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Holliston, MA Homes for Sale with Parking

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  • /42

    $1,350,000 Open Sun 11AM - 12:30PM

    • 4 Beds
    • 3.5 Baths
    • 5,356 Sq Ft

    138 Fairview St, Holliston, MA 01746

    Welcome to this grand brick-front Colonial, ideally situated in one of the most desirable neighborhoods near Pinecrest Golf Club. A striking two-story foyer greets you with a dramatic staircase that leads up to the open second floor and overlooks the elegant living room. The thoughtfully designed floor plan is perfect for entertaining, multi-use living, and multi-generational lifestyles. It

    Agent Photo

    Trina Macchi

    William Raveis R.E. & Home Services

    (508) 625-7756

    138 Fairview St, Holliston, MA 01746
  • /42

    $795,000 Open Sun 11AM - 12:30PM

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

    1 Dogwood Ln, Milford, MA 01757

    Stunning sun-splashed Colonial w/approx. 4,000sf of living space on a 1.06-acre lot in a desirable tree-lined cul-de-sac on Holliston line. Features 4+ bedrooms & 4 full baths, offering exceptional flexibility for multigenerational living. A dramatic 2-story foyer w/Palladian window sets the tone, flowing into formal spaces & an open-concept layout. 1st floor includes a cathedral-ceiling great

    Agent Photo

    Barrie Naji

    Coldwell Banker Realty - Canton

    (508) 794-8260

    1 Dogwood Ln, Milford, MA 01757
  • /36

    $940,000

    • 4 Beds
    • 2.5 Baths
    • 3,364 Sq Ft

    233 Willowgate Rise, Holliston, MA 01746

    Spacious center-entry colonial in sought-after double cul-de-sac location with 4-bdrm, 2.5-bth offers over 3,000 sq. ft. of comfortable & versatile living. The beautifully updated kitchen boasts modern cabinetry, stainless-steel appliances & is perfect for entertaining with a spacious dining area on one side and a fireplaced family room on the other. From the family room, step into incredible

    Lauren Davis Realty Executives Boston West

    233 Willowgate Rise, Holliston, MA 01746
  • /42

    $1,095,000 Open Sun 12PM - 2PM

    • 5 Beds
    • 5 Baths
    • 4,389 Sq Ft

    10 Jarr Brook Rd, Holliston, MA 01746

    Great opportunity to live in this magnificent house in a peaceful and lovely neighborhood dead end with cul-de-sac close to downtown and Excellent Schools. This beautiful home offers and abundance of natural lights, 5 generously sized bedrooms, 5 full bathroom, living room, dining room with fire place, kitchen, family room, storage room, music studio, home gym space, a large walk-out basement

    Joana Almeida Pablo Maia Realty

    10 Jarr Brook Rd, Holliston, MA 01746
  • /40

    $1,199,900 Open Sun 12PM - 2PM

    • 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 Open Sun 11AM - 12:30PM

    • 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
  • /41

    $945,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,842 Sq Ft

    37 Annetta Rd, Ashland, MA 01721

    Beautifully maintained Colonial in Hillside Farms, one of Ashland’s most sought-after neighborhoods. Set on a private corner lot with a yard on three sides. Enjoy the convenience of paved sidewalks and school bus pickup right at your door—just minutes from local stores, schools, childcare, restaurants, and more. The home features a brand-new roof (50-year transferable warranty), updated front

    Lynn Schreiner Realty Executives Boston West

    37 Annetta Rd, Ashland, MA 01721
  • /37

    $948,500 Open Sun 11AM - 1PM

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

    585 Chestnut St, Ashland, MA 01721

    Welcome to this stunning 2018-built Colonial in Ashland, blending style, comfort, and an unbeatable location. Featuring 3 bedrooms, an office, and a newly finished basement, this home perfectly suits today’s modern lifestyle. The first floor is an entertainer’s dream with an oversized living room boasting a vaulted ceiling and gas fireplace, flowing seamlessly into the elegant white kitchen with

    The Madden Team Keller Williams Realty Boston Northwest

    585 Chestnut St, Ashland, MA 01721
  • /33

    $759,900 Open Sun 12PM - 2PM

    • 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 refinished 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

    Vesta Real Estate Group Vesta Real Estate Group, Inc.

    329 Gorwin Dr, Holliston, MA 01746
  • /32

    $594,000 Open Sun 12:30PM - 2PM

    • 3 Beds
    • 1 Bath
    • 1,755 Sq Ft

    143 Oak St, Holliston, MA 01746

    Move-in ready ranch-style home that blends the comfort of single floor living with modern style, and convenience. With tasteful Pottery Barn-inspired touches throughout, this home offers a fresh and inviting interior. Enjoy peace of mind with major updates already completed, including new: roof, gas furnace, gas hot water heater, central AC, and maintenance-free composite decking and vinyl

    Susan McPherson Berkshire Hathaway HomeServices Commonwealth Real Estate

    143 Oak St, Holliston, MA 01746
  • /42

    $1,675,000 Open Sun 11:30AM - 1:30PM

    • 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 electric fireplace, large dining room, separate office or reading room, mudroom, and your dream

    Craig Morrison Realty Executives Boston West

    3 Danforth Dr, Holliston, MA 01746
  • /29

    $660,000

    • 2 Beds
    • 2.5 Baths
    • 1,974 Sq Ft

    39 Balancing Rock Dr, Holliston, MA 01746

    This lovely 55+ townhouse in Balancing Rock Village is ready for a new owner. Welcoming eat-in kitchen with new granite counters 2025, ss appliances, pantry and breakfast bar open to vaulted ceiling living room with gas fireplace and slider out to fantastic wood deck. Separate formal dining room at front of the unit and hardwood floors through much of main level. First floor primary en suite with

    Vesta Real Estate Group Vesta Real Estate Group, Inc.

    39 Balancing Rock Dr, Holliston, MA 01746
  • /15

    $869,000

    • 4 Beds
    • 2.5 Baths
    • 2,948 Sq Ft

    539 Fiske St, Holliston, MA 01746

    Welcome to 539 Fiske Street—this picture-perfect Center Entrance Colonial sits on over an acre of beautifully maintained, fully fenced land. With 4 bedrooms, 2.5 baths, and flexible living spaces, this home offers the perfect balance of charm, function, and comfort. The updated eat-in kitchen features granite countertops, new stainless appliances, and sliders to a new composite deck and patio. A

    Jamie Grossman MGS Group Real Estate LTD - Wellesley

    539 Fiske St, Holliston, MA 01746
  • /42

    $2,195,000

    • 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
  • /38

    $869,900

    • 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
  • /42

    $799,900

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

    1014 Highland St, Holliston, MA 01746

    Modern elegance and value meet at 1014 Highland St, now offered bellow market value! This brand-new 3 bed, 3.5 bath home sits on a private 1.3-acre lot in sought-after Holliston, just minutes from Pinecrest Golf Club. Enjoy a bright open-concept layout, designer kitchen with quartz counters, stainless appliances, and a spacious walk-in pantry—perfect for storing bulk purchases, freeing up

    Cristiano Jarbas Cristiano Jarbas, Inc.

    1014 Highland St, 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
  • /40

    $899,000

    • 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
  • /7

    $2,150,000 New Construction

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

    LOT 8 Pond View, Holliston, MA 01746

    * UNDER CONSTRUCTION * SHOWSTOPPER * 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 & POOL CAPABILITY W/ HUGE PRIVATE BACKYARD ~ Location ... Location ...

    Francis Vazza Four Season Homes, Llc

    LOT 8 Pond View, Holliston, MA 01746
  • /19

    $514,000

    • 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
  • /23

    $429,900

    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    38 Clark St, Medway, MA 02053

    Attention Builders, Investors, and Visionaries! Incredible opportunity to own over 7 acres of land with fantastic potential. Restore the existing 3-bedroom, 1.5-bath home to its former charm, or start fresh and build new. An oversized detached 2-car garage with office space adds even more value and versatility to this property. It is priced below assessed value due to the home's need for

    Team Rice RE/MAX Executive Realty

    38 Clark St, Medway, MA 02053
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