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Set at the end of a long driveway and surrounded by 13 acres, this 3,368-square-foot, five-bedroom home offers a truly distinctive living experience. Built in 1985, the octagonal design gives the property an architectural character that is rarely found in today's homes.The first floor features all five bedrooms, creating a dedicated and comfortable private space for family and guests. The second floor serves as the main gathering level, with the kitchen and living area arranged around the home's unique shape and design.A finished walkout basement adds another level of usable space with direct access to the outdoors, providing plenty of opportunity for recreation, hobbies, entertaining, or additional living needs.Beyond the home, the expansive acreage offers a rare sense of space and seclusion, with a long driveway providing a private approach to the property. The combination of substantial acreage, five bedrooms, multiple levels of living space, and unconventional architecture makes this a property with a character all its own. Open house rescheduled to September 14th 5-7pm.

5 Beds ⋅ 4 Baths ⋅ 73576195 MLS

Set at the end of a long driveway and surrounded by 13 acres, this 3,368-square-foot, five-bedroom home offers a truly distinctive living experience. Built in 1985, the octagonal design gives the property an architectural character that is rarely found in today's homes.The first floor features all five bedrooms, creating a dedicated and comfortable private space for family and guests. The second floor serves as the main gathering level, with the kitchen and living area arranged around the home's unique shape and design.A finished walkout basement adds another level of usable space with direct access to the outdoors, providing plenty of opportunity for recreation, hobbies, entertaining, or additional living needs.Beyond the home, the expansive acreage offers a rare sense of space and seclusion, with a long driveway providing a private approach to the property. The combination of substantial acreage, five bedrooms, multiple levels of living space, and unconventional architecture makes this a property with a character all its own. Open house rescheduled to September 14th 5-7pm.

243 Oak St, Holliston

$299,000

Welcome to Oakridge Condominiums! This spacious top-floor 2-bedroom unit an open floor plan and a gorgeous view in a peaceful setting at the end of a wooded cul-de-sac. Located in a garden-style building, this home offers comfortable, low-maintenance living. The building features on-site laundry, secure storage assigned to each unit, one assigned parking space, and ample guest parking. Enjoy a prime location just minutes from the commuter rail, grocery stores, shopping, parks, and the Charles River Rail Trail. For those seeking convenient, low-maintenance living, this condo is a great choice. With limited options at this price point, it is an excellent opportunity for a homeowner or investor.

2 Beds ⋅ 1 Baths ⋅ 73576026 MLS ⋅ ['Oakridge'] BLDG.

Welcome to Oakridge Condominiums! This spacious top-floor 2-bedroom unit an open floor plan and a gorgeous view in a peaceful setting at the end of a wooded cul-de-sac. Located in a garden-style building, this home offers comfortable, low-maintenance living. The building features on-site laundry, secure storage assigned to each unit, one assigned parking space, and ample guest parking. Enjoy a prime location just minutes from the commuter rail, grocery stores, shopping, parks, and the Charles River Rail Trail. For those seeking convenient, low-maintenance living, this condo is a great choice. With limited options at this price point, it is an excellent opportunity for a homeowner or investor.

49 Windsor Dr Unit 301, Holliston

$1,525,000

Wow! Spectacular sweeping East-facing views and exceptional craftsmanship define this one-of-a-kind custom home in the coveted Highlands at Holliston. Beautifully sited on over an acre above Old Cart Path, this stunning residence offers three levels of luxurious living and extraordinary spaces for both everyday living and entertaining. A welcoming farmer’s porch opens to a grand two-story foyer with brilliant hardwood floors and custom millwork. The expansive main level features a dramatic two-story family room with coffered ceiling, an enormous gourmet kitchen with custom cabinetry, center island and walk-in pantry, plus an exceptional media room with movie screen and projector. A gracious living room, formal dining room, oversized home office, and full bath complete the level. Upstairs, you'll find an expanded balcony, luxurious primary suite with grand bath, two walk-in closets, and sitting area, complemented by a princess suite, two additional bedrooms, full bath, and laundry. The finished lower level is an entertainer’s dream with full bar, game and bonus rooms, and full bath. Outside, enjoy manicured grounds, an expansive composite deck and oversized patio while taking in the amazing views. Ideally located in one of Holliston’s most desirable neighborhoods with access to the Charles River Rail Trail. A truly extraordinary offering where breathtaking views, exceptional finishes, remarkable scale, and sophisticated amenities create an exceptional luxury lifestyle. Seller Owned Solar transfers to Buyers.

4 Beds ⋅ 5 Baths ⋅ 73575584 MLS

Wow! Spectacular sweeping East-facing views and exceptional craftsmanship define this one-of-a-kind custom home in the coveted Highlands at Holliston. Beautifully sited on over an acre above Old Cart Path, this stunning residence offers three levels of luxurious living and extraordinary spaces for both everyday living and entertaining. A welcoming farmer’s porch opens to a grand two-story foyer with brilliant hardwood floors and custom millwork. The expansive main level features a dramatic two-story family room with coffered ceiling, an enormous gourmet kitchen with custom cabinetry, center island and walk-in pantry, plus an exceptional media room with movie screen and projector. A gracious living room, formal dining room, oversized home office, and full bath complete the level. Upstairs, you'll find an expanded balcony, luxurious primary suite with grand bath, two walk-in closets, and sitting area, complemented by a princess suite, two additional bedrooms, full bath, and laundry. The finished lower level is an entertainer’s dream with full bar, game and bonus rooms, and full bath. Outside, enjoy manicured grounds, an expansive composite deck and oversized patio while taking in the amazing views. Ideally located in one of Holliston’s most desirable neighborhoods with access to the Charles River Rail Trail. A truly extraordinary offering where breathtaking views, exceptional finishes, remarkable scale, and sophisticated amenities create an exceptional luxury lifestyle. Seller Owned Solar transfers to Buyers.

97 Old Cart Path, Holliston

$625,000

Charming antique Colonial in Holliston’s desirable Mudville neighborhood, filled with warmth, character, and classic New England appeal. Wide-plank pine floors run throughout the home, adding to its timeless charm. The bright and spacious eat-in kitchen features abundant natural light, cherry cabinetry, granite countertops, stainless steel appliances, and recessed lighting, with convenient access to the rear deck, perfect for relaxing or outdoor dining. The first floor also offers a comfortable living room, bedroom, and full bath, providing flexible living options. Upstairs are two additional bedrooms and a second full bath. Outside, enjoy a long, level yard with plenty of room for gardening, play, or entertaining. Enjoy the neighborhood lifestyle with a rail trail walking path just nearby, along with residential access to Lake Winthrop, where the beach, boat access, and playground offer another great spot to enjoy the outdoors. Ideally situated close to downtown Holliston’s shops, restaurants, and local amenities, this character-filled home offers a wonderful combination of antique charm, outdoor space, and a convenient location.

3 Beds ⋅ 2 Baths ⋅ 73575265 MLS

Charming antique Colonial in Holliston’s desirable Mudville neighborhood, filled with warmth, character, and classic New England appeal. Wide-plank pine floors run throughout the home, adding to its timeless charm. The bright and spacious eat-in kitchen features abundant natural light, cherry cabinetry, granite countertops, stainless steel appliances, and recessed lighting, with convenient access to the rear deck, perfect for relaxing or outdoor dining. The first floor also offers a comfortable living room, bedroom, and full bath, providing flexible living options. Upstairs are two additional bedrooms and a second full bath. Outside, enjoy a long, level yard with plenty of room for gardening, play, or entertaining. Enjoy the neighborhood lifestyle with a rail trail walking path just nearby, along with residential access to Lake Winthrop, where the beach, boat access, and playground offer another great spot to enjoy the outdoors. Ideally situated close to downtown Holliston’s shops, restaurants, and local amenities, this character-filled home offers a wonderful combination of antique charm, outdoor space, and a convenient location.

44 Exchange St, Holliston

$665,000

Unique residence offering space, character, and tremendous potential! Set on 5 acres with a large, private back yard surrounded by mature woods. This 3-bedroom, 2.5-bath home offers approximately 2,192 sqft of living space along with a 40x40 barn, 2-car garage, and a brand-new 3-bedroom septic system being installed prior to closing. The main level offers an open dining and kitchen area with island, range, black appliances, Woodmode dark walnut cabinetry, and imported Italian tile flooring. A spacious living room with laminate flooring, full bath, and screened porch with wood flooring. The primary bedroom includes a built-in AC unit and private half bath, with two additional bedrooms offering comfortable living space. The walk-out lower level adds 696 sqft including recessed lighting, laminate flooring, and a carpeted room that could serve as an office or studio. A full bath with tile flooring and tile shower completes the level. Oil-fired heat, 200-amp electrical service, and a 2017 water heater round out the mechanicals. The 40x40 barn is a standout feature, offering excellent potential for storage, workshop, hobbies, agricultural use, or other possibilities, subject to zoning and approvals. Part of the barn roof has been replaced. This home offers an excellent opportunity for buyers seeking fantastic land, substantial space, and the potential to make it their own — set in desirable Holliston, with a welcoming community, excellent schools, scenic conservation areas, and convenient access to major routes. A must see!

3 Beds ⋅ 3 Baths ⋅ 73575142 MLS

Unique residence offering space, character, and tremendous potential! Set on 5 acres with a large, private back yard surrounded by mature woods. This 3-bedroom, 2.5-bath home offers approximately 2,192 sqft of living space along with a 40x40 barn, 2-car garage, and a brand-new 3-bedroom septic system being installed prior to closing. The main level offers an open dining and kitchen area with island, range, black appliances, Woodmode dark walnut cabinetry, and imported Italian tile flooring. A spacious living room with laminate flooring, full bath, and screened porch with wood flooring. The primary bedroom includes a built-in AC unit and private half bath, with two additional bedrooms offering comfortable living space. The walk-out lower level adds 696 sqft including recessed lighting, laminate flooring, and a carpeted room that could serve as an office or studio. A full bath with tile flooring and tile shower completes the level. Oil-fired heat, 200-amp electrical service, and a 2017 water heater round out the mechanicals. The 40x40 barn is a standout feature, offering excellent potential for storage, workshop, hobbies, agricultural use, or other possibilities, subject to zoning and approvals. Part of the barn roof has been replaced. This home offers an excellent opportunity for buyers seeking fantastic land, substantial space, and the potential to make it their own — set in desirable Holliston, with a welcoming community, excellent schools, scenic conservation areas, and convenient access to major routes. A must see!

801 Winter St, Holliston

$975,000

Imagine coming home to a backyard that feels more like Vermont than MetroWest. Set on nearly four acres and abutting conservation land, 330 Marshall Street offers a wonderful connection to nature, yet remains close to everything that makes Holliston so desirable. This beautifully cared-for Colonial has a timeless quality, with warm wood floors, detailed trim and an inviting floor plan that works equally well for everyday life or a house full of family and friends. The kitchen, with granite counters and new tile floors, opens easily to the surrounding rooms, while French doors add character and allow spaces to be connected or separate when desired. Spend winter evenings by the fireplace and warmer days on the screened porch or deck, overlooking a yard that truly feels like a retreat. Beyond the lawn, the woods invite morning walks, hikes or snowshoeing after a fresh snowfall. Toward the back of the property, a small pond offers the possibility of ice skating when winter conditions allow—followed by hot chocolate and s’mores around the outdoor fire pit. Upstairs are four nicely sized bedrooms, including a generous primary suite with vaulted ceiling, walk-in closet and beautifully updated shower. It's a perfect place for quiet and a good book at the end of a long day. The walkout lower level offers finished living area along with plenty of additional room for a gym, media room, workshop or future expansion. An attached 2-car garage with new doors, excellent storage, central air and leased solar panels add to the home’s appeal. It’s a setting that feels wonderfully removed from it all, yet everyday conveniences are surprisingly close. Holliston High School—ranked #30 on Boston Magazine’s 2026 list of Greater Boston’s Top Public High Schools—Out Post Farm and Pinecrest Golf Club are all just minutes away, while I-495 and Milford’s wide selection of shopping and restaurants are within easy reach. For those who value a little more land, a little more nature and a little more room to breathe, this is a special place to call home.

4 Beds ⋅ 3 Baths ⋅ 73574969 MLS

Imagine coming home to a backyard that feels more like Vermont than MetroWest. Set on nearly four acres and abutting conservation land, 330 Marshall Street offers a wonderful connection to nature, yet remains close to everything that makes Holliston so desirable. This beautifully cared-for Colonial has a timeless quality, with warm wood floors, detailed trim and an inviting floor plan that works equally well for everyday life or a house full of family and friends. The kitchen, with granite counters and new tile floors, opens easily to the surrounding rooms, while French doors add character and allow spaces to be connected or separate when desired. Spend winter evenings by the fireplace and warmer days on the screened porch or deck, overlooking a yard that truly feels like a retreat. Beyond the lawn, the woods invite morning walks, hikes or snowshoeing after a fresh snowfall. Toward the back of the property, a small pond offers the possibility of ice skating when winter conditions allow—followed by hot chocolate and s’mores around the outdoor fire pit. Upstairs are four nicely sized bedrooms, including a generous primary suite with vaulted ceiling, walk-in closet and beautifully updated shower. It's a perfect place for quiet and a good book at the end of a long day. The walkout lower level offers finished living area along with plenty of additional room for a gym, media room, workshop or future expansion. An attached 2-car garage with new doors, excellent storage, central air and leased solar panels add to the home’s appeal. It’s a setting that feels wonderfully removed from it all, yet everyday conveniences are surprisingly close. Holliston High School—ranked #30 on Boston Magazine’s 2026 list of Greater Boston’s Top Public High Schools—Out Post Farm and Pinecrest Golf Club are all just minutes away, while I-495 and Milford’s wide selection of shopping and restaurants are within easy reach. For those who value a little more land, a little more nature and a little more room to breathe, this is a special place to call home.

330 Marshall Street, Holliston

$799,900

SUNDAY OPEN HOUSE CANCELLED. ACCEPTED OFFER. Welcome to 47 Jarr Brook Rd, a beautifully remodeled cape style home offering timeless character, modern updates, and exceptional indoor-outdoor living in desirable Holliston. The heart of the home is the fully remodeled kitchen, completed in 2020, featuring an open-concept design that seamlessly connects to the living room and eat in breakfast nook. Thoughtfully appointed with stainless steel appliances, quartz counter tops, built-in microwave, center island, and wine cooler, this inviting space is perfectly suited for both everyday living and entertaining. The living room offers a warm and welcoming atmosphere centered around a classic fireplace and custom built ins. The home features three well-appointed bedrooms and two updated full bathrooms, providing comfortable and versatile living space. Step outside and discover a truly special private retreat. The professionally landscaped grounds feature beautiful patio hardscaping, creating an ideal setting for outdoor dining, entertaining, and relaxing. A new deck and screened-in porch provide additional spaces to enjoy the outdoors throughout the seasons, while the private pool area offers the perfect escape for summer days. A dedicated fire pit adds another gathering space for those cool summar and fall evenings. An attached one-car garage adds convenience and additional storage. Ideally located on a quiet cul-de-sac, this home is a must see. Showings start Friday.

3 Beds ⋅ 2 Baths ⋅ 73574220 MLS

SUNDAY OPEN HOUSE CANCELLED. ACCEPTED OFFER. Welcome to 47 Jarr Brook Rd, a beautifully remodeled cape style home offering timeless character, modern updates, and exceptional indoor-outdoor living in desirable Holliston. The heart of the home is the fully remodeled kitchen, completed in 2020, featuring an open-concept design that seamlessly connects to the living room and eat in breakfast nook. Thoughtfully appointed with stainless steel appliances, quartz counter tops, built-in microwave, center island, and wine cooler, this inviting space is perfectly suited for both everyday living and entertaining. The living room offers a warm and welcoming atmosphere centered around a classic fireplace and custom built ins. The home features three well-appointed bedrooms and two updated full bathrooms, providing comfortable and versatile living space. Step outside and discover a truly special private retreat. The professionally landscaped grounds feature beautiful patio hardscaping, creating an ideal setting for outdoor dining, entertaining, and relaxing. A new deck and screened-in porch provide additional spaces to enjoy the outdoors throughout the seasons, while the private pool area offers the perfect escape for summer days. A dedicated fire pit adds another gathering space for those cool summar and fall evenings. An attached one-car garage adds convenience and additional storage. Ideally located on a quiet cul-de-sac, this home is a must see. Showings start Friday.

47 Jarr Brook Rd, Holliston

$599,900

Consider this your invitation to fall a little bit in love with Holliston! This beautifully maintained gem proves that 1,356 sq. ft. can live remarkably large. Step inside to a bright, inviting main level where gleaming hardwood floors create an effortless flow from the spacious living area into a cozy dining space. The charming kitchen brings plenty of personality with beautiful natural wood cabinetry, granite countertops, and a skylight that pours in natural light. Three comfortable bedrooms and a full bath round out the main level, while the delightful sunroom is ready for everything from morning coffee to quiet afternoons. Head downstairs to discover a versatile family room offering even more room to spread out, work from home, host guests, or create your favorite hangout space. Outside, the charm continues with a lovely white garden arbor, storage shed, and inviting yard space to enjoy in the warmer months. Recent improvements offer wonderful peace of mind, including a 2024 roof and newer heating and water heater systems, while fresh 2025 paint and 2026 washer and dryer add to the move-in-ready appeal. Enjoy all that Holliston has to offer, with Holliston High School, local shops and restaurants, parks, walking trails, and easy access to commuter routes all close by. Warm, welcoming, and wonderfully cared for, this is a home that makes everyday living feel easy!

3 Beds ⋅ 1 Baths ⋅ 73572997 MLS

Consider this your invitation to fall a little bit in love with Holliston! This beautifully maintained gem proves that 1,356 sq. ft. can live remarkably large. Step inside to a bright, inviting main level where gleaming hardwood floors create an effortless flow from the spacious living area into a cozy dining space. The charming kitchen brings plenty of personality with beautiful natural wood cabinetry, granite countertops, and a skylight that pours in natural light. Three comfortable bedrooms and a full bath round out the main level, while the delightful sunroom is ready for everything from morning coffee to quiet afternoons. Head downstairs to discover a versatile family room offering even more room to spread out, work from home, host guests, or create your favorite hangout space. Outside, the charm continues with a lovely white garden arbor, storage shed, and inviting yard space to enjoy in the warmer months. Recent improvements offer wonderful peace of mind, including a 2024 roof and newer heating and water heater systems, while fresh 2025 paint and 2026 washer and dryer add to the move-in-ready appeal. Enjoy all that Holliston has to offer, with Holliston High School, local shops and restaurants, parks, walking trails, and easy access to commuter routes all close by. Warm, welcoming, and wonderfully cared for, this is a home that makes everyday living feel easy!

93 Jerrold St, Holliston

$2,250,000

Welcome to 14 Fiske Pond Road! A dream home built w/the most unparalleled attention to detail, millwork & craftsmanship. The 5BR, 5BA house will appeal to today's modern families, multi-generational families, down sizers, & empty-nesters w/1st & 2nd floor primary options. The 1st floor open concept is the heart of the home w/soaring ceilings & natural light pouring in.The kitchen has SS high end appliances, walk-in custom pantry, 92 bottle wine chiller, 6 burner range, wall oven, center island & leads to LR w/gas FP, and DR. The primary BR is its own oasis w/luxurious spa BA & custom walk-in closet. 2nd BR/office & full BA also on 1st .The mudroom & laundry are have radiant floors & lead to 3 car garage. The 2nd floor is a surprise! 3 BR's (two ensuite), a 2nd FR w/gas FP, wet bar & vaulted ceilings + generous bonus room. 9ft ceilings. All BA's have radiant heat, speakers in most of house, fire pit. Conveniently located <10 miles many town centers: Sherborn, Dover, Natick, Wellesley.

5 Beds ⋅ 5 Baths ⋅ 73570164 MLS

Welcome to 14 Fiske Pond Road! A dream home built w/the most unparalleled attention to detail, millwork & craftsmanship. The 5BR, 5BA house will appeal to today's modern families, multi-generational families, down sizers, & empty-nesters w/1st & 2nd floor primary options. The 1st floor open concept is the heart of the home w/soaring ceilings & natural light pouring in.The kitchen has SS high end appliances, walk-in custom pantry, 92 bottle wine chiller, 6 burner range, wall oven, center island & leads to LR w/gas FP, and DR. The primary BR is its own oasis w/luxurious spa BA & custom walk-in closet. 2nd BR/office & full BA also on 1st .The mudroom & laundry are have radiant floors & lead to 3 car garage. The 2nd floor is a surprise! 3 BR's (two ensuite), a 2nd FR w/gas FP, wet bar & vaulted ceilings + generous bonus room. 9ft ceilings. All BA's have radiant heat, speakers in most of house, fire pit. Conveniently located <10 miles many town centers: Sherborn, Dover, Natick, Wellesley.

14 Fiske Pond Road, Holliston

$669,900

Privacy, acreage, and an incredible workshop—all in desirable Holliston! Set on 4.4 acres abutting town and conservation land, this well-maintained home offers a private, estate-like setting with space inside and out. Private 800+ foot driveway to the property. The home features a bright and comfortable layout, generous finished living space, a finished lower level, and covered decks perfect for enjoying the peaceful surroundings. The true showstopper is the massive multi-bay outbuilding with space for up to 6 vehicles—ideal for car enthusiasts, contractors, tradespeople, hobbyists, or anyone looking for a serious workshop right at home. With 4.4 acres, protected land along the property, abundant garage and workspace, and a convenient Holliston location, this is a unique property that’s increasingly difficult to find. Also conveniently located less than a half a mile from Holliston High school and Pinecrest Golf Club, and just 15 min to I-495.Newly installed septic, Title V Certificate of Compliance

3 Beds ⋅ 1 Baths ⋅ 73569184 MLS

Privacy, acreage, and an incredible workshop—all in desirable Holliston! Set on 4.4 acres abutting town and conservation land, this well-maintained home offers a private, estate-like setting with space inside and out. Private 800+ foot driveway to the property. The home features a bright and comfortable layout, generous finished living space, a finished lower level, and covered decks perfect for enjoying the peaceful surroundings. The true showstopper is the massive multi-bay outbuilding with space for up to 6 vehicles—ideal for car enthusiasts, contractors, tradespeople, hobbyists, or anyone looking for a serious workshop right at home. With 4.4 acres, protected land along the property, abundant garage and workspace, and a convenient Holliston location, this is a unique property that’s increasingly difficult to find. Also conveniently located less than a half a mile from Holliston High school and Pinecrest Golf Club, and just 15 min to I-495.Newly installed septic, Title V Certificate of Compliance

636 Highland St, Holliston

$1,475,000

263 South St contains five townhouse units, comprised of one (1) 3-Bedroom/2-Bathroom unit, one (1) 3-Bedroom/1-Bathroom unit, and three (3) 2-Bedroom/1-Bathroom units with 6,582 square feet of gross living area in 9,615 square feet of gross area. The Property is currently situated on 4.07 acres. Parking is readily available with nine (9) garage spaces, as well as ample surface parking spaces. With its bucolic nature surrounded by 25 acres of Conservation land and excellent tenant history, 263 South Street is truly a unique, one-of-a-kind investment property. 263 South Street features an attractive mix of spacious townhouse-style residences designed to appeal to today's renters. Units 1–4 offer desirable three-level layouts consisting of a full basement, main living level, and second floor, with sliding door access to a large, shared backyard with lush grounds. Unit 5 is a well-appointed single-level apartment situated above the Property's garage bays. Each residence is equipped with in-unit laundry, providing added convenience for tenants. Interior finishes include Formica countertops in Units 1, 2, 3, and 5, while Unit 4 features granite countertops. All apartments are separately metered, with tenants responsible for heat, hot water, central air conditioning, and electric service. 263 South Street presents the incoming investor ample opportunity toincrease the rental rates by programmatically renovating the remaining four units. In addition, the property is improved by a detached, two-story structure which features a Six-car garage parking as well as finished space above the garage. The potential exists to create an additional apartment at the site. Units 3 & 5 have received new heat pump systems over the last 2 years while all units have received new A/C systems over the last 10 years. Numerous appliances and water heaters have been replaced since current ownership took over, as well as an upgraded leeching field over the last 2 years. The opportunity exists for new ownership to separate out water utilities and put this onto tenants, as there are currently 5 water meters.

12 Beds ⋅ 6 Baths ⋅ 73568963 MLS

263 South St contains five townhouse units, comprised of one (1) 3-Bedroom/2-Bathroom unit, one (1) 3-Bedroom/1-Bathroom unit, and three (3) 2-Bedroom/1-Bathroom units with 6,582 square feet of gross living area in 9,615 square feet of gross area. The Property is currently situated on 4.07 acres. Parking is readily available with nine (9) garage spaces, as well as ample surface parking spaces. With its bucolic nature surrounded by 25 acres of Conservation land and excellent tenant history, 263 South Street is truly a unique, one-of-a-kind investment property. 263 South Street features an attractive mix of spacious townhouse-style residences designed to appeal to today's renters. Units 1–4 offer desirable three-level layouts consisting of a full basement, main living level, and second floor, with sliding door access to a large, shared backyard with lush grounds. Unit 5 is a well-appointed single-level apartment situated above the Property's garage bays. Each residence is equipped with in-unit laundry, providing added convenience for tenants. Interior finishes include Formica countertops in Units 1, 2, 3, and 5, while Unit 4 features granite countertops. All apartments are separately metered, with tenants responsible for heat, hot water, central air conditioning, and electric service. 263 South Street presents the incoming investor ample opportunity toincrease the rental rates by programmatically renovating the remaining four units. In addition, the property is improved by a detached, two-story structure which features a Six-car garage parking as well as finished space above the garage. The potential exists to create an additional apartment at the site. Units 3 & 5 have received new heat pump systems over the last 2 years while all units have received new A/C systems over the last 10 years. Numerous appliances and water heaters have been replaced since current ownership took over, as well as an upgraded leeching field over the last 2 years. The opportunity exists for new ownership to separate out water utilities and put this onto tenants, as there are currently 5 water meters.

263 South St, Holliston

$799,000

Far from your typical ranch! Gutted to the studs and completely reimagined in 2023, this home offers the look and feel of new construction with thoughtful design and high-end finishes throughout. The show stopping kitchen features vaulted ceilings, an oversized island, custom cabinetry, and quartzite countertops, opening seamlessly to the dining and living areas with custom built-ins. The primary bedroom offers a spacious walk-in closet, while the heated sunroom adds year-round living space. Extensive updates include a new roof, windows, whole-house spray foam insulation, prefinished hardwood floors, all-new electrical and panel, new plumbing throughout the home, HVAC, and water heater. A new driveway and back patio complete the improvements. Located in a desirable neighborhood close to shopping, parks, and trails, this move-in-ready home combines style, comfort, and the ease of single-level living.

3 Beds ⋅ 3 Baths ⋅ 73568151 MLS

Far from your typical ranch! Gutted to the studs and completely reimagined in 2023, this home offers the look and feel of new construction with thoughtful design and high-end finishes throughout. The show stopping kitchen features vaulted ceilings, an oversized island, custom cabinetry, and quartzite countertops, opening seamlessly to the dining and living areas with custom built-ins. The primary bedroom offers a spacious walk-in closet, while the heated sunroom adds year-round living space. Extensive updates include a new roof, windows, whole-house spray foam insulation, prefinished hardwood floors, all-new electrical and panel, new plumbing throughout the home, HVAC, and water heater. A new driveway and back patio complete the improvements. Located in a desirable neighborhood close to shopping, parks, and trails, this move-in-ready home combines style, comfort, and the ease of single-level living.

74 Westfield Dr, Holliston

$599,900

CHERISHED FAMILY HOME IN BRENTWOOD! Lovingly held by the same family since 1965, this classic Holliston property on Chamberlain Street offers a rare combination of long-held heritage, privacy and an extraordinary list of major brand-new improvements. Set in one of the town's most established neighborhoods, this home is ready for its next chapter to be written. At its heart is a bright kitchen featuring a convenient breakfast bar, dedicated eat-in dining area and ample counter space. Updates include the skylights with remote-controlled blinds (2026), dishwasher and oven (2025). The formal dining room and sprawling living room offer the ideal footprint to host holiday celebrations with NEW carpet (2026) while the finished lower level provides excellent, flexible bonus space. Upstairs, beautiful hardwood floors carry through all three bedrooms. A full bathroom has built-in storage that showcases the home’s authentic character. True peace of mind comes from the extensive list of big-ticket capital improvements completed by the sellers. ***Recent upgrades include a NEW roof, NEW septic system, NEW driveway, NEW 200-amp electrical panel, NEW wall-to-wall carpeting, NEW skylights, and FRESH interior paint — all completed in 2026 – with a NEW hot water tank (2024) and REBUILT AC condenser and furnace (2025).*** Exterior painted in 2022. Outside enjoy half an acre of land with plenty of room for outdoor play, gardening, or weekend entertaining. Move right in, relax, and start making your own memories from day one!

3 Beds ⋅ 1 Baths ⋅ 73567586 MLS

CHERISHED FAMILY HOME IN BRENTWOOD! Lovingly held by the same family since 1965, this classic Holliston property on Chamberlain Street offers a rare combination of long-held heritage, privacy and an extraordinary list of major brand-new improvements. Set in one of the town's most established neighborhoods, this home is ready for its next chapter to be written. At its heart is a bright kitchen featuring a convenient breakfast bar, dedicated eat-in dining area and ample counter space. Updates include the skylights with remote-controlled blinds (2026), dishwasher and oven (2025). The formal dining room and sprawling living room offer the ideal footprint to host holiday celebrations with NEW carpet (2026) while the finished lower level provides excellent, flexible bonus space. Upstairs, beautiful hardwood floors carry through all three bedrooms. A full bathroom has built-in storage that showcases the home’s authentic character. True peace of mind comes from the extensive list of big-ticket capital improvements completed by the sellers. ***Recent upgrades include a NEW roof, NEW septic system, NEW driveway, NEW 200-amp electrical panel, NEW wall-to-wall carpeting, NEW skylights, and FRESH interior paint — all completed in 2026 – with a NEW hot water tank (2024) and REBUILT AC condenser and furnace (2025).*** Exterior painted in 2022. Outside enjoy half an acre of land with plenty of room for outdoor play, gardening, or weekend entertaining. Move right in, relax, and start making your own memories from day one!

210 Chamberlain St, Holliston

$674,900

Nestled in a desirable Holliston neighborhood, this spacious raised ranch is set on a private lot abutting conservation land. The bright and welcoming main level features cathedral ceilings, abundant natural light, hardwood floors, and a wood-burning fireplace. The sunny, white-cabinet kitchen offers direct access to a large deck overlooking the private backyard, built-in pool, and beautiful patio—ideal for relaxing and entertaining. The main level also includes a tiled full bath, a primary bedroom with a private half bath, and two additional generously sized bedrooms. The finished lower level offers an open-concept family room with a second wood-burning fireplace, a versatile bonus room suitable for use as a fourth bedroom or home office, a well-appointed laundry room, and an additional half bath. Warm and inviting, this home offers abundant living space, privacy, numerous updates, and a newer septic system.

4 Beds ⋅ 3 Baths ⋅ 73567627 MLS

Nestled in a desirable Holliston neighborhood, this spacious raised ranch is set on a private lot abutting conservation land. The bright and welcoming main level features cathedral ceilings, abundant natural light, hardwood floors, and a wood-burning fireplace. The sunny, white-cabinet kitchen offers direct access to a large deck overlooking the private backyard, built-in pool, and beautiful patio—ideal for relaxing and entertaining. The main level also includes a tiled full bath, a primary bedroom with a private half bath, and two additional generously sized bedrooms. The finished lower level offers an open-concept family room with a second wood-burning fireplace, a versatile bonus room suitable for use as a fourth bedroom or home office, a well-appointed laundry room, and an additional half bath. Warm and inviting, this home offers abundant living space, privacy, numerous updates, and a newer septic system.

68 Gregory Rd, Holliston

$685,000

A touch of modern city but in the quiet suburbs. This 3-bedroom, 2 bath raised ranch offers both. Property is over 2 acres of privacy and quiet, with modern updates in the kitchen and baths. Upper level offers an open living room with fireplace, that leads into the dining area and kitchen. Take a moment sitting in the sun either on your deck off the kitchen or sunroom with skylights off the dining area. Move down the hall and you will find closet space, three bedrooms, and a full jack-and-jill bath attached to the main bedroom. Proceed to the lower level and you will find a fire placed family room, bonus room, full bath, storage, and access to the 2-car garage. As a surprise there is a finished space as well as storage in the pull-down attic. Some other bonuses include a covered patio on the lower level in the back, newer oil tank, storage shed, and small little pond.

3 Beds ⋅ 2 Baths ⋅ 73566661 MLS

A touch of modern city but in the quiet suburbs. This 3-bedroom, 2 bath raised ranch offers both. Property is over 2 acres of privacy and quiet, with modern updates in the kitchen and baths. Upper level offers an open living room with fireplace, that leads into the dining area and kitchen. Take a moment sitting in the sun either on your deck off the kitchen or sunroom with skylights off the dining area. Move down the hall and you will find closet space, three bedrooms, and a full jack-and-jill bath attached to the main bedroom. Proceed to the lower level and you will find a fire placed family room, bonus room, full bath, storage, and access to the 2-car garage. As a surprise there is a finished space as well as storage in the pull-down attic. Some other bonuses include a covered patio on the lower level in the back, newer oil tank, storage shed, and small little pond.

64 Marshall St, Holliston

$475,000

Welcome to 131 Goulding Street, a three-bedroom ranch offering the ease and convenience of one-level living on a level .48-acre lot. The home features a spacious living area, three bedrooms, and a full bath, along with a kitchen offering granite countertops and a gas stove. Additional features include replacement windows, vinyl siding, town water, and a one-car garage. The level lot provides plenty of outdoor space and offers the opportunity to create your own backyard setting. Conveniently located in Holliston, this property is a great opportunity for buyers looking for a ranch-style home with a practical layout and the potential to update and personalize the space to suit their needs.

3 Beds ⋅ 1 Baths ⋅ 73566520 MLS

Welcome to 131 Goulding Street, a three-bedroom ranch offering the ease and convenience of one-level living on a level .48-acre lot. The home features a spacious living area, three bedrooms, and a full bath, along with a kitchen offering granite countertops and a gas stove. Additional features include replacement windows, vinyl siding, town water, and a one-car garage. The level lot provides plenty of outdoor space and offers the opportunity to create your own backyard setting. Conveniently located in Holliston, this property is a great opportunity for buyers looking for a ranch-style home with a practical layout and the potential to update and personalize the space to suit their needs.

131 Goulding Street, Holliston

$769,000

A bright, showroom condition home in a community that is 8 years young and has matured into a beautiful location. In the immediate vicinity are two grocery stores, pharmacies, full service banks and a quintessential New England village downtown. The association has turned over to owner control meaning the priorities of the community are set by the residents while being young enough to be assessment free! This condominium, constructed in 2018, presents an immaculate property with two bedroom suites, one on the main level and a second in the upper level. A perfect condition home, offering a total of 2360 square feet of sophisticated living space. On the upper level one thousand square feet make up a suite of 3 areas and a full bath. A bedroom with walk-in closet, bonus room and loft connecting the two. The first floor consists of nearly fourteen hundred square feet is dedicated to a convenient easy floor plan to lead a single level lifestyle. This residence is thoughtfully designed for discerning individuals seeking a refined lifestyle within a private setting. The kitchen serves as the heart of this home, featuring an open-plan design that seamlessly integrates with the dining and living room. It is equipped with stainless steel appliances and a central island, with sink and dishwasher, providing both functional workspace and a focal point for social gatherings. The living room, adjacent to the kitchen/dining, is enhanced by a fireplace, offering an inviting atmosphere for relaxation and entertaining. An additional feature that enhances practical daily living, is the main level laundry room. Expanded living is available through the living room sliding door leading out to the deck with woodland views. The main bathroom is appointed with a double vanity and a walk-in shower, designed for both convenience and a touch of luxury. Additional amenities include a full basement, providing ample storage or potential for further customization. The property also benefits from an attached garage with space for two vehicles. Discover the exceptional living experience offered by this distinguished Holliston condominium. Quick closing possible.

2 Beds ⋅ 3 Baths ⋅ 73566269 MLS ⋅ ['Brooksmont Condominium'] BLDG.

A bright, showroom condition home in a community that is 8 years young and has matured into a beautiful location. In the immediate vicinity are two grocery stores, pharmacies, full service banks and a quintessential New England village downtown. The association has turned over to owner control meaning the priorities of the community are set by the residents while being young enough to be assessment free! This condominium, constructed in 2018, presents an immaculate property with two bedroom suites, one on the main level and a second in the upper level. A perfect condition home, offering a total of 2360 square feet of sophisticated living space. On the upper level one thousand square feet make up a suite of 3 areas and a full bath. A bedroom with walk-in closet, bonus room and loft connecting the two. The first floor consists of nearly fourteen hundred square feet is dedicated to a convenient easy floor plan to lead a single level lifestyle. This residence is thoughtfully designed for discerning individuals seeking a refined lifestyle within a private setting. The kitchen serves as the heart of this home, featuring an open-plan design that seamlessly integrates with the dining and living room. It is equipped with stainless steel appliances and a central island, with sink and dishwasher, providing both functional workspace and a focal point for social gatherings. The living room, adjacent to the kitchen/dining, is enhanced by a fireplace, offering an inviting atmosphere for relaxation and entertaining. An additional feature that enhances practical daily living, is the main level laundry room. Expanded living is available through the living room sliding door leading out to the deck with woodland views. The main bathroom is appointed with a double vanity and a walk-in shower, designed for both convenience and a touch of luxury. Additional amenities include a full basement, providing ample storage or potential for further customization. The property also benefits from an attached garage with space for two vehicles. Discover the exceptional living experience offered by this distinguished Holliston condominium. Quick closing possible.

65 Brooksmont Dr Unit 15, Holliston

$680,000

Welcome home to 203 Turner Road — a beautifully maintained split-level tucked on a quiet, tree-lined street in one of Holliston's most desirable neighborhoods, prized for top-rated schools, New England charm, and easy access to Rte 495 and the Mass Pike. Enjoy nearby Lake Winthrop for swimming, boating, and lakeside strolls, plus Ashland State Park just minutes away for hiking, trails, and outdoor recreation. All 3 bedrooms are situated on the main level, along with a full bath and a vaulted, beamed-ceiling living room centered on a brick fireplace and sunny bay window. Downstairs, the finished lower level adds incredible bonus space including a den or guest room, home office, separate workshop, second full bath, and laundry & pantry, perfect for remote work, hobbies, or guests. Step outside to a fully fenced, private 0.74-acre yard framed by mature trees, plus an incredible wraparound deck built for entertaining. An EV charging station is already installed, and with over $120,000 in work by the current owners: roof, furnace, septic, rebuilt chimney and more, this move-in-ready gem is not to be missed!

3 Beds ⋅ 2 Baths ⋅ 73562307 MLS

Welcome home to 203 Turner Road — a beautifully maintained split-level tucked on a quiet, tree-lined street in one of Holliston's most desirable neighborhoods, prized for top-rated schools, New England charm, and easy access to Rte 495 and the Mass Pike. Enjoy nearby Lake Winthrop for swimming, boating, and lakeside strolls, plus Ashland State Park just minutes away for hiking, trails, and outdoor recreation. All 3 bedrooms are situated on the main level, along with a full bath and a vaulted, beamed-ceiling living room centered on a brick fireplace and sunny bay window. Downstairs, the finished lower level adds incredible bonus space including a den or guest room, home office, separate workshop, second full bath, and laundry & pantry, perfect for remote work, hobbies, or guests. Step outside to a fully fenced, private 0.74-acre yard framed by mature trees, plus an incredible wraparound deck built for entertaining. An EV charging station is already installed, and with over $120,000 in work by the current owners: roof, furnace, septic, rebuilt chimney and more, this move-in-ready gem is not to be missed!

203 Turner Road, Holliston

$499,900

Opportunity knocks in this desirable neighborhood surrounded by higher-priced homes. This affordable three-bedroom ranch offers a smart layout with a fireplace living room, dining area, and an eat-in kitchen, plus three bedrooms and a full bath on the main level. The walk-out lower level expands your living space with a generous recreation room, workshop, and a half-bath/laundry area. Recent updates include newer gas heat, hot water (approx. one year old), and newer windows. With an expansive rear yard and solid bones, this original-owner home is a prime chance to build equity and customize to your vision. Act now.

3 Beds ⋅ 2 Baths ⋅ 73562180 MLS

Opportunity knocks in this desirable neighborhood surrounded by higher-priced homes. This affordable three-bedroom ranch offers a smart layout with a fireplace living room, dining area, and an eat-in kitchen, plus three bedrooms and a full bath on the main level. The walk-out lower level expands your living space with a generous recreation room, workshop, and a half-bath/laundry area. Recent updates include newer gas heat, hot water (approx. one year old), and newer windows. With an expansive rear yard and solid bones, this original-owner home is a prime chance to build equity and customize to your vision. Act now.

187 Turner Road, Holliston

$799,900

Discover the single-family home at 621 Marshall Street, offering the perfect blend of comfort, space, and privacy. This spacious 2,077-square-foot home sits on an expansive 80,150-square-foot lot, creating your own private retreat. Enjoy summer days by the inground pool, unwind in the hot tub, or relax in the peaceful outdoor setting. This home provides three bedrooms, two full bathrooms and an additional half bathroom, a beautifully updated kitchen, and more. Additional highlights include a three-car garage, providing abundant space for vehicles, storage, or hobbies. Conveniently located in desirable Holliston, this exceptional property offers the tranquility of a large lot while remaining close to shopping, dining, schools, and commuter routes. Don't miss the opportunity to add your personal touches and make this remarkable home your own! Home being sold as is.

3 Beds ⋅ 3 Baths ⋅ 73558504 MLS

Discover the single-family home at 621 Marshall Street, offering the perfect blend of comfort, space, and privacy. This spacious 2,077-square-foot home sits on an expansive 80,150-square-foot lot, creating your own private retreat. Enjoy summer days by the inground pool, unwind in the hot tub, or relax in the peaceful outdoor setting. This home provides three bedrooms, two full bathrooms and an additional half bathroom, a beautifully updated kitchen, and more. Additional highlights include a three-car garage, providing abundant space for vehicles, storage, or hobbies. Conveniently located in desirable Holliston, this exceptional property offers the tranquility of a large lot while remaining close to shopping, dining, schools, and commuter routes. Don't miss the opportunity to add your personal touches and make this remarkable home your own! Home being sold as is.

621 Marshall St, Holliston

$450,000

Don't miss the final opportunity to build your dream home in this exclusive Nantucket-style enclave on the Holliston/Sherborn town line. Restrictive covenants preserve the timeless character of this private community for generations to come. Enjoy over 25 acres of shared open space featuring scenic meadows, walking trails, and a peaceful pond. Bring your own architect and builder, or work with the seller to create your custom home. Seller has approved house plans and will provide septic designs, making it even easier to bring your vision to life.

73554651 MLS

Don't miss the final opportunity to build your dream home in this exclusive Nantucket-style enclave on the Holliston/Sherborn town line. Restrictive covenants preserve the timeless character of this private community for generations to come. Enjoy over 25 acres of shared open space featuring scenic meadows, walking trails, and a peaceful pond. Bring your own architect and builder, or work with the seller to create your custom home. Seller has approved house plans and will provide septic designs, making it even easier to bring your vision to life.

15 Fiske Pond Rd, Holliston

$1,249,000

Grand and glorious, this stately home is located in a double cul-de-sac neighborhood of refined homes, in a prime location on the Hopkinton line, close to Pinecrest golf course, Holliston High School, the Waseeka Wildlife Sanctuary (Audubon) and the commuter rail. Beautiful private setting abuts protected open space, with a gorgeous heated inground saltwater pool, cabana, large composite deck and spacious, flat backyard lawn area. Wonderful interior floor plan with front and back staircases is ideal for multi-generational living - finished 3rd floor with living area, bedroom and full bath. Main level features a large home office w/French doors and built-ins; sunny kitchen with white cabinetry and brand new stainless appliances; dramatic vaulted ceiling family room with floor-to-ceiling gas stone fireplace; fireplaced game/living room with custom molding and access to dreamy screened porch; dining room with crown molding; powder room with laundry and large mudroom. Second level features four bedrooms, showcased by the lovely, fireplaced primary with its spa bathroom and walk-in closet; oversized bedrooms offer lots of closet space. The walkup third level provides a multitude of possibilities for in-law living, work from home or teen hangout space; walkout lower level with home gym/exercise room. This home has plenty of room for all, while offering warm, cozy and inviting spaces, both inside and out. Be part of the lovely community of Holliston, which offers both Montessori and French Immersion programs as part of their exceptional school system.

5 Beds ⋅ 4 Baths ⋅ 73554074 MLS

Grand and glorious, this stately home is located in a double cul-de-sac neighborhood of refined homes, in a prime location on the Hopkinton line, close to Pinecrest golf course, Holliston High School, the Waseeka Wildlife Sanctuary (Audubon) and the commuter rail. Beautiful private setting abuts protected open space, with a gorgeous heated inground saltwater pool, cabana, large composite deck and spacious, flat backyard lawn area. Wonderful interior floor plan with front and back staircases is ideal for multi-generational living - finished 3rd floor with living area, bedroom and full bath. Main level features a large home office w/French doors and built-ins; sunny kitchen with white cabinetry and brand new stainless appliances; dramatic vaulted ceiling family room with floor-to-ceiling gas stone fireplace; fireplaced game/living room with custom molding and access to dreamy screened porch; dining room with crown molding; powder room with laundry and large mudroom. Second level features four bedrooms, showcased by the lovely, fireplaced primary with its spa bathroom and walk-in closet; oversized bedrooms offer lots of closet space. The walkup third level provides a multitude of possibilities for in-law living, work from home or teen hangout space; walkout lower level with home gym/exercise room. This home has plenty of room for all, while offering warm, cozy and inviting spaces, both inside and out. Be part of the lovely community of Holliston, which offers both Montessori and French Immersion programs as part of their exceptional school system.

25 Erin Way, Holliston

$950,000

Where timeless country living meets endless possibility- Once known as Kampersal Dairy Farm, this exceptional farm and home offer the space, charm and freedom you've been waiting for! The main house recently underwent a 1,000+ sq. ft. addition featuring an oversized 2 car garage w/ hydraulic lift. Kitchen, Bathrooms, Main Floor Primary Bedroom, Office, and Breezeways are all new. Renovations also include a full-length rear deck with sliders off the Kitchen and Primary BR. The wood stove efficiently heats the entire home, while portions of the original house have been preserved.Oversized three-story Barn recently received a board-and-batten facelift and offers abundant storage below. Set on just under 5 acres, Continue operating as a farm, Raise or board horses, Explore subdivision potential, or enjoy Country Living. Conveniently located near the Upper Charles Rail Trail, perfect for horse back riding and most outdoor activity, with easy access to Rts. 495, 109 &16

3 Beds ⋅ 3 Baths ⋅ 73552868 MLS

Where timeless country living meets endless possibility- Once known as Kampersal Dairy Farm, this exceptional farm and home offer the space, charm and freedom you've been waiting for! The main house recently underwent a 1,000+ sq. ft. addition featuring an oversized 2 car garage w/ hydraulic lift. Kitchen, Bathrooms, Main Floor Primary Bedroom, Office, and Breezeways are all new. Renovations also include a full-length rear deck with sliders off the Kitchen and Primary BR. The wood stove efficiently heats the entire home, while portions of the original house have been preserved.Oversized three-story Barn recently received a board-and-batten facelift and offers abundant storage below. Set on just under 5 acres, Continue operating as a farm, Raise or board horses, Explore subdivision potential, or enjoy Country Living. Conveniently located near the Upper Charles Rail Trail, perfect for horse back riding and most outdoor activity, with easy access to Rts. 495, 109 &16

85 Fisher Street, Holliston

$899,900

Gracious and stately, this sunny center entrance colonial offers a lovely updated main house plus two income generating apartments, making this a wonderful opportunity and investment. Located in the charming village of downtown Holliston, this home offers a coveted lifestyle of walking to schools, shops, cafes, playground, library, Upper Charles Rail Trail and Lake Winthrop. Updated kitchen features white cabinetry, wood flooring, granite counters, stainless appliances and an exposed beam; living room with pine flooring, built-ins and working fireplace; family room with lots of windows, built-ins, working fireplace and pine flooring; spacious dining room with beautiful original mantle and detailing, plus built-ins. The new screened porch & half bath complete the main level. Upstairs bedrooms are spacious and inviting, including the primary bedroom which offers the potential of being two rooms. Walk up 3rd floor provides either another bedroom or a fabulous home office space. A gem!

6 Beds ⋅ 4 Baths ⋅ 73549299 MLS

Gracious and stately, this sunny center entrance colonial offers a lovely updated main house plus two income generating apartments, making this a wonderful opportunity and investment. Located in the charming village of downtown Holliston, this home offers a coveted lifestyle of walking to schools, shops, cafes, playground, library, Upper Charles Rail Trail and Lake Winthrop. Updated kitchen features white cabinetry, wood flooring, granite counters, stainless appliances and an exposed beam; living room with pine flooring, built-ins and working fireplace; family room with lots of windows, built-ins, working fireplace and pine flooring; spacious dining room with beautiful original mantle and detailing, plus built-ins. The new screened porch & half bath complete the main level. Upstairs bedrooms are spacious and inviting, including the primary bedroom which offers the potential of being two rooms. Walk up 3rd floor provides either another bedroom or a fabulous home office space. A gem!

865 Washington St., Holliston

$749,990

Welcome to 660 Mayflower Landing — drastic price reduction for a quick closing. This beautifully maintained 2017-built colonial offers privacy and modern comfort on a secluded 0.73-acre lot at the edge of Fafard’s Constitution Village in desirable Holliston, MA, with large front and side yards and preserved woodlands wrapping the side and back yards. Tucked away yet conveniently located just minutes from Route 16, this home provides easy access to commuting routes, shopping, and local amenities while feeling worlds apart in its peaceful, wooded setting surrounded by conservation and open space land. Boasting 2,480 square feet of finished living space, this 3-bedroom, 2 full + 2 half bath home features an open and flexible floor plan perfect for today’s lifestyles. The main level offers a bright, sunny living room with fireplace, open kitchen/dinette area, and slider access to a spacious rear composite deck—ideal for outdoor entertaining and enjoying the private backyard. Hardwood floors flow throughout the primary living areas, while the carpeted bedrooms provide comfort and warmth. The finished basement adds significant additional living space and includes a half bath.

3 Beds ⋅ 4 Baths ⋅ 73545542 MLS

Welcome to 660 Mayflower Landing — drastic price reduction for a quick closing. This beautifully maintained 2017-built colonial offers privacy and modern comfort on a secluded 0.73-acre lot at the edge of Fafard’s Constitution Village in desirable Holliston, MA, with large front and side yards and preserved woodlands wrapping the side and back yards. Tucked away yet conveniently located just minutes from Route 16, this home provides easy access to commuting routes, shopping, and local amenities while feeling worlds apart in its peaceful, wooded setting surrounded by conservation and open space land. Boasting 2,480 square feet of finished living space, this 3-bedroom, 2 full + 2 half bath home features an open and flexible floor plan perfect for today’s lifestyles. The main level offers a bright, sunny living room with fireplace, open kitchen/dinette area, and slider access to a spacious rear composite deck—ideal for outdoor entertaining and enjoying the private backyard. Hardwood floors flow throughout the primary living areas, while the carpeted bedrooms provide comfort and warmth. The finished basement adds significant additional living space and includes a half bath.

660 Mayflower Landing, Holliston

$634,000

Welcome to 58 Wedgewood Drive, a beautifully maintained Holliston home offering over 2000 square feet of comfortable, versatile living and direct access to the Upper Charles Rail Trail. The well-appointed kitchen features stone countertop, stainless steel appliances, a center island, and plenty of space for everyday meals and entertaining. Rich hardwood flooring adds warmth and character to the inviting living room while comfortable bedrooms and 2 full baths complete the main living areas. Downstairs the spacious lower level offers even more room to gather and unwind. With an open layout and a dry bar, it's fantastic space for entertaining, movie nights, game days or simply relaxing with family and friends. Outside, the private backyard provides a peaceful setting for outdoor dining, gardening, or enjoying warm summer evenings,, And with direct access to the Upper Charles Rail Trail, miles of scenic walking and biking trails are almost right outside you door. Move-in ready and wonderfully located, this is a home designed t be enjoyed both inside and out.

3 Beds ⋅ 2 Baths ⋅ 73541116 MLS

Welcome to 58 Wedgewood Drive, a beautifully maintained Holliston home offering over 2000 square feet of comfortable, versatile living and direct access to the Upper Charles Rail Trail. The well-appointed kitchen features stone countertop, stainless steel appliances, a center island, and plenty of space for everyday meals and entertaining. Rich hardwood flooring adds warmth and character to the inviting living room while comfortable bedrooms and 2 full baths complete the main living areas. Downstairs the spacious lower level offers even more room to gather and unwind. With an open layout and a dry bar, it's fantastic space for entertaining, movie nights, game days or simply relaxing with family and friends. Outside, the private backyard provides a peaceful setting for outdoor dining, gardening, or enjoying warm summer evenings,, And with direct access to the Upper Charles Rail Trail, miles of scenic walking and biking trails are almost right outside you door. Move-in ready and wonderfully located, this is a home designed t be enjoyed both inside and out.

58 Wedgewood Dr, Holliston

$899,000

PRICE IMPROVEMENT!! Amazing opportunity to own New Construction in desirable Holliston on the Hopkinton line. This perfectly sized single-family home completed in 2026, offering 1813 square feet of meticulously designed living space, gleaming hardwood floors throughout. Upon entrance you will be greeted with an open floor of spacious luxury living room, cozy electric fireplace that flows into an open quartz filled kitchen, waterfall island, convenient pantry, spacious dining area, half bath and an easily accessible laundry room.Through the sliders onto the beautifully paved outdoor patio,its private, peaceful and great for entertaining.The residence features three thoughtfully appointed bedrooms, providing private retreats for all occupants, the primary suite offers a large custom closet, fireplace and modern full bath. Complementing other bedrooms an additional full bath. This exceptional property is poised to provide a refined living experience. We invite you to schedule a private showing to fully appreciate its distinctive qualities of this beautiful home.

3 Beds ⋅ 3 Baths ⋅ 73540173 MLS

PRICE IMPROVEMENT!! Amazing opportunity to own New Construction in desirable Holliston on the Hopkinton line. This perfectly sized single-family home completed in 2026, offering 1813 square feet of meticulously designed living space, gleaming hardwood floors throughout. Upon entrance you will be greeted with an open floor of spacious luxury living room, cozy electric fireplace that flows into an open quartz filled kitchen, waterfall island, convenient pantry, spacious dining area, half bath and an easily accessible laundry room.Through the sliders onto the beautifully paved outdoor patio,its private, peaceful and great for entertaining.The residence features three thoughtfully appointed bedrooms, providing private retreats for all occupants, the primary suite offers a large custom closet, fireplace and modern full bath. Complementing other bedrooms an additional full bath. This exceptional property is poised to provide a refined living experience. We invite you to schedule a private showing to fully appreciate its distinctive qualities of this beautiful home.

53 Louis St, Holliston

$1,795,000

Nestled in sought-after Cedarbrook, this exceptional 5-bed Colonial offers many updates including exterior painting, composite deck, new carpeting on upper and lower levels, and five new A/C condensers, offering exceptional living indoors and out. A two-story foyer with mahogany inlaid flooring sets the tone as you enter. Main level features elegant living and dining rooms, a great room with stone fireplace and custom built-ins, plus private home office with gas fireplace. Chef’s kitchen features Wolf gas range, double ovens, warming drawer, beverage fridge and butler’s pantry with sink and second dishwasher. Second floor offers five bedrooms including primary suite w/ a sitting room, three full baths, and convenient second-floor laundry. The finished walkout lower level with 8’ ceilings and full bath adds flexible living space. Outdoor living includes new deck overlooking saltwater pool, large front yard and farmer's porch. A truly remarkable home for everyday living and entertaining!

5 Beds ⋅ 6 Baths ⋅ 73538100 MLS

Nestled in sought-after Cedarbrook, this exceptional 5-bed Colonial offers many updates including exterior painting, composite deck, new carpeting on upper and lower levels, and five new A/C condensers, offering exceptional living indoors and out. A two-story foyer with mahogany inlaid flooring sets the tone as you enter. Main level features elegant living and dining rooms, a great room with stone fireplace and custom built-ins, plus private home office with gas fireplace. Chef’s kitchen features Wolf gas range, double ovens, warming drawer, beverage fridge and butler’s pantry with sink and second dishwasher. Second floor offers five bedrooms including primary suite w/ a sitting room, three full baths, and convenient second-floor laundry. The finished walkout lower level with 8’ ceilings and full bath adds flexible living space. Outdoor living includes new deck overlooking saltwater pool, large front yard and farmer's porch. A truly remarkable home for everyday living and entertaining!

16 Kingsbury Dr, Holliston

$1,275,000

Special 6.25% interest rate financing on 15/1 ARM on 30 year loan. Built in 2016 on a private 0.9-acre lot, this 4-bed, 3.5-bath Colonial offers over 4,000 sq ft of finished living space in an established neighborhood of newer homes. The 30-ft eat-in kitchen anchors the open main level with a large granite island, gas cooking, stainless appliances, a pantry and a slider to the composite deck and patio. Four fireplaces add warmth throughout, including the living room and the sunlit family room. Upstairs, the primary suite has a custom walk-in closet and a spa-style bath with a double vanity, plus three generous bedrooms, a flexible den/home office and 2nd-floor laundry. The finished lower level is made for entertaining: game room with wet bar and fireplace, media room with fireplace, exercise room and a full bath. Town water, Title 5 passed, 2-zone central air, solar for lower electric bills, irrigation and professional landscaping. Near trails, conservation land and major commuter routes.

4 Beds ⋅ 4 Baths ⋅ 73532141 MLS

Special 6.25% interest rate financing on 15/1 ARM on 30 year loan. Built in 2016 on a private 0.9-acre lot, this 4-bed, 3.5-bath Colonial offers over 4,000 sq ft of finished living space in an established neighborhood of newer homes. The 30-ft eat-in kitchen anchors the open main level with a large granite island, gas cooking, stainless appliances, a pantry and a slider to the composite deck and patio. Four fireplaces add warmth throughout, including the living room and the sunlit family room. Upstairs, the primary suite has a custom walk-in closet and a spa-style bath with a double vanity, plus three generous bedrooms, a flexible den/home office and 2nd-floor laundry. The finished lower level is made for entertaining: game room with wet bar and fireplace, media room with fireplace, exercise room and a full bath. Town water, Title 5 passed, 2-zone central air, solar for lower electric bills, irrigation and professional landscaping. Near trails, conservation land and major commuter routes.

120 Mohawk Path, Holliston

$700,000

Effortless living in this like-new 3BR 2.5BA, attached single family, set on a picturesque, level lot. Open-concept main level offers abundant natural light and a warm, inviting flow ideal for everyday living and entertaining. The kitchen features white cabinetry, center island, and granite countertops, opening to spacious living and dining areas. Upstairs includes three large bedrooms, two full baths, and a convenient laundry room. The primary suite offers a walk-in closet and bath with double vanity and tiled shower. Flexible layout allows one bedroom to serve as a home office or guest space. Additional highlights include a 2-car attached garage with EV charging, energy-efficient Pella windows, and an air purification system. Full basement provides excellent expansion potential and is already roughed for a bathroom. Enjoy no condo fees, but very young home! Prime location near downtown Holliston & Stoddard Park, blending luxury, comfort & convenience. Do not miss this great home!

3 Beds ⋅ 3 Baths ⋅ 73517320 MLS

Effortless living in this like-new 3BR 2.5BA, attached single family, set on a picturesque, level lot. Open-concept main level offers abundant natural light and a warm, inviting flow ideal for everyday living and entertaining. The kitchen features white cabinetry, center island, and granite countertops, opening to spacious living and dining areas. Upstairs includes three large bedrooms, two full baths, and a convenient laundry room. The primary suite offers a walk-in closet and bath with double vanity and tiled shower. Flexible layout allows one bedroom to serve as a home office or guest space. Additional highlights include a 2-car attached garage with EV charging, energy-efficient Pella windows, and an air purification system. Full basement provides excellent expansion potential and is already roughed for a bathroom. Enjoy no condo fees, but very young home! Prime location near downtown Holliston & Stoddard Park, blending luxury, comfort & convenience. Do not miss this great home!

228 Norfolk St Unit 228, Holliston

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