luxury properties with pool for sale Massachusetts, United States

Sophisticated country living inspired by classic New England style, perfectly sited on a rare and private two acre setting. Thoughtfully updated throughout, this exceptional property offers over three finished levels of beautifully designed living space, blending timeless architecture with today’s modern lifestyle. The main level features a renovated kitchen with new countertops and appliances that opens to a spacious family room with a gas fireplace and a beautiful screened-in porch, creating the perfect space to enjoy the peaceful surroundings in every season. A formal dining room, private office, mudroom, and versatile flex space ideal for a second office, home classroom, or creative retreat complete this level. Upstairs, the primary suite offers a peaceful escape with a sitting room, walk-in closet, and ensuite bath with soaking tub and separate shower. Three additional bedrooms and a second-floor laundry room complete this level, while the finished third floor provides endless possibilities as a playroom, media room, or bonus living space. A separate fifth bedroom with a full bath is perfect for guests, extended family, or an au pair.Designed for entertaining and creating lasting memories, the outdoor living spaces are truly exceptional. During their ownership, the sellers thoughtfully transformed the backyard into a private retreat featuring a heated saltwater pool with an automatic cover,pool house, professionally designed multi-sport court for basketball, tennis, and pickleball, expansive patios and hardscaping, a fire pit with landscape lighting, irrigation system,and beautifully landscaped grounds with fruit trees, flowering cherry trees, spring bulbs, and a charming chicken coop/greenhouse. The extensive list of seller improvements continues throughout the home and includes fresh interior paint, updated bathrooms, a remodeled garage, a dedicated art studio, new A/C condenser, water filtration system, radon mitigation system, an added electrical panel, and a seller-owned Tesla solar system with three Telsa Powerwalls, providing added efficiency and long-term value. A rare opportunity to own a turnkey property where luxury, recreation, and everyday living come together in one remarkable home!

Sophisticated elegance on approximately an acre of land in highly desirable neighborhood. A warmth upon entering through the grand foyer reveals an abundance of natural light and 76 impressive oversized windows. Beautiful architectural elements are revealed as the floor plan flows through an open concept chef's kitchen • butler's pantry • 5 entertaining rooms • 2 private home offices • media room • 6 en suite bedrooms • main level bedroom suite • fitness center • game room • sports bar with lounge • wine cellar and tasting room • 2 large stone patios • outdoor kitchen and fireplace • tranquil views of large flat private rear yard • 3 car heated garage. Nearby entrance to 150 acres of historic conservation land including trails, ponds, meadows, and antique stone walls. Just blocks to historic Lexington center and both elementary and middle schools. Easy commuter location to routes 3, 2 and I-95.

Set along the marsh front near the shores of Saquish and Standish Shore, this classic coastal colonial captures wide bay views. The heart of the home is a high-end kitchen with quartz surfaces, a generous island, Sub-Zero refrigeration, a six-burner Wolf cooktop, Wolf convection and steam ovens, and two Miele dishwashers all set atop Brazilian hardwood floors. Four fireplaces add character throughout. The primary suite offers a spacious retreat with a sitting area and bath with a walk-in steam shower. Outdoor living spans two levels of wraparound Trex decking. A finished walkout lower level includes a gym, full bath, and direct entry to a resort-style yard with a heated saltwater gunite pool, spa, outdoor shower. The 960 sf pool/guest house has an open floor plan with a large sleeping area on the second floor. Ready for summer occupancy!

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.

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Who could ask for anything more?

Charming, move-in ready side hall Colonial, a true ''dollhouse!'' Welcome home to this absolutely stunning, meticulously maintained side hall Colonial nestled in a super quiet, peaceful neighborhood. Combining classic charm with a long list of modern, high-ticket upgrades, this home is the definition of a turnkey property and is ready for its next chapter. Step inside to find a warm and inviting living space featuring a cozy wood-burning fireplace, perfect for chilly evenings. Classic hardwood floors run throughout the home, currently protected by brand new, plush carpeting that offers a fresh feel while preserving the beautiful wood underneath. The beautifully updated kitchen and dining area flow seamlessly together, creating an entertainer's dream space that is sure to please your guests. Through the sliding glass doors off the dining area, you will discover your own private outdoor oasis. The brand new deck overlooks a quiet, beautifully landscaped backyard that offers a peaceful escape from the daily grind. It is the ultimate setup for summer BBQs, morning coffee, and refreshing afternoon dips in the sparkling above-ground pool. The screened porch is another magnificent amenity to cozy up and read in the afternoon or sip cocktails in the evening. Beyond its picture-perfect aesthetic, this home offers incredible peace of mind with major mechanical upgrades designed to last for years to come. The property boasts a durable new metal roof, a high-efficiency wall-hung furnace, and a brand new hot water heater, saving you from any hidden, immediate expenses. From its exceptional curb appeal to its pristine, thoughtful interior, this home is simply a dollhouse that you have to see to believe. Properties this well-maintained do not stay on the market long, so schedule your private tour today before this gem is gone!

On the Weir River estuary in one of Hingham's most private enclaves, 8 Ringbolt Road is a meticulously maintained colonial ready to become the backdrop for the next chapter. A custom kitchen by Faneuil Kitchen Cabinet anchors the main level with shaker-style inset cabinetry, single-slab granite backsplash, and smart storage throughout. White oak hardwood floors with mahogany Celtic knot insets flow through the kitchen and informal dining area which opens into the family room with fireplace. A dedicated laundry room and main level office with French door access to the backyard complete the first floor. Upstairs, four bedrooms plus a versatile bonus room, two fully updated bathrooms with custom cabinetry, and generous closet space throughout. The partially finished lower level offers flexible space and ample storage. Outside, a heated in-ground pool sits within manicured private grounds. Two-car garage. Minutes to Hingham Square, the waterfront, and commuter boat and rail to Boston.

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.

Introducing a timeless European inspired mansion with a private gate and elegant marble fountain. This custom estate is situated on three acres. A spectacular pool and spa complemented by a fully equipped pool house with a kitchen adorn the grounds. A beautiful wrought iron fence embraces the entire estate which includes stone patios and tennis court. The grand entry and living and dining rooms boast beautiful granite floors for fine entertaining. Additionally, rich oak wood floors are throughout the house. Three custom marble fireplaces grace the sitting areas. A first floor primary suite, private office and sunroom complete the main level. Upstairs has four large bedroom suites while the finished third floor is ideal for a dual in-home office or guest bedroom. The tremendous lower level features a sauna, steam and home theater. This exceptional home embodies an elevated blend of refined and recreational living. This location provides excellent proximity to Boston and top-ranked schools.

Set on nearly two serene acres and abutting 150 acres of conservation land, this exceptional estate offers unmatched privacy and craftsmanship. Custom built by local developer Al Fiorenza as his personal residence, no detail was overlooked. A dramatic entry opens to sweeping views through floor-to-ceiling windows overlooking the manicured grounds, expansive patio, gunite pool, waterfall and gazebo. A stately wood-paneled office and elegant dining room flank the foyer, rich hardwood floors flow throughout the thoughtfully designed living spaces. Clean lines define the chef’s kitchen and vaulted living room, blending luxury and comfort. The oversized first floor suite is a true retreat, featuring a stunning, modern, spa-like bath. Three generously sized second floor bedrooms with walk in closets (2) and a new bath. The fully finished lower level provides incredible flexibility as a playroom, entertainment space, in-law apartment, or anything your lifestyle demands, all enhanced by its open floor and quality finishes.

To 205 Pleasant Street — “The Reserve” — an extraordinary custom estate designed by renowned builder Campbell Smith and set within one of Norwell’s most exclusive gated communities. Privately nestled on 11.75 picturesque acres within an intimate enclave of just ten distinguished residences spanning more than 80 acres, this exceptional Colonial offers timeless architecture, impeccable craftsmanship, and refined luxury throughout. Encompassing over 5,300 square feet, this elegant 11-room residence features 4 bedrooms, 3.5 baths, and a thoughtfully designed open floor plan ideal for both grand entertaining and comfortable everyday living. A gracious formal foyer with a sweeping staircase welcomes you into sun-filled interiors highlighted by over-sized true divided-light windows, exquisite custom millwork, and richly detailed finishes rarely found in newer construction. The heart of the home is a beautifully appointed chef’s kitchen that flows seamlessly into the dramatic 24' x 20' vaulted family room, where French doors open to an expansive patio and breathtaking grounds beyond. A well-designed mudroom and secondary staircase add both functionality and convenience. The luxurious 24' x 36' primary suite serves as a private retreat, complete with a spacious sitting area and serene views of the surrounding estate property. Outdoors, the professionally landscaped grounds create a resort-like setting featuring a heated Gunite saltwater pool, expansive lawn areas, and acres of surrounding land offering exceptional privacy and the potential for a private family compound. “The Reserve” is a rare offering — an elegant gated community with a private entrance, thoughtfully designed common drive, and convenient access to major highways, premier shopping, and top-rated schools. A remarkable opportunity to own a truly exceptional estate property in one of the South Shore’s most coveted locations.

Meticulously restored and ideally situated on Meriam Hill, just three blocks from the town center, this distinguished residence seamlessly blends historic elegance with modern amenities. Interiors by award-winning Boston designer showcase beautifully preserved architectural details throughout, with open living spaces bathed in natural light. A stately wraparound porch invites relaxation while offering stunning sunset views, seamlessly extending the living space outdoors. The grand foyer, anchored by the original staircase, opens to formal living and dining rooms and a study, each featuring a fireplace. A thoughtfully designed addition includes a chef’s kitchen with butler’s pantry and casual dining area, plus an office nook. The lower level boasts a media room, game room, fitness center with backyard access, and an additional mudroom. An attached three-car garage and two mudrooms complete this exceptional home. All of Lexingtons amenities, including schools, are within blocks.

Open Houses: Thur 4-6, Sat 2-4 Sun 11-1. Move right into this expansive center entrance Colonial in sought after Northwood Estates. This meticulously maintained five plus bedroom features four levels of living space with custom millwork and gleaming hardwood floors throughout. Enter into the two story foyer with office on right and formal living room & dining room on left. White kitchen with high-end appliances, island, breakfast/bar area and eat-in nook open to the two-story family room with floor to ceiling custom stone fireplace. Half bath, laundry and mudroom lead to three car garage. Exquisite primary suite with vaulted ceiling, fireplace, walk-in closet and stunning bath. Three additional bedrooms and bath complete 2nd floor. Third level features bedroom/office with exquisite bath and cedar closet. Lower level w/ half bath, playroom, gym or media room. Lush fenced in yard with heated pool & cabana w/ kitchenette, half bath & laundry are open & ready for your enjoyment.

This exceptional 6-acre estate offers supreme privacy and tranquility on a quiet cul-de-sac bordered by conservation land and completed fenced in with 3 gated driveways. The luxurious main residence includes 7 bedrooms, a gourmet kitchen with scenic views, solarium, library, private theater, billiards room, 2025 Built state-of-the-art Fitness Center with infrared room, juice bar, club house with a connecting wing to the Indoor Outdoor Heated Pool with full spa experience. Two greenhouses, multiple fruit tree orchards, tennis court w 4 Bed guest house, 2 add'l guest houses, commercial kitchen with live in chef's suite. A multi-car garage completes the offering. Just minutes from historic downtown Concord and top equestrian destinations, this secure, secluded retreat blends unmatched luxury with convenient New England access. Within minutes to Bedford Airport and New England's premier private boarding schools. Multi-Generational Living under one roof!

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.