luxury properties with pool for sale Massachusetts, United States

Discover an architecturally distinctive contemporary home where artistic design and natural beauty come together. Set on a secluded, beautifully landscaped lot, this one-of-a-kind residence offers four bedrooms and two-and-a-half baths, including a desirable first-floor primary en suite. In the living/dining area, a striking arched wood ceiling adds warmth and character, while expansive glass frames peaceful views of the treetops and pollinator garden. Custom cherry and shoji-paper pocket doors bring craftsmanship and flexibility to the interior. Outside, flowering plants and thoughtfully designed gardens attract birds, bees, and butterflies throughout the seasons. A spacious patio offers a lovely setting for entertaining, relaxing, or simply enjoying the tranquil surroundings. With exceptional privacy, distinctive architecture, and a wonderful connection to nature, this is a home that truly stands apart.

Luxury, privacy, and an extraordinary connection to nature come together at this beautifully updated Nantucket residence. Backing directly onto more than 110 acres of protected Nantucket Land Bank conservation land, this exceptional property enjoys an unparalleled sense of seclusion, where uninterrupted natural landscapes create a serene backdrop and neighboring development simply doesn't exist. Few properties offer the opportunity to experience such an expansive protected setting while remaining just minutes from Nantucket's beaches and Town. Thoughtfully renovated with high-end finishes and premium materials throughout, the home blends timeless coastal elegance with modern comfort. Designed for effortless indoor-outdoor living, the open-concept floor plan is filled with natural light and seamlessly connects the living, dining, and kitchen spaces, creating an ideal setting for both everyday living and entertaining. The resort-inspired backyard feels like a private retreat, featuring a sparkling pool with a waterfall, hot tub, expansive stone terrace, fire pit, covered outdoor living area, and a generous lawn, all set against a breathtaking backdrop of permanently protected open space. Perfectly positioned just five minutes from Nantucket's pristine ocean beaches and approximately ten minutes from Town's celebrated restaurants, boutiques, galleries, and harbor, this is a rare opportunity to enjoy luxury living in one of the island's most peaceful settings while remaining close to everything Nantucket has to offer.

A rare opportunity to become the next steward of an exceptional home or investment property in one of Southborough's most convenient locations. Set on an oversized 1.4-acre lot along a quiet neighborhood street, this versatile five bedroom, three and a half bath property (2,586 sq. ft. total) offers two attached living spaces — a four bedroom + office, two and a half bath main residence (approx. 2,078 sq. ft.) and a one bedroom, one bath in-law suite/ADU (approx. 508 sq. ft.). The configuration is nicely suited for multi-generational living, an au pair suite, income property potential, or whatever flexible arrangement fits your plans. The main residence offers a traditional floor plan with an eat-in kitchen with stainless steel appliances, dedicated first floor laundry room/pantry, a large formal dining room, separate family and living rooms, a primary suite with attached ensuite bath, three additional generously sized bedrooms with hardwood floors sharing a full hall bath with double vanity, and a bonus room perfect as home office, gym, or flex space of your choosing. The in-law unit includes an eat-in kitchenette, living room, bedroom, and full bath with tub. Outside, a composite deck overlooks the in-ground pool (in good working order), and the expansive lot leaves plenty of room to garden, play, entertain, or simply spread out. With this much space, land, and flexibility in a convenient Southborough location, there is significant upside for the right buyer ready to bring their vision to life. Ideally located with proximity and access to top-ranked schools and easy access to the Commuter Rail, Rt. 9, 495, and the Mass Pike.

Set on nearly four acres, 17 Ipswich Street offers exceptional privacy, expansive grounds, and distant Ocean views. The estate is composed of a five-bedroom main residence, a separate three-bedroom guest cottage, a pool cabana, and a 20' x 40' swimming pool, creating an estate designed for multi-generational living, gracious entertaining, and exceptional privacy. Beautifully landscaped grounds feature mature plantings, sweeping lawns, and stone patios that seamlessly connect the indoor and outdoor living spaces. The guest cottage is privately sited on its own landscaped acre, while the cabana, complete with a wet bar and half bath, serves the pool and surrounding outdoor entertaining areas. With nearly four acres and substantial living space across multiple structures, 17 Ipswich Street represents an increasingly rare opportunity to acquire this combination of scale, privacy, and value on Nantucket.

Built for Reuben and Grace Ropes, who according to her journal began housekeeping here on June 29, 1895. The house remained in the family until 2012, when it was exhaustively restored, new systems, plumbing, and electrics, while keeping its nostalgic soul. Set on a gentle knoll overlooking landscaped grounds, this traditional home suits how we live today, with rooms opening into one another and a circular first-floor flow at ease with family or enjoyed quietly. Upstairs are three bedrooms, a hall bath, and a primary suite with its bedroom in the tower bay window and a dressing room to the ensuite bath. The third-floor office offers water views and privacy. Outside, the grounds feel more expansive than their manageable half acre. The rear deck, ringed by river birches, suits entertaining, and a wild-life protected kitchen garden invites you to grow herbs and vegetables. A detached two-car garage with storage shed adds practicality, while the basement and attic, both easily reached by proper stairs, offer unusually accessible storage. Set in a pastoral setting, yet just minutes from the water, downtown Salem, the PEM, and the train station.

Brand-new construction scheduled for completion in Fall 2026, offering over 5,400+ square feet of thoughtfully designed living space across three finished levels on a 1.5 acre parcel of land. The open-concept first floor features a spacious living and dining area, a beautifully appointed kitchen, and a first-floor en suite bedroom, all flowing seamlessly to expansive decks, bluestone patios, indoor/outdoor dining area overlooking the 18x40 salt water pool, spa, and oversized backyard—an ideal setting for entertaining. The second floor offers four en suite bedrooms along with a generous secondary living room, providing the perfect space for family and guests to gather. The finished lower level includes an additional en suite bedroom, a large recreation room or gym, and an expansive family room, completing this exceptional new home designed for both comfortable everyday living in mind.

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

High on a hilltop in the Southern Berkshires stands East Hill Farm. 227 cultivated acres encompassing pristine forest, a spring-fed pond, a striking barn, verdant pastures, formal and vegetable gardens, a pool, and a tennis court. The centerpiece: a 1798 Georgian home, 5,000 SF with 5 bedrooms. Ready for private living, entertaining, horses, farming, a bespoke destination, or simply: tranquility. Includes a reimagined 6,000+ SF guest house, once an Arabian horse barn. 2½ hours to both NYC & Boston, yet a world apart. East Hill Farm offers what money rarely can buy: authenticity at scale. A 227 year-old house expanded, refined for 21st century life. Land, privacy, history, and a place of peace, which has endured through every chapter of American history. The next chapter begins with you. Reach out! Where The World Falls Away--227 acres. 227 years. One extraordinary hilltop farm. Drive up East Hill Road through Southfield village, past the store, climbing toward the top of Woodruff Mountain. The dirt road is well-maintained and lightly traveled. Sugar maples line your approach--massive, ancient trees that have watched over this land since before the house was built. Behind them, set back from the road, stands the kind of barn that makes photographers stop their cars. Three and a half stories of hand-hewn timber, painted proper New England red, moved here piece by piece from Amherst, Massachusetts, because the sellers understood that a farm needs a real barn. Not a replica. The real thing. The House Stops Your Heart--Federal period, 1798, when John Adams was president. This wasn't just another farmhouse. When Thomas Shepard commissioned John Collar to build this, he was making a statement. 8 rooms. 5 fireplaces. Ceilings higher than any farmer needed. Those distinctive 12-over-12 windows with hand-blown glass that turns the morning light liquid. A facade with sidelight windows and dentil cornice that announced to every traveler: here lives a person of substance. Walk through that front door and the wide center hall opens before you. Original wide-plank floors--King's boards, they called them, because timber this wide was supposed to be reserved for the Royal Navy's masts. Twin parlors flank the entrance, flooded with southern light. To your left, the original keeping room, now the dining room, where that massive cooking fireplace with its beehive oven still works perfectly after 227 years. The draft in these fireplaces is extraordinary. The woodwork throughout is original or crafted by hand precisely to match. Chair rails, wainscoting, built-in china cabinets with their original hardware. Those small cupboards tucked around the chimneys--John Collar's signature touch. Five Families in 227 Years--Jesse Hartwell married Thomas Shepard's niece and turned the house into a meeting place for progressive thinkers, and through the 19th century, the Hartwell family made this their home. Then came the Arabian horse breeders in the 1930s who added the newer rear ell and built what's now the guest house. The current sellers bought the house and five acres in 1969, then spent the next five decades not just restoring but thoughtfully expanding it. You'll be only the fifth resident to call East Hill Farm home--and despite its National Register status, free to shape its future as you see fit. That newer section? Radiant heat underfoot, a proper mudroom with laundry, a family room or perfect home office with its own kitchen, and an elevator up to a sun-filled library with built-in shelves and an ensuite bedroom and bath. A luminous sunroom framing year-round sunsets, with sweeping views across the formal gardens, horse pastures, and the shimmering pond below. Upstairs in the original part of the house, an additional four bedrooms, each with its own character. The canopy bedroom with its blue and white toile--that's not staging, that's how the family lives. Wide hallways, deep closets, and in that large upstairs hall above the front door, a perfect spot to sit and read while gazing out the neoclassical window over your barn, fields and forest, mountains in the distance. 5 full and 1 half baths in all--some original 1930s with their good bones, others from the 1980s restoration. The kitchen? Also 1980s, completely functional with good counter space, and a working wood-fired stove alongside modern appliances. Morning light streams in from the east, and sunset views are to the west, opening onto fieldstone patios on either side. Everything works: oil heat from a Viessman German boiler, cedar shake roof (much replaced in 2021), private well water so good they've bottled it up for guests, backup generator, fiber internet. The bones are so good and the mechanicals so solid that you can move in tomorrow or update to your taste--the house won't fight you either way. 227 Acres: A Complete World--East Hill Farm is more than the sum of its parts. From the original five-acre homestead, the current owners lovingly reunited land to create the breathtaking 227-acre estate it is today. 154 acres stretching across the north side of East Hill Road, and 73 tranquil acres to the south. To the north, a substantial portion of the property borders Sandisfield State Forest and thousands of acres of protected land. To the south, you have a section along Hotchkiss Road that is part of the New Marlborough Land Trust. Each acre is part of a dream fulfilled, a landscape that invites endless exploration and inspiration. Walk west from the kitchen patio between the formal gardens. Brick paths wind through perennial beds: heritage roses, peonies, iris. A long row of prolific blueberry bushes. In the vegetable garden, established asparagus and rhubarb come back stronger every year. Passing that perfect garden shed with its slate roof, as mist rises off the pond, becomes part of your morning coffee stroll. The pond--almost four acres, brook-fed, crystal clear. The family created it, and for decades it's been their private swimming hole, sailing spot, fishing paradise. Circle the pond and you'll find the big fishing rock on the west side, the perfect swimming spot on the east. Or head into the forest. Miles of trails, including a loop road that connects to Sandisfield State Forest. In spring, Lee Brook, the largest of several on the farm, roars with snowmelt. Up where the brook crosses the trail, it forms a waterfall after a hard rain. These are the headwaters of the Whiting River, and you own it. This isn't just acreage - it's a complete ecosystem. Meadows, forests, water, gardens, pastures, each flowing naturally into the next. Built for Whatever You Dream--That magnificent barn across the country road--3,550 SF on a full stone foundation, electricity, running water, lower level for equipment, main floor with stalls and work rooms, massive hay loft. Four pastures with water sources, run-in barns with power and water, and additional smaller outbuildings. The infrastructure is thoughtfully designed, whether your dreams include horses, alpacas, heritage sheep, a flourishing market garden, an orchard, festive celebrations, a tranquil retreat center, or simply savoring the seasons as they change across your land. The guest house tells its own story. Built as stables for those 1930s Arabians, it's now 6,668 SF divided into four independent residences, with cathedral ceilings and fireplaces. Some would use this for multi-generational living. Others might see a writers' or artists' retreat, a wedding venue, or wellness center. The bones are spectacular--soaring spaces and abundant light. Morning swims in the sparkling gunite pool with its serene fieldstone waterfall. Afternoons spent on the newly resurfaced tennis court. Evenings wandering down to the pond, soaking in the tranquility. Or embrace the rhythm of nature: January mornings breaking ice on water troughs, February afternoons tapping maples for syrup, and March evenings tending seedlings in the greenhouse, dreaming of summer tomatoes. The possibilities are manifold; life on East Hill Farm is generous and abundant. History You Can Touch--Walk these 227 acres and feel it: the weight of continuity. Five families in 227 years. Thomas Shepard, who helped found New Marlborough. The Hartwells, who held it for a century. Arabian horse breeders who landed their plane in the pasture. The current family, who pieced the scattered acres back together, whose daughters gathered eggs, boiled sap into syrup, grew the gardens that still bloom today. Some things do endure. That which matters can be preserved. In a disposable world, permanence is possible. The next chapter begins with you. The Berkshire Life, Perfected--Twenty minutes to Great Barrington's restaurants and shops. Less than ten to the Southfield Store. Tanglewood for summer concerts, Jacob's Pillow for dance, Butternut for winter skiing. Bradley Airport an hour away, Manhattan and Boston each two and a half hours. But honestly? Once you're here, leaving becomes the hard part. Mornings at East Hill Farm start with the mourning doves' lullaby that sounds like memory itself. The Sandhill Cranes return each spring to the lower pastures, their distinctive call announcing another season. Summer evenings, you'll sit on the west porch watching the sunset over your pond while fireflies rise from the meadows, and emerge from the woods. Winter nights, you'll build fires in those perfect fireplaces and be grateful they built that beehive oven so large. Everything here has been cared for with a deep knowledge of history and respect for nature and tradition. The heritage roses still bloom. The stone walls still stand true. The forest trails lead to hidden waterfalls and forgotten cellar holes. The gardens produce abundance. The pastures are ready to graze horses. Or you could simply walk your 227 acres knowing that in a world of constant change, you've found something real, something lasting, something irreplaceable. At $5.8 million, East Hill Farm offers what money rarely can buy: authenticity at scale. A genuine 18th-century house that works for 21st-century life. Land enough that you own your own hilltop. Buildings that tell the story of America. Privacy without isolation. History without the museum ropes. And beyond price, a place of profound peace that has endured through every chapter of American history, a hilltop sanctuary. Wake each morning in that otherworldly, untouchable tranquility that settles over the hilltop, where the rest of the world falls away, to watch the sun set where generations have watched it set, to be part of something larger than yourself, while making it entirely your own. 227 acres. 227 years. Some things are meant to be. Come see.

“Wait and See” is a stunning coastal retreat commanding extraordinary, unobstructed views of the Atlantic Ocean and Tom Nevers Pond. Perched on an elevated and beautifully landscaped acre, the property captures sweeping vistas and exceptional privacy. The first floor features two guest bedrooms with a shared bath, along with a serene primary suite complete with an en suite bath and direct access to a wraparound deck overlooking the landscape. The lower level offers a spacious family room, dedicated office, and walkout access to a private patio—ideal for relaxed indoor-outdoor living. The second floor is designed for gathering and entertaining, with an open-concept living room and a well-appointed gourmet kitchen. Expansive wraparound decks on this level provide seamless outdoor living spaces, perfectly positioned to take in the panoramic views and coastal breezes. A charming breezeway connects the three-bedroom main house to a two-bay garage, above which a private fourth bedroom suite with full bath enjoys its own elevated vantage point and beautiful views. The grounds are equally impressive, featuring a thoughtfully designed garden with a sunken patio and fire pit seating area. The outdoor experience is anchored by a stunning 18’ x 36’ pool, an 8’ x 8’ spa, and a generously sized outdoor shower, all complemented by multiple seating and lounging areas—creating an exceptional setting for summer living and entertaining. Additional amenities include access to two association tennis courts, located just one mile from the property.

75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. three upper bedrooms, office, large bonus room + finished walkout lower level. two-car garage with EV charger and generator backup. EQUESTRIAN: Professional nine-stall barn, heated tack room, wash stall & blanket laundry. 12,384 SF indoor arena (172'x72') + 130'x80' outdoor arena. 60' round pen & 15 turnout paddocks. Roof solar array on barn supplies powers to the property. WELLNESS & RESORT: Detached climate-controlled gym & solar yoga "She Shed." Heated, saltwater, gunite pool, hot tub, six-person barrel sauna. Outdoor kitchen with pizza oven. Meditation labyrinth, organic fruit orchards, and berry patches.