luxury properties for sale Holliston, United States

Imagine starting each morning with your coffee overlooking the private acre+ setting from the light-infused sunroom. This extension of the kitchen equally balances dining and relaxation, making entertaining and morning coffee enjoyable. Realize at the end of your busy day, this home has the amenities to restore peace and tranquility to even the busiest. Choose between the tiled glass shower (3 x 3) or the vaulted 2-person jacuzzi tub, but equally relaxing is floating by yourself in the (17 x 8) spa. Need to find more self-healing space? Try the chair in the back of the 23 x 8 dressing room. Realize the end of the day can be enhanced with a cozy fire and a good book. The rest of the home offers spacious rooms, a second fireplace, and a media room with a mini kitchen to keep snacks and beverages nearby. This is the home you have been waiting for. All these amenities, and the perfect location. Close to parks, walking trails, and stores.

Tucked at the end of a cul-de-sac in one of North Sherborn’s most sought-after neighborhoods, this exceptional Colonial sits on 2.16 private acres abutting Town Forest trails and is less than a mile from resident-only Farm Pond. A major renovation transformed the home with bright, open living spaces including a stunning chef’s kitchen and great room with panoramic backyard views. Features include custom cabinetry, double ovens, beverage bar, formal dining room with fireplace, living room with built-ins and fireplace, and a private home office. The architect-designed primary suite offers two luxurious bathrooms, a walk-in closet, and balcony. Four additional bedrooms, a second office, and spacious laundry room complete the upper level. The walk-out lower level includes a family room with fireplace, rec room, wine cellar, and workshop. Spectacular grounds and a welcoming neighborhood make this a rare forever home.

When the homeowners decided to build this home in 2012, they were looking for a neighborhood that offered larger lots and more space between homes. This nearly one-acre lot provided the opportunity to create the backyard they had always wanted. They installed an inground gunite pool which became their favorite place to spend summer days, and the yard still offers plenty of room for volleyball, cornhole, and a large tent for parties and special occasions. One of the details they prioritized was 9-foot ceilings throughout the first floor, second floor, and basement, enhancing the home’s spacious feel from top to bottom. They also expanded the original design by adding a great room off the family room, complete with a wet bar that includes a beverage refrigerator, and space for a pool table. With direct access to a 30’ x 28’ composite deck with hot tub, it has become one of their favorite spaces for entertaining.

Original Donnelly Estates mansion showcasing French-inspired architecture, timeless craftsmanship, on stunning, sophisticated private lot. This exceptional Dover home offers over 6,700 sq. ft. of finished living space with 15' ceilings, four wood-burning fireplaces, a grand foyer with curved staircase, and exquisite millwork throughout. Expansive living and dining rooms, an eat-in chef's kitchen with island, and a spectacular cathedral-ceiling family room with exposed brick and loft create ideal spaces for entertaining. Private library, bonus room, study/guest room, and finished lower level add flexibility. The spacious primary suite features a fireplace, plantation shutters, and two closets. Three additional bedrooms, two family baths, and finished lower level with dedicated laundry offers space for gym, TV or play space. Meticulously maintained by the current owners, this home is move-in ready or the perfect opportunity to update and personalize.

An absolute masterpiece of design and elite engineering by an award-winning local builder. As the crown jewel of the collection, this premier, unique floorplan is fully customizable. The high-performance, energy-efficient home features a supreme HERS score, an incredibly tight envelope insulation package, an ERV fresh air system, and a balanced Make-Up Air system. Inside, 4 white oak floors lead to a magnificent family room with coffered ceilings and a custom front-and-back kitchen boasting the Thermador Professional Collection, a 48 gas range, and handmade cabinetry. High-end, insulated Pella EnergyStar windows flood the massive 7,800+ SF layout with light, highlighting 5 bedrooms, 5.5 baths, an octagonal breakfast room, and a wet bar. The expansive finished walkout lower level is ideal for a future golf simulator or theater. Enjoy neighborhood access to 10 acres of protected Sudbury River trails. Walk to the commuter rail; 26 miles to Boston. Ask about builder incentives!

An absolute masterpiece of design and elite engineering by an award-winning local MA builder. This high-performance, energy-efficient home features a supreme HERS score, ERV fresh air system, and balanced Make-Up Air. Inside, 4 white oak floors lead to a magnificent family room with coffered ceilings and a chef's kitchen with handmade custom cabinetry. High-end Pella windows flood the sprawling 5,450 SF plan with light, highlighting 4 bedrooms—each with its own private en-suite bath! This weekend only: reserve by the end of June and choose 1 of 5 FREE builder luxury upgrade packages—Entertainment, Theater, Gym, Golf Lounge/Simulator, or Outdoor Living! Best of all, the builder provides, installs, and completes the entire package prior to closing. Positioned for beautiful scenic views with direct access to 10 acres of protected Sudbury River trails, yet just 26 miles from Boston and a short walk to the commuter rail. See firm remarks for incentive details!

Welcome home to 30 Stanhope Drive. Nestled on a gorgeous lot in one of Norfolk’s most desirable neighborhoods, this classic Colonial blends timeless design w/thoughtful updates. Heart of the home is a beautifully appointed eat-in kitchen w/granite countertops and SS appliances. Stunning custom fireplace/mantel w/beautiful backlit built-in shelves anchors the sunny family room. French doors open to separate sunroom with slider to deck-ideal for grilling and container gardening. Perfectly appointed mudroom off oversized two-car garage completes the home’s “west wing.” Generous foyer separates a dedicated formal dining room and enormous front-to-back living room with magnificent floor-to-ceiling bay window. A bath with shower completes this level. Upstairs, three large bedrooms w/meticulous hardwood floors share renovated bath. Second floor laundry? Check! A serene primary suite w/walk-in closet and updated private bath completes second level. Versatile finished LL for fitness, media, or play. Just 1.2 miles to commuter rail.

Sited along the Sudbury River, this enchanting four to five bedroom, three and a half bath Colonial offers 3,344 square feet of refined living and outdoor space that feels like a hidden gem. A large deck and bluestone patio overlooking serene surroundings create a sense of true indoor-outdoor living. Inside, a soaring two-story foyer sets the tone of the gracious residence. The expansive family room opens through glass pocket doors, and the inviting fireplaced dining room with built-ins adds warmth and character. The sprawling kitchen impresses with a granite island, eat-in peninsula, cooktop, wall oven, and full wall of pantry storage. The primary suite features a window seat with panoramic views, three walk-in closets, and a high-style remodeled bathroom with soaking tub, tiled shower, and double vanity. The versatile lower level offers a great room plus an additional potential bedroom and remodeled full bath. More than a home - this is a lifestyle of nature, privacy, and elevated living.

Welcome home to a stunning Colonial in a coveted cul-de-sac neighborhood. The dramatic two-story foyer opens to an expansive first floor layout featuring 9' ceilings, front-to-back living/dining rooms, dedicated home office, and showstopping family room with stone fireplace. The eat-in kitchen boasts granite counters, large island, wine fridge, ample cabinetry/storage, and slider to the large deck overlooking a beautiful flat backyard on the acre+ lot. Upstairs, the sprawling primary retreat offers two large walk-in closets, attached bonus room, and a spa bath with double vanity. Three additional bedrooms and another full bath complete the upper level. Major upgrades include a $35K high-efficiency heat pump HVAC system (10-yr transferrable warranty), fully-owned solar panels, all-electric home, hardwood flooring, refreshed full baths with quartz vanities, & partial roof replacement. All this, with access to top-rated schools and minutes to the Commuter Rail, Rt. 9, Mass Pike, and 495.

42 North Street offers the rare combination of privacy, acreage, and turnkey living on over six secluded acres just moments to the Franklin/Foxboro commuter rail, town center, and Gillette Stadium. This beautifully maintained 4-year-young home features a stunning chef’s kitchen with Thermador and Bosch appliances, oversized quartz island, two refrigerators, walk-in pantry, and abundant prep space. A formal dining room with French doors opens to the 26’ x 31’ great room with gas fireplace, ideal for hosting large gatherings so everyone feels comfortable. The spacious primary suite offers vaulted ceilings, gas fireplace, oversized custom walk-in closet, and spa-like bath with soaking tub. Three additional bedrooms, finished third floor bonus space, and an impressive 1,000+ sq ft barn/shed with two garage bays, electricity, and concrete floors complete this exceptional property. OPEN HOUSE Sunday 5/31 1:30-3:30.

Put your mark on a dream home by Southborough’s premier builder. This new construction home combines a sleek, open-concept design with the exquisite craftsmanship expected at this level. A grand two-story foyer leads to a gourmet kitchen featuring custom inset cabinetry, Quartz countertops, and an oversized social island. The family room, anchored by a modern fireplace, creates a sophisticated yet warm gathering spot.The thoughtful first-floor layout includes both a private Study and a Home Office, each with an adjacent bathroom. Upstairs, the primary suite serves as a serene retreat with a boutique-style walk-in closet and spa bath. The unfinished basement offers soaring ceilings—ideal for a golf simulator or gym. Set on a rare, flat cul-de-sac lot, you’ll enjoy a private yard with easy access to the MBTA Commuter Rail, Boston/Worcester routes 90, 495, and 9, and Breakneck Hill trails. Experience Southborough’s top-rated public schools and prestigious private schools and a lifestyle of refined tranquility. Photos are of similar homes; early-stage buyers may customize.

A private garden estate overlooking the Upton State Forest, where a winding paver driveway meanders through mature gardens before arriving at an extraordinary custom home. Created by combining three lots into one remarkable homesite, this custom-built residence offers exceptional privacy while remaining just minutes from Route 495, the Mass Pike, shopping, and dining. Nearly two years in the making, every aspect of the home was carefully planned, from its architectural details to its placement on the property to maximize views of the mature gardens and the Upton State Forest beyond. Beautifully landscaped grounds create a remarkable sense of arrival and a peaceful retreat in every season.

Situated in a sought-after Hopkinton neighborhood, this thoughtfully designed Colonial offers quality craftsmanship, modern finishes, and an exceptional setting surrounded by natural beauty. The main level features an open-concept floor plan with hardwood flooring, a gas fireplace, and a well-appointed kitchen showcasing quartz countertops, stainless steel appliances, a center island, and pantry. The spacious primary suite includes a walk-in closet and private bath, while two additional bedrooms and a flexible bonus space provide versatility for today's lifestyles. Enjoy a fenced backyard, patio, and stone firepit. Ideally located near Whitehall Reservoir, conservation trails, major commuter routes, and Hopkinton's highly regarded schools, this home offers the perfect blend of privacy, recreation, and convenience.

Tucked along beautiful scenic Pine Hill Road, this stunning Southborough Colonial sits on a peaceful acre lot abutting conservation land: the kind of setting that makes every day feel like a retreat. Inside, the recently renovated magazine-quality kitchen (~$100K) steals the show: professionally designed with quartz counters, premium stainless appliances, large island, and a custom beverage center/coffee bar. Stylish modern bathrooms, fresh carpets throughout the upper level, and gleaming hardwoods and attractive tile throughout the first floor complete the polished interior. Four spacious bedrooms, front-to-back family AND living rooms, gracious foyer with double closets, an oversized lower-level mudroom, and a flexible finished basement room (ideal for a home office, gym, or playroom) offer spaces for every need. Meticulously maintained home; see extensive list of updates and improvements attached to MLS. Easy access to Rt. 9 and the Mass Pike makes this a commuter's dream!

Welcome to 45 Blueberry Lane, a timeless Colonial set on a picturesque 1.08-acre lot in one of Westwood's most sought-after neighborhoods. Tucked away on a quiet side street, this home is a peaceful retreat, offering a rare combination of privacy, luxury, and convenience, just minutes from top-rated schools, shopping, parks, commuter rail, and major highways. From the moment you arrive, you'll appreciate the home's cozy and inviting atmosphere, and classic New England charm. Inside, a freshly painted interior in today's neutral tones, rich hardwood floors, and elegant crown molding throughout the first floor create a warm and sophisticated setting. The spacious living room, highlighted by a stunning bay window, flows effortlessly into the formal dining room, perfect for holiday gatherings, celebrations, and everyday entertaining. The heart of the home is the expansive kitchen featuring granite countertops, stainless steel appliances, a center island, pantry, and spacious dining area where family and friends excitedly gather. Just beyond, the inviting family room is anchored by a beautiful brick fireplace with custom built-in cabinetry, creating the perfect place to unwind after a long day. Step outside to the screened porch, where you'll enjoy summer dinners, morning coffee, or simply relaxing while overlooking the peaceful yard. Upstairs, the spacious primary suite offers a walk-in closet and private bath, while two additional generously sized bedrooms share a well-appointed full bath, providing comfortable accommodations for family and guests. As you venture outside to the backyard, you’ll see how it truly sets this property apart. Designed for the nature enthusiast and adventure seeker, this private wooded setting offers endless opportunities to explore, create walking paths, build a firepit gathering area, or simply enjoy the serenity of your own backyard retreat. Scale the rocky hilltop and you'll be rewarded with breathtaking elevated views, a hidden gem that makes this property truly special and unlike anything else in the neighborhood. Additional highlights include a convenient mudroom with first-floor laundry off the attached two-car garage, two-zone central air, 200-amp electrical service, a full basement with radon remediation system offering future expansion potential, an enclosed patio, and an oversized paved driveway with parking for multiple vehicles.

Welcome to 18 Benvenue Street! This sun-filled Colonial in the coveted Dana Hall neighborhood offers thoughtful updates and exceptional living space throughout. The open-concept first floor features an updated eat-in kitchen with custom cabinetry, quartz countertops, stainless steel appliances, tiled backsplash, and peninsula, flowing seamlessly into the dining and family rooms. A fireplaced living room, half bath, and spacious laundry room with built-ins complete the main level. Upstairs are four generously sized bedrooms, including a primary suite with a walk-in closet and private bath, plus an additional full bath in the hallway. The finished lower level offers a large gym/playroom, fifth bedroom, and full bath, ideal for guests or extended family. Enjoy the beautifully landscaped backyard with your own private oasis patio and level lawn, perfect for entertaining. Central A/C, one-car garage and newer shed complete this exceptional home.

Built in 1996 this three level home abutting the Bay State Rail Trail has a very flexible floor plan for the living level. Sitting room off of the kitchen has a wood burning fireplace and deck with sweeping woodsy views. First floor has a garage, workshop, den (exercise room) and laundry, second floor has an open kitchen and family room. Kitchen has a great layout, plenty of granite countertops with a peninsula for breakfast bar seating. Flexible floor plan allows for different uses of the living level. Living room has bow window and small office. Third floor has the primary bedroom suite with double closets and a five-piece bath with soaking tub, shower and two vanities. There are two more bedrooms and full bath. Pull down ladder for attic storage. Garage with interior access. Large yard stretches along the Bay State Rail Trail. Professional greenhouses in backyard can stay or we can remove them prior to closing. Fabulous setting back from the road. Six minute drive to Needham Junction for commuter rail.

Enjoy panoramic views of Dudley Pond from this beautifully crafted 2019 Dutch Colonial offering the perfect condo alternative. The open floor plan features a spacious living room with a gas fireplace, open dining area for eight, a stunning white kitchen with center island seating for four, Thermador appliances, and a first-floor office or third guest bedroom. Upstairs are two ensuite bedrooms, including a luxurious primary suite with a fireplace and private deck overlooking the water. A wraparound porch, second-floor laundry, oversized two-car garage+added storage room and generous yard complete the home. Pond access provides year-round recreation including kayaking, canoeing, swimming, and skating.

Welcome to one of Mendon's most coveted neighborhoods! Tucked away on a picturesque cul-de-sac in desirable King Philip Path, this custom-built Colonial has been impeccably maintained by its original owners. Offering over an acre of professionally maintained grounds w/ in ground pool, hardwood flooring throughout, freshly painted interior & exterior, & countless renovations. The main level offers quality custom built-ins w/ electrical & a wood burning fireplace in the family room, formal dining room, & living room/study. The kitchen features stainless steel appliances, granite countertops, & a spacious eat-in dining area. Four bedrooms incl. the primary w/ en suite & walk-in closet complete the 2nd level. The finished lower level is complemented by hardwood flooring in an open plan entertaining space, including ample storage. System updates include; new furnace, Andersen™ windows & exterior doors, well pump, new exterior lighting, water softener system, & so much more. Welcome Home!

Glen Echo is a most desirable neighborhood close to Rt 495, MA Pike & Westborough. This pristine & spacious 4 bedroom, 3.5 bath Chatsworth Model Colonial has been impeccably maintained by its original owners. Enter to dramatic 2 story foyer w/ wainscoting & balcony. Open floor plan, 9 ft ceilings & tons of windows give this home an airy & roomy feel. Main level boasts hardwoods throughout. Gourmet eat-in kitchen is a cook's dream - granite, SS appliances, dbl oven, vented out hood vent, walk-in pantry, expansive island, butler's nook, desk area & sliders to composite deck overlooking private yard w/ woodland views. Spacious family room w/ FP. Large office w/ French doors, living room, dining room & laundry/mud room complete 1st floor. Added convenience - a 2nd staircase. Spectacular Primary Suite w/ sitting area, gorgeous bath, jetted tub & updated tiled shower. Jack & Jill bath connects two good size bedrooms. 3rd full bath in 4th bedroom. ~2000 sq ft unfinished basement w/ sliders.

Stately and spacious, this 5-bedroom Georgian Colonial in sought-after Olde Jackstraw Village offers timeless character, exceptional versatility, and a wonderful west-side neighborhood setting. A gracious curved staircase welcomes you into the open foyer, leading to a front-to-back fireplaced living room, private first-floor office, formal dining room, and inviting fireplaced family room. The oversized eat-in kitchen is ideal for those who love to cook, featuring extensive cabinetry, two dishwashers, and two stoves. Each bedroom is generously sized, including a finished walk-up third level with a full bedroom, perfect for guests, hobbies, or additional living space. One bedroom offers a wonderful surprise: an alcove of closets plus a bonus room over the garage. Wide-pine floors add warmth and character throughout this reproduction-style home, a signature look of this beloved neighborhood. A young roof, town water/sewer, and a charming screened porch complete this special offering.

Heritage Meets Modern Comfort....Welcome to idyllic Olde Jackstraw Village—where timeless charm meets thoughtful updates! This 5BR Colonial stuns with wide pine floors, built-ins, and five fireplaces. Four bedrooms feature two large closets each. The huge walk-up attic (10-ft ceilings, insulated floor) offers 800+ sq ft of potential living space. Cook like a pro in the large kitchen with fireplace, vented hood, and freshly painted cabinets. Central A/C upstairs, Nest thermostats, smart lighting, and many 2022–2025 upgrades reflect pride of ownership. Enjoy a newer roof, windows, oil tank, water heater, heating system and New driveway. Outdoors: a serene 2-tier yard with firepit, trail, raised beds, and a shaded creek side area. Entertain on the deck or shoot hoops on the flat driveway with pro-grade system. The oversized 2-car garage has epoxy floors, painted walls, shelves, and ample storage. Quiet cul-de-sac near top-rated Fales School—immaculate, move-in ready, and truly special!

Custom-built Colonial inspired by classic Connecticut Valley design, thoughtfully positioned on a private wooded lot with a picturesque brook running through the property. With over 6,733 square feet under the roof, the home offers both immediate livability and meaningful expansion potential. Approximately 3,534 square feet of finished living space is complemented by a walk-up attic and full basement, each ready for future finishing. This creates a rare opportunity to grow into the home over time rather than outgrow it. The layout is designed with flexibility in mind, offering a range of possible living arrangements, including multigenerational use, along with dedicated spaces that support today’s work-from-home needs. The first floor includes a private office and an additional den that could easily function as a bedroom, giving the home adaptability without requiring structural changes. At the center of the home, the updated kitchen serves as both a functional workspace and a natural gathering point. Features include granite countertops, upgraded cabinetry, stainless steel appliances, a wine chiller, pot filler, and Italian porcelain flooring. The combination of materials and layout reflects both durability and thoughtful design. Bathrooms throughout the home are finished with marble flooring, stone surfaces, and consistent upgrades that reinforce a cohesive, elevated feel across all levels. Outdoor living is equally considered. A large composite deck overlooks the wooded surroundings and the natural movement of the brook, creating a space that feels connected to the landscape rather than imposed on it. The privacy of the lot enhances this experience, making the outdoor areas as usable as the interior. Beyond the home itself, there is an optional community pool, offering an additional recreational amenity without the maintenance responsibilities of private ownership. This property presents a distinctive opportunity for buyers seeking scale, flexibility, and long-term potential in a setting that offers both privacy and character.

This welcoming, warm, 4-bedroom Dutch Gambrel-style Colonial home is located on the desirable East side of Westborough. This recognizable property has outstanding curb appeal. It has had great caretakers for the last two decades who have made continuous updates throughout their ownership both inside and out. It boasts a spacious front to back family room with a center wall fireplace, which abuts a generously sized dining room. Across the foyer there is a flex room currently used as a private office.There is hardwood and ceramic tile flooring throughout, and solid-surface countertops in the eat-in kitchen along with a stunning backsplash with subway tiles stacked on the half. Great thought and love went into making this house a home. There is also a cozy, wood paneled mudroom through the side entrance. As you walk out onto the deck you'll be pleasantly surprised to find a large, flat, private backyard. It is conveniently situated on the corner of the Hundreds Road neighborhood offering fast and convenient access to nearby commuter highways including private access to Route 9 east directly from the neighborhood.