luxury house with pool for sale East Chatham, United States

Escape the hustle of city life and discover Bellavista Country Estate, a grand 12,000-square-foot Georgian brick residence set on over 25 private acres in the foothills of the Berkshires, ideally situated between the Hudson River Valley and the Berkshires. Offering 6 to 9 beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, and both a fully stocked eat-in kitchen and a formal dining room, the estate blends elegance and comfort with ease. Recreation and relaxation abound, with a spacious in-ground pool, a serene pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, guests enjoy a full gym, a game and entertainment room with arcade favorites, a home theater, a library of hundreds of books, and a finished attic, while a 4,500-square-foot barn with foosball, ping pong, and bar space provides additional room for gatherings and events. Perfect for weddings, anniversaries, family celebrations, and private retreats, Bellavista also offers access to private chefs, caterers, and event planning support, with every detail—from fiber-optic internet and full-house generators to weekly pool and grounds maintenance—thoughtfully attended to. Since 2011, the estate has been a successful luxury rental for vacations and retreats, equally suited to private full- or part-time residence, a hybrid work-from-home escape, or an unforgettable destination getaway. Just minutes from Chatham, Hudson, and Kinderhook, and a short drive to Lenox, Stockbridge, and Great Barrington, the estate is surrounded by farm-to-table dining, art galleries, organic markets, and the renowned Crandell Theater, with easy access via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, or Albany International Airport.

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room.Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional guest bedrooms share a Jack and Jill bathroom, providing comfort and privacy for friends.The finished lower level is dedicated to leisure and repose, crafted with the ultimate goal of relaxation in mind. Here, in this tranquil setting, you'll find the peace and privacy you desire, all within a home that exudes charm and character.

This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

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.

Experience the perfect balance of grand-scale architecture and tranquil nature in this stunning 6,000+ sq. ft. modern Colonial. Nestled on 3.42 manageable acres within a private enclave near Onota Lake, this 5-bedroom, 5.5-bath estate offers sweeping meadow views just minutes from the world-class arts of Tanglewood and The Clark. The entry is marked by dramatic dry-laid stonework, leading into an interior defined by soaring heights. The heart of the home is a two-story living room featuring vaulted ceilings and a floor-to-ceiling stone fireplace. The expansive living space of the great room flows effortlessly into a gourmet chef's kitchen equipped for high-end entertaining with dual refrigerators, double wall ovens, and a center island cooktop with a built-in griddle. High-top island seating allows for social cooking and a sizable breakfast area flanked by a wall-to-wall credenza—ideal for buffet-style hosting. The home's floor plan thoughtfully blends communal areas with distinct privacy across three levels. The main level is designed for complete convenience and the primary suite is a true sanctuary. It features a private egress to the pool and a hidden back staircase leading to a secluded loft—perfect for a library or reading nook overlooking the suite. The upper level offers a sweeping gallery balcony overlooking the great room, leading to four spacious bedrooms. This includes two private ensuites and two additional bedrooms serviced by a full bath and a dedicated laundry room. The lower level is an entertainment hub featuring a home theater, gaming space, gym, full bath, and a secondary egress for easy garage access. The fully-fenced backyard makes for a resort-style oasis. Host movie nights on the expansive deck, or relax by the heated inground pool and custom-finished patio. The designer firepit is anchored by a unique stone compass inlay, and a poolside full bathroom ensures guests never need to track water through the main house. For the automotive hobbyist or enthusiast, a high-end, three-bay attached garage is professionally finished with epoxy floors, industrial-style metal cabinets, and an EV charger. You will also find a massive, 50x40 detached shop with four bays and oversized doors. Whether for housing a car collection, an RV, or a professional art studio, the possibilities of this space are endless. Embrace the Berkshire landscape in a home where every detail has been considered. Whether you are heading out for fine dining or staying in to enjoy your private oasis, Blythewood Estates offers a lifestyle of unparalleled peace and sophistication.

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.

Built in 1974 by an engineer, this mid century modern residence resembles a French chateau in concept yet retains all the modern flourishes true to the period. Once two identical houses then combined employing steel beam construction, the symmetry inside soothes the soul of the connoisseur but it is the 12’x 60’ lap pool and accompanying screened pool house that grabs the attention. Surrounded by hedges of hydrangeas and a tidy boxwood garden that lends to the European flair of this property, florals fall over all the edges of the sensational long lawn while providing a tucked-in experience of privacy. This 3 bedroom 2 bathroom house boasts lofty, two story atriums with dramatic, modern glass windows with vertical mullions casting inviting sunlight over the living spaces while the whole house white painted interiors add a lightness of being within all the rooms. The open kitchen with its mid mod mosaic tiles offer the clean lines you come to expect from this architectural specimen while also being warm and entertaining. This property is especially good at throwing parties as it lends itself to both indoor and outdoor lifestyle activities with patios in both the front and back lawns. Stuyvesant NY is a scenic, rural town tucked away in the northwestern corner of Columbia County. It is defined by its pristine agricultural landscape, deep-rooted Dutch history, and striking waterfront geography along the eastern shore of the Hudson River, all the while enjoying its unique proximity to the village of Kinderhook NY. Shop for CSA farm to table foodstuffs at Samascot just 5 miles away or hit up the Chatham Berry Farm for your groceries and never step foot into a box store again. Dining out in the evening is provided by the many lovely Kinderhook hotspots.

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.

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?

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.

Charming in-town Cape on a spacious lot with inground pool. Located in a delightful neighborhood close to town, this inviting home built in 1951 offers 5 bedrooms and 2 full baths. Inside, the residence seamlessly balances ample room to spread out with warm, light-filled spaces tailored for everyday living and entertaining. Timeless architectural details throughout bring character and charm, including a wood-burning fireplace, graceful arched doorways, and custom built-in cabinetry. Outdoors, a private in-ground pool is set within a large, sunny yard, creating a wonderful oasis. Turn-key peace of mind is provided by recent upgrades, including a newer furnace, water heater, and pool filter. Town water, town sewer, and natural gas from the street. Close to everything; a must see!

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.

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

Haas Hill is a rare opportunity to own an expertly envisioned, sprawling country compound on 148 pristine acres amidst the verdant foothills of the Catskill Mountains. The Setting The lush acreage is home to three structures originally built in the late 1940s and all recently renovated: a 2,700 sq ft main house, a two-story cottage with a full bath and kitchenette, and the large pool house/cabin with a loft, full bath, and kitchenette. The land is populated with an in-ground pool, a fenced wildflower garden, a barn, many mature gardens and trees, and acres and acres of rolling hills and ecologically diverse forests. The Main House The main house is overflowing with natural light and charm, with a layout designed to serve rest and play equally; large primary living areas and a spacious, inherently social kitchen are a frequent entertainer's dream, while the cozy family room, tucked-away office, and serene bedrooms with far-reaching views of the surrounding landscape offer a quiet respite for a family. When you enter, you're greeted by the mudroom, with slate floors, wood paneling, a long peg rail and bench for everyday storage, and an extra-large closet for coats and sports equipment. Through a sliding door is the utility room, with laundry, a worktop and shelves, and a large utility sink. The kitchen features brand-new appliances, a beautiful charcoal AGA range, a hand-painted tile backsplash, terracotta radiant-heat tile floors, and ample built-in storage, including a pantry. The built-in breakfast nook in the corner of this space looks out onto the pool and an ancient Catalpa tree, and a door from the kitchen leads out to the back deck's dining area. Flooding with light from morning until evening, the double-height living-dining room centers around an original fireplace with built-in wood storage. Completing the ground floor is the powder room, a wallpapered office, and a more intimate family/media room. The second floor has the most commanding views on the property, with unobstructed views from the primary suite of the Mid-Hudson Valley's prominent hills and mountains. The wallpapered kids' room, an additional full bath, and a charming guest room round out the second floor. The Cottage Down a meandering stone path from the main house lies the two-floor cottage, with beautiful pine floors, exposed wood beams, a kitchenette and full bath, and ample living, sleeping, and storage space. The Cabin Just around the corner from the pool area is the cabin - a charming space with green-painted floors, shelving and peg rails throughout, and vaulted ceilings with thick wood beams. Currently used as a pool house and for sleepovers by the youngest generation, the cabin can also be easily remixed into an art studio, office, or additional (grown-up) guest quarters, and features a kitchenette with abundant storage, a full bath, and a cozy loft. The Surroundings While you won't need to leave your own grounds to get a healthy dose of nature and adventure, the surroundings are filled with opportunities for long, scenic hikes, boating trips along the Hudson, skiing in the Catskills, jaunts through fruit orchards, and many other outdoor pursuits. The nearby town of Coxsackie is home to a perfectly-stocked General Store (Coxsackie General), our favorite spot to grab a delicious bottle of wine (Reed Street Bottle Shop), a delightful antique store/bar/creative collective (UnQuiet), and a beloved supplier, maker, and curator of delicious Italian goodies (Via Ravioli). Haas Hill is just a few minutes from the town of Coxsackie, 15 minutes from the village of Catskill, 30 minutes from Albany International Airport, 30 minutes from Hudson (and Amtrak), and just under 2.5 hours from New York City.