053

Property at 9 Adams Ln #9, Sherborn, MA 01779, 4 beds, 4.5 baths

$1,599,000

4 beds4.5 baths3,800 sq ft

9 Adams Ln #9, Sherborn, MA 01779

Property at 7 Nason Hill Ln, Sherborn, MA 01770

$850,000

— beds— baths— sq ft

7 Nason Hill Ln, Sherborn, MA 01770

Luxury Homes for Sale in Holliston

There are currently 6 luxury homes for sale in Holliston at a median listing price of $740K. 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 31 days and receive 1 offers. This map is refreshed with the newest listings in Holliston every 15 minutes.

In the past month, 7 homes have been sold in Holliston. In addition to houses in Holliston, there were also 5 condos, 2 townhouses, 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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