luxury houses with pool for sale Pittsfield, United States

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.

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.

Set on eight acres, between the Hudson Valley and the Berkshires, this idyllic, light-filled house offers ample opportunity for living, work, and entertaining. With three bedrooms, four full baths, and a recent addition, the property has stunning views of the surrounding hills, a large deck, a two-car garage, a creative studio, and a picturesque pond. Enter through a breezeway with floor-to-ceiling windows and a tiled floor. The foyer leads into the living room, with a wood burning fireplace, and a large dining area. The kitchen and the adjacent great room make it easy to host gatherings. Wide-board floors are throughout the house. French doors open from the great room to the large deck outside, overlooking the pond. The first floor bedroom, which is currently used as an office, has an ensuite full bath. Upstairs, comfort and convenience are a priority for both the primary bedroom and the guest bedroom, which have ensuite bathrooms and large walk-in closets. The primary bedroom looks out over the Berkshire hills, including views of Jiminy Peak. The recent two-story, 1,433 square-foot addition conveniently connects via the breezeway to the main section of the house. The first floor of the addition has a very large, flex room, which can be additional living or work space or as a place for entertaining. It opens to a separate area that is currently being used as an exercise room. Upstairs is a spectacular studio space with vaulted ceilings, walls of windows, and features a full bath that includes a Japanese style soaking tub. It has been used as an artist's studio, but could easily be repurposed for meditation, yoga, music--the possibilities are endless. Outside, you can relax on the deck, looking out at the pond, enjoying the hot tub or walking the trails on the property; a small bridge leads you to a gazebo. Just minutes away is the farm market store and The Blueberry Café for delicious breakfast, lunch and dinner. Chatham Village has restaurants, The Crandell movie theater, bookstore, along with many other shops. A short drive into The Berkshires for music and theater or head the other direction to Hudson for the vibrant scene on Warren Street and access to Amtrak. Only a two-and-a-half-hour car ride to NYC. This peaceful, scenic and spacious house offers so much for the next owner.

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?

Commanding one of the highest residential elevations in the Hudson Valley, this extraordinary custom residence enjoys breathtaking, uninterrupted views across the Catskill Mountains and Hudson Valley, offering spectacular sunsets, endless skies, and extraordinary stargazing from the privacy of your own mountaintop retreat. Thoughtfully designed for luxurious everyday living and effortless entertaining, the home features a chef's kitchen appointed with premium Bosch, Sub-Zero, and other high-end stainless steel appliances, a gas cooktop, a handsome butler's bar, and exceptional custom cabinetry and built-ins handcrafted by renowned local artisan Vormer Cabinetry of Hillsdale. Superb craftsmanship is evident throughout, complemented by high-performance insulated Pella windows that enhance comfort and energy efficiency while framing the spectacular views. The dramatic great room is anchored by a striking stone fireplace with a reclaimed wood mantel, while a marble gas fireplace with a wood mantel creates an inviting atmosphere in the den. The spacious primary suite enjoys magnificent views and is complemented by an open spa-inspired bath, laundry, and generous closet space. The spacious two-car garage offers abundant storage for outdoor equipment, bicycles, paddleboards, and kayaks, perfectly complementing the property's proximity to Queechy Lake, Stockbridge Bowl, and the region's exceptional outdoor recreation. Modern conveniences include app-controlled security cameras and heating and cooling systems, allowing effortless remote management of the home. Outdoor living is equally impressive, with expansive decks and patios positioned to capture the extraordinary views, multiple barbecue and fire pit areas, and a heated saltwater swimming pool creating an exceptional setting for entertaining or quiet relaxation. A charming pool house with its own outdoor grilling patio extends the outdoor living experience, while the walkout lower level opens to an additional stone patio and fire pit--another spectacular vantage point from which to enjoy unforgettable Catskill sunsets beneath expansive evening skies. Raised garden beds, ornamental flower gardens, and fenced vegetable gardens with programmable drip irrigation provide an ideal setting for growing vegetables, herbs, and flowers. Flexible living space offers additional guest accommodations, while a backup generator provides year-round peace of mind. An additional five-acre parcel is included in the sale, presenting an exceptional opportunity to construct a guest house, studio, office, or other accessory structure, subject to approvals. Located within an exclusive community with privately maintained roads, the property offers exceptional privacy while remaining just minutes from Chatham, Hudson, and the Berkshires. Enjoy easy access to acclaimed dining, boutique shopping, yoga and Pilates studios, organic markets, farm stands, theater, antiquing, and renowned cultural destinations including Tanglewood, Jacob's Pillow, Stockbridge, Lenox, Egremont, Great Barrington, and the Shainman Gallery. Convenient to the Taconic State Parkway, Interstate 90, New York City, Boston, and Albany International Airport, this remarkable residence offers the very best of Hudson Valley luxury living.

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.

Berkshire ridge views and ten private acres set the scene for this distinctive log contemporary on George Carter Road in Becket. Set on a quiet country road just beyond Jacob's Pillow Dance Festival and within easy reach of Lee and Lenox, the home offers generous gathering spaces, a private guest suite, and a wonderful setting for a four-season Berkshire getaway. At the heart of the home is a dramatic great room with soaring cathedral ceilings, massive exposed log beams and trusses, and a floor-to-ceiling brick fireplace. A wall of windows rises to the roofline, filling the space with natural light and framing the Berkshire ridges beyond. Generous living and dining areas offer plenty of room to gather, while glass doors open directly to a wraparound deck overlooking the grounds and pool The kitchen features wood cabinetry, a butcher-block island with gas cooktop, double wall ovens, and brick floors. A walk-in pantry with laundry provides additional utility. The main level also includes a first-floor bedroom with exposed log walls and a full bath, a powder room, and a large heated bonus room currently used for recreation. Upstairs, an open loft overlooking the great room offers space for a family room or office, along with the primary bedroom and a full bath with a separate soaking-tub room. Above the oversized attached two-car garage, a spacious guest suite features vaulted ceilings, exposed beams, skylights, and large windows, creating a bright, open space with its own private bathroom. Set apart from the main bedrooms, it's an ideal space for visiting friends or extended family. The walkout lower level includes a fourth bedroom, a recreation room (or potential fifth bedroom), a full bath, sauna, and flexible space for exercise or other uses. A workshop area provides additional utility. Outside, the deck takes in the distant views, while the lawn rolls gently downhill to the swimming pool, surrounded by woods on either side. A private retreat with room to spread out, spaces to gather, and views to enjoy through all four beautiful Berkshire seasons.

Welcome to Red Rock House, a remarkable architectural compound privately set on 16 acres in the historic hamlet of Red Rock in East Chatham, New York. Designed by Anmahian Winton Architects with landscapes by Studio Reed-Hilderbrand, this extraordinary retreat seamlessly blends contemporary design with the surrounding natural landscape, creating an exceptional sanctuary. A winding driveway through the forest leads to the main house and guest house, both clad in darkened cedar wood with latticed privacy screens that blend effortlessly into their surroundings. A bluestone pathway connects the structures, leading to a terraced pergola with multiple seating areas, a wood-burning fireplace, sweeping meadow views, and a 60-foot heated saltwater pool. Just beyond, a secluded cottage overlooks a rushing creek, while a woodland trail leads to an elevated treehouse-perfect for yoga, meditation, or quiet reflection. Spanning three levels, the main house is a masterclass in modern minimalist design. Crisp white interiors create a gallery-like backdrop for art while framing spectacular four-season views through expansive walls of glass. A stone-paved foyer leads to a dramatic loft-like entertaining space anchored by a double-height living room with floor-to-ceiling windows overlooking the treetops. Nearby, a cozy lounge with a wood-burning fireplace opens to a wraparound terrace cantilevered into the forest. The windowed chef's kitchen with center island flows seamlessly into the dining area and features Vermont Danby marble countertops, abundant custom cabinetry, premium appliances by Wolf, Sub-Zero, and Miele, plus a balcony overlooking the pool and meadow. A tasteful powder room completes this level. A sculptural staircase leads up to the private primary suite level, an airy retreat filled with natural light. The king-sized bedroom includes a sitting area with a gas fireplace and a spa-like bathroom with double vanities, a rain shower, and a deep soaking tub for two. A spacious dressing room with custom built-ins offers exceptional storage, while a hallway with a laundry closet leads to a comfortable media room featuring a fireplace and custom bookshelves. The walk-out lower level opens directly to the pool and includes two bedrooms, a study, and a full bathroom. These flexible spaces can also serve as a gym, home office, or studio. A large mechanical room is also located on this level. Privately positioned from the main residence, the contemporary guest house offers bright open living spaces, oversized picture windows, two spacious bedrooms, a full bathroom, and a kitchenette. Below, a two-car garage provides abundant storage and a Tesla charging station. The entire compound is meticulously maintained and offers exceptional privacy and premium amenities, including multi-zone HVAC, radiant heated floors, custom architectural lighting, a central vacuum system, and a 22KW generator for the ultimate in comfort and security. This unique and remarkable offering is ideal for those who appreciate world-class modern architecture and are seeking a true refuge from the world outside. Though completely immersed in nature, the property sits just 10 minutes from the town of Chatham and 25 minutes from Hudson and the Berkshires, with easy access to renowned restaurants, farmers markets, Tanglewood, P.S. 21, and the highly anticipated Art Omi Pavilions. Red Rock House: not just a home, but a holistic and restorative experience!

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.

Your own sports compound and sanctuary tucked away on a quiet Great Barrington road: this private four-acre retreat centers around an in-ground heated swimming pool and a dedicated tennis/pickleball court framed by natural landscape. Inside, clean mid-century architectural lines deliver remarkable flow, highlighted by two fireplaces, four bedrooms, three baths, space to work from home, and a sunroom overlooking the grounds. Substantial energy upgrades include a high-output ground-mount solar array and an updated heating system that keep operational costs remarkably low, offering a turnkey private playground just minutes from downtown dining, skiing, and cultural landmarks.

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!