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Holliston, MA Homes for Sale

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  • /41

    $1,900,000 Open Fri 4PM - 6PM

    • 4 Beds
    • 4.5 Baths
    • 4,995 Sq Ft

    36 Connelly Hill Rd, Hopkinton, MA 01748

    Set in Hopkinton’s coveted Connelly Hill Estates this pristine home checks every box, inside and out. The floor plan is open and bright with front-to-back living / dining room, a private office, built-ins, mudroom, and a gorgeous kitchen with Sub-Zero and Wolf appliances. Upstairs, the spacious primary suite is a true retreat, and there’s a bonus room perfect as a fifth bedroom or second office.

    Agent Photo

    Trina Macchi

    William Raveis R.E. & Home Services

    (508) 786-8623

    36 Connelly Hill Rd, Hopkinton, MA 01748
  • /37

    $1,150,000 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 3 Baths
    • 3,518 Sq Ft

    81 Linden St, Holliston, MA 01746

    This meticulously maintained Mid Century Modern home is flooded with natural light d/t open floor plan & enlarged Pella windows. Completely remodeled in 2010 the homeowners thought of everything you need so you can move right in. Gorgeous hardwood floors flow throughout the main level. The kitchen's custom cabinets, quartz countertops & large island are ideal for gatherings. The living room

    Melissa Kaspern RE/MAX Executive Realty

    81 Linden St, Holliston, MA 01746
  • /39

    $1,149,000

    • 3 Beds
    • 2 Baths
    • 2,297 Sq Ft

    279 Norfolk St, Holliston, MA 01746

    Welcome to this beautifully maintained Royal Barry Wills Cape! This stunning property offers a spacious layout perfect for families or those seeking extra space. As you step inside, you'll be greeted by a bright and airy LR adorned with large windows, ample natural light and a gas lit fireplace. The recently added 32x18 addition to the home features a stunning Chefs kitchen offering Modern

    Meeghan Ford Berkshire Hathaway HomeServices Commonwealth Real Estate

    279 Norfolk St, Holliston, MA 01746
  • /41

    $975,000 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 2 Baths
    • 3,366 Sq Ft

    35 Church St, Holliston, MA 01746

    A true oasis, this stunning farmhouse is beautifully sited on its *double* lot in the heart of Holliston's downtown - close to schools, Rail Trail, shops, lake & cafes. Incredible, large flat backyard is ideal for a pool, pickleball court, soccer, play or potential ADU. New 4BR septic, updated plumbing & electrical. Updated and sun filled, magazine worthy kitchen features custom cabinetry,

    Kathy Chisholm Realty Executives Boston West

    35 Church St, Holliston, MA 01746
  • /37

    $1,199,900

    • 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
  • /42

    $985,500

    • 3 Beds
    • 3.5 Baths
    • 3,088 Sq Ft

    585 Chestnut St, Ashland, MA 01721

    Welcome to this stunning 2018-built Colonial in Ashland, offering the perfect blend of style, comfort, and convenience. With 3 bedrooms, an office, and a newer finished basement, this home is designed for today’s modern lifestyle. The first floor is an entertainer’s dream, featuring an oversized living room with a vaulted ceiling, gas fireplace, and seamless flow into the elegant white kitchen

    The Madden Team Keller Williams Realty Boston Northwest

    585 Chestnut St, Ashland, MA 01721
  • /42

    $1,050,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 3,624 Sq Ft

    85 S Mill St, Hopkinton, MA 01748

    Lovingly maintained Colonial offers a sought after open floor plan with 2 car attached garage sited on a picturesque, well-landscaped 1.07 acres offering 2 decks, Screened Porch & Storage Shed! Pretty Kitchen w/ granite counters, range, micro, dishwasher, refrigerator, tile floor & large breakfast bar! Kitchen leads to fireplaced Family Room w/ mounted TV above mantel & slider leading to

    Kathleen Williamson Berkshire Hathaway HomeServices Commonwealth Real Estate

    85 S Mill St, Hopkinton, MA 01748
  • /2

    $1,295,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,056 Sq Ft

    1 Nirvana Way, Medway, MA 02053

    Wonderful New Construction in Medway. Private home on 6+ acres of pristine land. Summer 2025 delivery. Wonderful open floor plan with over 4000sq ft of living space on three floors. Gorgeous family boasts 11 foot cathedral ceiling. Large custom kitchen with island, stainless steel appliances, Quartz counters, and a full pantry. 2nd floor has separate laundry, and 3 bedrooms with spacious

    Darla Prentice Prentice Realty Group

    1 Nirvana Way, Medway, MA 02053
  • /38

    $869,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 3,436 Sq Ft

    328 Washington St, Holliston, MA 01746

    A true gem! This custom-built colonial offers an unparalleled blend of luxury and comfort with 3,400 sq. ft nestled on a generous lot! The expansive main bedroom features a private balcony with serene backyard views, double closets,and a spa-like bath with jacuzzi tub and separate shower. The heart of the home is a chef-inspired gourmet kitchen boasting double-ovens, an island perfect for

    Jerry Mazzola Congress REALTORS®

    328 Washington St, Holliston, MA 01746
  • /30

    $699,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    1874 Washington St, Holliston, MA 01746

    Welcome to this beautifully cared-for home that offers direct access to the Upper Charles Rail Trail – perfect for outdoor enthusiasts and those who love a private oasis! Already upgraded and move-in ready with acacia solid hardwood flooring, an efficient gas furnace and hot water heater (both 2018), energy-efficient Pella windows (2014), a vinyl privacy fence, two fireplaces, central AC, an

    Matt Gorman EDGE Realty Advisors

    1874 Washington St, Holliston, MA 01746
  • /41

    $600,000 Open Fri 5PM - 6:30PM

    • 4 Beds
    • 1.5 Baths
    • 1,906 Sq Ft

    108 Prentice St, Holliston, MA 01746

    Welcome to 108 Prentice Street Holliston! This well-loved home comes to market after 60+ years! The amount of space & flexible use of the rooms makes this house exciting & unique! 4-bedroom septic system was completed in May of 2024. Most windows were replaced in 2018. Glowing hardwoods throughout! The spacious eat in kitchen boasts Corian brand countertops & maple wood cabinets w/cherry

    Lydia Rajunas RE/MAX Executive Realty

    108 Prentice St, Holliston, MA 01746
  • /42

    $875,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 3.5 Baths
    • 3,277 Sq Ft

    166 Willowgate Rise, Holliston, MA 01746

    Fantastic opportunity to own a wonderful, contemporary home in the coveted Willow Gate Rise neighborhood. Lovely eat-in kitchen (2004) w/granite counters, ss appliances, oversized island w/range, abundant cabinets. Open to phenomenal cathedral ceiling great room (added 2004) w/gas fireplace, built ins & slider to wonderful screened porch. Gleaming hdwd flrs thru much of home. Vaulted living rm

    Vesta Real Estate Group Vesta Real Estate Group, Inc.

    166 Willowgate Rise, Holliston, MA 01746
  • /17

    $999,000

    • Land
    • 1.00 Acre
    • $999,000 per Acre

    147 N Mill St, Holliston, MA 01746

    Imagine your new home, nestled in the heart of a serene, rolling pastoral landscape, This picturesque one-acre parcel offers the perfect blend of tranquility and opportunity. Your home would be surrounded by soft, undulating hills and wide open skies, with long, peaceful views of the land stretching into the distance and the nearby pond.. A brand-new, beautifully constructed 1,675+ sq. ft.

    Stephen DeConto Cameron Real Estate Group

    147 N Mill St, Holliston, MA 01746
  • /10

    $999,000

    • Land
    • 5 Acres
    • $186,729 per Acre

    177 N Mill St, Holliston, MA 01746

    Welcome to a stunning 5-acre parcel-offering panoramic pastoral views and endless possibilities. This is the perfect canvas to build your dream home surrounded by nature's beauty and tranquility. The gently sloped terrain offers multiple ideal building sites, whether you're envisioning a luxurious main residence, a spacious garage for your car collection, a well-equipped workshop for your

    Stephen DeConto Cameron Real Estate Group

    177 N Mill St, Holliston, MA 01746
  • /42

    $849,900 Open Sat 4PM - 5:30PM

    • 3 Beds
    • 3.5 Baths
    • 2,034 Sq Ft

    1014 Highland St, Holliston, MA 01746

    Modern Comfort Meets Classic Charm! Welcome to this beautifully crafted 3-bedroom, 3.5-bath single-family home, where space, style, and smart design come together effortlessly.Enjoy a bright, open-concept kitchen with sleek finishes and seamless flow into the living and dining areas—perfect for entertaining. Each bedroom offers generous space and privacy, including two en-suites for elevated

    Cristiano Jarbas Cristiano Jarbas, Inc.

    1014 Highland St, Holliston, MA 01746
  • /33

    $755,000 Open Sat 11AM - 12:30PM

    • 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
  • /32

    $849,000

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    1282 Highland St, Holliston, MA 01746

    Stunning 2020 townhome with a single family feel! This home features an open floor plan with a show-stopping kitchen, complete with a massive center island, luxury finishes, and a gas cooktop, making it a dream for any culinary enthusiast. The first-floor primary suite is a true sanctuary, boasting a walk-in California Closet, a luxurious bath with double vanity sinks, a jacuzzi tub, and separate

    The Movement Group Compass

    1282 Highland St, Holliston, MA 01746
  • /30

    $849,000

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    1282 Highland St, Holliston, MA 01746

    This modern retreat, built in 2020, offers 2800 SF of sophisticated, move-in ready living space. This home features an open floor plan with a stunning kitchen, complete with a massive center island, luxury finishes, and a gas cooktop, making it a dream for any culinary enthusiast. The first-floor primary suite is a true sanctuary, boasting a walk-in California Closet, a luxurious bath with double

    The Movement Group Compass

    1282 Highland St, Holliston, MA 01746
  • /41

    $1,399,000 Open Sat 2:30PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 5,364 Sq Ft

    138 Fairview St, Holliston, MA 01746

    This elegant home, nestled in a premier neighborhood, offers refined living. A grand driveway leads to a brick facade and meticulously landscaped grounds. Inside, soaring ceilings and intricate crown molding frame bright, spacious living areas. The gourmet kitchen, a chef's dream, features top-tier appliances and a central island. A recently finished basement (2023) adds significant value with a

    Marina Korenblyum Redfin Corp.

    138 Fairview St, Holliston, MA 01746
  • /19

    $449,900

    • Land
    • 6 Acres
    • $78,108 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
  • /39

    $1,649,000

    • 4 Beds
    • 4.5 Baths
    • 5,648 Sq Ft

    75 Mohawk Path, Holliston, MA 01746

    NEW PRICE! Nestled on nearly 1 acre in the Highlands at Holliston, this exceptional property offers everything you've been searching for! Seamlessly combining elegance & functionality, you’ll find a spacious, open floor plan across 3 levels of luxurious living space. This home is made for entertaining! Upon entry, you'll be greeted by a grand 2-story foyer leading to an expansive main level,

    Tara D'Amato Engel & Völkers Wellesley

    75 Mohawk Path, Holliston, MA 01746
  • /37

    $899,000

    • 4 Beds
    • 2.5 Baths
    • 2,860 Sq Ft

    539 Fiske St, Holliston, MA 01746

    Move right into this beautiful Center Entrance Colonial nestled in the woods of East Holliston. Set on 1.17 acres of peaceful, fully fenced land, this inviting home has over 2800 sf of living space, with 4 bdrms, 2.5 baths, & eat-in kitchen w/sliders to a new deck and patio. Cook with new stainless appliances, granite countertops and tiled backsplash. Entertain in your dining room, with custom

    deb@jamaicahill. Gallaga Jamaica Hill Realty, Inc.

    539 Fiske St, Holliston, MA 01746
  • /41

    $925,000 Open Sat 2PM - 3:30PM

    • 4 Beds
    • 3.5 Baths
    • 3,894 Sq Ft

    655 Central St, Holliston, MA 01746

    Step into a world of sleek sophistication and modern comfort in this stunning 4-bedroom, 3.5-bathroom contemporary home. Designed with an eye for clean lines and open spaces, this residence offers a unique blend of style and functionality, perfect for today's discerning homeowner. From the moment you enter, you'll be captivated by the airy ambiance and natural light that floods the spacious

    The Platinum Team Mathieu Newton Sotheby's International Realty

    655 Central 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
  • /2

    $500,000

    • Land
    • 10 Acres
    • $50,968 per Acre

    0 Hill St, Holliston, MA 01746

    +9 acre lot. Message listing agent for more information.

    Fahd Khan Keller Williams Realty Boston South West

    0 Hill St, Holliston, MA 01746
  • /3

    $2,150,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 4,903 Sq Ft

    LOT 8 Pond View, Holliston, MA 01746

    ** UNDER CONSTRUCTION ** SHOWSTOPPER NEW CONSTRUCTION MODERN FARMHOUSE COLONIAL at 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 & SWIMMING POOL CAPABILITY W/ HUGE PRIVATE BACKYARD

    Francis Vazza Four Season Homes, Llc

    LOT 8 Pond View, Holliston, MA 01746

About Holliston

Holliston is a small Boston suburb with a highly rated school system, beloved local businesses and a diverse housing stock. “It really has a Norman Rockwellian feel,” says Executive Partner, Lauren Davis with Realty Executives Boston West, who has about 20 years of experience in the area. Home to a neighborhood named Mudville and several other connections to the famous poem, "Casey at the Bat,” the community takes pride in its role in Boston’s deep-rooted baseball history. The town also has a CAP Index crime score of 1, which is significantly l ...

Frequently Asked Questions

What is the average home price in Holliston, MA?
Homes for sale in Holliston, MA have an average home price of $821,594.
How many homes have sold over the last 12 months in Holliston, MA?
164 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 02116, 02118, 02895, 02135 and 02130.
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 6.81%, your estimated principal and interest payment would be $3,790 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $162K 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

Home Trends

Median Price (12 Mo)
$717,500
Median Single Family Price
$750,000
Median Townhouse Price
$720,000
Median 2 Bedroom Price
$632,000
Median 1 Bedroom Price
$247,500
Average Price Per Sq Ft
$340
Number of Homes for Sale
14
Last 12 months Home Sales
164
Months of Supply
1.00
Median List Price
$725,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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