luxury house with pool for sale Sandisfield, United States

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.

An incredible opportunity to be the next steward of Ledgehurst, a historic c.1780 estate once owned by founding family of Monterey, and perched above the charming village. Spanning over 4,000 sq. ft., the residence features bright living spaces, a primary suite plus 3 guest bedrooms, and a rare indoor pool complex w/ a sauna. Massive outbuildings offer endless potential for ADU's, workshops, creative studios, or car collections. Enjoy a short stroll to Lake Garfield's sandy beach, and under 15 minutes drive from downtown Great Barrington. The property is being sold in as-is condition. Buyers are encouraged to perform their due diligence and verify all information on condition and intended uses. This will be a project, but with the right vision, the property can be spectacular once again!

Experience 225 years of preserved grandeur on Nodin Farm. Nestled on 130 sprawling acres of rolling countryside, this Greek Revival has been lovingly stewarded by only four owners across more than two centuries, ensuring its soul remains as original as its architecture. The Manor House: The interior seamlessly blends the romance of the 19th century with the sophisticated comforts of the 21st. Rich wide-plank wood flooring, bespoke built-ins, hand-carved woodwork, seven fireplaces, these are just some of the original details. The gourmet kitchen has premium, professional-grade appliances, the home's bathrooms are renovated, and the estate is equipped with state-of-the-art climate control systems. The Grounds and Out Buildings: The "Farm" moniker only hints at the magnitude of this estate's amenities. You'll find a brick patio and a shimmering inground pool, perfect for summer afternoons. The Main Barns- A majestic gambrel-roof brick barn and a classic wooden barn, both fully restored. The Bull Barn- A charming, standalone brick structure with existing architectural plans for a luxury guest house. Auto Gallery- A massive, 7-bay brick garage complete with a professional-grade gym and a private executive office. This entire barn complex was meticulously repaired and outfitted with premium roofing in 2024. Nodin Farm is a rare convergence of history, scale, and meticulous preservation. It is an invitation to own a piece of the American story. Schedule your private tour of this 130-acre legacy estate today.

Introducing: Katsura. It might surprise you to learn that the ultimate lake wilderness retreat you've been searching for in Maine, Vermont, or Montana is actually hidden right here in the foothills of Connecticut. Perfectly positioned just over two hours from NYC, Katsura Lodge is a masterclass in privacy, offering a rare opportunity to truly escape into nature. Set at the end of a gated, long private crushed stone driveway, this 118-acre unspoiled woodland sanctuary offers approximately a mile of pristine frontage on Winchester Lake. It is the ultimate luxury camp. A place to unplug, exhale, and reconnect with family and friends. Offering over 5,000 square feet of sophisticated living space, this custom built, 5 bedroom contemporary residence integrates beautifully with its surroundings. Exceptional craftsmanship including heart pine and stone floors, custom cherry cabinetry, and soaring cathedral ceilings creates an elevated, warm aesthetic. In the great room, an impressive double-height fireplace, crafted from stones sourced directly from the property, anchors the space, while a cozy windowed reading nook invites quiet afternoons. Seemingly endless Albertini sliding glass doors erase the line between indoors and out, framing captivating views of the manicured grounds and the water. The home is designed for seamless entertaining on any scale. A gourmet chef's kitchen features top-of-the-line appliances, an adjoining wet bar, and a spacious wine cellar. The glass wrapped breakfast room flows effortlessly into an expansive screened-in porch with a built-in grill. Here, the lake-facing wall opens completely to a covered patio, providing flawless indoor-outdoor lounging and dining, regardless of the weather. The 1st floor primary suite is a true sanctuary, featuring vaulted ceilings, a second property sourced stone fireplace, a whirlpool jetted soaking tub, and access to a private terrace. Ascend the sculptural staircase to find an art-lover's landing overlooking the great room, leading to four generously sized upper-level bedrooms - each with extensive custom cherry built-ins - alongside three full bathrooms and a relaxed loft. A media/game room, mudroom, laundry room, and temperature-controlled three-car garage complete the home's flawless functionality. The outdoor amenities rival any private resort. Spend long summer afternoons fishing in peaceful Winchester Lake, a 229-acre body of water celebrated for its untouched shoreline and superior bass fishing. Grab your kayak from the boathouse and head to the captivating stone inlet. Paddle out into the larger of the two coves to your own private island. Serve up a match on your private tennis court. Warm afternoons are best spent by the gunite pool and pool house, complete with a wet bar, full bath, changing room, outdoor shower, and a sauna-ready room. End the day roasting s'mores around the firepit. When the seasons turn, the estate transforms into a winter wonderland. Strap on your snowshoes or cross-country skis to explore your private trails and expansive meadows, go ice skating on the lake, or take a quick 30-minute drive to the local ski slopes. Katsura Lodge - a luxurious four-season lakefront estate settled in unspoiled wilderness, just over two hours from NYC.

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot with almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen and bathrooms, as well as the furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for its next owners to create their own Berkshire journey and memories. Replaced/Updated Within the Last 3 Years: furnace, central AC, kitchen, bathrooms, all exterior doors, basement improvements Community Details: -8 homes in the community -$1,500 transfer fee due at closing from buyers to the Association -HOA dues will decrease to $900 per quarter ($300 per month) after two loans are paid off in July and October 2027 Rental Policy: -First rental term has a 28-day minimum -Second rental term has a 7-day minimum -Maximum rental term is 1 year -Lease extensions must be approved by the Association

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio above the den--offering an ideal, quiet space for an executive home office or fitness room. Outdoor living is built for relaxation, featuring an expansive wrap-around deck with scenic views, a stone patio, and a spectacular 3-season screened porch overlooking mature perennial gardens. Modern mechanicals include central air and a full backup generator system for ultimate peace of mind. As a resident of this coveted neighborhood, you'll enjoy exclusive access to the heated community pool. Simply lock up, leave, and enjoy nearby Tanglewood, local ski mountains, and Main Street dining.

Set on just under an acre along one of Lee's most desirable roads, this beautifully maintained home combines timeless design, quality craftsmanship, and exceptional outdoor living. Overlooking peaceful meadows with stunning sunset views, the setting offers the perfect balance of privacy and natural beauty. Designed for both entertaining and everyday living, the backyard is truly the centerpiece of the property. A tiered bluestone patio creates multiple spaces to gather and relax, featuring a built-in outdoor kitchen, gas fire pit, and a heated saltwater plunge pool by Soake Pools. Mature landscaping, professionally designed landscape lighting, and a charming storage building complete the outdoor space, creating a backyard that feels like your own private retreat. Inside, the home is warm, inviting, and thoughtfully designed. The eat-in kitchen is the heart of the home with a large center island, custom cabinetry, premium JennAir appliances, and direct access to the patio for seamless indoor-outdoor living. Just off the kitchen, the family room offers a comfortable place to unwind, while the formal living and dining rooms provide the perfect setting for holidays and entertaining. A powder room and first-floor laundry add convenience to the main level. Upstairs, the spacious primary suite offers a walk-in closet and a beautifully appointed en-suite bathroom featuring a soaking tub and walk-in shower. Two additional bedrooms share a full bath, while the oversized bonus room provides incredible flexibility. Filled with natural light from a dramatic picture window overlooking the backyard and rolling meadows with distant mountain views, it's the perfect space for a media room, playroom, home office, or fourth bedroom/guest suite. A second staircase offers easy access and enhances the home's thoughtful layout. Additional features include a new roof in 2022, an attached two-car garage and a full basement with radiant heat, providing ample storage and endless potential for future finishing. From the quality craftsmanship and thoughtfully designed floor plan to the incredible outdoor spaces and picturesque setting, this is a home that has been exceptionally cared for and is ready to be enjoyed for years to come.

Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings--a two-car garage and a garden house. The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined, restorative bath, and walk-in closet/dressing room. To the right, a spacious dining room, well-appointed kitchen, screened porch, and hallway to two bedrooms and full bath. The U-shaped floor plan embraces a secluded formal garden, reflecting pool with fountain, patio with pergola, and 40' lap pool. Completed in 1998, every element of the residence attests to architectural intelligence, superior craftsmanship, and love for the bucolic landscape. The high level of quality is evident in the visually commanding millwork, true stucco exterior, lath-and plaster walls in the principal rooms, east and south pergolas, west-facing screened porch, and sensitive choreography of space. With roots in the classical architecture of ancient Rome, this is a thoroughly modern dwelling replete with whole-house fan, air conditioning, generator, security system, 630-foot drilled well, and chef-ready appliances. The result is a home that feels both sculptural and deeply connected to its setting. With protected views, total privacy, and proximity to South County amenities (7 minutes to Guido's), this is a rare Berkshire offering -- serene, architecturally stunning, and eminently livable.

The Dean House, a/k/a The Horsford Homestead, a/k/a The Howe's Home is arguably the oldest residence in Falls Village (Canaan), CT. The original structure was built in 1735, with a major, two story addition added in 1804. Many details have withstood the test of time, and this home is a stunning statement for any old-house enthusiast. If you envy the history as a preservationist, conservationist, or restorationist, you just found your personal Xanadu. From the original fireplaces and paneling to the structural "bones" in the attic and basement, all the right features are here, as spacious rooms, cozy environs, and heartfelt warmth are the mantras. Much of the original trim, flooring, doors, and moldings are prevalent, and that impact speaks volumes. The bathrooms are recently updated, and there are newer appliances. The cedar roofs are no more than 7 years old. The outdoor environment is lush and well maintained. There's a kidney shaped in-ground pool, beautiful gardens, and even a large flat lawn that once served as a home to a full-sized English croquet court. The large old barn dates well back in time, and there's a gazebo for quiet reflection and outdoor meals. Several other smaller buildings exist for all types of storage. And then there's the newer building (1997) - a combination of a two-car garage, a huge studio/workshop, a smaller storage room, and a roughly 1700 sq. ft. in-law apartment on the second floor. Approximately 30 acres of farmland is organic. Drive-bys are welcomed, but please do not pull in the driveway without a confirmed appointment.

Offered fully furnished and ready to enjoy, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions.

This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace. The adjoining kitchen and dining areas are designed for gathering, with cherry floors, custom pine cabinetry, a large island, and stainless appliances. A large screened porch and wraparound deck extend the living space outdoors and take in the wooded setting and ridge views. The luxurious first-floor primary suite offers private porch access and a spacious bath with soaking tub and separate shower. First-floor laundry completes the main-level living arrangement. Upstairs are three additional bedrooms and two full baths. The walk-out lower level includes a dedicated home gym and additional flexible space. Beyond the pool area are several other amenities, including a dramatic fire pit tucked into a natural rock outcropping, a children's playground, and open lawn for games and play. Private but not remote, the property is just minutes from downtown West Stockbridge, with Stockbridge, Lenox, Great Barrington, and Tanglewood all within easy reach.

This one-of-a-kind custom designed home is a peaceful sanctuary, situated on top of a hill on 18 secluded acres (that is subdividable) and bordered by conservation land. To access the home, you drive over a bridge and up a paved and gravel driveway. The home is fine for entertaining, featuring a cook's kitchen with stainless steel appliances, a breakfast bar and granite leather suede countertops. The expansive dining area includes a gas fireplace, and the living room boasts a soaring ceiling and a wood burning fireplace. A large deck provides amazing views, and you can enjoy swimming all year round with the indoor 18x36 inground saltwater pool, complete with a dehumidifying system and alarm. The main level is completed by a laundry room, mud room and attached two-car garage. For a retreat, the primary bedroom suite offers a sitting room with custom crafted Mahoghany doors and ceiling fan, with a luxurious primary bath featuring a soaking tub, tile shower and dual sinks. The lower level includes a wine cellar, a full bath, a tandem two-car garage and a walkout patio. An elevator which serves all three levels of the home. Mechanical features of the property include energy efficient geothermal heat and air conditioning, a generator and underground utilities. The grounds are thoughtfully cultivated featuring fruit trees, blueberry and raspberry bushes, fenced in gardens, a stone walkway and the paved driveway. A beautiful place to reside in the Litchfield Hills.

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.