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Homes for Sale near Holliston High School

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  • 15 Fiske Pond Rd, Holliston, MA 01746
    15 Fiske Pond Rd, Holliston, MA 01746
    15 Fiske Pond Rd, Holliston, MA 01746
    /8

    $599,990

    • Land
    • 0.92 Acre
    • $652,163 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

    Agent Photo

    Bela Kasas

    Choice Realty RES

    (508) 593-1468

    15 Fiske Pond Rd, Holliston, MA 01746
  • 56 Paul Rd, Holliston, MA 01746
    56 Paul Rd, Holliston, MA 01746
    56 Paul Rd, Holliston, MA 01746
    /35

    $829,900 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,798 Sq Ft

    56 Paul Rd, Holliston, MA 01746

    Contractors & Savvy Buyers – Don’t Miss This Rare Opportunity! Discover this beautifully updated 3-bed, 2-bath Holliston gem, nestled on a peaceful cul-de-sac. The main home features a stunning maple cabinet kitchen with granite countertops and stainless-steel appliances, two stylishly renovated baths, and versatile finished lower-level rooms. Enjoy peace of mind with a newer roof, vinyl siding,

    Agent Photo

    Michelle Sebio Savje

    Coldwell Banker Realty - Franklin

    (508) 715-3642

    56 Paul Rd, Holliston, MA 01746
  • 14 Fiske Pond Rd, Holliston, MA 01746
    14 Fiske Pond Rd, Holliston, MA 01746
    14 Fiske Pond Rd, 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 -

    Agent Photo

    Bela Kasas

    Choice Realty RES

    (508) 980-2978

    14 Fiske Pond Rd, Holliston, MA 01746
  • 266 Willowgate Rise, Holliston, MA 01746
    266 Willowgate Rise, Holliston, MA 01746
    266 Willowgate Rise, Holliston, MA 01746
    /42

    $1,037,900 Open Sun 12PM - 2PM

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

    266 Willowgate Rise, Holliston, MA 01746

    Looking for a stunning home in one of Holliston’s most sought-after neighborhoods? This stately garrison colonial, in a desirable double cul-de-sac, offers exceptional living with a blend of elegance and comfort! Enjoy cozy evenings in the great room with its stunning stone fireplace, or gather in the kitchen featuring granite countertops, SS appliances, double oven, and butler’s pantry—ideal for

    Carolyn Chiantera RE/MAX Executive Realty

    266 Willowgate Rise, 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
  • 156 Mitchell Rd, Holliston, MA 01746
    156 Mitchell Rd, Holliston, MA 01746
    156 Mitchell Rd, Holliston, MA 01746
    /41

    $1,274,900

    • 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
  • 110 Bonney Dr, Holliston, MA 01746
    110 Bonney Dr, Holliston, MA 01746
    110 Bonney Dr, Holliston, MA 01746
    /31

    $1,599,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,469 Sq Ft

    110 Bonney Dr, Holliston, MA 01746

    Welcome to The Homes on Bonney Drive – a private three-home cul-de-sac in Holliston! 110 Bonney Drive offers ~3,500 sq. ft. of beautifully designed living space on over an acre. This 4-bedroom, 3.5-bath home blends modern luxury with energy-efficient living: all-electric, solar-ready, and roughed for EV charging. Open-concept layout features a gourmet kitchen, spacious family room, home office,

    Stephen O'leary O'Leary Homes

    110 Bonney Dr, Holliston, MA 01746
  • 133 Brooksmont Dr Unit 43, Holliston, MA 01746
    133 Brooksmont Dr Unit 43, Holliston, MA 01746
    133 Brooksmont Dr Unit 43, Holliston, MA 01746
    /20

    $709,000 Open Thu 4PM - 5:30PM

    • 2 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    133 Brooksmont Dr Unit 43, Holliston, MA 01746

    Beautiful Sorrento/Milan TWO story design at Brooksmont, a 55+ Adult Community in Holliston. Excellent scenic views from back deck and Main Bedroom. Single owner since built, this condo has Main Bedroom and Bath Suite on first floor with 2nd bedroom, bath AND LOFT area on second floor. Two heat/AC zones. Open floor plan with kitchen - dining - and living room. Convenient first floor laundry.

    Marjorie Levy Coldwell Banker Realty - Canton

    133 Brooksmont Dr Unit 43, Holliston, MA 01746
  • 107 Richard Rd, Holliston, MA 01746
    107 Richard Rd, Holliston, MA 01746
    107 Richard Rd, Holliston, MA 01746
    /42

    $559,000

    • 5 Beds
    • 2.5 Baths
    • 2,306 Sq Ft

    107 Richard Rd, Holliston, MA 01746

    Attention first time Homebuyers & Contractors! Large Multi-Level Home in a very desirable neighborhood – LOTS of Potential to put your own design style into this home! So many possibilities with this spacious 5-bedroom, 2.5-bath home located in one of the area's most sought-after neighborhoods. With multiple levels of living space, this property offers both functionality and flexibility for a

    Michelle Theriault Laffely Real Estate Associates

    107 Richard Rd, Holliston, MA 01746
  • 195 High St, Holliston, MA 01746
    195 High St, Holliston, MA 01746
    195 High St, Holliston, MA 01746
    /31

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,686 Sq Ft

    195 High St, Holliston, MA 01746

    Welcome to this inviting Cape-style home filled w/warmth, character + thoughtful updates throughout. The light filled family room w/vaulted beamed ceiling, feels like the heart of the home - offering views of the private backyard + walkout to the deck surrounded by stone gardens. Updated white kitchen w/granite counters + tile backsplash opens to both the family + dining rooms, creating a natural

    Ritucci & Swift - Your Home Team Realty Executives Boston West

    195 High St, Holliston, MA 01746
  • 131 Jennings Rd, Holliston, MA 01746
    131 Jennings Rd, Holliston, MA 01746
    131 Jennings Rd, Holliston, MA 01746
    /34

    $739,900

    • 3 Beds
    • 1.5 Baths
    • 1,748 Sq Ft

    131 Jennings Rd, Holliston, MA 01746

    Suburban Lifestyle:Nestled in a peaceful wooded setting, this 3-bedroom, 1.5-bath Saltbox Colonial combines classic charm with thoughtful updates. Built in 1989 with durable post & beam oak timber construction, the home features wide 12-inch pine floors and a warm, open layout. The updated kitchen offers quartz slab countertops, high-quality Shaker cabinets, and an under-counter microwave. The

    Karen McDermott Realty ONE Group Suburban Lifestyle

    131 Jennings Rd, Holliston, MA 01746
  • 54 Westfield Dr, Holliston, MA 01746
    54 Westfield Dr, Holliston, MA 01746
    54 Westfield Dr, Holliston, MA 01746
    /37

    $749,900

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    54 Westfield Dr, Holliston, MA 01746

    COMPLETELY RENOVATED 4 Br/2 bath 1 car garage colonial in a highly desirable East Holliston Neighborhood! Brand New Shaker style kitchen cabinets with recessed light, 2 pantry closets and a large 10 foot island! Kitchen opens to both the family room and dining room making this home great for entertaining! Brand new LVP flooring throughout first floor. Brand New Full 1st floor bathroom off kitchen

    Marcello Trolio Custom Realty Solutions

    54 Westfield Dr, Holliston, MA 01746
  • 0 Hill St, Holliston, MA 01746
    0 Hill St, Holliston, MA 01746
    /2

    $350,000

    • Land
    • 9.81 Acres
    • $35,678 per Acre

    0 Hill St, Holliston, MA 01746

    9+ Acre Parcel in Holliston, MA – Endless Possibilities.Discover the perfect opportunity to own over 9 acres of beautiful, versatile land in the highly sought-after town of Holliston. Nestled in a quiet, scenic setting with mature trees and natural landscapes, this expansive parcel offers the ideal canvas for your vision—whether it's a private estate, equestrian retreat, or potential development

    Fahd Khan Keller Williams Realty Boston South West

    0 Hill St, Holliston, MA 01746
  • 95 Brooksmont Dr Unit 26, Holliston, MA 01746
    95 Brooksmont Dr Unit 26, Holliston, MA 01746
    95 Brooksmont Dr Unit 26, Holliston, MA 01746
    /38

    $709,900

    • 2 Beds
    • 2 Baths
    • 2,431 Sq Ft

    95 Brooksmont Dr Unit 26, Holliston, MA 01746

    Beautiful Trentino One Story Design at Brooksmont of Holliston, a 55+ active Adult Community. This condo has everything you are looking for with convenient one level living. Open Floor Plan with Kitchen, Dining Area and Living Room great for gatherings! The Kitchen features huge center island with built-ins, custom soft close cabinets, granite countertops, tiled backsplash, upgraded stainless

    Karen Piedra Realty Executives Boston West

    95 Brooksmont Dr Unit 26, Holliston, MA 01746
  • 43 Bittersweet Cir Unit 43, Holliston, MA 01746
    43 Bittersweet Cir Unit 43, Holliston, MA 01746
    43 Bittersweet Cir Unit 43, Holliston, MA 01746
    /35

    $925,000

    • 2 Beds
    • 2.5 Baths
    • 2,384 Sq Ft

    43 Bittersweet Cir Unit 43, Holliston, MA 01746

    Nestled in a serene country setting, this impeccably maintained detached home is located in the highly sought-after 55+ community of Hollis Hills Preserve. Designed for comfort and easy living, the home features a spacious open-concept layout combining the kitchen, dining, and living areas—ideal for both everyday living and entertaining. You'll find two generously sized bedrooms, 2.5 bathrooms,

    Christine Norcross William Raveis R.E. & Home Services

    43 Bittersweet Cir Unit 43, Holliston, MA 01746
  • 1014 Highland St, Holliston, MA 01746
    1014 Highland St, Holliston, MA 01746
    1014 Highland St, Holliston, MA 01746
    /41

    $780,000

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

    1014 Highland St, Holliston, MA 01746

    This home blends modern comfort with future-ready features, making it a standout in Holliston’s competitive market. Modern elegance and value meet at 1014 Highland St. 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,

    Cristiano Jarbas Cristiano Jarbas, Inc.

    1014 Highland St, Holliston, MA 01746
  • 147 Turner Rd Unit 80, Holliston, MA 01746
    147 Turner Rd Unit 80, Holliston, MA 01746
    147 Turner Rd Unit 80, Holliston, MA 01746
    /22

    $224,900

    • 1 Bed
    • 1.5 Baths
    • 705 Sq Ft

    147 Turner Rd Unit 80, Holliston, MA 01746

    Spacious 1-bedroom condo on the first floor of the desirable Crestview Condominiums in Holliston. This bright unit features an open-concept kitchen and living area with white cabinets, matching appliances, and plenty of counter space. The generously sized bedroom offers a large walk-in closet for excellent storage. A full bath completes the layout. Laundry is conveniently located just down the

    Joe Norton Realty Executives Boston West

    147 Turner Rd Unit 80, Holliston, MA 01746
  • 62 Ashland St, Holliston, MA 01746
    62 Ashland St, Holliston, MA 01746
    62 Ashland St, Holliston, MA 01746
    /35

    $909,000

    • 4 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    62 Ashland St, Holliston, MA 01746

    Put a sparkle in your eye! BEST BACKYARD in Holliston! This house, is fully rebuilt, customized & expanded in ALL the right ways to support ease of family life, entertaining, cooking together, work at home, backyard fun, storage, versatility & low maintenance. This chefs kitchen with pantry and open dining is truly the heart of this home, FR has 2 generous sliders inviting outside in, with

    Susan Mogren Realty Executives Boston West

    62 Ashland St, 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

    Kathleen McBride RE/MAX Executive Realty

    Lot 2 Hanlon Rd, Holliston, MA 01746
  • 30 Powderhorn Ln, Holliston, MA 01746
    30 Powderhorn Ln, Holliston, MA 01746
    30 Powderhorn Ln, Holliston, MA 01746
    /39

    $850,000

    • 4 Beds
    • 2.5 Baths
    • 2,416 Sq Ft

    30 Powderhorn Ln, Holliston, MA 01746

    Attractive, well maintained 4 bedroom, 2 1⁄2 bath home located in a private setting at the end of a small cul-de-sac. Large living and dining rooms offer multiple configurations for entertainment and family gatherings. Wired ethernet installed for fast home networking. Heated sunroom overlooks a fenced in backyard great for kids and pets. Upstairs includes 4 bedrooms and a recently upgraded

    Greg Richard Realty Executives Boston West

    30 Powderhorn Ln, Holliston, MA 01746
  • 75 Ridge Rd, Holliston, MA 01746
    75 Ridge Rd, Holliston, MA 01746
    75 Ridge Rd, Holliston, MA 01746
    /34

    $529,000

    • 3 Beds
    • 1 Bath
    • 1,180 Sq Ft

    75 Ridge Rd, Holliston, MA 01746

    Opportunity knocks in one of Holliston’s most sought-after neighborhoods! This classic ranch offers single-level living with solid bones and many important updates already done, including vinyl siding, a newer hot water heater, central A/C, a newer generator, and more. Bring your vision and creativity—cosmetic updates throughout will make this home shine! Set on a generous lot, this property

    Team Rice RE/MAX Executive Realty

    75 Ridge Rd, Holliston, MA 01746
  • 152 Turner Rd Unit 14, Holliston, MA 01746
    152 Turner Rd Unit 14, Holliston, MA 01746
    152 Turner Rd Unit 14, Holliston, MA 01746
    /18

    $220,000

    • 1 Bed
    • 1 Bath
    • 693 Sq Ft

    152 Turner Rd Unit 14, Holliston, MA 01746

    Located at 152 Turner Road U:14, Holliston, MA, this condominium offers an opportunity to embrace comfortable living within a well-established community. This property presents a canvas for personalization and enjoyment. The living area, encompassing 693 square feet, provides a flexible space to create an environment tailored to your individual lifestyle and preferences. Imagine arranging your

    Linn Butler Afonso Real Estate

    152 Turner Rd Unit 14, Holliston, MA 01746
  • 104 Brooksmont Dr Unit 104, Holliston, MA 01746
    104 Brooksmont Dr Unit 104, Holliston, MA 01746
    104 Brooksmont Dr Unit 104, Holliston, MA 01746
    /26

    $639,000

    • 2 Beds
    • 2 Baths
    • 1,516 Sq Ft

    104 Brooksmont Dr Unit 104, Holliston, MA 01746

    Brooksmont at Holliston – This Florence model is set in a Serene 55+ community surrounded by mature woods and friendly neighbors who look out for one another. With just over 65 beautifully crafted condos built by Plute in four styles, This pet-friendly neighborhood offers the perfect blend of privacy, safety, and connection. Enjoy the community garden, nearby Ashland State Park for outdoor

    Cindy Laughrea Engel & Völkers Wellesley

    104 Brooksmont Dr Unit 104, Holliston, MA 01746
  • 45 Wendy Ln, Holliston, MA 01746
    45 Wendy Ln, Holliston, MA 01746
    45 Wendy Ln, Holliston, MA 01746
    /42

    $2,075,000

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

    45 Wendy Ln, Holliston, MA 01746

    NEW PRICE!!! 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

    Kimberly Collins Berkshire Hathaway HomeServices Robert Paul Properties

    45 Wendy Ln, 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
  • LOT 8 Pond View, Holliston, MA 01746
    LOT 8 Pond View, Holliston, MA 01746
    LOT 8 Pond View, Holliston, MA 01746
    /6

    $2,250,000 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 ~ CALL OFFICE FOR INFO & WALK THRU ** 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
Massachusetts Middlesex County Holliston Holliston High School

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