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$814,000
3 Beds ⋅ 2 Baths ⋅ 73375340 MLS
OPEN HOUSE CANCELLED offer accepted!!! Wow! Welcome to 263 Ashland Street, this remarkable stone villa-style ranch set on a beautifully private 2.4-acre corner lot in the sought-after town of Holliston. This amazing property blends distinctive architecture, character-rich details, and exceptional space, all in a tranquil, nature-filled setting. Step inside and be captivated by vaulted ceilings, stone and tile flooring, and three fireplaces that create a cozy and inviting atmosphere. The spacious living room, bathed in natural light from oversized picture windows, opens seamlessly into a dining room with direct access to the outdoors, ideal for relaxing or entertaining.The primary suite is a true sanctuary featuring its own fireplace, beamed ceilings, exterior access, and a full en suite bath with plenty of storage and natural light. Two additional bedrooms provide versatility for family, guests, or a home office.

263 Ashland Street, Holliston

Listing courtesy of Listing Agent: Walsh Fine Homes Team from Listing Office: eXp Realty.
$293,000
2 Beds ⋅ 1 Baths ⋅ 73360927 MLS ⋅ ['The Oakridge Condominium'] BLDG.
This clean and well-maintained 2-bedroom home presents an excellent opportunity for both homeowners and investors. Situated at the quiet end of a wooded cul-de-sac, residents enjoy a peaceful tranquil setting. The property offers the convenience of on-site laundry facilities and secure storage allocated to each unit, along with one assigned parking space and generous visitor parking. This makes for a comfortable and practical living experience or a straightforward rental investment. Access to Holliston schools and parks, with area shopping and restaurants nearby. A great value!

49 Windsor Dr Unit 105, Holliston

Listing courtesy of Listing Agent: Scott Driscoll from Listing Office: Redfin Corp..
$1,575,000
4 Beds ⋅ 5 Baths ⋅ 73358083 MLS
Look no further! Situated in one of Holliston's coveted neighborhoods, this stunning, young (2022) "Smart Home" features a light and bright, open floorplan, gorgeous finishes, handsome expresso floors and high ceilings throughout. The chef's dream kitchen with Thermador appliances, 6-burner range,, two sinks and sunny breakfast area opens to both the spacious and inviting dining and living areas. A versatile1st floor room with beautiful French doors and adjacent shower bath is the ideal home office or in-law/ guest suite.Upstairs you'll find a deluxe Primary Suite with convenient coffee bar, spa-like bath and large his.and hers walk-in closet.Three generous bedrooms, one shower and one tub bath and laundry complete the 2nd floor. Perfect for game day or movie night is the recently finished lower level with its great space, custon built-ins, wet bar and half bath. Just minutes to downtown Holliston, the High School and Pinecrest Golf Club, this home is definitely a Must-See!

115 Fairview Street, Holliston

Listing courtesy of Listing Agent: The Walsh Team & Partners from Listing Office: William Raveis R.E. & Home Services.
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 73351271 MLS
Truly in a class all its own, this exceptional waterfront property with 400' of frontage offers a coveted and unsurpassed lifestyle that is a Metrowest Boston treasure. This custom crafted home is enveloped by water, wrapped in nature, featuring seamless integration between its interior and exterior spaces, with commanding views from every window. Open floor plan offers a brand new kitchen with cherry flooring; dining and living space w/gas FP. The oversized entry, home office/bedroom & powder room complete the main level. Upstairs, the primary bedroom will take your breath away - imagine waking up to the sights and sounds of Lake Winthrop, including occasional bald eagle sightings, and is complimented by its magazine worthy spa bathroom and dreamy walk-in closets. Two additional generously sized bedrooms upstairs; marble bath & laundry. Finished walkout lower level with exercize/sitting room, office/bedroom & full bath. Stunning professional landscaping enhances the natural beauty.

1 Norfolk Lane, Holliston

Listing courtesy of Listing Agent: Kathy Chisholm from Listing Office: Realty Executives Boston West.
$950,000
4 Beds ⋅ 2 Baths ⋅ 73347379 MLS
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, heated HW floors, granite counters, walls of windows, built-ins, 6 burner Wolf cooktop, SubZero fridge and large island w/wet bar. Dramatic floor to ceiling marble gas FP in family room; gracious living & dining rooms; dreamy screened porch; 2nd staircase & updated full bath complete the main level. Beautiful front staircase leads upstairs to the generously sized bedrooms, including the primary BR with its wall of custom closets & direct access to the stunning bath w/large tiled shower. Walk up 3rd floor offers more living space w/many possibilities. Zoned Village Residential & likely subdividable

35 Church Street, Holliston

Listing courtesy of Listing Agent: Kathy Chisholm from Listing Office: Realty Executives Boston West.
$347,500
1 Beds ⋅ 1 Baths ⋅ 73326361 MLS
Exceptional waterfront property on Lake Winthrop. Nice deck overlooking the lake makes for great entertaining or relaxation. Original 764 sf. bungalow currently sits on this site. Find out requirements to build new, expand or renovate. A property like this does not come around often. Come relax and enjoy the peaceful setting.

57 Lake Shore Drive, Holliston

Listing courtesy of Listing Agent: Jeffrey Fontaine from Listing Office: Fontaine Real Estate, Inc..
$703,000
2 Beds ⋅ 2 Baths ⋅ 73358119 MLS
Nestled on over a half acre in the heart of downtown Holliston, this enchanting home exudes peace and tranquility. The fenced-in side yard offers privacy, while the expansive back & side yards are perfect for summer cookouts. Step through the front door into a sun-drenched Sitting Room & Living Room, where warmth and coziness welcome you home. The first floor also features a beautiful Dining Room & spacious, open Kitchen-Family Room with a stunning wall of windows that fill the space w/natural light. The Kitchen, complete w/center island, a gas cooktop & stainless steel appliances, is a perfect gathering spot for everyone. A 2nd staircase leads to the generous Primary Suite & Bath, as well as a beautiful 2nd bedroom & main bath. The 3rd room offers flexibility for a home office or guest room. Located just minutes from Goodwill Park, shops, coffee shops, cafe's, top-rated schools, the library, & The Upper Charles Rail Trail make this a perfect location for all. New Septic System 2025!!

29 Austin Lane, Holliston

Listing courtesy of Listing Agent: Diane Regan from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.
$630,000
3 Beds ⋅ 2 Baths ⋅ 73377997 MLS
Already special — and ready to become extraordinary. This unique 3-level split is full of character and bursting with potential. Set on over 6 acres in sought-after Holliston, it offers a rare blend of privacy and convenience. With solid bones and functional systems, this property is the perfect canvas for contractors, investors, or creative homeowners ready to make their mark. Whether you're dreaming of a full renovation or just updating with your personal touch, the possibilities here are endless.Enjoy the charm of the existing features: an attached screen porch for summer evenings, a whimsical gazebo-style playhouse, and a spacious barn — all adding charm and opportunity. In addition to 3 bedrooms, 2 full baths, and a sprawling family room, there are two bonus rooms just off the living room, waiting to be reimagined. Sold AS IS, AS SEEN. Open House Sat 5/24 is on! OFFER DEADLINE IS MONDAY 5/26 at NOON! Please make offers good til 5PM on Tues 5/27. Seller will review all on Tues.

650 Marshall, Holliston

Listing courtesy of Listing Agent: Joselle Turner from Listing Office: ERA Key Realty Services.
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73372443 MLS
Discover this exquisite Colonial nestled in sought-after White Pines Estates neighborhood. An open, airy layout with sun-drenched spaces overlooks the professionally landscaped yard. The first floor centers around a remodeled kitchen with gleaming granite countertops, newer S/S appliances, a dining area and a pantry. This flows seamlessly to a fireplaced family room and a screened porch, and deck – ideal for entertaining. Formal living room, dining room, ½ bath, office, and garage access complete this level. Upstairs, a luxurious primary suite offers a spa-like bath with soaking tub, dual vanities, shower, as well as a walk-in closet and bonus room. Three well-sized bedrooms, a second full bath, and laundry complete this floor.The finished walk-out basement expands your living space and includes a stylish wet bar, offering endless possibilities for recreation and relaxation.The newer paver patio provides a perfect transition to the backyard, an ideal space for relaxation and enjoyment.

72 Kim Place, Holliston

Listing courtesy of Listing Agent: Alyssa Spear O'Grady from Listing Office: Lamacchia Realty, Inc..
$726,000
4 Beds ⋅ 2 Baths ⋅ 73363794 MLS
Enjoy all the charm of yesteryear in this lovingly maintained 4-bedroom farmhouse colonial, peacefully set on over 2 acres of land in a popular and convenient Holliston location. This inviting home welcomes you with a charming front porch and features a spacious kitchen with a generous dining area, updated appliances, and custom cabinetry. Relax in the wonderful sunroom or entertain guests in the formal dining room. The large living room, complete with a cozy fireplace, offers an inviting space to gather with family and friends. Upstairs, you'll find four good sized bedrooms and a full bath, providing comfortable living space for all. Outside, the long driveway offers ample parking and leads to a two-story barn with a basement—ideal for storage, hobbies, or future possibilities. A wonderful property!

390 Central Street, Holliston

Listing courtesy of Listing Agent: Ned Mahoney from Listing Office: eXp Realty.
$943,000
4 Beds ⋅ 3 Baths ⋅ 73358043 MLS
The perfect blend of old and new, this gracious waterfront home offers a wonderful floor plan with refined finishes and architectural detailing. The custom kitchen boasts a vaulted ceiling, dining area with slider to deck, commercial grade gas range, stainless appliances, large island, gardener's window and beverage fridge; inviting family room with box window and built-ins; lovely sitting/living room with French door and wood stove; sunny office with fireplace, beadboard and built-ins; fabulous mudroom and oversized full bath complete the main level. Upstairs are all four bedrooms, highlighted by the dreamy primary bedroom with its vaulted ceiling, water views, HW floors and multiple closets. Second bedroom is oversized, with water views and its own sitting/lounge area; other bedrooms also have wood flooring and closets. Outdoor spaces feature a bluestone patio, 3 season porch, mahogany decks & mature plantings. Oversized garage w/walk-up. Close to shopping, trails & major routes.

234 Courtland St., Holliston

Listing courtesy of Listing Agent: Kathy Chisholm from Listing Office: Realty Executives Boston West.
$1,800,000
4 Beds ⋅ 5 Baths ⋅ 73356005 MLS
Coveted residence at Summit Pointe exceeds expectations! The Home everyone wants to be invited to! Stunning Modern Farmhouse w/close to 5000SF on 2+ acres & gorgeous sunsets! The architectural details are breathtaking! Dreamy chef's kitchen inspires your inner gourmet w/custom shaker cabinetry, top of the line appliances, wine chiller, potfiller, fantasy grey granite & backsplash plus an entertainment size Isle to gather at. Sun drenched FR w/sophisticated coffered ceiling & gas FP.. Just imagine making memories for a lifetime! The Primary Retreat w/Hdwd, Sitting area & Spa like Ensuite w/soaking tub, custom shower plus his/hers closets. 4 Ensuite BR's! 4.5 BA's! 3rd flr walkup for expansion! Experience the famous Summit Pointe Pub in the FAB Lower level & take in a game of pool! Add a home office, media area & gym then step outside to a backyard OASIS w/custom stone patio & walls, firepit & uplighting, you'll never leave! Smart home feats, Solar, Tesla generators, Irrig & 3 car gar.

11 Summit Pointe Dr, Holliston

Listing courtesy of Listing Agent: The Real Estate Ladies Team from Listing Office: RE/MAX Executive Realty.
$2,800
1 Beds ⋅ 1 Baths ⋅ 73388309 MLS
Lakefront living at it's best! This rare and charming 1 bedroom house is set on the shores of Lake Winthrop and offers a serene and peaceful setting that you won't find in apartment living. Enjoy an open concept kitchen/dining area and living room that overlook the water through a wall of windows. You'll have access to the water and there is a dock if you would like to have a canoe or kayak. Driveway parking and detached 1 car garage space that is located directly across the street. The house is being offered with partial furnishings or without furnishings as needed. Electricity, propane for cooking, Internet, Water/Sewer are all included. Tenants pay for Oil to heat the house. Tenants to handle snow/ice removal and the lawn and garden maintenance. No pets, no smoking of any kind. Close to Patoma/Stoddard park with beach access, playground, hiking trails, baseball/soccer fields, tennis and basketball courts. See attached video tour!

53 Lakeshore Drive Unit ., Holliston

Listing courtesy of Listing Agent: Lynn A. Schreiner from Listing Office: Realty Executives Boston West.
$825,000
4 Beds ⋅ 3 Baths ⋅ 73378780 MLS
Staycation Ready! This 4-bedroom Colonial Is your own private oasis. Offering the perfect blend of comfort, style, and private outdoor space. Enjoy beautiful hardwood floors, a spacious eat-in kitchen ideal for gatherings, a formal living room, and a cozy family room with a fireplace. Spend your summer in the sun-drenched vaulted-ceiling sunroom, with its walls of sliders. It opens directly to the deck, leading to a spectacular fenced backyard with a stunning in-ground pool. Upstairs you'll find four generously sized bedrooms with hardwood flooring, including a primary suite with dual closets & en suite bath with an updated toilet and vanity. Updated main bath. Central air. Basement with garage entry, laundry hookups, and Buderus boiler. Wonderful, quiet neighborhood with sidewalks. Fantastic location, and top-rated Holliston school system!

69 Stonybrook Dr, Holliston

Listing courtesy of Listing Agent: Megan Tolland from Listing Office: Realty Executives Boston West.
$610,000
3 Beds ⋅ 2 Baths ⋅ 73360795 MLS
Welcome to this thoughtfully upgraded ranch-style home, offering comfort, efficiency, and convenience all on a single level. With a well-designed living space, this home offers easy living with modern amenities. Step inside to discover a newly renovated kitchen, perfect for cooking and entertaining. The freshly updated half bath adds a modern touch, while the full bath remains practical and bright. The flexible floor plan includes three bedrooms, with the third bedroom ideal as a home office, guest room, or creative space, offering privacy and natural light for those working from home. The home features solar electricity and solar hot water, supporting a sustainable lifestyle. Plus, an electric car charger is already installed, making it a dream for eco-conscious homeowners. Outside, enjoy a spacious backyard ideal for outdoor gatherings and gardening. Located in a quiet neighborhood yet close to amenities, this home is a smart blend of charm, value, and forward-thinking upgrades.

236 High St, Holliston

Listing courtesy of Listing Agent: Itisha Venugopal from Listing Office: Coldwell Banker Realty - Wellesley.
$1,475,000
3 Beds ⋅ 3 Baths ⋅ 73374207 MLS
Tucked at the end of a peaceful cul-de-sac, this exquisite Cape-style home sits on 7.8 acres of manicured grounds with a stunning heated saltwater pool—ideal for elegant entertaining or quiet relaxation. Renovated in 2010, the home blends timeless charm with modern sophistication. The chef’s kitchen features walnut and granite islands, high-end appliances, and a spacious butler’s pantry with second dishwasher, Sub-Zero 78-bottle wine fridge, generous cabinetry, and pool views. The second-floor primary suite is a true retreat with a spa-like bath—freestanding tub, walk-in shower, and double vanities. A private first-floor guest suite offers added comfort. Additional highlights include a home office, dual-sided fireplace, central air, full-house generator, cobblestone driveway with granite light posts. A rare opportunity to own a luxurious private sanctuary just moments from everyday conveniences.

91 Gretchen Lane, Holliston

Listing courtesy of Listing Agent: Jamie Grossman from Listing Office: MGS Group Real Estate LTD - Wellesley.
$710,000
3 Beds ⋅ 3 Baths ⋅ 73367883 MLS
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 attached garage with interior access, and new gutters (2025). The primary suite features an updated private bath. All bathrooms have been stylishly remodeled with stone countertops and modern finishes. Two finished bonus rooms on the lower level offer flexible space for an additional guest room, home office, or media room. The backyard is private and inviting, perfect for entertaining or quiet evenings outdoors. Ideally located is just a mile up the Rail Trail from local dining, shops, and ice cream. Don't miss out!

1874 Washington St, Holliston

Listing courtesy of Listing Agent: Matt Gorman from Listing Office: EDGE Realty Advisors.
$753,000
3 Beds ⋅ 2 Baths ⋅ 73369836 MLS
Serenity abounds in this classic Cape on cul-de-sac! Thoughtfully renovated, while retaining the original rustic charm. Open floor plan includes country kitchen with indoor grill & generous-sized dining area. Step-down great room has 9' ceiling, hardwood floors, and raised hearth fireplace. Main floor office has a sunroom feel, with loads of windows & tiled floor. Large 1st floor primary bedroom with built-in bookcases & beamed ceiling. The baths on each floor have custom-crafted cabinetry, tiled tub/shower. Convenient mudroom connects the new, 2-c garage to the kitchen, & offers a door to the patio overlooking the peaceful back yard. Basement presents an opportunity for additional living space, with a fireplace, and a craft room. Great town, great schools, great neighborhood!

145 Hemlock, Holliston

Listing courtesy of Listing Agent: Margo Otey from Listing Office: RE/MAX Executive Realty.
$625,000
3 Beds ⋅ 2 Baths ⋅ 73363331 MLS
Do not miss the opportunity to see this lovingly cared for property, owned for 50+ years by the sellers. Expanded kitchen in the 1980s to fantastic, cathedral ceiling w/ skylight, Corian island w/ seating & 2nd sink, wall oven, pantry, amazing cabinet space. SS appliances in last few years. Slider to terrific composite deck w/ auto retractable awning & steps down to stone patio. Sparkling hdwd flrs thru main level, just refinished. Dining & living rms w/ fireplace. Three bedrooms w/ closet systems. Upgraded main bath w/ double wide tile shower, pedestal sink & tile flr. Lower level offers family rm w/ brand new carpet & 2nd fireplace. Great half bath & laundry. Amazing basement storage & walk out to access back yard. Fresh interior paint 2025, brand new 3 bed septic, new electrical panels 2023, roof 2016 & windows approx. 10 yrs old, on demand H2O, HVAC 1996. Lush yard filled w/ mature plantings. Two car garage, awesome neighborhood, walkable to town!

48 Pinecrest Rd, Holliston

Listing courtesy of Listing Agent: Vesta Group from Listing Office: Vesta Real Estate Group, Inc..
$850,000
3 Beds ⋅ 3 Baths ⋅ 73357017 MLS
Step right in to this stunning, updated and sun filled home located in one of Holliston's most popular neighborhoods - great commuting location close to shops, commuter rail and major routes. Jaw dropping kitchen features custom white cabinetry, granite counters, stainless appliances & beverage fridge, flowing seamlessly to the dining area and dreamy sunroom/family room with vaulted ceiling and walls of windows overlooking the beautiful yard. Fireplaced living room; updated hallway bathroom with skylight & granite. Spectacular primary bedroom with vaulted ceiling, abundance of windows, custom walk-in closet, French door to deck and private full bathroom. Two other generously sized bedrooms complete the main level. The lower level offers a second fireplaced family/game room; a great office or 4th bedroom; half bath with laundry, plus lots of storage. Composite deck; lovely backyard; newer windows; brand new septic in 2020; solid interior doors. Move right in and enjoy the summer!

70 Orchard Lane, Holliston

Listing courtesy of Listing Agent: Kathy Chisholm from Listing Office: Realty Executives Boston West.
$665,000
2 Beds ⋅ 3 Baths ⋅ 73363197 MLS ⋅ ['Balancing Rock Village'] BLDG.
Charming 55+ Condo in Desirable Balancing Rock Village,Welcome to effortless living in this beautifully maintained condo located in the sought-after Balancing Rock Village. This spacious home offers a thoughtfully designed open floor plan that blends comfort with style. With a first-floor Primary Bedroom, enjoy the ease of single-level living with a generously sized primary suite featuring ample closet space and a private bath. The gorgeous Sunroom flooded with natural light, is the perfect spot to relax with your morning coffee or entertain guests year-round. Soaring ceilings in the main living area create a bright, airy atmosphere that enhances the open layout. The modern kitchen the updated kitchen features sleek finishes, plenty of cabinetry, and a functional layout ideal for both casual meals and entertaining. There are gleaming hardwood floors flowing throughout the main living areas, adding warmth and elegance. Brand new central AC and hot water heater installed 4/25!

53 Balancing Rock Dr Unit 53, Holliston

Listing courtesy of Listing Agent: Anthony Balzarini from Listing Office: LAER Realty Partners.
$3,400
4 Beds ⋅ 2 Baths ⋅ 73348417 MLS
Welcome to this beautifully renovated 4-bedroom + bonus room home, nestled on a quiet street near downtown Holliston. Thoughtfully updated by the owner as their own family home, it seamlessly blends modern upgrades with original charm. The home features new flooring, carpeting, freshly painted walls, updated windows, electrical, plumbing, siding, and basement work—all completed with care. Spacious bedrooms and a bright kitchen with updated floors offer versatility for families, guests, or a home office. The fully renovated bathroom feels fresh and modern, while the expansive yard is perfect for entertaining or relaxing beneath mature trees. Additional perks include in-unit laundry hookups, off-street parking, and pet-friendly options (case by case). Ideally located near parks, trails, schools, and Holliston’s quaint downtown, with easy access to Route 16, Route 126, and and commuter rail stations in Ashland and Natick.

49 Church St Unit 1, Holliston

Listing courtesy of Listing Agent: Entela Tase from Listing Office: Coldwell Banker Realty - Westwood.
$665,000
4 Beds ⋅ 2 Baths ⋅ 73367575 MLS
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 finish. Entertain in the dining room w/hardwoods & chair rails. The front to back living room has a fireplace & sliders out to the deck, running the length of the house. The den also has sliders out to the deck. The massive 2 car garage has a pull-down staircase to extra storage. The half bath completes this floor. Upstairs find a charming wrap around hallway with all bedrooms & the full bath. The 4th bedroom has charming small cape style storage/closets. The walkout finished basement has full windows a fireplace & wood stove. A nice level yard for gatherings. Close to ALL! Welcome home!

108 Prentice Street, Holliston

Listing courtesy of Listing Agent: Lydia Rajunas from Listing Office: RE/MAX Executive Realty.
$710,000
2 Beds ⋅ 3 Baths ⋅ 73363607 MLS ⋅ ['The Orchards At Holliston'] BLDG.
Here is the one you have wanted! This spacious, light filled 2014 end unit townhouse offers you choice of 1st or 2nd floor primary suites, granite/stainless eat-in kitchen with island seating & gas cooking, flowing easily into the cathedral ceilinged living room with gas fireplace, picture window & sliders to a large deck. The open floor plan is a delight, with hardwoods throughout the entertaining area.The entry & dining room feature decorative molding & bay window. The powder room, laundry & entrance to 2 car garage invite convenience. Upstairs - a generous loft, bonus room with French doors & walk in closet. The closets are abundant. A full basement adds even more storage & gives buyers the option of finishing. This lovely home faces east & backs west onto green space providing views & privacy. The Orchards - professionally managed, pet friendly, with high owner occupancy. Charming Holliston features great schools, outdoor open recreational spaces, major route access. Home.

106 Garett Way Unit 106, Holliston

Listing courtesy of Listing Agent: Connie Kickham from Listing Office: Coldwell Banker Realty - Newton.
$720,000
3 Beds ⋅ 2 Baths ⋅ 73344666 MLS
Beautifully maintained home with 3 levels of living space or enjoy 1st floor living. First floor enjoys a fireplace living room, dining room, kitchen w breakfast bar with wood block counters and new appliances. Main bedroom and full bath complete 1st floor. Second floor has 2 good size bedrooms and half bath. Lower level is fully finished adding @600 more sq ft of livable space. Entertainment room w built in bar and wine fridge w barn doors covering laundry and sink. In home office and separate gym. Newer windows, Hardwood flooring recently sanded and stained, Central AC, New bathroom vanities, new patio, recently interior painted. New water mitigation system w French drains. Beautiful fenced in yard with a gentle slope. 1 car detached garage. Easy access to highway/495, walking trails, golf course and Lake Winthrop.

35 Underwood St., Holliston

Listing courtesy of Listing Agent: Christopher M. Byrne from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$835,000
4 Beds ⋅ 3 Baths ⋅ 73363157 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home, close to top-rated schools and town amenities, this property offers the perfect blend of comfort and convenience for modern living. Step inside to discover three levels of sun-filled living space. The open-concept kitchen flows effortlessly into a cozy living room with a wood-burning fireplace—perfect for everyday living and relaxing evenings. A separate dining room provides an elegant setting for entertaining and special occasions. Upstairs, you’ll find three spacious bedrooms along with a primary suite featuring an en suite bath. The finished lower level offers endless flexibility—ideal for a home office, gym, playroom, or media space. Outside, enjoy an expansive deck overlooking a large, level backyard complete with a greenhouse—perfect for gardening, gatherings, or simply soaking up the seasons. Don’t miss the opportunity to make this exceptional property your forever home.

365 Highland St, Holliston

Listing courtesy of Listing Agent: Brian O'Keefe from Listing Office: Redfin Corp..
$695,000
3 Beds ⋅ 2 Baths ⋅ 73353909 MLS
**open house canceled**. Updated Multi-Level Home on Private 1.88-Acre Lot. Set behind a privacy fence and nestled on nearly 2 acres, this beautifully updated multi-level offers space, style, and seclusion. Fully remodeled in 2016 and recently refreshed with new carpeting and paint, the home features 3 bedrooms, 2 bathrooms, and a flexible layout that suits today’s lifestyle. The main level offers an inviting living room with fireplace and a large picture window, leading to an open eat-in kitchen with direct access to a spacious deck overlooking peaceful wooded views—perfect for outdoor entertaining or relaxing in nature. Upstairs, you'll find three comfortable bedrooms and a full bath. The finished lower level includes a second full bath and bonus space ideal for a family room, home office, or guest area—plus additional unfinished space for storage, workshop, or gym. Additional highlights include central air, 1-car garage, and a private, tree-lined lot just minutes to town.

2332 Washington Street, Holliston

Listing courtesy of Listing Agent: Alison Borrelli from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$690,000
4 Beds ⋅ 3 Baths ⋅ 73347508 MLS
This beautifully updated, downtown property presents with 4-bedrooms, 2.5-bathrooms, a garage and central air. It is a perfect blend of comfort and style. The first floor includes a modern kitchen, cozy living room, formal dining room, and separate family room all providing plenty of options for both relaxation and entertaining. On the second level is the primary suite, an additional bedroom and full bathroom. On the third floor are two bonus rooms, currently used as bedrooms, with tons of closet space. You will find beautiful hardwoods throughout the home. In addition, there is an amazing home office w separate entry over the detached one-car garage which is perfect for remote work, study or hobbies. This property also boasts a lovely yard that is ideal for outdoor activities, complete with a convenient shed for extra storage. The prime downtown location ensures an easy walk to shops, schools, rail trail and Lake Winthrop. Also listed as MLS#73347958.

20 Prospect St Unit 20, Holliston

Listing courtesy of Listing Agent: Lauren Davis from Listing Office: Realty Executives Boston West.
$2,250
2 Beds ⋅ 1 Baths ⋅ 73368547 MLS
Well maintained two bedroom apartment in desirable Holliston. Updated kitchen, new heating system, new septic system and extra storage make this apartment stand out from the rest. Located on a quiet street near nature trails and the center of town.

72 Jennings Rd. Unit 1, Holliston

Listing courtesy of Listing Agent: James Bruce from Listing Office: RE/MAX Executive Realty.
$656,000
4 Beds ⋅ 2 Baths ⋅ 73358270 MLS
Charming New England Cape nestled on a beautifully landscaped lot with stone wall on a quiet dead end with cul-de-sac close to town. Classic layout features a cozy living room with wood-burning fireplace insert that efficiently heats the entire home, plus a large bay window for abundant natural light. The updated kitchen offers granite countertops, stainless steel appliances, and flows to a spacious deck and patio overlooking a large level backyard designed for entertaining — complete with built-in firepit and plenty of room for play. Flexible first-floor layout provides options for 1st floor bedroom with adjacent full bath, home office and/or mudroom. Upstairs offers two generous bedrooms and a half bath. The partially finished lower level is perfect for a family room, home gym, or additional office space. Fantastic location with easy access to town, local shopping and just a short stroll to Rossini Corner stores.

23 Jarr Brook Rd, Holliston

Listing courtesy of Listing Agent: Team Lynch Real Estate Consultants from Listing Office: William Raveis R.E. & Home Services.

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