luxury houses for sale Holliston, United States

Stately and grand meets modern luxury and comfort. This impressive home has been meticulously renovated to maintain timeless charm while offering contemporary finishes and amenities. Step into timeless elegance with this incredibly charming Colonial home, designed in 1910. This stunning stucco residence boasts soaring ceilings & 8 fireplaces across 3 floors of living space. The front door welcomes you to a breathtaking foyer, leading to a library, formal dining room, living room & eat-in kitchen. The first floor of the home has fine ceiling moldings and wainscoting. With 6 plus bedrooms, 8 baths & a primary suite w/ dressing room, this home offers unmatched space. A three -car garage & beautifully landscaped yard w/ patio completes the exterior. Set on over 7 acres with a carriage house and barn. The long driveway offers great privacy. Minutes to town, shopping and restaurants. Call for your private tour!

An exceptional opportunity to own a beautifully sited waterfront property in one of Hopkinton's most desirable neighborhoods. Nestled on a picturesque pond and surrounded by mature landscaping, 28 South Mill Street offers a rare combination of privacy, natural beauty, and convenience. Pride of ownership is evident throughout the property, with extensive renovations and improvements made over the years that have enhanced both its functionality and long-term appeal. The home's striking exterior presence is complemented by outdoor spaces designed to take full advantage of the serene water views. Enjoy morning coffee overlooking the pond, entertain guests outdoors, or simply appreciate the changing seasons from this special setting. Featuring owned solar panels for long-term energy savings and sustainability, the property is also located near top-rated schools, shopping, dining, recreation, and major commuting routes.

Exceptional historic estate in the heart of Sherborn Center, the iconic Calvin Sanger House (c.1819) is a gracious Federal-style Colonial, thoughtfully renovated for modern living while preserving the character and craftsmanship that make this home so distinctive. Set on just over two beautifully landscaped acres, this landmark residence offers a rare combination of history, elegance and modern luxury. Period details include soaring ceilings, beautiful hardwood floors, refined millwork and multiple fireplaces. Gracious formal living room with window seat with original pocket doors to dining room with French doors to bluestone patio. This all complemented by a stunning renovated chef’s kitchen with stainless steel appliances, custom cabinetry and generous workspace. A flexible first-floor office or bedroom with bay windows and adjacent full bath is ideal for guests or working from home and could be utilized as a two-room in-law suite. The spacious family room features a fireplace, wet bar and French doors to an upper deck. A walk-out lower level with recreation space and full bath offers additional flexibility for guests, fitness or entertaining. Upstairs are four generous bedrooms and beautifully updated baths throughout. The renovated primary suite is a serene retreat with a luxurious bath and dressing area. Two additional bedrooms share an updated connecting bath, while the fourth bedroom has a dedicated full bath just across the hall. Upstairs laundry adds another modern convenience. Outside, mature landscaping, classic New England stonewalls to an in-ground pool create a private retreat in the heart of the village. An exceptional location, just steps from Sherborn’s newly expanded Library and soon-to-open History Center, with brand-new tennis and pickleball courts just down the street. Enjoy easy access to Sherborn’s renowned trail system, Farm Pond, consistently top-ranked Dover-Sherborn school system, restaurants, Town Hall, houses of worship and village amenities. A rare opportunity to own one of Sherborn’s most distinguished historic residences, where more than two centuries of New England character and beautifully renovated modern living come together.

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.

One of 13 estates in Dover’s magnificent Snow’s Hill neighborhood, 5 Hamlin’s Crossing includes 3.2+ impeccably manicured acres overlooking and abutting gorgeous conservation land. Privacy, timeless finish/craftsmanship, brilliant entertaining spaces and outstanding value distinguish this extraordinary property. Dover Land Conservation Trust manages 138 acres of trails adjacent to the neighborhood. Stunning stone walls outline the two-tiered front lawn and the generous circular drive creates a dramatic approach. Exhale and enjoy the unequaled peace and privacy Snow’s Hill residents enjoy. French-inspired architecture, incl. multiple brick porticos and pretty dormered windows, reveals a home built with no detail spared. Inside, a two-story foyer with marble floors and sensational dome ceiling is anchored by a dramatic curved staircase. Windows everywhere provide abundant direct views of the backyard and pool. Magnificent. Richly lined with custom bookshelves, the home office includes a fireplace and generous seating area. Multigenerational households take note: the west wing offers a rare first-floor four-room primary suite, effortlessly accommodating family or long-term guests. Dedicated billiard room with deluxe bar and egress to the side-yard putting green is a playful, beloved gathering spot. Beautiful sunken living room and enormous family room with cathedral ceiling and custom architectural beams are the main gathering spaces. Designed for holidays and family parties, the open-concept kitchen/family room is where everyone gathers. Eat-in dining area with island and peninsula seating + comfortable built-in window seat accommodates the crowd. This is the heart of the home. Priceless. Royal formal dining room, mudroom off spotless four-car garage and two half bathrooms complete the main level. 2nd level is accessed by one of two staircases and connected by wide hallways and elegant catwalk. West side includes a 2nd primary suite with rich, spacious bath, two walk-in closets, dressing room and bonus custom closet. Four ensuite BRs with spotless hardwood floors, generous laundry room with awesome storage and folding spaces + media room with Savant AV projector/screen ideal for family movie nights and game days complete the 2nd level. Glorious sun-splashed deck is steps from the saltwater pool. Insta-worthy slide and waterfall + fully equipped pool house with bath, full kitchen and laundry make end-of-year parties and cocktail hours effortless. Expensive recent improvements incl. high-efficiency gas furnaces, Tesla Power wall/solar panels, Crestron lighting system and extensive landscaping/hardscaping.

Experience the pinnacle of luxury in this stunning, high-performance custom-built home featuring 7,802 finished square feet of living space, grand-sized rooms, and a spectacular, unique floor plan situated at the end of a private cul-de-sac. This rare offering presents a special opportunity to customize your dream home and add your personal touches—including custom appliance selections—using the builder's generous allowances. Engineered for superior efficiency, low maintenance, and high quality, the home is equipped with a rare and highly sought-after NATURAL GAS heating system alongside an exceptionally tight envelope insulation package, supreme HERS score, ERV fresh air system with 4" HEPA filters, and a balanced Make-Up Air system for ultimate climate control. Set on a bright and sunny lot surrounded by serene open space at the end of a private cul-de-sac, you are just minutes from the commuter rail, Hopkinton State Park, and top-rated schools—all just 26 miles from Boston. The heart of the home is a custom chef's kitchen complete with a separate pantry, handmade cabinetry, double wall ovens, an elegant octagonal breakfast room, and space for a professional 48" natural gas range and 36" French door refrigerator. The open-concept family room showcases classic design elements like white oak wood flooring, a stone fireplace mantel, deck access, and a wet bar with a paneled beverage fridge. With 5 oversized bedrooms, 5.5 designer baths, a giant primary suite with double closets and a spa-like bath, and a sprawling finished WALKOUT basement, there is incredible room for everyone. Enjoy a bright setting with direct access to 10 acres of protected Sudbury River trails in this extraordinary value for discerning luxury buyers.

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 to a masterpiece of design and elite engineering on a private lot, where this entire home has been upgraded and meticulously curated for effortless luxury. Built by an award-winning local MA builder, this high-performance, low-maintenance home offers highly sought-after natural gas heating. This is paired with ultimate climate control and extraordinary energy efficiency, powered by an exceptionally tight envelope insulation package, supreme HERS score, ERV fresh air system with 4" HEPA filters, and a balanced Make-Up Air system. A grand foyer with an impressive staircase introduces an open-concept layout featuring four-inch white oak hardwood floors, high-end Pella EnergyStar windows, and an elegant family room with a natural gas fireplace, stone mantle, and coffered ceilings. Every finish was hand-selected by a professional interior designer, including custom handmade cabinetry, designer tile, architectural lighting, and premium plumbing fixtures throughout. Set behind French doors is a spacious home office, and you'll enjoy sunsets from the Formal Dining Room. The chef's kitchen is a culinary work of art anchored by a 36” professional natural gas range, double ovens, wet bar with beverage fridge, and quartz counters, all anchored by an expansive island. The main level also offers a second home office or flex room with vaulted ceiling and an adjacent full bath, while the Mudroom is what dreams are made of with charming built-ins, a large coat closet, powder room, and tile floors in a herringbone pattern. Upstairs, you will find a magazine-worthy laundry room with custom cabinets, space for a double washer and dryer, tons of counter space, and a large storage closet, along with en-suite bedrooms and a primary suite sanctuary featuring a lavish bath with a large shower, soaking tub, and expansive custom vanity, and a spectacular walk-in closet centered around a custom island with a quartz countertop. The expansive lower level adds 1,450 sq ft of finished living space with high ceilings and a full bathroom, ideal for a media room, fitness space, or lounge. Set on a supreme lot with a private, level backyard, direct access to 10 acres of protected Sudbury River trails, and minutes to the commuter rail, Hopkinton State Park, and top-rated schools—just 26 miles from Boston. Don't miss this opportunity!

Move-in ready five bedroom, three and a half bath renovated residence in South Natick near the Dover/Wellesley line with Charles River views. Lives like a true single-family with a bright, open layout, brand-new kitchen, updated baths, new roof, windows, systems, and solar to lower energy costs. Flexible space for a home office, guest suite, or multi-generational living. The game-changer? A first-floor professional space with an active long-term lease and tenant-paid utilities—built-in income that offsets your carrying costs. Operating strictly during weekday business hours, the tenant leaves your evenings and weekends quiet and private. Set on 0.52 acres with nine parking, steps from Broadmoor Wildlife Sanctuary, waterfalls, and village parks. Minutes to Wellesley College, Natick shopping, Wellesley boutiques, local bistros, library, and Hunnewell Estate with fast access to Rts 135, 495, and Mass Pike. A rare opportunity to own more home in a prime MetroWest location. Home AND income—done right. Schedule your tour today!

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.

Exceptional newer construction in the heart of South Natick lives like a single family home. A welcoming front porch introduces this stunning home, which showcases superior craftsmanship, sophisticated finishes & thoughtful design across three beautifully finished levels. The exceptional chef's kitchen features high-end appliances, an expansive island & abundant workspace, flowing seamlessly into fresh, sun-filled living & entertaining spaces. A private first-floor office, fabulous walk-in pantry & beautifully designed laundry room enhance everyday living. All four bedrooms are thoughtfully located together on the second floor, along w/ an inviting loft area ideal for reading, gaming, or relaxing. Gorgeous primary suite w/ spa-like bath. The expansive finished lower level offers outstanding flexibility for guests, fitness, recreation or media. Enjoy a walkable lifestyle near Riverbend School, Memorial Elementary, South Natick village, Elm Bank Reservation, trails & the Charles River, plus easy access to Wellesley & Natick Centers, commuter rail, shopping & dining. Spacious two-car garage. Distinctive design, exceptional functionality & an enviable location-a true gem!

Universally admired, 25 Dover Road is an enchanting yellow shingle colonial with an unbeatable location. Timeless architecture, lush landscaping, elegant stonework and an inviting front porch all contribute to the home's exceptional curb appeal. Inside, the dramatic double-height sunlit foyer opens to graciously proportioned rooms, abundant windows, sparkling hardwood floors, and an open, airy floor plan. The expansive renovated chef’s kitchen flows into a stunning breakfast room framed by a curved wall of windows and an inviting fireplaced family room with custom built-ins. A handsome office with custom cabinetry, elegant living and dining rooms, and a mudroom and powder room, both with radiant heat for frosty New England winters, complete the first floor. Upstairs, the magnificent front-to-back primary suite is a true retreat featuring a fireplace, private balcony, and spa-inspired bath. Two additional spacious bedrooms and a full bath complete the 2nd level. The fully finished lower level offers a versatile game/rec room, along with a private walkout guest suite with full bath—ideal for au pair or in-laws. Enjoy fresh air spring through fall in the beautifully finished 3-season porch. Entertain on the spacious two-level deck and stone terrace, all with glorious views of the large private backyard with enormous lawn. Four-bedroom septic. Ideally located near the town centers of Natick, Wellesley, and Needham, with convenient access to train stations and local destinations Elm Bank and Lookout Farm. Natick town water and natural gas. With its top-ranked schools and low property taxes, Dover remains one of the region’s most desirable towns, and this exceptionally pretty home offers the perfect blend of classic design, modern comfort, and an embrace of nature for the quintessential Dover lifestyle.

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.

Once in a lifetime opportunity to own in Wellesley's most coveted premier historic location, Pond Road. Featuring the finest custom craftsmanship throughout, professionally engineered mechanical systems, smart house and professionally designed ultra high end finishes. Over 9400 sq ft of living space on 3 floors. The floor plan everybody wants with a 1200 sq ft great room and over 10 foot ceilings. Oversized mudroom and pantry. First floor includes white oak herring bone hardwoods. 2nd floor ceilings 14-20 feet! An incredible main suite. All bedrooms en-suite with walk-in closets. Plus a 2nd floor lounge room or incredible guest suite. Lower level is unprecedented with 17 ft ceiling in 1/2 court basketball/ rec room (size of space also work for squash) with viewing room including wet bar. Theatre/media room with additional wet bar plus a gym with full bath including steam shower. Large flat yard. Close to Wellesley trails and town center.

Spectacular opportunity to own this newer construction set on a rare one-acre lot in a desirable cul-de-sac location. Offering 7 bedrooms and 5 full baths, this exceptional home is designed for both everyday living and effortless entertaining. The stunning chef's kitchen features a large center island, premium Wolf range, and oversized walk-in pantry. Sun-filled living and dining spaces with elegant French doors open to a custom patio and private backyard oasis. The second floor offers five spacious bedrooms with walk-in closets, including a luxurious primary suite with balcony access overlooking the backyard and a versatile loft space. The walk-up third level includes two additional bedrooms, a full bath, and a generous bonus/play space. Welcome Home!

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.

Four-bedroom multi-level home on a peaceful Cochituate cul-de-sac. The front living room is filled with natural light and features a picture window and wood-burning fireplace. The updated cherry kitchen has granite countertops and opens to the dining room and window-lined family room. The second floor offers three bedrooms and a full bath, with two and a half updated baths in total. The lower level includes an office/den, bedroom, second full bath, and laundry.Recent updates include a 2017 high-efficiency Veissmann boiler with on-demand hot water heater, a 2023 roof, and a 2024 whole-home water purification system. Fresh paint throughout and newly refinished hardwood flooring. A new four-bedroom septic system will be installed at the seller’s expense prior to closing. Located near Cochituate ball field and Wayland Town Beach

Custom-built home on 1.53 acres abutting conservation land offering privacy & tranquil repose. Refined finishes not seen in today's real estate market! Exterior hardscape by Sudbury Land Design & Kitchen Design featured in Boston Magazine. Mahogany Doors lead you to the Foyer w/ curved staircase, Living Rm w/ limestone fireplace, Dining Rm & Family Rm all w/ Southern Pine Flooring. Gourmet kitchen w/ chef grade appls, Butlers Pantry & Italian Limestone flooring. Stunning 3-season Sunroom w/ glass & screen inserts and access to brick/bluestone patio. First flr Primary Bedroom w/ French Doors leading to covered Veranda. Second flr w/ 3 bedrooms each w/ private baths. Second flr office w/ Mahogany built-ins. Lower level w/ 3 entertainment rms, gas fireplace, a large work-out rm, a full bathroom, unfinished storage space & access to the 3-car garage complete w/ separate Workshop. 11' first floor ceilings, 10' second floor ceilings, Bevolo exterior lighting, custom Pella windows & doors.

Situated in the sought-after Saxonville area, this thoughtfully updated Colonial offers a flexible floor plan designed for modern living. The first floor flows seamlessly from the living and dining areas to a custom kitchen, creating an inviting setting for both everyday living and entertaining. A convenient laundry area and oversized powder room complete the main level, while multiple decks and balconies extend the living space outdoors and provide an easy connection for gatherings, dining and relaxation with spectacular treetop green views. Upstairs, the spacious primary suite features a vaulted ceiling and private bath, accompanied by two additional bedrooms and a bright, sun-filled full bath. The walk-out lower level offers valuable flexible space with potential for a home office, gym, media room, guest space or additional living area. A deep two-car garage provides generous parking and storage. For buyers considering condo living, 106 Danforth offers a compelling alternative, move-in-ready style, flexible space and convenient access to area amenities, with the added benefits of a two-car garage, multiple outdoor spaces and the privacy of a single-family home. Thoughtfully curated by a professional interior designer, the home offers a move-in-ready feel with furnishings available for added convenience. Located close to schools, trails, shopping, dining and major commuter routes, 106 Danforth Street combines comfort, flexibility and accessibility in the heart of Saxonville.

Gracious Shingle Style Mansion in coveted estate neighborhood is a rare combination of privacy and grandeur. With soaring ceilings and spanning over 8,800 square feet of living space, this house meets the desires of families, or entrepreneurial spirits with a love of larger homes. Beautifully crafted with custom details, millwork, moldings, and fine cabinetry throughout. A formal living room with stone fireplace and gorgeous dining room flanks a 2-story entrance hall. Further in a massive chef's kitchen flows effortlessly into the great family room, perfect for large gatherings and entertainment. A handsome library exudes sophistication. 5 bedrooms, 7 baths, a third-floor game room, and a lower level featuring an additional rec room, full bar, movie theater, and wine cellar complete the home. Privately sited on 2.65 acres and surrounded by stone walls with mature lush landscaping and gardens. An elegant Manor on one of the prettiest streets in Dover.

Set on a beautifully flat lot in one of Wellesley's most desirable neighborhoods, this exceptional Colonial offers a rare combination of luxury, space, and timeless design. Located in a special community with a picturesque meadow at its center, providing a peaceful setting. Featuring 7 bedrooms, 7 full and 2 half bathrooms, this thoughtfully designed home offers flexibility for today's lifestyle. The stunning chef's kitchen features a center island, top-of-the-line appliances, custom cabinetry, and separate walk-in pantry. Spacious living areas, elegant formal rooms, high ceilings, natural light, and beautiful finishes create an inviting atmosphere. The luxurious primary suite offers a private retreat, while the generous secondary bedrooms provide comfort for family and guests. Multiple spaces allow for work, recreation, and entertaining. The expansive backyard is ideal for outdoor enjoyment, conveniently located near Wellesley's top-rated schools, town center, train, and major routes.

Welcome to a lifestyle reimagined at Baiting Brook Farm, a brand-new 55+ active adult community in the scenic countryside of North Framingham. As Massachusetts' first Agrihood, residents have a choice of three single-family home styles & three duplex variations. Residences are thoughtfully sited for breathtaking views & natural light, while boasting 1st floor primary suites, chef’s kitchens & modern high-end finishes. Experience the ultimate farm lifestyle with luxurious amenities including pickleball, clubroom and fitness center. Enjoy the bounty of community-grown produce & farm-fresh eggs, while taking in the beauty of 46 acres of meadows and pastures with grazing cows. Access to over 800 acres of hiking and walking trails at Callahan State Park make this the perfect blend of leisure and nature! Eastleigh single-family homes provide 2 beds, 2.5 baths, featuring home office, an open concept kitchen, living room & dining room, 1st floor laundry, 2 car garage & unfinished basement.

Tucked along scenic Pine Hill Road in Southborough, this stunning colonial sits on a peaceful, park-like acre lot abutting conservation land. Inside, the recently renovated (2025) magazine-quality kitchen steals the show: professionally designed with quartz counters, premium brand stainless appliances, ample cabinetry with custom interior organization, a large island with built-in microwave that seats four, natural gas cooking with vent hood, and a custom beverage center/coffee bar. From the kitchen, step out to the composite deck to take in the tranquil, wooded views. Stylish modern bathrooms, gleaming hardwoods and attractive tile throughout the first floor, and fresh carpets throughout the upper-level complete the polished interior. Four spacious bedrooms include a sprawling primary suite with ensuite bathroom and a large walk-in closet. The flexible floorplan offers a front-to-back family room and a separate front-to-back living room, a large dining room open to the kitchen for hosting and entertaining, a gracious foyer with double closets, an oversized lower-level mudroom, and a flexible finished basement room ideal for a home office, gym, or playroom - spaces for truly every need. The home's location is exceptionally convenient, with easy access to Rt. 9 and the Mass Pike, making it a commuter's dream. Enjoy Callahan State Park just moments away, offering miles of trails and hundreds of acres of parkland, plus additional trails nearby along the Sudbury Reservoir as part of the Bay Circuit Trail. All this, plus access to a welcoming community and highly regarded schools in Southborough. 63 Pine Hill Road has been meticulously maintained and shows extreme pride of ownership; see the extensive list of updates and improvements attached to MLS - including exterior painting just completed September 2026!