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Holliston, MA Homes for Sale

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  • 261 Rolling Meadow Dr, Holliston, MA 01746
    261 Rolling Meadow Dr, Holliston, MA 01746
    261 Rolling Meadow Dr, Holliston, MA 01746
    /36

    $950,000

    • 4 Beds
    • 2.5 Baths
    • 2,484 Sq Ft

    261 Rolling Meadow Dr, Holliston, MA 01746

    Nicely updated and very well maintained 4 bedroom, 2.5-bath colonial nestled in a terrific neighborhood with access to Holliston Open Space (Wenakeening Woods) as well as shopping, restaurants and major routes. The home features a bright and spacious layout, including a remodeled kitchen that opens to an elegant dining room. A comfortable family room with vaulted ceiling and gas fireplace has

    Lisa Paulette Coldwell Banker Realty - Framingham

    261 Rolling Meadow Dr, Holliston, MA 01746
  • 1366 Washington St, Holliston, MA 01746
    1366 Washington St, Holliston, MA 01746
    1366 Washington St, Holliston, MA 01746
    /19

    $429,900

    • Land
    • 5.76 Acres
    • $74,635 per Acre

    1366 Washington St, Holliston, MA 01746

    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 Kattman Team ERA Key Realty Services-Bay State Group

    1366 Washington St, Holliston, MA 01746
  • 140 Goulding St, Holliston, MA 01746
    140 Goulding St, Holliston, MA 01746
    140 Goulding St, Holliston, MA 01746
    /42

    $1,199,900

    • 4 Beds
    • 3 Baths
    • 4,130 Sq Ft

    140 Goulding St, Holliston, MA 01746

    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

    Kathy Chisholm Realty Executives Boston West

    140 Goulding St, Holliston, MA 01746
  • 35 Peter St, Holliston, MA 01746
    35 Peter St, Holliston, MA 01746
    35 Peter St, Holliston, MA 01746
    /38

    $1,070,000

    • 4 Beds
    • 2.5 Baths
    • 3,224 Sq Ft

    35 Peter St, Holliston, MA 01746

    Welcome to 35 Peter St, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for chilly evenings. The kitchen is a chef's dream, boasting a functional island, an accent backsplash, and stainless steel appliances. The primary bedroom is a sanctuary with a spacious walk-in closet. The primary bathroom is a spa-like retreat featuring a separate tub and

    DANIEL BEIRNE OpenDoor Brokerage LLC

    35 Peter St, Holliston, MA 01746
  • 33 Garett Way Unit 33, Holliston, MA 01746
    33 Garett Way Unit 33, Holliston, MA 01746
    33 Garett Way Unit 33, Holliston, MA 01746
    /42

    $639,000

    • 2 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    33 Garett Way Unit 33, Holliston, MA 01746

    Beautifully Maintained Townhome in The Orchards of Holliston. Welcome to this stunning townhome offering comfort, style, and convenience in one of Holliston’s most desirable communities. Main Level with shining hardwood floors throughout first floor. Modern kitchen with granite countertops, stainless steel appliances, and peninsula seating, Dining area with sliders leading to a private deck

    Prasad Anem Key Prime Realty LLC

    33 Garett Way Unit 33, Holliston, MA 01746
  • 37 Garett Way Unit 37, Holliston, MA 01746
    37 Garett Way Unit 37, Holliston, MA 01746
    37 Garett Way Unit 37, Holliston, MA 01746
    /24

    $710,000

    • 2 Beds
    • 2.5 Baths
    • 2,161 Sq Ft

    37 Garett Way Unit 37, Holliston, MA 01746

    Nestled at The Orchards, in the charming town of Holliston, this inviting 2011 townhouse provides an elegant, serene living experience catering to a modern lifestyle. Within the thoughtfully designed condominium, you will discover a light-filled, open floor plan, cathedral ceiling, cozy gas fireplace, French doors, walk out lower level, picture windows, skylights, hardwood floors throughout the

    Connie Kickham Coldwell Banker Realty - Newton

    37 Garett Way Unit 37, Holliston, MA 01746
  • Lot 2 Hanlon Rd, Holliston, MA 01746
    Lot 2 Hanlon Rd, Holliston, MA 01746
    Lot 2 Hanlon Rd, Holliston, MA 01746
    /4

    $450,000

    • Land
    • 0 Acre

    Lot 2 Hanlon Rd, Holliston, MA 01746

    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.

    Katie McBride REMAX Executive Realty

    Lot 2 Hanlon Rd, Holliston, MA 01746
  • 3 Danforth Dr, Holliston, MA 01746
    3 Danforth Dr, Holliston, MA 01746
    3 Danforth Dr, Holliston, MA 01746
    /42

    $1,625,000

    • 5 Beds
    • 4.5 Baths
    • 4,610 Sq Ft

    3 Danforth Dr, Holliston, MA 01746

    Located in a cozy cul-de-sac with an awesome yard and gorgeous views of the woods with walking trails! This home has 4610 sqft of living space NOT including a walk-up 3rd level ready to be finished. The 1st floor has 9' ceilings and a wide open floor plan with lots of natural light. Family room with fireplace, large dining room, separate office or reading room, mudroom, and your dream kitchen

    Craig Morrison Realty Executives Boston West

    3 Danforth Dr, Holliston, MA 01746
  • 66 Lakeshore Dr, Holliston, MA 01746
    66 Lakeshore Dr, Holliston, MA 01746
    66 Lakeshore Dr, Holliston, MA 01746
    /3

    $420,000

    • 2 Beds
    • 1 Bath
    • 1,060 Sq Ft

    66 Lakeshore Dr, Holliston, MA 01746

    Property is available for online auction only. See Realty Bid for property, auction, showing & bidding information.

    Brian Brockman Bang Realty

    66 Lakeshore Dr, Holliston, MA 01746
  • 140 Concord St, Holliston, MA 01746
    140 Concord St, Holliston, MA 01746
    140 Concord St, Holliston, MA 01746
    /41

    $549,900

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    140 Concord St, Holliston, MA 01746

    This fabulous, sunny Cape style home with a full basement is on a corner lot, located in a fabulous commuter location and is move in ready. Brand new 3 bedroom septic system installed in October 2025. Front to back living room features beautiful hardwood flooring, fireplace, sunny bay window and plenty of space to spread out. Kitchen offers hickory cabinets, plenty of counter space and exterior

    Kathy Chisholm Realty Executives Boston West

    140 Concord St, Holliston, MA 01746
  • 74 Meeting House Path, Ashland, MA 01721
    74 Meeting House Path, Ashland, MA 01721
    74 Meeting House Path, Ashland, MA 01721
    /41

    $488,000 Open Sat 11:30AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    74 Meeting House Path, Ashland, MA 01721

    Move in Ready 3 Bed , 2 bath townhome in the Ledgemere Country Condominium of Ashland. Building within the community is at a nice locaation. Grand 2 story foyer and staircase leading to the second floor. Generous living space and ample kitchen cabinetry with eat in space. Open Layout. Sun drenched dining & Living space with a slider that leads to a private yard. First floor bed and full bathroom

    Kiran Kumar Gundavarapu Key Prime Realty LLC

    74 Meeting House Path, Ashland, MA 01721
  • 306 Trailside Way, Ashland, MA 01721
    306 Trailside Way, Ashland, MA 01721
    306 Trailside Way, Ashland, MA 01721
    /19

    $454,000

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    306 Trailside Way, Ashland, MA 01721

    Welcome to this beautifully maintained 2-bedroom, 2-bath condo located in desirable Spyglass Hill. This inviting home offers a range of recent upgrades, including newer carpet, water heater, washer and dryer, refrigerator, updated kitchen countertops, and refreshed bathroom fixtures, providing a move-in ready opportunity for its next owner. The condo includes two garage spaces in a convenient

    Boaz McMahon Blue Fin Realty

    306 Trailside Way, Ashland, MA 01721
Massachusetts Middlesex County Holliston

Real Estate & Homes for Sale in Holliston, MA

Why Live in Holliston

Holliston, MA, is a small Boston suburb located 23 miles southwest of Downtown Boston, known for its highly rated school system and diverse housing options. The town features classic New England architecture, including antique colonials, Cape Cods, ranch styles, and new constructions, often situated on spacious lots. Holliston Public Schools, including Fred Miller Elementary, Robert Adams Middle, and Holliston High School, are well-regarded, offering a variety of extracurricular activities and a Montessori program. The downtown area along Central and Washington Streets is home to popular local businesses like Casey’s Pub, Coffee Haven, and Holliston Superette, fostering a strong sense of community. Residents enjoy numerous things to do, such as events organized by the Holliston Newcomers & Neighbors Club, steam engine train rides with the Waushakum Live Steamers, and seasonal farmers markets at Blair Square. Outdoor enthusiasts can explore Lake Winthrop, the Upper Charles Rail Trail, and Brentwood Conservation Land. Holliston has a lower crime risk compared to the national average. For transportation, the closest commuter rail is 6 miles north in Ashland, and Boston Logan International Airport is about 32 miles away. The town's proximity to Interstate 495 and Interstate 90 provides convenient access to Boston and other areas.

Learn more about living in Holliston

Frequently Asked Questions

What is the average home price in Holliston, MA?
Homes for sale in Holliston, MA have an average home price of $784,595.
How many homes have sold over the last 12 months in Holliston, MA?
171 homes have sold in Holliston, MA over the last 12 months.
What are the most popular zip codes in Holliston, MA?
The most popular zip codes in Holliston, MA include 01746, 02053, 02054, 01721 and 01748.
How much do you need to make to afford a house in Holliston?
The median home price in Holliston is $725,000. If you put a 20% down payment of $145,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $3,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $154K a year to afford the median home price in Holliston. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Holliston, MA?
Holliston, MA has highly rated public and private schools. Some of the best schools in Holliston based on Niche Grades are Dover-Sherborn Regional High School, Elmwood Elementary School and Hopkinton High School. Browse all the schools in Holliston, MA to learn more.

Home Trends in Holliston, MA

On average, homes in Holliston, MA sell after 18 days on the market compared to the national average of 53 days. The median sale price for homes in Holliston, MA over the last 12 months is $725,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$725,000
Median Single Family Sale Price
$741,900
Median Townhouse Sale Price
$694,950
Median 2 Bedroom Sale Price
$657,500
Median 1 Bedroom Sale Price
$225,000
Average Price Per Sq Ft
$356
Number of Homes for Sale
8
Last 12 months Home Sales
171
Months of Supply
0.60
Median List Price
$725,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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