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741 Winter St., Holliston
$650,000
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
105 Dodd Drive, Holliston
$695,000
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
72 Alden Road, Holliston
$649,900
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
423 South St, Holliston
$685,000
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
1093 Washington St Unit 1093, Holliston
$699,900
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
1093 Washington St Unit 1093, Holliston
$699,900
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
468 Underwood St, Holliston
$650,000
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
35 Jerrold Street, Holliston
$625,000
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
44 Exchange St, Holliston
$625,000
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
801 Winter St, Holliston
$665,000
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
636 Highland St, Holliston
$669,900
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
68 Gregory Rd, Holliston
$674,900
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
64 Marshall St, Holliston
$685,000
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
58 Wedgewood Dr, Holliston
$634,000
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
228 Norfolk St Unit 228, Holliston
$700,000
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
228 Norfolk St Unit 228, Holliston
$700,000
3 Beds ⋅ 3 Baths ⋅ 73510333 MLS ⋅ ['228-230 Norfolk Street Holliston Condo'] BLDG.
Effortless living in this like-new 3BR 2.5BA townhouse-style condo 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 and a prime location near downtown Holliston and Stoddard Park, blending luxury, comfort and convenience. Do not miss this great condo!

228 Norfolk St Unit 228, Holliston
186 Locust St, Holliston
$649,000
3 Beds ⋅ 2 Baths ⋅ 73328308 MLS
Escape to this beautifully maintained, sun-drenched 3-bed, 2-bath Raised Ranch on scenic 1/2-acre lot! The open-concept main level features gleaming hardwood floors, fireplaced living room, and a seamless flow to the dining area. Gourmet kitchen boasting granite countertops, tiled backsplash, stainless steel appliances with center island / breakfast bar. French doors off the kitchen lead to a screened-in porch overlooking the private, lush backyard. The lower level offers a spacious family room with fireplace, recessed lighting, full bath with laundry, and direct access to the attached garage. Recent updates include roof, windows, vinyl siding, electrical, heating, central A/C, kitchen, baths, septic system and more. Conveniently located near all that Holliston has to offer, this turn-key home is ready for you to move right in!

186 Locust St, Holliston

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