6,116

Middlesex, MA Homes

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  • /42

    $1,350,000 Pending

    • 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
  • /7

    $1,850 per month

    • 1 Bed
    • 1 Bath
    • 697 Sq Ft
    • Apartment for Rent

    152 Turner Rd Unit 7, Holliston, MA 01746

    Spacious and very well maintained 1 bedroom unit located in the most desirable Crestview Condominium Complex. Open floor plan kitchen/dining/living room combination. Large bedroom with oversized custom walk-in closet. Fully air conditioned with 2 mini splits. Close and easy access to Ashland and Framingham train stations and many major highways. Available September 1st! DON'T MISS OUT

    Sylwia Brucker Coldwell Banker Realty - Sharon

    152 Turner Rd Unit 7, Holliston, MA 01746
  • /26

    $692,434 Sold Aug 08, 2025

    • 1,278 Sq Ft
    • $542/SF
    • 2 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1952

    2 Rich Rd, Holliston, MA 01746

    Welcome Home!! This spacious charming cute Cape offers 3 bedrooms with cozy living room with NEW ENGLAND fireplace. Newer Roof, sun filled Pella Windows, Pella remote skylights, knotty Pine porch. BRAND NEW SEPTIC prior to closing. Surrounded by private wooded cul-de-sac road near conservation land. Conveniently located near highway access and shops downtown. Make your appointment to see this

    Lindsey Sarah Widak-Emanuel Lindsey Sarah Realty Group

    2 Rich Rd, Holliston, MA 01746
    • /24

      Est $468,115 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,086 Sq Ft

      9 Gregory Rd, Holliston, MA 01746

      9 Gregory Rd, Holliston, MA 01746
  • /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
  • /8

    $2,050 per month

    • 2 Beds
    • 1.5 Baths
    • 777 Sq Ft
    • Apartment for Rent

    26 Burnap Rd Unit 6, Holliston, MA 01746

    Great 2 bedroom apartment situated in a quiet place amidst beautiful natural vegetation. Some renovations were made during the seller's ownership such as high quality laminate flooring throughout the home, painting, and a recent refrigerator. This condo also offers private attic space, extra storage, and laundry room. Minutes to major routes 126, 495 and Mass pike

    Arleuza Maia Pablo Maia Realty

    26 Burnap Rd Unit 6, Holliston, MA 01746
  • /39

    $1,100,000 Sold Aug 08, 2025

    • 3,518 Sq Ft
    • $313/SF
    • 33 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1960

    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
    • /30

      Est $1,441,569 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 4,766 Sq Ft

      195 Mohawk Path, Holliston, MA 01746

      195 Mohawk Path, 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
  • /8

    $1,850 per month

    • 1 Bed
    • 1 Bath
    • 715 Sq Ft
    • Condo for Rent

    147 Turner Rd Unit 106, Holliston, MA 01746

    Freshly painted and recently updated third floor unit available for rent in desirable Crestview Condominium Development in Holliston. The beautiful updated kitchen has newer granite countertops and stainless steel appliances. Storage is never a problem as this unit has several closets. A washer and dryer is in the building for your convenience. Relax on your private personal balcony, or enjoy

    Eliot VanDam Coldwell Banker Realty - Sharon

    147 Turner Rd Unit 106, Holliston, MA 01746
  • /36

    $700,000 Sold Aug 07, 2025

    • 1,698 Sq Ft
    • $412/SF
    • 5 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1963

    124 South St, Holliston, MA 01746

    You do not want to miss this stunning split-level with updates galore! Enter the gorgeous, eat-in kitchen w/ quartz counters, oversized island, ss appliances, induction cooktop floating shelves open to living rm w/brick fireplace w/wood insert & bay window. Sun drenched dining rm w/beamed ceiling & wonderful natural light. Gleaming hdwds thru much of the home. Upstairs you will enjoy three

    Vesta Real Estate Group Vesta Real Estate Group, Inc.

    124 South St, Holliston, MA 01746
    • /34

      Est $1,424,377 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,096 Sq Ft

      607 Prentice St, Holliston, MA 01746

      607 Prentice 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
  • /42

    $1,006,000 Sold Aug 07, 2025

    • 3,362 Sq Ft
    • $299/SF
    • 7 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1960

    1221 Highland St, Holliston, MA 01746

    This meticulously cared for home in a jaw dropping 2.71 acre setting close to Holliston's downtown, Rail Trail and schools is a true delight. Sun filled, and thoughtfully expanded upon in 2002, with refined detailing and fine craftsmanship. Stunning family room with vaulted ceilings, floor to ceiling stone (gas) fireplace, HW flooring and walls of windows; beautiful kitchen (2012) with custom

    Kathy Chisholm Realty Executives Boston West

    1221 Highland St, Holliston, MA 01746
    • /38

      Est $1,368,276 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,096 Sq Ft

      589 Prentice St, Holliston, MA 01746

      589 Prentice St, Holliston, MA 01746
  • /38

    $869,900 Pending

    • 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
  • /27

    $752,500 Sold Aug 07, 2025

    • 2,022 Sq Ft
    • $372/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1968

    10 Temi Rd, Holliston, MA 01746

    This beautifully maintained ranch-style home is located in a welcoming neighborhood and oozes a true sense of pride in ownership.Inside you’ll find a sunken living room with cozy wood-burning fireplace.The kitchen features maple cabinetry and a breakfast bar with stool seating which seamlessly connects the dining and living areas.This main level also includes versatile spaces,such as a den and a

    Kate Swenson William Raveis R.E. & Home Services

    10 Temi Rd, Holliston, MA 01746
    • /42

      Est $797,470 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 2,457 Sq Ft

      43 Brooksmont Dr Unit 8, Holliston, MA 01746

      43 Brooksmont Dr Unit 8, Holliston, MA 01746
  • /40

    $899,000 Pending

    • 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
  • /42

    $1,195,000 Sold Aug 01, 2025

    • 3,977 Sq Ft
    • $300/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1996

    257 Underwood St, Holliston, MA 01746

    Set on a bucolic 10-home private drive, bordered by peaceful conservation land, this one-of-a-kind Southern Cape-style home on 3.7 acres blends timeless charm with refined comfort. From the inviting front porch, step into the exquisite two-story foyer with its custom open staircase. A wall of French door sliders fills the open-concept kitchen and family room w/incredible sunlight, creating

    Diane Regan Berkshire Hathaway HomeServices Robert Paul Properties

    257 Underwood St, Holliston, MA 01746
    • /39

      Est $722,717 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,028 Sq Ft

      21 Garett Way Unit 21, Holliston, MA 01746

      21 Garett Way Unit 21, Holliston, MA 01746
  • /42

    $939,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,124 Sq Ft

    535 Prentice St, Holliston, MA 01746

    Discover this rare contemporary retreat set on 14 private acres along scenic Prentice Street. Architecturally unique with soaring cathedral ceilings, this home offers a remodeled kitchen and baths, cozy living spaces, and a dedicated office. Perfect for entertaining and peaceful living, the expansive wrap-around deck with pergola overlooks a 20x40 Lazy L-shaped pool, fire pit area, greenhouse,

    Maria Babakhanova Redfin Corp.

    535 Prentice St, Holliston, MA 01746
  • /41

    $753,700 Sold Aug 01, 2025

    • 2,414 Sq Ft
    • $312/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1846

    21 Mechanic St, Holliston, MA 01746

    You will not want to miss this pristine Mudville antique in the heart of downtown Holliston. Wonderful beamed ceiling, eat-in kitchen w/tile flr & maple cabinets. Sparkling hdwd flrs through much of the home. Formal dining rm includes lovely built-in hutch. Amazing addition 2007-08 of fantastic family rm w/ wood insert & ceiling fan as well as tiled mudroom & gorgeous deck. Convenient 1st flr

    Vesta Real Estate Group Vesta Real Estate Group, Inc.

    21 Mechanic St, Holliston, MA 01746
    • /42

      Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 2,435 Sq Ft

      49 Brooksmont Dr Unit 10, Holliston, MA 01746

      49 Brooksmont Dr Unit 10, Holliston, MA 01746
  • /42

    $1,049,900 Pending

    • 4 Beds
    • 4 Baths
    • 2,578 Sq Ft

    35 Morgans Way, Holliston, MA 01746

    Discover this inviting colonial nestled on just under 1 acre in one of Holliston's most sought-after neighborhoods. Built in 1994, this well-maintained home features a newer roof, furnace, and hot water tank, all updated within the last 8 years. Offering four spacious bedrooms, including a primary suite that boasts an expansive bathroom with a soaking tub and a generous walk-in closet, this

    Leanne McCormick Milestone Realty, Inc.

    35 Morgans Way, Holliston, MA 01746
  • /42

    $550,000 Sold Jul 30, 2025

    • 1,092 Sq Ft
    • $504/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1958

    456 Prentice St, Holliston, MA 01746

    One level living made easy in this meticulously updated full basement ranch with AC, sited on over a half acre, flat lot. Beautiful kitchen with custom cherry cabinetry, stainless appliances, granite countertops and a spacious eating area overlooking the pretty backyard. Large living room with fireplace, hardwood flooring, oversized windows and arched doorways; nice dining room with hardwood

    Kathy Chisholm Realty Executives Boston West

    456 Prentice St, Holliston, MA 01746
    • /42

      Est $655,300 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,725 Sq Ft

      519 Fiske St, Holliston, MA 01746

      519 Fiske St, Holliston, MA 01746
  • /36

    $940,000 Pending

    • 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
  • /33

    $625,000 Sold Jul 30, 2025

    • 1,340 Sq Ft
    • $466/SF
    • 3 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1964

    4 Roberta Cir, Holliston, MA 01746

    OPEN HOUSE CANCELED 6/15 - OFFER ACCEPTED. Welcome to Roberta Circle—a charming and affordable home featuring 3 comfortable bedrooms and 1.5 baths. Enjoy cozy evenings in the fireside living room, perfect for relaxing or gathering with friends. The formal dining room adds a touch of elegance for special meals and celebrations.You'll love the warm hardwood flooring throughout, and the fully,

    Lynn Rossini RE/MAX Executive Realty

    4 Roberta Cir, Holliston, MA 01746
    • /42

      Est $665,332 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,320 Sq Ft

      15 Hill St, Medway, MA 02053

      15 Hill St, Medway, MA 02053
  • /42

    $1,095,000 Pending

    • 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
  • /41

    $940,000 Sold Jul 30, 2025

    • 3,542 Sq Ft
    • $265/SF
    • 26 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    54 Indian Ridge Rd S, Holliston, MA 01746

    This 4 bedroom Colonial has absolutely stunning curb appeal! Set in a nice neighborhood on 1.2 acres with a huge level fenced-in backyard, above ground pool, and an awesome farmer's porch! Nice size kitchen with dining area, center island, stainless steel appliances and sliders that lead to a deck overlooking an amazing backyard! Large family room with a fireplace, formal dining room, 1st floor

    Craig Morrison Realty Executives Boston West

    54 Indian Ridge Rd S, Holliston, MA 01746
    • /35

      Est $1,443,338 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 5,207 Sq Ft

      28 Mohawk Path, Holliston, MA 01746

      28 Mohawk Path, Holliston, MA 01746
  • /15

    $869,000 Pending

    • 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
  • /41

    $700,000 Sold Jul 30, 2025

    • 1,362 Sq Ft
    • $514/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1950

    29 Regal St, Holliston, MA 01746

    This stunning, completely renovated ranch, exudes impeccable style and quality, with no detail left untouched!! Nestled alongside the scenic Upper Charles Rail Trail, this home offers both tranquility and privacy, w/a New Trex Deck & Paver Patio and beautifully fenced in yard, perfect for hosting friends, relaxing with family or letting pets roam freely! As you step inside this sun filled home,

    Diane Regan Berkshire Hathaway HomeServices Robert Paul Properties

    29 Regal St, Holliston, MA 01746
    • /28

      Est $1,349,237 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,500 Sq Ft

      7 Tea Party Ln, Holliston, MA 01746

      7 Tea Party Ln, Holliston, MA 01746
  • /38

    $875,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,305 Sq Ft

    81 N Mill St, Holliston, MA 01746

    Discover the charm and elegance of this beautifully restored Antique Colonial, perfectly nestled on a private and serene 2-acre lot. This 3-bedroom, 2.5-bath home features rich hardwood floors, tile and marble, a bright and inviting kitchen with stainless steel appliances, sun-filled sitting room, dining room and an oversized living room with a wood-burning stove. A large bonus room offers

    Jennifer French RE/MAX Executive Realty

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

    $1,100,000 Sold Jul 29, 2025

    • 3,524 Sq Ft
    • $312/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2018

    41 Pleasant St, Holliston, MA 01746

    Stunning custom-built colonial perfectly situated in the heart of Holliston’s beloved Mudville neighborhood, close to downtown, the scenic Rail Trail, and Lake Winthrop.With 3,600+ square feet of thoughtfully designed living space, this home blends elegance with functionality. Wide-plank 7” oak flooring & oversized windows create a sun-drenched warm ambiance throughout. The gourmet kitchen

    Angela Caruso Realty Executives Boston West

    41 Pleasant St, Holliston, MA 01746
    • /34

      Est $1,275,793 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 4,844 Sq Ft

      27 Old Cart Path, Holliston, MA 01746

      27 Old Cart Path, Holliston, MA 01746
  • /25

    $739,000

    • 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

Showing Results 1 - 40, Page 1 of 18

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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