Holliston, MA homes for sale & real estate

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ABOUT THIS HOME
Holliston, MA Homes for Sale
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 desig

$749,900

3 beds2 baths1,894 sq ft

160 Winter, Holliston, MA 01746

Open floor plan • Expanded log home • Cozy fireplace

ABOUT THIS HOME
Holliston, MA Homes for Sale
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

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ABOUT THIS HOME
Holliston, MA Homes for Sale
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
Holliston, MA Homes for Sale
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

$699,000

3 beds2 baths1,772 sq ft

625 Norfolk St, Holliston, MA 01746

Oversized kitchen • Sunroom • Large island

ABOUT THIS HOME
Holliston, MA Homes for Sale
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 reaso

$785,000

4 beds2.5 baths2,416 sq ft

30 Powderhorn Ln, Holliston, MA 01746

Fenced area • Entertainment space • Cul-de-sac road

Property at 1014 Highland St, Holliston, MA 01746, 3 beds, 3.5 baths

$769,900

3 beds3.5 baths2,034 sq ft

1014 Highland St, Holliston, MA 01746

Property at 131 Jennings Rd, Holliston, MA 01746, 3 beds, 1.5 baths

$724,900

3 beds1.5 baths1,748 sq ft

131 Jennings Rd, Holliston, MA 01746

Property at 110 Bonney Dr, Holliston, MA 01746, 4 beds, 3.5 baths

$1,599,900

4 beds3.5 baths3,469 sq ft

110 Bonney Dr, Holliston, MA 01746

Property at 1366 Washington St, Holliston, MA 01746

$429,900

— beds— baths— sq ft

1366 Washington St, Holliston, MA 01746

Property at Lot 2 Hanlon Rd, Holliston, MA 01746

$450,000

— beds— baths— sq ft

Lot 2 Hanlon Rd, Holliston, MA 01746

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ABOUT THIS HOME
Holliston, MA Homes for Sale
Welcome to this beautifully maintained townhouse in Ashland’s desirable Ledgemere Condominiums. This spacious home features two large bedrooms, each with its own full bathroom and generous closet space. The primary bedroom offers a new modern vanity, updated lighting, and a walk-in closet. The tiled entryway opens to a warm and inviting living room with gleaming hardwood floors and a cozy fireplace. A separate bonus room provides flexibility for a formal dining area, home office, or additional living space. The updated kitchen shines with new white cabinetry, quartz countertops, stainless steel appliances, and a new floor. A convenient half bath completes the main level. Additional hi

$509,900

2 beds2.5 baths1,344 sq ft

157 Leland Farm Rd #157, Ashland, MA 01721

New modern vanity • Walk-in closet • Cozy fireplace

NEW CONSTRUCTION

ABOUT THIS HOME
Holliston, MA Homes for Sale
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 TODAY, 12PM TO 1:30PM

ABOUT THIS HOME
Holliston, MA Homes for Sale
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
Holliston, MA Homes for Sale
Don’t miss this pristine cape style home nestled within the sought-after Spyglass Hill Association. A harmonious blend of comfort and style awaits you in this thoughtfully designed residence. The open-concept living and dining area boasts newer flooring and is an inviting space for relaxation or entertaining guests. The updated kitchen features stainless steel appliances, granite countertops, and ample storage. Retreat to the main suite, adorned with a generous walk-in closet and a private bath. The second bedroom provides flexibility for a home office or a guest suite with a full bathroom. Enjoy the convenience of in-unit main floor laundry and tandem garage parking for 2 cars. With

$495,900

2 beds2.5 baths1,312 sq ft

84 E Bluff Rd #84, Ashland, MA 01721

Walk-in closet • Cape style home • Updated kitchen

ABOUT THIS HOME
Holliston, MA Homes for Sale
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

OPEN TODAY, 11:30AM TO 1:30PM

ABOUT THIS HOME
Holliston, MA Homes for Sale
Welcome to 25 Prospect St — a spacious 4-bedroom, 2-bath home in the heart of Ashland. Tastefully remodeled in 2001 and freshly painted throughout, this inviting property features two cozy fireplaces, a bright and open layout, and generous living space perfect for entertaining. Enjoy a large backyard, ample parking, and a convenient location near schools, parks, and major commuter routes. A true gem with charm, comfort and room to add your personal touch.

$600,000

4 beds2 baths1,788 sq ft

25 Prospect St, Ashland, MA 01721

Ample parking • Large backyard • Two cozy fireplaces

Property at 68 E Main St, Hopkinton, MA 01748, 2 beds, 3 baths

$819,900

2 beds3 baths2,304 sq ft

68 E Main St, Hopkinton, MA 01748

Property at 6 April Way, Millis, MA 02054, 4 beds, 2.5 baths

$1,049,000

4 beds2.5 baths2,808 sq ft

6 April Way, Millis, MA 02054

Property at 45 Half Crown Cir #45, Ashland, MA 01721, 2 beds, 2.5 baths

$644,900

2 beds2.5 baths2,143 sq ft

45 Half Crown Cir #45, Ashland, MA 01721

Property at 1 Emerald Dr, Hopkinton, MA 01748, 5 beds, 5.5 baths

$2,399,000

5 beds5.5 baths5,357 sq ft

1 Emerald Dr, Hopkinton, MA 01748

Property at 72 Meeting House Path #72, Ashland, MA 01721, 3 beds, 2 baths

$449,800

3 beds2 baths1,454 sq ft

72 Meeting House Path #72, Ashland, MA 01721

Property at 2 Country Village Way #2, Millis, MA 02054, 2 beds, 1.5 baths

$419,900

2 beds1.5 baths1,591 sq ft

2 Country Village Way #2, Millis, MA 02054

Property at 27 Pollard Dr, Millis, MA 02054, 6 beds, 3.5 baths

$799,999

6 beds3.5 baths3,532 sq ft

27 Pollard Dr, Millis, MA 02054

Property at 176 Main St #3, Medway, MA 02053, 2 beds, 2 baths

$590,000

2 beds2 baths2,140 sq ft

176 Main St #3, Medway, MA 02053

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 63 Trailside Way #63, Ashland, MA 01721, 3 beds, 2.5 baths

$425,000

3 beds2.5 baths1,796 sq ft

63 Trailside Way #63, Ashland, MA 01721

Property at 67 Spyglass Hill Dr #67, Ashland, MA 01721, 2 beds, 2.5 baths

$459,999

2 beds2.5 baths1,624 sq ft

67 Spyglass Hill Dr #67, Ashland, MA 01721

Property at 277 Meeting House Path #277, Ashland, MA 01721, 2 beds, 2.5 baths

$449,000

2 beds2.5 baths1,456 sq ft

277 Meeting House Path #277, Ashland, MA 01721

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

Average home prices near Holliston, MA

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Holliston, MA real estate trends

All Home Types trends in Holliston, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$650,000

-3.5% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Holliston, MA

$650,000

-3.5%

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