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Holliston, MA Homes for Sale

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  • /42

    $770,000

    • 4 Beds
    • 4 Baths
    • 3,978 Sq Ft

    1 Dogwood Ln, Milford, MA 01757

    BEST DEAL Per Sq Ft in MILFORD! Buyer got cold-feet. Beautifully maintained 4BR/4BA Colonial w/nearly 4,000sf on a private 1.06-acre lot, ideal for MULTIGENERATIONAL living. 1ST FL offers a guest/in-law BDRM & full BA, laundry rm, playrm/office, and open kitchen w/GRANITE, wall oven & PANTRY. Dramatic 2-story foyer flows into a sun-filled GREAT ROOM w/cathedral ceiling & oversized windows.

    Agent Photo

    Barrie Naji

    Coldwell Banker Realty - Canton

    (508) 794-8260

    1 Dogwood Ln, Milford, MA 01757
  • /39

    $1,325,000

    • 4 Beds
    • 2.5 Baths
    • 3,926 Sq Ft

    169 Pinecrest Rd, Holliston, MA 01746

    Elegant brick-front Colonial in one of Holliston’s premier Toll Brothers neighborhoods—originally the model home with every upgrade. Set on a cul-de-sac corner lot across from hiking trails and walkable to Pinecrest Golf Club. Over 3,900sqft includes a vaulted family room with fireplace, formal living and dining rooms, and a granite kitchen with hardwoods and built-ins. The expansive primary

    Joshua Shalin ERA Key Realty Services-Bay State Group

    169 Pinecrest Rd, Holliston, MA 01746
  • /40

    $1,199,900

    • 4 Beds
    • 3.5 Baths
    • 3,664 Sq Ft

    662 Concord St, Holliston, MA 01746

    Welcome to this stunning residence, where timeless charm meets modern comfort! Step inside and experience the warmth and spaciousness designed for today's lifestyle.The heart of the home, a gorgeous chef's kitchen, offers high-end finishes and ample space to create unforgettable meals. Entertain effortlessly in the expansive dining room, or by the cozy gas fireplace in the elegant living room on

    Sue Sindoni Keller Williams Elite

    662 Concord St, Holliston, MA 01746
  • /41

    $1,174,900

    • 4 Beds
    • 2.5 Baths
    • 3,764 Sq Ft

    156 Mitchell Rd, Holliston, MA 01746

    Set at the end of winding Mitchell Road, with views behind of vast farmland, this grand three-story home has had vast improvements added both inside and out since its original construction. An oversized family room with vaulted ceiling, stone chimney and fireplace, and large picture windows overlooking the back yard is the centerpiece of the first floor's open-concept design. The grand kitchen is

    Richard Wilcox Distinctly New England

    156 Mitchell Rd, Holliston, MA 01746
  • /38

    $525,000

    • 3 Beds
    • 1 Bath
    • 1,141 Sq Ft

    58 Front St, Holliston, MA 01746

    Charming antique Colonial on a sunny corner lot in Holliston’s beloved Mudville! This 3-bedroom home blends historic character with thoughtful updates—featuring wide-plank hardwood floors, a light-filled layout, and a versatile bonus room ideal for a home office, studio, or playroom. The warm, inviting kitchen flows into spacious dining and living areas. Upstairs, find three bedrooms with

    Janine Wuschke Keller Williams Realty

    58 Front St, Holliston, MA 01746
  • /41

    $750,000

    • 4 Beds
    • 2 Baths
    • 1,911 Sq Ft

    86 Christopher Rd, Holliston, MA 01746

    Situated at the end of a quiet cul-de-sac with direct access to the Upper Charles Rail Trail and Hopping Brook, this recently expanded and renovated home is ready for its lucky new owners! Outdoor enthusiasts and nature lovers will enjoy a private sanctuary nestled in a neighborhood setting, with park-like grounds steps from the trail and water views. The home boasts a 36x16’ addition with garage

    Kathy Murray Coldwell Banker Realty - Westwood

    86 Christopher Rd, Holliston, MA 01746
  • /42

    $584,900

    • 3 Beds
    • 1 Bath
    • 1,399 Sq Ft

    464 Gorwin Dr, Holliston, MA 01746

    Charming 3-bedroom, 1-bath ranch in the sought-after Brentwood neighborhood of Holliston, MA. This well-maintained home offers 1,399 sq ft of comfortable living on a generous 0.41-acre lot. Featuring beautiful hardwood floors, a tiled full bath, and efficient forced hot air gas heat! Enjoy the outdoors on the beautiful tiered composite deck (2019), perfect for entertaining or relaxing while

    John Kokocinski The Neighborhood Realty Group

    464 Gorwin Dr, Holliston, MA 01746
  • /38

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,039 Sq Ft

    1884 Washington St, Holliston, MA 01746

    OPEN HOUSE SAT AUG 2 from 11am-12:30pm * Welcome to 1884 Washington Street — a highly sought-after ranch offering privacy, space, and convenience. Set back from the road, this 3-bedroom, 2-bath home features an open-concept layout with a spacious front-to-back living room, an eat-in kitchen, and a dedicated dining area. The primary bedroom includes a private 3⁄4 bath, while two additional

    Kimberley Tufts eXp Realty

    1884 Washington St, Holliston, MA 01746
  • /42

    $2,500,000

    • 5 Beds
    • 5 Baths
    • 5,740 Sq Ft

    14 Fiske Pond Rd, Holliston, MA 01746

    Construction just completed. This is your chance to be part of a unique and idyllic private enclave on the Holliston/Sherborn town line. Enjoy 25 acres of common areas - meadows, trails and a pond. Designed for todays modern life style, no detail was overlooked and no expense was spared to make this gorgeous 5 BR; 5 bath contemporary colonial masterpiece. This "Smart Home" has two master suites -

    Bela Kasas Choice Realty RES

    14 Fiske Pond Rd, Holliston, MA 01746
  • /32

    $759,900

    • 4 Beds
    • 2 Baths
    • 1,969 Sq Ft

    329 Gorwin Dr, Holliston, MA 01746

    You must see this gorgeously updated raised-ranch in the coveted Brentwood neighborhood. Lovely brand new kitchen - cabinets, ss appliances, quartz counters & oversized island open to fireplace living rm & dining rm. Sparkling hdwd floors throughout the main level. Three of the four bedrms & fabulous main bathroom w/ tile shower/bath, tile flr & solid surface vanity. Phenomenal added space in the

    Vesta Real Estate Group Vesta Real Estate Group, Inc.

    329 Gorwin Dr, Holliston, MA 01746
  • /42

    $1,675,000

    • 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
  • /5

    $599,000

    • 5 Beds
    • 2.5 Baths
    • 3,130 Sq Ft

    52 Jasper Hill Rd, Holliston, MA 01746

    Incredible Opportunity on 6 Private Acres in Holliston!Builders and investors take note — this is a rare chance to own a stunning 6-acre wooded lot perched on Jasper Hill, offering sweeping views of Holliston’s town center. The property features a single-family home in need of extensive renovation or tear-down, making it an ideal site for new construction.Imagine building a custom dream home or

    Enis Shehu Cameron Real Estate Group - Framingham

    52 Jasper Hill Rd, Holliston, MA 01746
  • /42

    $2,195,000 Open Sun 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 5,737 Sq Ft

    45 Wendy Ln, Holliston, MA 01746

    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,

    Kimberly Collins Berkshire Hathaway HomeServices Robert Paul Properties

    45 Wendy Ln, Holliston, MA 01746
  • /33

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    14 Day Rd, Holliston, MA 01746

    Welcome to 14 Day Road — a stunning 4-bedroom, 2.5-bath home that seamlessly blends timeless charm with modern upgrades in one of Holliston’s most sought-after neighborhoods. Step inside to a stunning new kitchen featuring quartz countertops, LG stainless steel appliances, and custom cabinetry. The open layout flows seamlessly into bright living spaces, highlighted by new oak flooring and fresh

    Razmig Panossian Coldwell Banker Realty - Waltham

    14 Day Rd, Holliston, MA 01746
  • /19

    $429,900

    • Land
    • 6 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
  • /8

    $649,990

    • Land
    • 0.92 Acre
    • $706,511 per Acre

    15 Fiske Pond Rd, Holliston, MA 01746

    Ready to build with approved plans; No Cash - No problem - Land purchase financing available - This is your last chance to be part of a unique and idyllic private enclave on the Holliston/Sherborn town line. Restrictive covenants ensure the character of this "Nantucket Style" village community will be preserved for the next generation. Enjoy the 25 acres of common areas - meadows, trails and a

    Bela Kasas Choice Realty RES

    15 Fiske Pond Rd, Holliston, MA 01746
  • /3

    $2,150,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 4,959 Sq Ft

    LOT 8 Pond View, Holliston, MA 01746

    ** UNDER CONSTRUCTION ** TIME TO CUSTOMIZE YOUR PERSONAL TOUCH SO CALL OFFICE FOR INFO & WALK THROUGH ** MODERN FARMHOUSE COLONIAL @ STUNNING "The Homes at Pond View" 5 Bedrooms ~ 4 1/2 Bathrooms ~ 3 Cars Garages ~ Town Water ~ Natural Gas Heating & Cooking ~ GORGEOUS TALL PINES ESTATE HOMESITE w/ 3.62 ACRES w/ NO CONSERVATION WETLANDS ~ Family Neighborhood ~ Excellent Schools ~ SPORTS COURT &

    Francis Vazza Four Season Homes, Llc

    LOT 8 Pond View, Holliston, MA 01746
  • /36

    $749,900

    • 3 Beds
    • 3 Baths
    • 1,792 Sq Ft

    283 Hayden Rowe St, Hopkinton, MA 01748

    Set on over an acre in beautiful Hopkinton, this split-level ranch offers an unbeatable combination of space, privacy, and location. With 3 generous bedrooms and 3 baths, this home is ideal for comfortable living and entertaining. Inside, vaulted ceilings and sun-filled rooms create an open, airy feel, while the expansive lot offers endless potential for outdoor enjoyment or potential expansion.

    Justin Lussier Lamacchia Realty, Inc.

    283 Hayden Rowe St, Hopkinton, MA 01748
  • /19

    $504,000

    • 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
  • /38

    $998,900

    • 2 Beds
    • 2.5 Baths
    • 2,485 Sq Ft

    27 Richardson Dr Unit 27, Millis, MA 02054

    This highly sought-after unit is in immaculate condition and offers all the essentials for enjoying adult community living at its best. If your home search emphasizes brightness and spaciousness, this expansive open floor plan unit, complete with exquisite features, is sure to captivate you. It boasts large windows that allow for ample natural light, soaring ceilings, and a stunning, centrally

    Shelly Armstrong Redfin Corp.

    27 Richardson Dr Unit 27, Millis, MA 02054

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.

Frequently Asked Questions

What is the average home price in Holliston, MA?
Homes for sale in Holliston, MA have an average home price of $1,108,963.
How many homes have sold over the last 12 months in Holliston, MA?
58 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, 01748 and 01770.
How much do you need to make to afford a house in Holliston?
The median home price in Holliston is $1,149,000. If you put a 20% down payment of $229,800 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $5,940 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $255K a year to afford the median home price in Holliston.
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, Hopkinton High School and Elmwood Elementary School. Browse all the schools in Holliston, MA to learn more.

Home Trends in Holliston, MA

Housing Trends

Median Sale Price
$1,060,000
Median Single Family Sale Price
$1,170,000
Median Townhouse Sale Price
$699,900
Median 2 Bedroom Sale Price
$699,900
Average Price Per Sq Ft
$342
Number of Homes for Sale
1
Last 12 months Home Sales
58
Months of Supply
0.20
Median List Price
$1,149,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
47%
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