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Charming 3-bedroom Ranch beautifully situated on over an acre of land! Surrounded by woodlands, the expansive backyard offers a peaceful, private retreat with plenty of space for outdoor entertaining, gardening, recreation and relaxation. A spacious screened porch opens to a large deck overlooking the picturesque grounds, while a dedicated fire pit area provides another inviting spot to gather with family and friends. Inside, this warm and welcoming home features hardwood flooring, an updated kitchen with center island and a delightful dining area with built-in bench seating. The sun-filled, generously sized living room boasts a beautiful stone fireplace and distinctive wide-plank flooring, creating an inviting space for everyday living and entertaining. Three bedrooms and an updated full bath complete the main level. The finished lower level adds exceptional versatility, offering flexible space ideal for a playroom, home office or guest quarters, along with a second full bath. Additional highlights include central AC, a new furnace, new driveway, 1-car garage and numerous other updates. Offering far more than meets the eye, this delightful home combines comfortable, manageable living spaces with a versatile finished lower level and exceptional outdoor amenities. Perfect for first-time buyers, those looking to downsize or anyone seeking a home filled with charm, functionality and wonderful spaces for entertaining and relaxation. A special property with so much to offer! A must-see!

3 Beds ⋅ 2 Baths ⋅ 73596485 MLS

Charming 3-bedroom Ranch beautifully situated on over an acre of land! Surrounded by woodlands, the expansive backyard offers a peaceful, private retreat with plenty of space for outdoor entertaining, gardening, recreation and relaxation. A spacious screened porch opens to a large deck overlooking the picturesque grounds, while a dedicated fire pit area provides another inviting spot to gather with family and friends. Inside, this warm and welcoming home features hardwood flooring, an updated kitchen with center island and a delightful dining area with built-in bench seating. The sun-filled, generously sized living room boasts a beautiful stone fireplace and distinctive wide-plank flooring, creating an inviting space for everyday living and entertaining. Three bedrooms and an updated full bath complete the main level. The finished lower level adds exceptional versatility, offering flexible space ideal for a playroom, home office or guest quarters, along with a second full bath. Additional highlights include central AC, a new furnace, new driveway, 1-car garage and numerous other updates. Offering far more than meets the eye, this delightful home combines comfortable, manageable living spaces with a versatile finished lower level and exceptional outdoor amenities. Perfect for first-time buyers, those looking to downsize or anyone seeking a home filled with charm, functionality and wonderful spaces for entertaining and relaxation. A special property with so much to offer! A must-see!

478 Prentice Street, Holliston

$729,900

Welcome to 29 Garett Way, a Parkland end-unit townhouse at The Orchards with two bedrooms, two and a half baths, and flexible living spaces across three levels. A backyard abutting conservation land provides privacy and a natural backdrop to the home. Enjoy morning coffee, outdoor dining, or time to unwind on the sun deck overlooking the adjoining conservation land. Inside, the living room opens beneath an 18-foot cathedral ceiling, with two skylights bringing in natural light and a gas fireplace creating a focal point. Sliding doors connect the living room to the deck, extending the gathering space outdoors. Hardwood floors connect the main living areas, while nine-foot ceilings add to the open feel. The kitchen combines granite countertops, stainless steel appliances, a center island, and a breakfast area. A separate dining room provides space for everyday meals and larger gatherings. The first-floor primary suite offers the convenience of main-level living, with a walk-in closet and a private bath with granite finishes. Upstairs, an additional bedroom, an open loft suited to office space, and a separate bonus room can serve as a third bedroom, hobby room, or workspace. Modular California Closets, along with eave storage, provide practical organization and storage options. The finished lower level offers generous room for entertaining, from movie nights to gatherings with friends. Alongside the family room, a separate enclosed room provides flexibility as an office, game room, gym, or media room, with potential for a guest bedroom. Separate spaces allow room for recreation and focused activities without taking over the main living areas. EV charger in the garage and new water heater being installed. From the open living room and first-floor primary suite to the versatile finished lower level, this home balances gathering spaces with places to retreat. The end-unit setting, private rear outdoor space, and adjoining conservation land complete the setting at The Orchards.

2 Beds ⋅ 3 Baths ⋅ 73596436 MLS ⋅ ['The Orchards At Holliston Condominium'] BLDG.

Welcome to 29 Garett Way, a Parkland end-unit townhouse at The Orchards with two bedrooms, two and a half baths, and flexible living spaces across three levels. A backyard abutting conservation land provides privacy and a natural backdrop to the home. Enjoy morning coffee, outdoor dining, or time to unwind on the sun deck overlooking the adjoining conservation land. Inside, the living room opens beneath an 18-foot cathedral ceiling, with two skylights bringing in natural light and a gas fireplace creating a focal point. Sliding doors connect the living room to the deck, extending the gathering space outdoors. Hardwood floors connect the main living areas, while nine-foot ceilings add to the open feel. The kitchen combines granite countertops, stainless steel appliances, a center island, and a breakfast area. A separate dining room provides space for everyday meals and larger gatherings. The first-floor primary suite offers the convenience of main-level living, with a walk-in closet and a private bath with granite finishes. Upstairs, an additional bedroom, an open loft suited to office space, and a separate bonus room can serve as a third bedroom, hobby room, or workspace. Modular California Closets, along with eave storage, provide practical organization and storage options. The finished lower level offers generous room for entertaining, from movie nights to gatherings with friends. Alongside the family room, a separate enclosed room provides flexibility as an office, game room, gym, or media room, with potential for a guest bedroom. Separate spaces allow room for recreation and focused activities without taking over the main living areas. EV charger in the garage and new water heater being installed. From the open living room and first-floor primary suite to the versatile finished lower level, this home balances gathering spaces with places to retreat. The end-unit setting, private rear outdoor space, and adjoining conservation land complete the setting at The Orchards.

29 Garett Way Unit 29, Holliston

$1,499,900

Luxury curated for the way you live!! A thoughtfully designed home with all the bells and whistles! Top brands like Subzero, Wolf, are a dream for a chef inspired kitchen with beautiful quartz countertops and backsplashes. Skylights let the sunshine pour in while your studio McGee Audrine sink helps with clean up. The dining area leads to an outside oversized blue stone patio which invites you to enjoy nature and migrate dinners from the table to meaningful patio conversations. High end plumbing fixtures such as Waterworks, Kohler, Toto, Signature, and Brizo kitchen faucets are featured throughout the home. Relax in your sun-drenched family room that features built in cabinetry with a gas fireplace. This home also has a lower-level room with a full bath and full walk-out for anyone seeking accommodations for an in-law, or home office, or secondary family room. Drive up your driveway with stone walls to come home to your personal oasis. Finally, after a long day retreat to your primary bedroom with your private spa like bath featuring a soaking tub and tiled shower to unwind from life's demands. This environment is created to calm the mind and restore the spirit. This parcel abuts 2 large tracts of restricted conservation land assuring you that you will always hear the birds singing.

4 Beds ⋅ 4 Baths ⋅ 73595472 MLS

Luxury curated for the way you live!! A thoughtfully designed home with all the bells and whistles! Top brands like Subzero, Wolf, are a dream for a chef inspired kitchen with beautiful quartz countertops and backsplashes. Skylights let the sunshine pour in while your studio McGee Audrine sink helps with clean up. The dining area leads to an outside oversized blue stone patio which invites you to enjoy nature and migrate dinners from the table to meaningful patio conversations. High end plumbing fixtures such as Waterworks, Kohler, Toto, Signature, and Brizo kitchen faucets are featured throughout the home. Relax in your sun-drenched family room that features built in cabinetry with a gas fireplace. This home also has a lower-level room with a full bath and full walk-out for anyone seeking accommodations for an in-law, or home office, or secondary family room. Drive up your driveway with stone walls to come home to your personal oasis. Finally, after a long day retreat to your primary bedroom with your private spa like bath featuring a soaking tub and tiled shower to unwind from life's demands. This environment is created to calm the mind and restore the spirit. This parcel abuts 2 large tracts of restricted conservation land assuring you that you will always hear the birds singing.

10 Laurel Glen Ct, Holliston

$2,500,000

Northeast Private Client Group is pleased to present 459-465Washington St, a six-suite retail plaza on 1.53 acres in Holliston,Massachusetts, in the MetroWest region. The 1967 plaza holds 7,063rentable square feet along Washington Street.Five suites are home to everyday businesses: Subway, Kings Pizza,Jings Garden, a liquor store and a jewelry store, in suites from 563 to1,900 square feet. Three food operators and a package store give theplaza reasons for repeat, daily visits from the surroundingneighborhood.The value-add starts with one 1,600 SF suite. A new owner can choosethe tenant that best rounds out the mix and strengthens the plaza'sdraw. The plaza's next chapter is shaped by one leasing decision.The plaza's buildings, dating to 1967, cover roughly 11% of the 1.53-acresite, which gives a hands-on owner room to reposition the propertyover time.

73595425 MLS

Northeast Private Client Group is pleased to present 459-465Washington St, a six-suite retail plaza on 1.53 acres in Holliston,Massachusetts, in the MetroWest region. The 1967 plaza holds 7,063rentable square feet along Washington Street.Five suites are home to everyday businesses: Subway, Kings Pizza,Jings Garden, a liquor store and a jewelry store, in suites from 563 to1,900 square feet. Three food operators and a package store give theplaza reasons for repeat, daily visits from the surroundingneighborhood.The value-add starts with one 1,600 SF suite. A new owner can choosethe tenant that best rounds out the mix and strengthens the plaza'sdraw. The plaza's next chapter is shaped by one leasing decision.The plaza's buildings, dating to 1967, cover roughly 11% of the 1.53-acresite, which gives a hands-on owner room to reposition the propertyover time.

459-465 Washington St, Holliston

$650,000

Unlock the potential of this hidden gem in Holliston! Tucked away and privately set back from the road, this home offers a rare opportunity to create your dream sanctuary on a spectacular 2.73-acre lot. Nature lovers will appreciate the tranquility of this location, which borders expansive conservation land, providing ultimate privacy and a peaceful backdrop. The property features a large, flat yard perfect for outdoor activities, gardens, or recreation. Inside, the home provides a versatile floor plan with 3 bedrooms and 2 full bathrooms. The first floor layout includes 2 bedrooms, a full bath and a large fireplaced living room. The second floor features the primary bedroom, a second full bath and a spacious second living room that offers excellent flexibility for a home office, media room, or guest retreat. A new septic system is being installed, the roof, heating system and hot water heater have all been updated in recent years and the large full basement provides ample storage and is already partially finished. This home is ready for a modern transformation and your personal touch, the expansive lot, and the coveted, secluded location make this a truly unique find. Bring your vision to reimagine this property and make it your own.

3 Beds ⋅ 2 Baths ⋅ 73594125 MLS

Unlock the potential of this hidden gem in Holliston! Tucked away and privately set back from the road, this home offers a rare opportunity to create your dream sanctuary on a spectacular 2.73-acre lot. Nature lovers will appreciate the tranquility of this location, which borders expansive conservation land, providing ultimate privacy and a peaceful backdrop. The property features a large, flat yard perfect for outdoor activities, gardens, or recreation. Inside, the home provides a versatile floor plan with 3 bedrooms and 2 full bathrooms. The first floor layout includes 2 bedrooms, a full bath and a large fireplaced living room. The second floor features the primary bedroom, a second full bath and a spacious second living room that offers excellent flexibility for a home office, media room, or guest retreat. A new septic system is being installed, the roof, heating system and hot water heater have all been updated in recent years and the large full basement provides ample storage and is already partially finished. This home is ready for a modern transformation and your personal touch, the expansive lot, and the coveted, secluded location make this a truly unique find. Bring your vision to reimagine this property and make it your own.

741 Winter St., Holliston

$300,000

Land Opportunity In Holliston, 11.27acres. Abuts the Mellen St conservation, and Winter Street. Buyers and Buyers agents to do their own due diligence. best to use mapping, town hall, and engineer to discuss all the possibilities. Likely use would be a single lot.

73593884 MLS

Land Opportunity In Holliston, 11.27acres. Abuts the Mellen St conservation, and Winter Street. Buyers and Buyers agents to do their own due diligence. best to use mapping, town hall, and engineer to discuss all the possibilities. Likely use would be a single lot.

Winter St, Holliston

$849,999

Welcome to 543 Central Street, a beautifully updated 4-bedroom home that proves you don’t have to choose between charm, spacious rooms, and eco-friendly efficiency. Tucked away on a private lot that backs directly to conservation land, this property feels like a hidden retreat while remaining just moments from the heart of Holliston. Inside, the home is bathed in natural light, featuring a versatile layout with generously sized rooms that easily adapt to your lifestyle, whether you need a quiet home office or space to spread out. The renovated kitchen flows right into a stunning great room, where cathedral ceilings, exposed beams, and a massive picture window frame the greenery outside. The sustainability features here are a total game-changer. With owned solar panels and a high-efficiency heat pump installed in 2022, the home’s energy system is so effective that the current owners actually generate more electricity than they consume. Imagine a home that handles all your heating and cooling and still sends you a check at the end of the month.The second floor offers four spacious bedrooms, while the lower level adds even more flexibility with a bonus room and a full bathroom. Outside, the property is a true oasis. With over three acres of land, direct trail access, and an updated gunite pool, it’s a dream setting for hosting summer gatherings or enjoying a quiet morning coffee on the deck. Recent capital improvements, including a newer roof, windows, siding, and insulation, mean you can move in with total peace of mind. Whether you’re drawn to the privacy, the trail-side location near Lake Winthrop, or the incredible energy savings, 543 Central Street is a rare find in the wonderful town of Holliston. Come see it for yourself!

4 Beds ⋅ 4 Baths ⋅ 73593792 MLS

Welcome to 543 Central Street, a beautifully updated 4-bedroom home that proves you don’t have to choose between charm, spacious rooms, and eco-friendly efficiency. Tucked away on a private lot that backs directly to conservation land, this property feels like a hidden retreat while remaining just moments from the heart of Holliston. Inside, the home is bathed in natural light, featuring a versatile layout with generously sized rooms that easily adapt to your lifestyle, whether you need a quiet home office or space to spread out. The renovated kitchen flows right into a stunning great room, where cathedral ceilings, exposed beams, and a massive picture window frame the greenery outside. The sustainability features here are a total game-changer. With owned solar panels and a high-efficiency heat pump installed in 2022, the home’s energy system is so effective that the current owners actually generate more electricity than they consume. Imagine a home that handles all your heating and cooling and still sends you a check at the end of the month.The second floor offers four spacious bedrooms, while the lower level adds even more flexibility with a bonus room and a full bathroom. Outside, the property is a true oasis. With over three acres of land, direct trail access, and an updated gunite pool, it’s a dream setting for hosting summer gatherings or enjoying a quiet morning coffee on the deck. Recent capital improvements, including a newer roof, windows, siding, and insulation, mean you can move in with total peace of mind. Whether you’re drawn to the privacy, the trail-side location near Lake Winthrop, or the incredible energy savings, 543 Central Street is a rare find in the wonderful town of Holliston. Come see it for yourself!

543 Central Street, Holliston

$899,000

Welcome to 1419 Washington Street in Holliston! This well-maintained three-family Colonial presents a fantastic opportunity for investors and owner-occupants alike. The property features two spacious 2-bedroom units and one lofted 1-bedroom apartment, each complete with its own private deck, in-unit washer and dryer, and dishwasher. Separately metered utilities offer added convenience, while a large driveway provides ample parking. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other two, this property offers excellent flexibility. One unit will be delivered vacant at closing, the property is particularly appealing to owner-occupants. Conveniently located near downtown Holliston, local shops, restaurants, and major routes. Don't miss this opportunity to own a versatile multifamily property in Holliston! OPEN HOUSE SATURDAY, 10/31

5 Beds ⋅ 3 Baths ⋅ 73593644 MLS

Welcome to 1419 Washington Street in Holliston! This well-maintained three-family Colonial presents a fantastic opportunity for investors and owner-occupants alike. The property features two spacious 2-bedroom units and one lofted 1-bedroom apartment, each complete with its own private deck, in-unit washer and dryer, and dishwasher. Separately metered utilities offer added convenience, while a large driveway provides ample parking. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other two, this property offers excellent flexibility. One unit will be delivered vacant at closing, the property is particularly appealing to owner-occupants. Conveniently located near downtown Holliston, local shops, restaurants, and major routes. Don't miss this opportunity to own a versatile multifamily property in Holliston! OPEN HOUSE SATURDAY, 10/31

1419 Washington St, Holliston

$1,025,000

Welcome to this beautifully maintained Colonial, ideally situated on a lovely 1+ acre lot in a wonderful neighborhood on a quiet cul-de-sac! An inviting farmer’s porch, lush lawn and lovely plantings create exceptional curb appeal. Inside, a tiger maple hardwood entry leads to a living room with hardwood flooring and an elegant dining room featuring random width wide pine floors installed with historical cut nails and crown molding. The spacious eat-in kitchen offers quartz countertops, center island, stainless steel appliances, refinished hardwood floors, recessed lighting, tile backsplash and pantry. Relax in the inviting family room with wood-burning fireplace, skylight, ceiling fan and French doors leading to a low-maintenance Trex deck overlooking the private, gorgeous backyard, complete with irrigation, vegetable garden and storage shed. A convenient mudroom and half bath complete the first floor. Upstairs, the primary suite features a cathedral ceiling, walk-in closet and private bath with stone-topped double vanity and custom double shower. Three additional bedrooms, a full bath and convenient laundry area complete the second floor. Walk-up access to the unfinished attic provides additional storage space. The finished lower level offers fantastic flexibility with brand-new luxury vinyl flooring, recessed lighting, bonus room and private home office with separate heating zone and double-hung windows for maximum natural light. Recent 2026 improvements include new carpeting on the stairs, hallway and primary bedroom, beautifully refinished hardwood floors in the entryway and kitchen, and fresh interior paint in many rooms. Additional updates include new microwave, refrigerator & dryer 2026, vinyl windows 2022, heat pump for AC 2024, roof 2013 and boiler/hot water heater 2014. Complete with an attached two-car garage and security system, this exceptionally cared-for home offers comfort, charm and room to spread out inside and out! Enjoy all that Holliston has to offer, from its charming downtown shops and restaurants to Lake Winthrop, the Upper Charles Rail Trail and a vibrant community atmosphere.

4 Beds ⋅ 3 Baths ⋅ 73593616 MLS

Welcome to this beautifully maintained Colonial, ideally situated on a lovely 1+ acre lot in a wonderful neighborhood on a quiet cul-de-sac! An inviting farmer’s porch, lush lawn and lovely plantings create exceptional curb appeal. Inside, a tiger maple hardwood entry leads to a living room with hardwood flooring and an elegant dining room featuring random width wide pine floors installed with historical cut nails and crown molding. The spacious eat-in kitchen offers quartz countertops, center island, stainless steel appliances, refinished hardwood floors, recessed lighting, tile backsplash and pantry. Relax in the inviting family room with wood-burning fireplace, skylight, ceiling fan and French doors leading to a low-maintenance Trex deck overlooking the private, gorgeous backyard, complete with irrigation, vegetable garden and storage shed. A convenient mudroom and half bath complete the first floor. Upstairs, the primary suite features a cathedral ceiling, walk-in closet and private bath with stone-topped double vanity and custom double shower. Three additional bedrooms, a full bath and convenient laundry area complete the second floor. Walk-up access to the unfinished attic provides additional storage space. The finished lower level offers fantastic flexibility with brand-new luxury vinyl flooring, recessed lighting, bonus room and private home office with separate heating zone and double-hung windows for maximum natural light. Recent 2026 improvements include new carpeting on the stairs, hallway and primary bedroom, beautifully refinished hardwood floors in the entryway and kitchen, and fresh interior paint in many rooms. Additional updates include new microwave, refrigerator & dryer 2026, vinyl windows 2022, heat pump for AC 2024, roof 2013 and boiler/hot water heater 2014. Complete with an attached two-car garage and security system, this exceptionally cared-for home offers comfort, charm and room to spread out inside and out! Enjoy all that Holliston has to offer, from its charming downtown shops and restaurants to Lake Winthrop, the Upper Charles Rail Trail and a vibrant community atmosphere.

6 Beaver Brook Dr, Holliston

$695,000

Tucked away in a much-desired Holliston neighborhood, while offering convenient access to local amenities, you’ll find an impressive split-level home w an abundance of space. Beginning in the living room on the main level where a large picture window fills the space w natural light, you’ll find beautiful hardwood floors that go throughout most of the main level. The living room & dining room are open concept just off the kitchen. Past the kitchen, prepare to be wowed by the expansive great room, complete w beamed vaulted ceilings, skylights, a pellet stove, & sliding-doors to an oversized deck, perfect for outdoor entertaining. Also on the main level you’ll find 3BRs w 2 full BAs which includes the primary suite, w a walk-in closet & private BA. The lower level delivers even more flexibility w a home office, large recreation room featuring a fireplace & built in, as well as an additional space that would make a great meditation room, playroom or craft room. An additional half bathroom & laundry area round out the lower level. This home’s flexible and versatile floor plan make this a wonderful home for extended guest visits w excellent space for entertaining, work, or everyday living. Outside, the fenced yard provides a private setting playing fetch with the dog or just relaxing. Notable improvements include mini-splits installed in 2021, as well as double-pane windows & new skylights installed in 2022. This spacious & versatile Holliston home is one you won’t want to miss!

3 Beds ⋅ 3 Baths ⋅ 73593545 MLS

Tucked away in a much-desired Holliston neighborhood, while offering convenient access to local amenities, you’ll find an impressive split-level home w an abundance of space. Beginning in the living room on the main level where a large picture window fills the space w natural light, you’ll find beautiful hardwood floors that go throughout most of the main level. The living room & dining room are open concept just off the kitchen. Past the kitchen, prepare to be wowed by the expansive great room, complete w beamed vaulted ceilings, skylights, a pellet stove, & sliding-doors to an oversized deck, perfect for outdoor entertaining. Also on the main level you’ll find 3BRs w 2 full BAs which includes the primary suite, w a walk-in closet & private BA. The lower level delivers even more flexibility w a home office, large recreation room featuring a fireplace & built in, as well as an additional space that would make a great meditation room, playroom or craft room. An additional half bathroom & laundry area round out the lower level. This home’s flexible and versatile floor plan make this a wonderful home for extended guest visits w excellent space for entertaining, work, or everyday living. Outside, the fenced yard provides a private setting playing fetch with the dog or just relaxing. Notable improvements include mini-splits installed in 2021, as well as double-pane windows & new skylights installed in 2022. This spacious & versatile Holliston home is one you won’t want to miss!

105 Dodd Drive, Holliston

$799,900

Room for everyone at 631 Central Street! Set on three-quarters of an acre, this home offers a true in-law setup with a heated in-ground pool, making it ideal for multi-generational living or anyone who wants space to spread out. The main house features hardwood floors, an open living and dining area with a brick fireplace and rustic wood mantel, and an updated kitchen with white cabinetry, granite counters, stainless appliances, and a planked wood ceiling. Three bedrooms and a full bath on the main level, plus a lower-level family room, additional bedroom, half bath, laundry room, and garage, give you plenty of flexibility. The in-law suite has its own private entrance and features a stunning vaulted kitchen with rich wood cabinetry, granite, a large center island, opening to a bright living and dining area. It also includes a bedroom, a full bath with a tiled walk-in shower, in-unit laundry, and a lower-level den with generous storage. Step outside to enjoy summers by the heated pool, surrounded by a paver patio, pool house, and vinyl privacy fencing with a peaceful wooded backdrop. Solar panels, two driveways, and ample parking add to the appeal. Conveniently located near downtown Holliston, the rail trail, shopping, restaurants, and Routes 16 and 495, this is a rare opportunity to own a versatile home with space, privacy, and room to grow. First Showing Open House Saturday October, from 11AM to 12:30PM

4 Beds ⋅ 3 Baths ⋅ 73593357 MLS

Room for everyone at 631 Central Street! Set on three-quarters of an acre, this home offers a true in-law setup with a heated in-ground pool, making it ideal for multi-generational living or anyone who wants space to spread out. The main house features hardwood floors, an open living and dining area with a brick fireplace and rustic wood mantel, and an updated kitchen with white cabinetry, granite counters, stainless appliances, and a planked wood ceiling. Three bedrooms and a full bath on the main level, plus a lower-level family room, additional bedroom, half bath, laundry room, and garage, give you plenty of flexibility. The in-law suite has its own private entrance and features a stunning vaulted kitchen with rich wood cabinetry, granite, a large center island, opening to a bright living and dining area. It also includes a bedroom, a full bath with a tiled walk-in shower, in-unit laundry, and a lower-level den with generous storage. Step outside to enjoy summers by the heated pool, surrounded by a paver patio, pool house, and vinyl privacy fencing with a peaceful wooded backdrop. Solar panels, two driveways, and ample parking add to the appeal. Conveniently located near downtown Holliston, the rail trail, shopping, restaurants, and Routes 16 and 495, this is a rare opportunity to own a versatile home with space, privacy, and room to grow. First Showing Open House Saturday October, from 11AM to 12:30PM

631 Central St, Holliston

$549,900

ATTENTION INVESTORS, FIRST TIME BUYERS & THOSE LOOKING TO DOWNSIZE!! This charming ranch is move-in ready, while offering an excellent opportunity to add your own personal touches and cosmetic updates to make it truly your own. 36 Regal offers comfortable single-level living in a desirable Holliston neighborhood, just moments from the Rail Trail. The bright and inviting living room features beautiful hardwood floors and a large bay window. The spacious kitchen offers ample cabinetry, counter space, and stainless steel appliances, with a versatile bonus space perfect for a home office, dining area, playroom, or flex space.Three bedrooms and a full bath complete the main level. But the real showstopper may be outside! Set on a large, level lot, the private backyard is made for summer entertaining, complete with a spacious deck and above-ground pool. A storage shed provides additional space for gardening equipment and outdoor essentials. Central air, natural gas heating, and a fantastic location close to schools, shopping, the Rail Trail, Route 16, Route 109, and major commuter routes add to the appeal. Homes like this don't come around often, move-in ready and perfectly positioned for enjoying everything this wonderful community has to offer, this is one you won't want to miss!

3 Beds ⋅ 1 Baths ⋅ 73593307 MLS

ATTENTION INVESTORS, FIRST TIME BUYERS & THOSE LOOKING TO DOWNSIZE!! This charming ranch is move-in ready, while offering an excellent opportunity to add your own personal touches and cosmetic updates to make it truly your own. 36 Regal offers comfortable single-level living in a desirable Holliston neighborhood, just moments from the Rail Trail. The bright and inviting living room features beautiful hardwood floors and a large bay window. The spacious kitchen offers ample cabinetry, counter space, and stainless steel appliances, with a versatile bonus space perfect for a home office, dining area, playroom, or flex space.Three bedrooms and a full bath complete the main level. But the real showstopper may be outside! Set on a large, level lot, the private backyard is made for summer entertaining, complete with a spacious deck and above-ground pool. A storage shed provides additional space for gardening equipment and outdoor essentials. Central air, natural gas heating, and a fantastic location close to schools, shopping, the Rail Trail, Route 16, Route 109, and major commuter routes add to the appeal. Homes like this don't come around often, move-in ready and perfectly positioned for enjoying everything this wonderful community has to offer, this is one you won't want to miss!

36 Regal Street, Holliston

$500,000

A rare opportunity in Holliston: a 2+ acre estate homesite at the end of a brand-new cul-de-sac, offering the privacy and quiet of a wooded setting, with room for the kind of home and yard that are hard to find in town. The lot is for sale, and the seller will build your home as well: choose from our collection of custom floor plans, designed for luxury living and entertaining, or bring your own plans and we’ll bring them to life. Our in-house designer is there to help guide you through layouts, finishes, and details, taking you from first sketch to final walkthrough. Contact the listing agent for plans, pricing, and timeline.

73592610 MLS

A rare opportunity in Holliston: a 2+ acre estate homesite at the end of a brand-new cul-de-sac, offering the privacy and quiet of a wooded setting, with room for the kind of home and yard that are hard to find in town. The lot is for sale, and the seller will build your home as well: choose from our collection of custom floor plans, designed for luxury living and entertaining, or bring your own plans and we’ll bring them to life. Our in-house designer is there to help guide you through layouts, finishes, and details, taking you from first sketch to final walkthrough. Contact the listing agent for plans, pricing, and timeline.

000 Undisclosed, Holliston

$1,175,000

Welcome home to this beautiful Colonial, set on a private 3-acre lot in Holliston's sought-after Cedarbrook neighborhood. With plenty of room to gather with friends and family or find a quiet place to unwind, this home offers a wonderful balance of comfortable living spaces and thoughtful design. The spacious kitchen features granite countertops, a large center island, double wall ovens and a sunny dining area for morning coffee or casual meals. Just beyond, the inviting family room features a cathedral ceiling, gas fireplace and a stunning wall of glass sliders that fills the room with natural light and brings the beauty of the outdoors right into your living space. Imagine curling up by the fire on a chilly New England evening, surrounded by views of the changing seasons. Step outside to the expansive deck with a covered seating area, perfect for summer dinners, entertaining friends or simply enjoying the peaceful wooded surroundings. A fenced yard offers comfort that little ones or furry friends won't wander. Back inside, the adjoining game room with wet bar and wine refrigerator makes entertaining easy while the formal dining room is ready for holidays and special occasions. A separate living room/office offers a comfortable space to relax or work from home. Surround sound speakers throughout downstairs and all season speakers on deck are all ready for you to connect a surround system to! Upstairs, the generous primary suite with new carpet includes two walk-in closets, a private office area and a spacious bath with soaking tub, tiled shower and double vanity. There are three additional bedrooms, a full bath and separate laundry room. A charming loft with built-in shelving and window seat is a lovely spot to read or enjoy a little quiet time. The large unfinished basement offers possibilities for future living space, while the three-car garage, walk-up attic and updated heating and cooling systems add everyday convenience. It's rare to find a home with this much privacy in such a wonderful neighborhood, with shopping, schools and major routes nearby!

4 Beds ⋅ 3 Baths ⋅ 73592000 MLS

Welcome home to this beautiful Colonial, set on a private 3-acre lot in Holliston's sought-after Cedarbrook neighborhood. With plenty of room to gather with friends and family or find a quiet place to unwind, this home offers a wonderful balance of comfortable living spaces and thoughtful design. The spacious kitchen features granite countertops, a large center island, double wall ovens and a sunny dining area for morning coffee or casual meals. Just beyond, the inviting family room features a cathedral ceiling, gas fireplace and a stunning wall of glass sliders that fills the room with natural light and brings the beauty of the outdoors right into your living space. Imagine curling up by the fire on a chilly New England evening, surrounded by views of the changing seasons. Step outside to the expansive deck with a covered seating area, perfect for summer dinners, entertaining friends or simply enjoying the peaceful wooded surroundings. A fenced yard offers comfort that little ones or furry friends won't wander. Back inside, the adjoining game room with wet bar and wine refrigerator makes entertaining easy while the formal dining room is ready for holidays and special occasions. A separate living room/office offers a comfortable space to relax or work from home. Surround sound speakers throughout downstairs and all season speakers on deck are all ready for you to connect a surround system to! Upstairs, the generous primary suite with new carpet includes two walk-in closets, a private office area and a spacious bath with soaking tub, tiled shower and double vanity. There are three additional bedrooms, a full bath and separate laundry room. A charming loft with built-in shelving and window seat is a lovely spot to read or enjoy a little quiet time. The large unfinished basement offers possibilities for future living space, while the three-car garage, walk-up attic and updated heating and cooling systems add everyday convenience. It's rare to find a home with this much privacy in such a wonderful neighborhood, with shopping, schools and major routes nearby!

35 Johnson Drive, Holliston

$314,900

Welcome to this beautiful unit at Regency Park Condominium. Very well-maintained two bedrooms townhouse, both on the second floor. Hardwood flooring throughout the living room and bedrooms. Finished basement with extra room for work or entertainment and laundry. Washer and dryer will stay. Backyard for a fresh air and relaxing. Great location unit! Minutes from the downtown where you will find coffee shops, pharmacy and stores. Lake Winthrop and the walk trail are right there for spring and summer days. Don't miss the opportunity to see this unit, it won't last. Schedule a visit now, easy to show! Open house Saturday October 17th from 11:30am to 1pm.

2 Beds ⋅ 1 Baths ⋅ 73590913 MLS

Welcome to this beautiful unit at Regency Park Condominium. Very well-maintained two bedrooms townhouse, both on the second floor. Hardwood flooring throughout the living room and bedrooms. Finished basement with extra room for work or entertainment and laundry. Washer and dryer will stay. Backyard for a fresh air and relaxing. Great location unit! Minutes from the downtown where you will find coffee shops, pharmacy and stores. Lake Winthrop and the walk trail are right there for spring and summer days. Don't miss the opportunity to see this unit, it won't last. Schedule a visit now, easy to show! Open house Saturday October 17th from 11:30am to 1pm.

43 Regency Dr Unit 43, Holliston

$725,000

Welcome to 16 Roy Ave, a fully renovated 4-bedroom, 2-full-bath raised ranch on nearly half an acre with an in-ground pool located in a quaint setting. The bright, open main level features engineered hardwood floors, a sun-filled living room with a painted-brick fireplace flowing into the dining area, and a brand-new kitchen with a quartz waterfall island, two-tone cabinetry, tile backsplash and stainless steel appliances. The main level also offers a renovated full bath and three of the home's four bedrooms. The finished lower level adds a spacious bedroom with a slat accent wall and built-in brick shelving, a new tiled full bath and a two-car drive-under garage. Updates include a new roof, new septic system, new electric, new plumbing, a new gas boiler with hot water baseboard heat and a new water heater. The home also has central AC. Outside, enjoy a large yard with an in-ground pool, a storage shed and parking for eight. Close to Rt 126, downtown Holliston and the rail trail. Move right in!

4 Beds ⋅ 2 Baths ⋅ 73590909 MLS

Welcome to 16 Roy Ave, a fully renovated 4-bedroom, 2-full-bath raised ranch on nearly half an acre with an in-ground pool located in a quaint setting. The bright, open main level features engineered hardwood floors, a sun-filled living room with a painted-brick fireplace flowing into the dining area, and a brand-new kitchen with a quartz waterfall island, two-tone cabinetry, tile backsplash and stainless steel appliances. The main level also offers a renovated full bath and three of the home's four bedrooms. The finished lower level adds a spacious bedroom with a slat accent wall and built-in brick shelving, a new tiled full bath and a two-car drive-under garage. Updates include a new roof, new septic system, new electric, new plumbing, a new gas boiler with hot water baseboard heat and a new water heater. The home also has central AC. Outside, enjoy a large yard with an in-ground pool, a storage shed and parking for eight. Close to Rt 126, downtown Holliston and the rail trail. Move right in!

16 Roy Ave, Holliston

$1,699,000

Experience the art of exceptional living at 30 Mill Street, where timeless elegance, modern sophistication, and thoughtful design come together in this stunning 2026 luxury Colonial. Beautifully situated on nearly an acre along the Holliston–Hopkinton line, this remarkable residence offers approximately 4,587 sq. ft. of refined living space. An exquisite chef’s kitchen with a dramatic quartz waterfall island flows effortlessly into elegant entertaining areas, complemented by rich hardwood floors, architectural detailing, and three fireplaces. Four beautifully appointed en-suite bedrooms include a magnificent primary sanctuary featuring a fireplace, spa-inspired bath, and spacious dressing room. A private library, inviting second-floor lounge, and expansive finished lower level provide exceptional flexibility. Outdoors, a spectacular stone patio with a built-in kitchen creates the perfect setting for unforgettable gatherings. Complete with a three-car garage and proximity to golf, this is luxury living at its finest.

4 Beds ⋅ 5 Baths ⋅ 73590622 MLS

Experience the art of exceptional living at 30 Mill Street, where timeless elegance, modern sophistication, and thoughtful design come together in this stunning 2026 luxury Colonial. Beautifully situated on nearly an acre along the Holliston–Hopkinton line, this remarkable residence offers approximately 4,587 sq. ft. of refined living space. An exquisite chef’s kitchen with a dramatic quartz waterfall island flows effortlessly into elegant entertaining areas, complemented by rich hardwood floors, architectural detailing, and three fireplaces. Four beautifully appointed en-suite bedrooms include a magnificent primary sanctuary featuring a fireplace, spa-inspired bath, and spacious dressing room. A private library, inviting second-floor lounge, and expansive finished lower level provide exceptional flexibility. Outdoors, a spectacular stone patio with a built-in kitchen creates the perfect setting for unforgettable gatherings. Complete with a three-car garage and proximity to golf, this is luxury living at its finest.

30 Mill St, Holliston

$400,000

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 to. Cost is buyers, but homeowner is willing to be involved with the town. Beautiful parcel. Sliver of land owned by another goes along Alpine Road, so no access/driveway to Alpine without purchasing from them. Unknown as to price for said piece, nor willingness to sell. As it stands now, it is one legal lot. Paperwork with attorney who is registering land at the registry, but it's not yet done. Please do not walk without permission as there are dogs on adjacent property who also walk on this land.

73590343 MLS

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 to. Cost is buyers, but homeowner is willing to be involved with the town. Beautiful parcel. Sliver of land owned by another goes along Alpine Road, so no access/driveway to Alpine without purchasing from them. Unknown as to price for said piece, nor willingness to sell. As it stands now, it is one legal lot. Paperwork with attorney who is registering land at the registry, but it's not yet done. Please do not walk without permission as there are dogs on adjacent property who also walk on this land.

76B Hanlon Road, Holliston

$1,500,000

Discover a distinguished single-family country estate, meticulously crafted in 1975, offering 4834 square feet of refined living space. This property stands as a testament to enduring design & thoughtful construction, providing a harmonious blend of comfort and functionality. The residence features 2 well-proportioned primary suites, each designed to offer privacy & tranquility. One suite is located in a newer home addition & is handicap accessible by way of an interior elevator & ramp, a curbless oversize shower & barrier-free roll under sink. In addition this space offers a large custom closet and sitting room, the perfect respite for those requiring these enhancements as well as discerning buyers that appreciate large, gracious spaces. The second primary suite features a very comfortable bedroom & sitting room, lots of closet space & a gorgeous designer en suite perfect for teens wanting "their own space" or live- in help Complementing these sleeping quarters are two additional bedrooms, one with a customized walk-in closet, providing ample convenience & personal space for residents & guests alike. Further enhancing the property's appeal is a chef's kitchen featuring stainless steel Thermador appliances, granite tops, peninsula seating space & a butlers pantry with an abundance of storage. The adjoining dining room/living room features an open floor plan, custom built-in cabinetry, a Harman Frost Enamel pellet stove & access to a beautiful screen porch. The great room is a show piece of its own - soaring ceiling, hardwood floor with inlay border & custom rug, built-in cabinetry, large Palladium window with custom motorized shades & access to the outer deck. The lower level features a large game room with natural brick flooring & a coffered ceiling, a pellet stove, an adjoining wine cellar & space for a dedicated gym/art studio/craft room. Another bonus in this home is a beautiful & bright home office with Palladium window, motorized shades, radiant heat & a separate entrance. A spacious 3-car garage offers significant utility for vehicle storage & additional organizational needs. This home is conveniently located at the Hopkinton line, with easy access to Routes 85, 126 and 495. The expansive lot provides a generous outdoor environment, ideal for various recreational pursuits or simply enjoying the natural surroundings. To truly appreciate the sophisticated design & unique scale of this property, we invite your private viewing.

4 Beds ⋅ 4 Baths ⋅ 73590193 MLS

Discover a distinguished single-family country estate, meticulously crafted in 1975, offering 4834 square feet of refined living space. This property stands as a testament to enduring design & thoughtful construction, providing a harmonious blend of comfort and functionality. The residence features 2 well-proportioned primary suites, each designed to offer privacy & tranquility. One suite is located in a newer home addition & is handicap accessible by way of an interior elevator & ramp, a curbless oversize shower & barrier-free roll under sink. In addition this space offers a large custom closet and sitting room, the perfect respite for those requiring these enhancements as well as discerning buyers that appreciate large, gracious spaces. The second primary suite features a very comfortable bedroom & sitting room, lots of closet space & a gorgeous designer en suite perfect for teens wanting "their own space" or live- in help Complementing these sleeping quarters are two additional bedrooms, one with a customized walk-in closet, providing ample convenience & personal space for residents & guests alike. Further enhancing the property's appeal is a chef's kitchen featuring stainless steel Thermador appliances, granite tops, peninsula seating space & a butlers pantry with an abundance of storage. The adjoining dining room/living room features an open floor plan, custom built-in cabinetry, a Harman Frost Enamel pellet stove & access to a beautiful screen porch. The great room is a show piece of its own - soaring ceiling, hardwood floor with inlay border & custom rug, built-in cabinetry, large Palladium window with custom motorized shades & access to the outer deck. The lower level features a large game room with natural brick flooring & a coffered ceiling, a pellet stove, an adjoining wine cellar & space for a dedicated gym/art studio/craft room. Another bonus in this home is a beautiful & bright home office with Palladium window, motorized shades, radiant heat & a separate entrance. A spacious 3-car garage offers significant utility for vehicle storage & additional organizational needs. This home is conveniently located at the Hopkinton line, with easy access to Routes 85, 126 and 495. The expansive lot provides a generous outdoor environment, ideal for various recreational pursuits or simply enjoying the natural surroundings. To truly appreciate the sophisticated design & unique scale of this property, we invite your private viewing.

457 Hanlon Rd, Holliston

$775,000

Welcome to 85 Alden Road, where modern updates, thoughtful design, and comfortable living come together. Beautifully renovated throughout, this 4-bedroom, 2.5-bath home offers an inviting open-concept layout that seamlessly connects the kitchen, dining, and living areas, creating the perfect setting for both everyday living and entertaining. The beautifully redesigned kitchen is the heart of the home, featuring quartz countertops, stylish new cabinetry, and a generous center island ideal for gathering with family and friends. New hardwood floors bring warmth and character to the main level, while new windows throughout fill the home with natural light. The finished lower level offers even more flexibility, featuring a fourth bedroom, half bath, and additional living space that can easily adapt to your needs. Step outside to enjoy the renovated deck and backyard, perfect for relaxing, entertaining, or simply enjoying the outdoors. Beyond the beautiful finishes, major improvements include a new roof, new septic system, and new furnace with central air conditioning, offering comfort and peace of mind for years to come. Enjoy convenient access to the Upper Charles Rail Trail, Lake Winthrop, and major commuter routes. With so many updates already completed, all that’s left to do is move in and make it your own!

4 Beds ⋅ 3 Baths ⋅ 73588728 MLS

Welcome to 85 Alden Road, where modern updates, thoughtful design, and comfortable living come together. Beautifully renovated throughout, this 4-bedroom, 2.5-bath home offers an inviting open-concept layout that seamlessly connects the kitchen, dining, and living areas, creating the perfect setting for both everyday living and entertaining. The beautifully redesigned kitchen is the heart of the home, featuring quartz countertops, stylish new cabinetry, and a generous center island ideal for gathering with family and friends. New hardwood floors bring warmth and character to the main level, while new windows throughout fill the home with natural light. The finished lower level offers even more flexibility, featuring a fourth bedroom, half bath, and additional living space that can easily adapt to your needs. Step outside to enjoy the renovated deck and backyard, perfect for relaxing, entertaining, or simply enjoying the outdoors. Beyond the beautiful finishes, major improvements include a new roof, new septic system, and new furnace with central air conditioning, offering comfort and peace of mind for years to come. Enjoy convenient access to the Upper Charles Rail Trail, Lake Winthrop, and major commuter routes. With so many updates already completed, all that’s left to do is move in and make it your own!

85 Alden Rd, Holliston

$649,900

Welcome to 72 Alden Rd, a classic split level on a stunning half-acre lot located in a quiet, closed-loop neighborhood. In Law Potential! 3 bedrooms, 2 1/2 baths, & a flowing floor plan that makes everyday living effortless. Generous, light-filled rooms move naturally from one to the next, with three spacious bedrooms on the main level & a flexible living area on the lower level with it's own full bath and entry point- perfect for an in-law suite. Hardwood floors & a wood-burning fireplace bring warmth to every gathering. The dining room opens directly to the brand new wood deck & fenced-in backyard for seamless indoor-outdoor flow. The refreshed basement adds versatile bonus space - perfect as a playroom, home office, or full in law suite. Outside, the brand new deck anchors a stunning fenced-in backyard with a full in ground pool -made for outdoor living at its best. This backyard oasis invites you to linger long after the sun goes down. Easy access to Rt 16 or Rt 27, parks & trails completes this special home.

3 Beds ⋅ 3 Baths ⋅ 73588024 MLS

Welcome to 72 Alden Rd, a classic split level on a stunning half-acre lot located in a quiet, closed-loop neighborhood. In Law Potential! 3 bedrooms, 2 1/2 baths, & a flowing floor plan that makes everyday living effortless. Generous, light-filled rooms move naturally from one to the next, with three spacious bedrooms on the main level & a flexible living area on the lower level with it's own full bath and entry point- perfect for an in-law suite. Hardwood floors & a wood-burning fireplace bring warmth to every gathering. The dining room opens directly to the brand new wood deck & fenced-in backyard for seamless indoor-outdoor flow. The refreshed basement adds versatile bonus space - perfect as a playroom, home office, or full in law suite. Outside, the brand new deck anchors a stunning fenced-in backyard with a full in ground pool -made for outdoor living at its best. This backyard oasis invites you to linger long after the sun goes down. Easy access to Rt 16 or Rt 27, parks & trails completes this special home.

72 Alden Road, Holliston

$685,000

This distinguished home offers a unique blend of historical charm and contemporary appointments, setting the stage for refined living. The kitchen is thoughtfully designed for both culinary pursuits and social gatherings, featuring stainless steel appliances, stone counters, an island, and a peninsula, providing an ideal space for meal preparation and informal dining. The living room serves as a central gathering point, enhanced by a fireplace that offers warmth and ambiance, complemented by elegant wide pine flooring that extends throughout the first floor. The large primary bedroom with its oversized walk in closet, offers a balcony overlooking your expansive backyards adds seamless connection to the outdoors, while another bedroom is distinguished by built-in shelves, adding both character and practical storage solutions. The property further benefits from a private yard, offering a tranquil retreat, and a brick patio, perfect for outdoor entertaining or quiet relaxation. A large carriage house provides additional storage and the potential for expanding with either a home office/craft room/or ADU on the second floor. We invite you to discover the distinctive appeal of this exceptional Holliston residence. Brand New Septic system just installed! Other updates are attached to the listing. Showings start Friday morning.

3 Beds ⋅ 2 Baths ⋅ 73587965 MLS

This distinguished home offers a unique blend of historical charm and contemporary appointments, setting the stage for refined living. The kitchen is thoughtfully designed for both culinary pursuits and social gatherings, featuring stainless steel appliances, stone counters, an island, and a peninsula, providing an ideal space for meal preparation and informal dining. The living room serves as a central gathering point, enhanced by a fireplace that offers warmth and ambiance, complemented by elegant wide pine flooring that extends throughout the first floor. The large primary bedroom with its oversized walk in closet, offers a balcony overlooking your expansive backyards adds seamless connection to the outdoors, while another bedroom is distinguished by built-in shelves, adding both character and practical storage solutions. The property further benefits from a private yard, offering a tranquil retreat, and a brick patio, perfect for outdoor entertaining or quiet relaxation. A large carriage house provides additional storage and the potential for expanding with either a home office/craft room/or ADU on the second floor. We invite you to discover the distinctive appeal of this exceptional Holliston residence. Brand New Septic system just installed! Other updates are attached to the listing. Showings start Friday morning.

423 South St, Holliston

$970,272

Imagine coming home to a place where there is room for everyone, space for everything, and something special around every corner. Welcome to 272 Mill St in Holliston, a home made for living, gathering, creating, and making memories. Set on a beautiful, level one-acre lot, this spacious 4-bedroom, 4-bath home offers over 2,000 square feet of living space, but it’s everything beyond the numbers that makes this home so special. Picture summer days spent around the gorgeous in-ground pool, friends and family gathered in the backyard, and quiet mornings or relaxing evenings in the oversized sunroom overlooking it all. Beyond the pool, the expansive yard offers room for backyard games, summer cookouts, gardening, entertaining, or simply spreading out and enjoying the outdoors. Have cars, projects, hobbies, or simply wish you had more space? The incredible attached 4-car garage is a car enthusiast’s, mechanic’s, or hobbyist’s dream, while the workshop and abundant storage offer even more room to create, work, and organize. Downstairs, discover an entirely different level of possibilities with its own living room, kitchenette, bedroom, and full bath. It’s an ideal setup for extended family, guests, a private retreat, or potential future ADU use, subject to town approval. There’s room here for everyone to have a space of their own and plenty of places to come together. Located near Pinecrest Golf Club with convenient access for commuters, 272 Mill St offers a rare combination of space, versatility, privacy, and outdoor living. This isn’t simply a house with great features. It’s the kind of place where summers are spent by the pool, projects come to life in the workshop, family and friends always have a place to stay, and home becomes the place everyone wants to be.

4 Beds ⋅ 4 Baths ⋅ 73585683 MLS

Imagine coming home to a place where there is room for everyone, space for everything, and something special around every corner. Welcome to 272 Mill St in Holliston, a home made for living, gathering, creating, and making memories. Set on a beautiful, level one-acre lot, this spacious 4-bedroom, 4-bath home offers over 2,000 square feet of living space, but it’s everything beyond the numbers that makes this home so special. Picture summer days spent around the gorgeous in-ground pool, friends and family gathered in the backyard, and quiet mornings or relaxing evenings in the oversized sunroom overlooking it all. Beyond the pool, the expansive yard offers room for backyard games, summer cookouts, gardening, entertaining, or simply spreading out and enjoying the outdoors. Have cars, projects, hobbies, or simply wish you had more space? The incredible attached 4-car garage is a car enthusiast’s, mechanic’s, or hobbyist’s dream, while the workshop and abundant storage offer even more room to create, work, and organize. Downstairs, discover an entirely different level of possibilities with its own living room, kitchenette, bedroom, and full bath. It’s an ideal setup for extended family, guests, a private retreat, or potential future ADU use, subject to town approval. There’s room here for everyone to have a space of their own and plenty of places to come together. Located near Pinecrest Golf Club with convenient access for commuters, 272 Mill St offers a rare combination of space, versatility, privacy, and outdoor living. This isn’t simply a house with great features. It’s the kind of place where summers are spent by the pool, projects come to life in the workshop, family and friends always have a place to stay, and home becomes the place everyone wants to be.

272 Mill St, Holliston

$699,900

Welcome to this stunning, like-new 2020 townhome that lives like a single-family home, set far back from the road on @ 1 acre in total, in a serene, wooded setting with a fully fenced-in, private yard. High ceilings and an open-concept design create a bright, spacious feel throughout. Wood flooring enhances the main living areas, while the finished walkout lower level, completed in 2022, adds two versatile rooms and approximately 700 SF of additional living space, all with high ceilings. The main bedroom features a spacious ensuite bath with a double vanity, a custom-tiled shower, and a large walk-in closet with a custom closet system. Convenient second-floor laundry is located near the bedrooms. Enjoy low-maintenance outdoor living with a composite front porch and rear deck overlooking the large, private fenced backyard. Additional highlights include a 2-car garage with an EV charger. 2 unit HOA $325/month covers exterior maintenance, landscaping, and snow removal. A beautifully maintained, like-new home offering comfort, flexibility, privacy, and modern convenience! See townhouse listing at MLS#73584502

2 Beds ⋅ 3 Baths ⋅ 73584532 MLS

Welcome to this stunning, like-new 2020 townhome that lives like a single-family home, set far back from the road on @ 1 acre in total, in a serene, wooded setting with a fully fenced-in, private yard. High ceilings and an open-concept design create a bright, spacious feel throughout. Wood flooring enhances the main living areas, while the finished walkout lower level, completed in 2022, adds two versatile rooms and approximately 700 SF of additional living space, all with high ceilings. The main bedroom features a spacious ensuite bath with a double vanity, a custom-tiled shower, and a large walk-in closet with a custom closet system. Convenient second-floor laundry is located near the bedrooms. Enjoy low-maintenance outdoor living with a composite front porch and rear deck overlooking the large, private fenced backyard. Additional highlights include a 2-car garage with an EV charger. 2 unit HOA $325/month covers exterior maintenance, landscaping, and snow removal. A beautifully maintained, like-new home offering comfort, flexibility, privacy, and modern convenience! See townhouse listing at MLS#73584502

1093 Washington St Unit 1093, Holliston

$699,900

Welcome to this stunning, like-new 2020 townhome that lives like a single-family home, set far back from the road on @ 1 acre in total in a serene, wooded setting with a fully fenced-in, private yard. High ceilings and an open-concept design create a bright, spacious feel throughout. Wood flooring enhances the main living areas, while the finished walkout lower level, completed in 2022, adds two versatile rooms and approximately 700 SF of additional living space, all with high ceilings. The main bedroom features a spacious ensuite bath with a double vanity, a custom-tiled shower, and a large walk-in closet with a custom closet system. Convenient second-floor laundry is located near the bedrooms. Enjoy low-maintenance outdoor living with a composite front porch and rear deck overlooking the large, private fenced backyard. Additional highlights include a 2-car garage with an EV charger and a low $325/month HOA covering exterior maintenance, landscaping, and snow removal. A beautifully maintained, like-new home offering comfort, flexibility, privacy, and modern convenience! Also listed as single-family MLS 73584532.

2 Beds ⋅ 3 Baths ⋅ 73584502 MLS

Welcome to this stunning, like-new 2020 townhome that lives like a single-family home, set far back from the road on @ 1 acre in total in a serene, wooded setting with a fully fenced-in, private yard. High ceilings and an open-concept design create a bright, spacious feel throughout. Wood flooring enhances the main living areas, while the finished walkout lower level, completed in 2022, adds two versatile rooms and approximately 700 SF of additional living space, all with high ceilings. The main bedroom features a spacious ensuite bath with a double vanity, a custom-tiled shower, and a large walk-in closet with a custom closet system. Convenient second-floor laundry is located near the bedrooms. Enjoy low-maintenance outdoor living with a composite front porch and rear deck overlooking the large, private fenced backyard. Additional highlights include a 2-car garage with an EV charger and a low $325/month HOA covering exterior maintenance, landscaping, and snow removal. A beautifully maintained, like-new home offering comfort, flexibility, privacy, and modern convenience! Also listed as single-family MLS 73584532.

1093 Washington St Unit 1093, Holliston

$495,000

This bright & sunny home is situated on a 1/2 acre lot located in a popular Holliston neighborhood, close to shops, commuter rail and major routes. You will find and appreciate that this home was designed for easy and comfortable living. Featuring 3 bedrooms and 2 full baths, fireplace & slider to deck with wonderful elevated views of the back yard, one car garage and a circular driveway for easy entry and exit. You will love time spending in the kitchen with its many features including a skylight, granite countertop, recessed lighting, and stainless appliances. Much of the home offers gleaming hardwood floors. Top ranked schools. Only a few miles to Ashland or Framingham Train Stations.

3 Beds ⋅ 2 Baths ⋅ 73582102 MLS

This bright & sunny home is situated on a 1/2 acre lot located in a popular Holliston neighborhood, close to shops, commuter rail and major routes. You will find and appreciate that this home was designed for easy and comfortable living. Featuring 3 bedrooms and 2 full baths, fireplace & slider to deck with wonderful elevated views of the back yard, one car garage and a circular driveway for easy entry and exit. You will love time spending in the kitchen with its many features including a skylight, granite countertop, recessed lighting, and stainless appliances. Much of the home offers gleaming hardwood floors. Top ranked schools. Only a few miles to Ashland or Framingham Train Stations.

2 Ashland Street, Holliston

$650,000

Welcome to 468 Underwood Street, a 4-bedroom, 1.5-bath Colonial in Holliston's desirable Brentwood neighborhood. Nestled on a nearly half-acre lot, this home has been extensively updated over the past five years, blending classic colonial character with modern, move in ready appeal. Accentuated by brand new granite stairs and a stunning paver entrance, this property offers exceptional curb appeal. Upon entering you are invited into the kitchen where sunlight streams in highlighting a perfect balance of contemporary style and bright, airy design. Crisp, porcelain floors serves a brilliant foundation, effortlessly reflecting light across the room. At the center of it all is a stunning new kitchen island, providing a focal point and a welcoming gathering spot. Topped with pristine quartz countertops, every surface gleams with a polished luster that maximizes brightness from day to night. Ensuring year round comfort, the entire open area is efficiently cooled by a sleek, modern mini-split system (2024). The second floor features a seamless layout with four well lit bedrooms, all boasting hardwood flooring and a renovated full bath (2021). Enjoy the beauty of every season from the comfort of a brand new 4-season porch with plenty of light to enjoy whether entertaining family and friends or just cozying up with a good book. Step directly from the sun filled 4 season porch into a charming new back patio (2024) offering an intimate, low maintenance outdoor nook perfect for your morning coffee. Many major essentials have been updated recently as well: a 1500-gallon, 4-bedroom septic system (2021), highly durable Hardie board siding (2024), fascia, and gutters (2024), double pane windows (2023), an asphalt driveway with an installed EV charger (2024) and a brand new hot water heater (2026). The entire property has been elevated by extensive landscape improvements framing the house in beautiful greenery with crisp and clean stonework (2022-2026). This delightful home sits in a highly desirable location just moments away from Holliston's famous Out Post Farm and beautiful Pinecrest Golf Club, bringing premier farm to table treats and weekend tee times right to your door steps.

4 Beds ⋅ 2 Baths ⋅ 73581958 MLS

Welcome to 468 Underwood Street, a 4-bedroom, 1.5-bath Colonial in Holliston's desirable Brentwood neighborhood. Nestled on a nearly half-acre lot, this home has been extensively updated over the past five years, blending classic colonial character with modern, move in ready appeal. Accentuated by brand new granite stairs and a stunning paver entrance, this property offers exceptional curb appeal. Upon entering you are invited into the kitchen where sunlight streams in highlighting a perfect balance of contemporary style and bright, airy design. Crisp, porcelain floors serves a brilliant foundation, effortlessly reflecting light across the room. At the center of it all is a stunning new kitchen island, providing a focal point and a welcoming gathering spot. Topped with pristine quartz countertops, every surface gleams with a polished luster that maximizes brightness from day to night. Ensuring year round comfort, the entire open area is efficiently cooled by a sleek, modern mini-split system (2024). The second floor features a seamless layout with four well lit bedrooms, all boasting hardwood flooring and a renovated full bath (2021). Enjoy the beauty of every season from the comfort of a brand new 4-season porch with plenty of light to enjoy whether entertaining family and friends or just cozying up with a good book. Step directly from the sun filled 4 season porch into a charming new back patio (2024) offering an intimate, low maintenance outdoor nook perfect for your morning coffee. Many major essentials have been updated recently as well: a 1500-gallon, 4-bedroom septic system (2021), highly durable Hardie board siding (2024), fascia, and gutters (2024), double pane windows (2023), an asphalt driveway with an installed EV charger (2024) and a brand new hot water heater (2026). The entire property has been elevated by extensive landscape improvements framing the house in beautiful greenery with crisp and clean stonework (2022-2026). This delightful home sits in a highly desirable location just moments away from Holliston's famous Out Post Farm and beautiful Pinecrest Golf Club, bringing premier farm to table treats and weekend tee times right to your door steps.

468 Underwood St, Holliston

$799,900

INTEREST RATE BUY DOWNS AVAILABLE! Welcome home to this exceptional fully renovated residence, ideally situated in one of Holliston's most desirable neighborhoods. Every inch of this home has been thoughtfully transformed from top to bottom, offering the rare combination of a turn-key home within a warm, established community.This gut renovation leaves nothing to chance — a new roof, new windows, all-new mechanical systems, and a new septic system provide complete peace of mind for years to come. No detail was overlooked, ensuring worry-free ownership from day one.Step inside to discover a bright, sun-filled interior with a spacious, open feel throughout. The brand-new kitchen is a true showstopper, featuring gorgeous solid quartz countertops, high-end fixtures, and premium finishes that blend timeless style with everyday function — perfect for cooking, entertaining, and gathering.The beautifully renovated bathrooms continue the home's elevated aesthetic, showcasing elegant tile showers and designer fixtures that create a spa-like retreat right at home.With its generous layout, abundant natural light, and meticulous attention to detail, this home offers move-in-ready luxury in a location that's second to none. Enjoy the charm and convenience of one of Holliston's premier neighborhoods, close to top-rated schools, scenic parks, and easy commuter access.This is a rare opportunity to own a completely renovated home where every system, surface, and finish is brand new — combining modern luxury with an unbeatable location. Don't miss your chance to make this exceptional property your own!

3 Beds ⋅ 2 Baths ⋅ 73580836 MLS

INTEREST RATE BUY DOWNS AVAILABLE! Welcome home to this exceptional fully renovated residence, ideally situated in one of Holliston's most desirable neighborhoods. Every inch of this home has been thoughtfully transformed from top to bottom, offering the rare combination of a turn-key home within a warm, established community.This gut renovation leaves nothing to chance — a new roof, new windows, all-new mechanical systems, and a new septic system provide complete peace of mind for years to come. No detail was overlooked, ensuring worry-free ownership from day one.Step inside to discover a bright, sun-filled interior with a spacious, open feel throughout. The brand-new kitchen is a true showstopper, featuring gorgeous solid quartz countertops, high-end fixtures, and premium finishes that blend timeless style with everyday function — perfect for cooking, entertaining, and gathering.The beautifully renovated bathrooms continue the home's elevated aesthetic, showcasing elegant tile showers and designer fixtures that create a spa-like retreat right at home.With its generous layout, abundant natural light, and meticulous attention to detail, this home offers move-in-ready luxury in a location that's second to none. Enjoy the charm and convenience of one of Holliston's premier neighborhoods, close to top-rated schools, scenic parks, and easy commuter access.This is a rare opportunity to own a completely renovated home where every system, surface, and finish is brand new — combining modern luxury with an unbeatable location. Don't miss your chance to make this exceptional property your own!

33 Cheryl Ln, Holliston

$1,250,000

More than a home—this private retreat offers exceptional space for living, working and entertaining! Sited down a long private drive off a cul-de-sac neighborhood, this spacious 4-bedroom Colonial enjoys a wonderfully private setting while remaining convenient to Holliston Town Center and major commuting routes. The home features updated kitchen and baths, 4 full baths, gas heat and central air. A large, thoughtfully designed laundry room features custom built-ins and convenient access from both the mudroom and the outside deck—an especially practical feature for everyday living and summer days by the pool. The finished lower level provides terrific versatility with a kitchen area and flexible living space currently used for extended-family living, along with plenty of additional storage. Outdoor living is a highlight of this special property. A lovely, sun porch provides the perfect spot for relaxing, while overlooking the private grounds. Step outside and enjoy your own backyard oasis complete with an expansive deck and in-ground Gunite pool, creating your own backyard retreat for summer gatherings. A full bath conveniently located just off the deck provides easy access from the pool area. The attached 3-car garage features exceptionally high ceilings, easily accommodating larger SUVs and trucks, while one heated and air-conditioned bay offers the perfect space for a home gym, workshop or hobby area. The detached barn is an incredible bonus, offering finished, heated and air-conditioned space ideal for a private home office, yoga or fitness studio, art/craft space or other creative pursuits. Below, car enthusiasts will love the additional 2-bay garage featuring soaring ceilings along with heat and air conditioning—ideal for a car collection, workshop or additional recreational storage. With five garage bays, multiple flexible-use spaces, a pool and a wonderfully private setting, this is a truly unique property offering room to live, work, entertain and pursue your passions—all just minutes from the heart of Holliston.

4 Beds ⋅ 5 Baths ⋅ 73580243 MLS

More than a home—this private retreat offers exceptional space for living, working and entertaining! Sited down a long private drive off a cul-de-sac neighborhood, this spacious 4-bedroom Colonial enjoys a wonderfully private setting while remaining convenient to Holliston Town Center and major commuting routes. The home features updated kitchen and baths, 4 full baths, gas heat and central air. A large, thoughtfully designed laundry room features custom built-ins and convenient access from both the mudroom and the outside deck—an especially practical feature for everyday living and summer days by the pool. The finished lower level provides terrific versatility with a kitchen area and flexible living space currently used for extended-family living, along with plenty of additional storage. Outdoor living is a highlight of this special property. A lovely, sun porch provides the perfect spot for relaxing, while overlooking the private grounds. Step outside and enjoy your own backyard oasis complete with an expansive deck and in-ground Gunite pool, creating your own backyard retreat for summer gatherings. A full bath conveniently located just off the deck provides easy access from the pool area. The attached 3-car garage features exceptionally high ceilings, easily accommodating larger SUVs and trucks, while one heated and air-conditioned bay offers the perfect space for a home gym, workshop or hobby area. The detached barn is an incredible bonus, offering finished, heated and air-conditioned space ideal for a private home office, yoga or fitness studio, art/craft space or other creative pursuits. Below, car enthusiasts will love the additional 2-bay garage featuring soaring ceilings along with heat and air conditioning—ideal for a car collection, workshop or additional recreational storage. With five garage bays, multiple flexible-use spaces, a pool and a wonderfully private setting, this is a truly unique property offering room to live, work, entertain and pursue your passions—all just minutes from the heart of Holliston.

57 Carl Road, Holliston

$625,000

NEW PRICE! HOLLISTON's Favorite BRENTWOOD NEIGHBORHOOD! Lovingly maintained Raised Ranch built in 1964 with 1933 SF of living space. Foyer recently painted also has a Ceiling Fan, Sunny Formal Dining Room with Hardwood Floors, leads to an amazing Kitchen with wood floors, Maple Cabinets, Dual Fuel Double Oven, Ceramic Tile Back Splash, Skylight, 5 Burner Cook Top, Quartize Countertops which were done in 2024, Kitchen Appliances will stay new in 2020, Wall to Wall Carpet in Spacious Family Room, Three Bedrooms all with Hardwood Floors, One Car Garage, Screened Porch, Shed, Back Yard Play Area (w Rubber Mulch) 2021, plus many Recent Updates including Interior Painting 2025, 2026, C/A added 2022, Leaf Filter Gutters 2023, 2 furnaces, one new in 2024 and located in the garage, new Harvey Windows 2013, Exterior painted 2025, deck painted 2026, 200 AMP Board 2022, Water heater approx. 2 years old, Septic System 2023, Pentair Whole House Water Filter System 2023, Primary Bathroom Hardware (Sinks, Showers & Tub) 2024 This home is ready for immediate occupancy. WELCOME HOME!!

3 Beds ⋅ 2 Baths ⋅ 73579102 MLS

NEW PRICE! HOLLISTON's Favorite BRENTWOOD NEIGHBORHOOD! Lovingly maintained Raised Ranch built in 1964 with 1933 SF of living space. Foyer recently painted also has a Ceiling Fan, Sunny Formal Dining Room with Hardwood Floors, leads to an amazing Kitchen with wood floors, Maple Cabinets, Dual Fuel Double Oven, Ceramic Tile Back Splash, Skylight, 5 Burner Cook Top, Quartize Countertops which were done in 2024, Kitchen Appliances will stay new in 2020, Wall to Wall Carpet in Spacious Family Room, Three Bedrooms all with Hardwood Floors, One Car Garage, Screened Porch, Shed, Back Yard Play Area (w Rubber Mulch) 2021, plus many Recent Updates including Interior Painting 2025, 2026, C/A added 2022, Leaf Filter Gutters 2023, 2 furnaces, one new in 2024 and located in the garage, new Harvey Windows 2013, Exterior painted 2025, deck painted 2026, 200 AMP Board 2022, Water heater approx. 2 years old, Septic System 2023, Pentair Whole House Water Filter System 2023, Primary Bathroom Hardware (Sinks, Showers & Tub) 2024 This home is ready for immediate occupancy. WELCOME HOME!!

35 Jerrold Street, Holliston

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