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Holliston, MA Homes for Sale

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

    Agent Photo

    Bela Kasas

    Choice Realty RES

    (508) 593-1468

    15 Fiske Pond Rd, Holliston, MA 01746
  • 2 Towne Lyne Rd, Sherborn, MA 01770
    2 Towne Lyne Rd, Sherborn, MA 01770
    2 Towne Lyne Rd, Sherborn, MA 01770
    /34

    $1,150,000

    • 4 Beds
    • 2.5 Baths
    • 2,739 Sq Ft

    2 Towne Lyne Rd, Sherborn, MA 01770

    Spacious and bright Cape style home on one of the prettiest cul-de-sac streets in town. Sunny eat-in kitchen with plenty of storage, stainless appliances, step down to fireplaced family room, hardwood floors, 2-story living room with open staircase, first floor bedroom/office and huge deck with slider access from both kitchen and family room. This home has been nicely maintained with numerous

    Agent Photo

    Maryann Clancy

    Berkshire Hathaway HomeServices Commonwealth Real Estate

    (508) 691-7865

    2 Towne Lyne Rd, Sherborn, MA 01770
  • 121 Bullard St, Holliston, MA 01746
    121 Bullard St, Holliston, MA 01746
    121 Bullard St, Holliston, MA 01746
    /42

    $985,806

    • 4 Beds
    • 4 Baths
    • 3,775 Sq Ft

    121 Bullard St, Holliston, MA 01746

    Exceptional two-level home with two remarkable expansions, designed for entertaining and everyday living. The main level, the social hub, features formal dining and living rooms with fireplace, flowing into a carefully crafted eat-in kitchen with granite, abundant storage, and breakfast bar. The cathedral family room stuns with soaring wood-planked vaulted ceilings, dramatic floor-to-ceiling

    Ann Atamian Gibson Sotheby's International Realty

    121 Bullard St, Holliston, MA 01746
  • 14 Andrew Ln, Holliston, MA 01746
    14 Andrew Ln, Holliston, MA 01746
    14 Andrew Ln, Holliston, MA 01746
    /42

    $925,000 Open Fri 4PM - 5:30PM

    • 5 Beds
    • 3 Baths
    • 3,140 Sq Ft

    14 Andrew Ln, Holliston, MA 01746

    This spacious home in a highly coveted Holliston neighborhood offers a wonderfully flexible floor plan, with plenty of room for all. Brand new 5 bedroom septic system; 3 full baths, 2 fireplaces, updates galore and a gorgeous, private, flat backyard. Entertain with ease and style in the huge, magazine worthy kitchen, featuring hardwood floors, custom cabinetry, lots of counter space, oversized

    Kathy Chisholm Realty Executives Boston West

    14 Andrew Ln, Holliston, MA 01746
  • 30 Powderhorn Ln, Holliston, MA 01746
    30 Powderhorn Ln, Holliston, MA 01746
    30 Powderhorn Ln, Holliston, MA 01746
    /39

    $875,000 Open Sun 2PM - 3PM

    • 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
  • 30 Arthur St, Holliston, MA 01746
    30 Arthur St, Holliston, MA 01746
    30 Arthur St, Holliston, MA 01746
    /39

    $875,000

    • 4 Beds
    • 2.5 Baths
    • 2,584 Sq Ft

    30 Arthur St, Holliston, MA 01746

    Set on over 3 acres at the end of a cul-de-sac, this beautiful 4-bedroom Garrison Colonial offers both privacy and charm in the desirable town of Holliston. Meticulously maintained, the home features many recent updates including a new high-efficiency heating system (2023), roof (2017), fresh interior paint (2025), and brand-new bedroom carpets (2025). A spacious family room addition creates an

    Campos Homes RE/MAX Real Estate Center

    30 Arthur St, Holliston, MA 01746
  • 169 Pinecrest Rd, Holliston, MA 01746
    169 Pinecrest Rd, Holliston, MA 01746
    169 Pinecrest Rd, Holliston, MA 01746
    /39

    $1,295,000

    • 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 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 suite offers a

    Joshua Shalin ERA Key Realty Services-Bay State Group

    169 Pinecrest Rd, 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
  • 62 Carl Rd, Holliston, MA 01746
    62 Carl Rd, Holliston, MA 01746
    62 Carl Rd, Holliston, MA 01746
    /41

    $725,000 Open Sat 11AM - 12:30PM

    • 4 Beds
    • 1.5 Baths
    • 1,870 Sq Ft

    62 Carl Rd, Holliston, MA 01746

    Fabulous four bedroom colonial in one of Holliston's most sought after neighborhoods, close to shopping, commuter rail and major routes. Sited on a private corner lot, on a cul-de-sac, this home has been meticulously updated and maintained. Stunning kitchen with granite counters, custom cabinetry, built-in window seat, brand new double oven, Fisher Paykel dishwasher, walk-in pantry and crown

    Kathy Chisholm Realty Executives Boston West

    62 Carl Rd, Holliston, MA 01746
  • 56 Roy Ave, Holliston, MA 01746
    56 Roy Ave, Holliston, MA 01746
    56 Roy Ave, Holliston, MA 01746
    /40

    $549,000 Open Fri 5PM - 6:30PM

    • 4 Beds
    • 1.5 Baths
    • 1,901 Sq Ft

    56 Roy Ave, Holliston, MA 01746

    Attention Contractors! Charming Multi-Level Home in a Desirable Neighborhood – Great Potential!! Discover the possibilities with this spacious 4-bedroom, 1.5-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 variety of lifestyles. Step outside and enjoy the large backyard

    Team Metrowest Berkshire Hathaway HomeServices Commonwealth Real Estate

    56 Roy Ave, 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
  • 85 Water St, Holliston, MA 01746
    85 Water St, Holliston, MA 01746
    85 Water St, Holliston, MA 01746
    /28

    $449,000

    • 2 Beds
    • 1 Bath
    • 1,428 Sq Ft

    85 Water St, Holliston, MA 01746

    Welcome to Holliston! This charming Antique Colonial is the perfect opportunity to make your mark in the heart of Mudville. Ideally located just a short walk to downtown Holliston, Lake Winthrop, and local schools, this home blends classic character with modern updates.Enjoy the open-concept family and dining room addition (2005), a fully remodeled kitchen and bath (2008), updated electrical, and

    Street Property Team Keller Williams Realty Boston Northwest

    85 Water St, Holliston, MA 01746
  • 485 Central St, Holliston, MA 01746
    485 Central St, Holliston, MA 01746
    485 Central St, Holliston, MA 01746
    /32

    $669,900 Open Sat 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,512 Sq Ft

    485 Central St, Holliston, MA 01746

    Welcome to this charming Cape-style 4-bedroom/2 bath home with a 1-car garage. This property, w/over a half-acre of amazing outdoor space including newly planted gardens, features a 1st floor living room & fireplace that flows perfectly into the eat in kitchen with stainless steel appliances. The 1st floor is rounded out with a full bathroom & 2 bedrooms. Off the kitchen area, step into to the

    Amy Uliss MDM Realty, Inc

    485 Central St, Holliston, MA 01746
  • 15 Whispering Ln, Holliston, MA 01746
    15 Whispering Ln, Holliston, MA 01746
    15 Whispering Ln, Holliston, MA 01746
    /42

    $1,800,000

    • 4 Beds
    • 5 Baths
    • 6,498 Sq Ft

    15 Whispering Ln, Holliston, MA 01746

    Meticulous craftsmanship defines this exceptional home in the coveted Deer Creek community. Built as the builder’s own residence, every detail reflects superior design and quality. A dramatic entry sets the tone with elegant millwork, gleaming hardwood floors, and abundant natural light. The main level offers a dining room, private office, family & living room, both w/ fireplace & custom built-in

    Kathleen McBride RE/MAX Executive Realty

    15 Whispering 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
    /9

    $225,000

    • 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
  • 175 Westfield Dr, Holliston, MA 01746
    175 Westfield Dr, Holliston, MA 01746
    175 Westfield Dr, Holliston, MA 01746
    /39

    $639,900 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,336 Sq Ft

    175 Westfield Dr, Holliston, MA 01746

    This charming 3-BR, 2.5-bath Cape-style home offers a perfect blend of comfort and space. Second-floor and back-of-house additions make this home much larger than it appears.The welcoming front LR features a large picture window filling the room w/natural light, and the DR is an ideal setting for special occasions while the eat-in kitchen is perfect for everyday meals. A cozy fireside FR

    Lynn Rossini RE/MAX Executive Realty

    175 Westfield Dr, Holliston, MA 01746
  • 9 Ruth Ellen Rd, Holliston, MA 01746
    9 Ruth Ellen Rd, Holliston, MA 01746
    9 Ruth Ellen Rd, Holliston, MA 01746
    /35

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 2,118 Sq Ft

    9 Ruth Ellen Rd, Holliston, MA 01746

    Welcome to 9 Ruth Ellen Rd! This single-family residence in presents a remarkable opportunity to establish roots in a desirable neighborhood. This property offers a blend of classic charm and the potential for modern enhancements. The residence features four bedrooms and two full bathrooms, along with a conveniently located half bathroom, providing ample space for comfortable living. With 2118

    Gustavo Villatoro Coldwell Banker Realty - Framingham

    9 Ruth Ellen Rd, 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
    /25

    $689,000

    • 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
  • 880 Washington St, Holliston, MA 01746
    880 Washington St, Holliston, MA 01746
    880 Washington St, Holliston, MA 01746
    /26

    $725,000

    • 4 Beds
    • 3 Baths
    • 2,056 Sq Ft

    880 Washington St, Holliston, MA 01746

    Discover this this beautifully maintained Italianate Colonial, ideally located in the heart of Holliston. Light-filled with high ceilings and open concept, the first floor welcomes you with a large front entry.This legal two-family home offers the best of both worlds—functioning seamlessly as a spacious single-family residence with the added bonus of a flexible private exterior entry, lower-level

    Stephanie Sugden Compass

    880 Washington St, Holliston, MA 01746
  • 58 Front St, Holliston, MA 01746
    58 Front St, Holliston, MA 01746
    58 Front St, Holliston, MA 01746
    /38

    $499,900

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

    58 Front St, Holliston, MA 01746

    **Back on the market to due Buyer Cold Feet** 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

    Janine Wuschke Keller Williams Realty

    58 Front St, Holliston, MA 01746
  • 329 Gorwin Dr, Holliston, MA 01746
    329 Gorwin Dr, Holliston, MA 01746
    329 Gorwin Dr, Holliston, MA 01746
    /30

    $739,900 Open Sun 11:30AM - 1PM

    • 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
  • 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
  • 52 Jasper Hill Rd, Holliston, MA 01746
    52 Jasper Hill Rd, Holliston, MA 01746
    52 Jasper Hill Rd, Holliston, MA 01746
    /5

    $499,000

    • 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
  • 45 Wendy Ln, Holliston, MA 01746
    45 Wendy Ln, Holliston, MA 01746
    45 Wendy Ln, 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
  • 0 Hill St, Holliston, MA 01746
    0 Hill St, Holliston, MA 01746
    /2

    $400,000

    • Land
    • 9.81 Acres
    • $40,775 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
  • 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
  • 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
  • LOT 8 Pond View, Holliston, MA 01746
    LOT 8 Pond View, Holliston, MA 01746
    LOT 8 Pond View, Holliston, MA 01746
    /3

    $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 & POOL

    Francis Vazza Four Season Homes, Llc

    LOT 8 Pond View, Holliston, MA 01746
  • 9 South St, Ashland, MA 01721
    9 South St, Ashland, MA 01721
    9 South St, Ashland, MA 01721
    /40

    $774,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    9 South St, Ashland, MA 01721

    Welcome to this beautifully maintained center entrance colonial, perfect blend of classic charm and modern finishes. This 4 bedroom, 2.5 bath home is truly in a nature lover's paradise. Very close distance you will find Ashland Woods,120 acres of natural beauty, an ideal place to hike and enjoy nature. Less than 2 minutes away is the Ashland Reservoir where you can kayak, swim and fish, and hike

    John Szolomayer RE/MAX Executive Realty

    9 South St, Ashland, MA 01721
  • 8 Raymond Way, Ashland, MA 01721
    8 Raymond Way, Ashland, MA 01721
    8 Raymond Way, Ashland, MA 01721
    /37

    $799,900 Open Sat 4:30PM - 5:30PM

    • 4 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

    8 Raymond Way, Ashland, MA 01721

    Discover elegance and comfort at 8 Raymond Way, Ashland, MA — a beautifully maintained 4-bedroom, 3-bathroom home that blends style, space, and functionality in one of Ashland’s most coveted neighborhoods. With light-filled, inviting living areas, an open layout ideal for entertaining, and quality finishes throughout, this property offers both immediate move-in appeal and long-term value. The

    John Grande Media Realty Group Inc.

    8 Raymond Way, Ashland, MA 01721
  • 84 Meeting House Path Unit 84, Ashland, MA 01721
    84 Meeting House Path Unit 84, Ashland, MA 01721
    84 Meeting House Path Unit 84, Ashland, MA 01721
    /42

    $489,900

    • 2 Beds
    • 1.5 Baths
    • 1,316 Sq Ft

    84 Meeting House Path Unit 84, Ashland, MA 01721

    WELCOME TO THIS DESIRABLE UNIT IN A QUIET NEIGHBORHOOD. WELL-MAINTAINED UNIT, WITH TWO BEDROOMS AND ONE AND A HALF BATHROOMS. MAIN LEVEL OFFERS LIVING ROOM WITH HARDWOOD FLOORS, FIREPLACE, ONE HALF BATHROOM AND SLIDER DOOR TO DECK. UPDATED KITCHEN WITH GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, DINING ROOM AREA AND EXTERIOR ACCESS. ON THE SECOND FLOOR ARE TWO GOOD SIZED BEDROOMS WITH

    Eusa Pessote RE/MAX One Call Realty

    84 Meeting House Path Unit 84, Ashland, MA 01721
  • 306 Trailside Way, Ashland, MA 01721
    306 Trailside Way, Ashland, MA 01721
    306 Trailside Way, Ashland, MA 01721
    /19

    $499,999

    • 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
  • 27 Richardson Dr Unit 27, Millis, MA 02054
    27 Richardson Dr Unit 27, Millis, MA 02054
    27 Richardson Dr Unit 27, Millis, MA 02054
    /38

    $988,900

    • 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
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 $832,300.
How many homes have sold over the last 12 months in Holliston, MA?
163 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 $725,000. If you put a 20% down payment of $145,000 and had a 30-year fixed mortgage with an interest rate of 6.35%, your estimated principal and interest payment would be $3,610 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $155K 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

On average, homes in Holliston, MA sell after 20 days on the market compared to the national average of 52 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
$751,250
Median Townhouse Sale Price
$694,950
Median 2 Bedroom Sale Price
$650,000
Median 1 Bedroom Sale Price
$240,000
Average Price Per Sq Ft
$354
Number of Homes for Sale
24
Last 12 months Home Sales
163
Months of Supply
1.80
Median List Price
$725,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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