luxury houses for sale Berkshire County, United States

Have you been dreaming of year round fun on Stockbridge Bowl? The time is now! Built in 2011, this lovely home is directly across the street from the beloved town beach and affords water views from most windows. Offering single-level living, 3 BR, 1 full BA, a well appointed kitchen and gracious living spaces. The unfinished walk-out lower level is the perfect place to store your kayaks, and could be finished to offer more living space. There is plenty of off-street parking above and below the home. You are mere moments to Tanglewood's Lions Gate and the very best of the Berkshires. Would make a great rental, or a wonderful family retreat to make memories for years to come. Town sewer, private well, radiant heat, and energy efficient construction, all in a location that can't be be beat!

Welcome to this well maintained 3-bedroom, 1-bath home tucked away at the end of a quiet side street, offering privacy, convenience, and a beautiful connection to nature. Inside, hardwood floors run throughout most of the home, reflecting years of attentive care and pride of ownership. Step outside to a spacious, fully fenced backyard featuring a deck with a remote-controlled retractable awning, perfect for relaxing or entertaining. Abutting protected land through Berkshire Natural Resources Council, this property offers easy access to hiking trails leading to The Boulders and beyond. A move in ready home in a peaceful setting that you'll love coming home to.

Welcome home to this sweet and petite one level easy living ranch style home. Sun-filled bright spaces invite you to relax and enjoy the end of each day in this thoughtfully planned layout. Boasting a king size bedroom, two other bedrooms, and an updated full bath. The galley style kitchen is comfortable for baking and creating all the dinner gatherings you wish. Comfortable everyday dining is open to living and a lovely added sunroom for extra living space and enjoyment. French doors lead to a generously sized back yard with perennial plantings and a shade tree for an outdoor cool evening escape and playtime. Central to all that is Berkshire and Lee with a quaint downtown, shopping, schools, dining, and antiques. Close to parks, playgrounds and October Mountain State Forest for fun!

Comfort, privacy, and easy Berkshire charm on nearly four acres, just five minutes from downtown Great Barrington. Set well back from Division Street on a quiet road, this inviting home feels tucked away but not remote. A tree-lined drive winds through the property to a home surrounded by colorful gardens and mature trees. Inside, the house opens up and keeps surprising. A thoughtful expansion by noted Berkshire architect John James added volume, light, and a more contemporary flow while still feeling connected to the original home. The living room, with its wood-burning fireplace, connects to an updated kitchen, dining room, and sunken great room. With oversized windows and views into the trees, the great room gives the home a bright, open feel while still keeping a sense of definition between spaces. The large vaulted screened porch may be the best room in the house. Surrounded by trees and birdsong, it feels peaceful and immersed in nature -- easy to imagine using all summer. Just beyond, a stone patio overlooks the backyard and offers a great spot for outdoor dining and relaxing. The flexible floor plan includes a first-floor bedroom and full bath, offering the option for one-level living. Upstairs, the large primary suite includes generous closet space and a private bath with soaking tub and separate shower. Two additional bedrooms share a third full bath. A detached two-stall barn/garage with overhead storage provides useful space for vehicles, tools, garden equipment, hobbies, or recreational gear. Close to downtown Great Barrington, but with the feel of a country setting, this is a comfortable, open, good-feeling home in one of the Berkshires' most convenient locations.

Beautifully renovated historic farm house available in Lenox, Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst,'' one of the famed Berkshire ''cottages,'' this former guest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2-car garage. Luxurious traditional decor throughout the home but with all the modern conveniences including AC, wifi, whole house generator and more. A flagstone terrace overlooks the lush backyard and fully planted walled garden. The house benefits from the rolling landscaped vistas of the beautifully maintained estate property it abuts. Minutes to the town of Lenox and to Tanglewood!

Set on 4.7 beautifully landscaped acres with distant views. This impeccably maintained home offers generous space, thoughtful craftsmanship, and remarkable indoor-outdoor living. Located just minutes from so many of the Berkshires' most beloved attractions, including only 15 minutes from the main gate at Tanglewood, this Richmond property also boasts easy access to major traffic routes connecting you conveniently to both New York and Boston. Your ability to enjoy the region's culture, adventure, and cuisine starts right here.

Welcome to the historic Simmons Cottage located at 2 Melrose Street in Adams, MA. This Victorian gem, completed in 1901, perfectly blends its 19th-century character with modern convenience. Situated on a .24-acre lot in the heart of Adams, the 2,406-square-foot residence features 4 bedrooms, three bathrooms, office, and full attic. The home's historic elegance shines through its preserved curved front porch, original woodwork, stained-glass windows, and rare Lincrusta ceilings. This home has been updated to provide efficiency, including a new roof, upgraded heating system, and a modernized kitchen. A standout feature is the unique historic carriage barn, relocated and repurposed into an incredible five-car detached garage for your vehicles and hobbies!

Move right into this beautifully renovated mid-century Cape, where modern updates blend seamlessly with timeless charm. Designed for easy single-floor living, this bright and airy home features an open-concept kitchen, dining, and living area that creates an inviting space for both everyday living and entertaining. The living room is highlighted by a soaring cathedral ceiling and abundant natural light, enhancing the home's spacious feel. The thoughtfully designed layout includes a private primary suite with an en suite bath,offering comfort and convenience. French doors open from the living room to a rear deck overlooking a fire pit area, creating the perfect setting for outdoor gatherings, relaxing evenings, and enjoying the surrounding landscape. Ideally located just minutes from downtown Great Barrington, Ski Butternut, and the public boat launch at Lake Buel, this move-in-ready home provides easy access to the best of the Berkshires, from outdoor recreation to dining, shopping, and cultural attractions. Excellent rental history.

Offering the rare and coveted 'lake life' on Lake Buel, this unique property presents an extraordinary opportunity to establish your own Berkshire footprint on an expansive 2-acre parcel. Comprising 90% sun-drenched, open meadow, the large lot serves as the ultimate blank canvas with potential for a stunning architectural expansion, a custom family compound, or agricultural designs. While the existing cottage provides a peaceful, private retreat set back from the road, the true crown jewel is the property's dedicated lake access--offering the right to install your own private dock or boat slip on one of the Berkshires premier motorized lakes. Bring your vision to this exceptional property and start living the Berkshire lakeside dream today.

Embrace the ease of single-level living in this enchanting 3-bedroom, 2-full-bath cottage nestled in historic Stockbridge. Perfect as a year-round residence or a peaceful weekend getaway, this home perfectly blends cozy charm with modern convenience.

Enjoy the best of the Berkshires from this beautifully maintained contemporary Colonial, privately set on more than 2.5 acres with deeded access to Otis Reservoir, Massachusetts' largest recreational lake. Spend your summers boating, swimming, and fishing, then return home to relax in the peace and privacy of your own wooded retreat. Built in 2000, this spacious home offers four bedrooms and three full baths, including a first-floor primary suite with a private en suite bath. The open-concept living area features soaring cathedral ceilings, a cozy gas stove, and a seamless flow into the well-appointed kitchen, creating an inviting space for everyday living and entertaining. A generous screened porch overlooks the expansive yard, while the stone terrace and newer hot tub provide the perfect setting to unwind after a day on the lake or slopes. The finished lower level offers a comfortable media room or family room, providing flexible space for movie nights, games, or guests. An oversized attached two-car garage offers abundant storage for vehicles and recreational gear. Ideally located just minutes from Otis Ski Ridge, Big Pond Beach, local restaurants, hiking trails, and year-round outdoor recreation, this home also features fast fiber-optic internet for those who work remotely. Combined with low property taxes and an exceptional location, this property offers the perfect blend of comfort, convenience, and Berkshire adventure.

Step back in time and discover the timeless charm of this classic 19th-century New England home, ideally situated on a generous .66-acre corner lot on a quiet street just minutes from the heart of downtown Great Barrington. Rich in character, this antique home retains many of its original architectural details, offering an exceptional opportunity for restoration and reimagination.The inviting, old-fashioned front porch welcomes you to a home filled with history and potential. A classic barn adds versatility for storage, hobbies, or future creative use, while recent updates--including a new boiler and barn roof in 2025 and the convenience of natural gas--provide a solid foundation for your vision. Whether you're looking to restore a beloved antique or create your dream Berkshire retreat, this property offers endless possibilities in an unbeatable in-town location. Bring your imagination and breathe new life into this historic gem. Property is being sold as is.

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.

Nestled on over 3 private acres with an extraordinary 650 feet of frontage on Hayes Pond, this exceptional waterfront retreat offers sweeping elevated views, a private dock, sandy beach, and direct access to swimming, kayaking, and fishing. Designed to embrace its stunning natural setting, the home features expansive windows and multiple outdoor living spaces, including a wraparound deck, waterside gazebo, and screened porch with hot tub connection--perfect for entertaining or relaxing in every season. The bright open-concept interior includes 4 bedrooms and 3 full baths, highlighted by a dramatic great room with knotty pine ceilings, a wood-burning stove with stone hearth, and direct deck access overlooking the water. The spacious primary suite also opens to the deck and features its own and features its own wood-burning stove and en suite bath. The walkout lower level offers additional living space with a family room, full bath, and two bedrooms ideal for guests or extended family. Additional features include solid wood floors throughout, an attached two-car garage with EV charging, and easy access to the very best of the Berkshires. Located just minutes from Lee and Lenox, with nearby hiking, skiing, dining, Tanglewood, and year-round cultural attractions, this is a rare opportunity to enjoy the ultimate Berkshire waterfront lifestyle. Sale includes lots 34 and 35.

2 bed, 2 full bath Berkshire retreat. The bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch and 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand new back deck, an ideal setting for summer evenings. 2 bedrooms on the second floor, with a full bath and dreamy tub. Meticulously-maintained home with a new 200-amp electrical service, this turnkey retreat ensures total peace of mind. Expansive back yard with basketball court and shed. Whether you're enjoying the classic rocking-chair porch or exploring nearby trails and boutiques, this sweet sanctuary is a rare find in the heart of Berkshires.

Step into effortless Berkshire living in this design-forward mid-century ranch. Perfectly positioned on a quiet downtown dead-end road, this 3-bedroom, 1-bathroom home seamlessly blends crisp, modern style with classic architectural character. Inside, original hardwood floors guide you through a bright, fluid one-level layout. The living room serves as a comfortable anchor for cozy mountain evenings, featuring a striking wood stove that pairs perfectly with the home''s fresh, stylish aesthetic. Outside, the generous 0.41-acre level lot offers a private, shaded yard surrounded by mature trees-a fantastic feature for a property this close to the action. Beyond its residential charm, this property boasts coveted Business zoning, making it perfect for an ideal live-work lifestyle. Antonio M Segalla [email protected] 413-329-4075 WILLIAM PITT SOTHEBY''S - GT BARRINGTON

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.

Light-filled contemporary Cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area, and living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom and a balcony overlooking the living area. The four-season sunroom (heated and cooled for year-round use) opens to the level backyard. Lovely front entrance with Bluestone steps into an ample mudroom. Enjoy year-round comfort with zone-controlled mini-splits. Close to vibrant Great Barrington, Stockbridge, and Lenox. A quick drive to Tanglewood, cultural venues, and abundant outdoor recreation including hiking and lakes, this modern retreat blends style, comfort, and an exceptional Berkshires location.

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 a corner lot in a well-established neighborhood, this home offers a practical layout, thoughtful updates, and plenty of outdoor space. This 2-bedroom, 1.5 bath split-level home features hardwood floors throughout the main living spaces and bedrooms, creating a warm and cohesive feel. The kitchen opens directly into the dining room, offering an easy flow while overlooking the spacious backyard with a laundry and half bathroom right off the side entrance for convenience. The lower level offers excellent potential for partial finishing--ideal for additional living space, a home office, gym, or recreation area. Outside, the large backyard provides ample room for entertaining, gardening, or play, and the detached one-car garage adds convenience and storage. Well-maintained and full of opportunity, this home combines comfort, charm, and future potential in a desirable setting.

Be wowed by this southeast sleeper that presents as a traditional-style colonial where you'll be pleasantly surprised by all the upgrades. This home offers custom luxury features and stylish finishes with exceptional indoor-outdoor living. 145 Leona is modernized inside and out. It is situated on a unique lot with a welcoming front porch, spacious side lawn ideal for play plus a bonus hilltop wooded retreat. You get the best of all worlds here. Begin your tour inside with the awe-inspiring heart of the home, a beautifully designed kitchen with quality cabinetry, top-of-the-line Bosch appliances, marble counters, and a sleek tile backsplash that blends artistic symmetry with everyday function. The centrally placed coffee-bar buffet is perfect for morning coffee, casual entertaining, or signature summer cocktails with friends and neighbors. Radiant heated floors add cozy comfort throughout the family room, kitchen and everyday dining area. The mudroom features an updated Kohler half bath/powder room, laundry, and entry from the garage. The dining area and fireplaced family room overlook the full-span TREX deck and 2 goshen stone patios with a firepit--an ideal setting for s'mores, campfires, and memorable evenings outdoors. The east-side backyard lawn is perfect for outdoor sports and a swing set. A stairway built into the hillside leads up to the wooded hilltop and your own backyard forest escape, complete with a stand of trees, picnic table, hammock, and tent area for at-home adventures. As the night wanes and it's time to wander indoors, you will discover a beautiful sweeping circular staircase leading you to the bedroom level. Enjoy four bedrooms and two updated custom finished baths. Choose the designer deep soaking Kohler bathtub to soak and unwind, creating a luxury spa experience before slipping into the freshly carpeted cozy bedroom of your choice. The primary suite is queen-sized for comfort ensuring a restful ending to your day with the soothing water in motion rain shower experience in the designer bath which also has a radiant heated floor. Start the day with a spacious well planned walk in closet and enjoy the central locale for a quick and easy morning commute to school and work. Updated mechanicals complete the quality and value of this home with a lower level family room and an abundance of storage. Everything you need is ready for you to move right in. Join this welcoming neighborhood and the Friends of Leona community, where you can enjoy the perfect blend of comfortable living, nearby parks, city conveniences, and two levels of outdoor space on a manageable wooded home site. This home is a treasure to be discovered.

The road ends here. At the end of quiet Old Quarry Road, still much as it felt 150 years ago, sits a circa 1840 farmhouse overlooking its own broad lawn, with sixty acres of woodland stretching beyond. Thoughtfully expanded over time, the original farmhouse and later addition are seamlessly integrated, yet retain separate entrances, giving everyone a little space of their own. Three bedrooms are in the original house, two more in the addition, and every bedroom has its own private bath. No sharing necessary. Multiple wood-burning fireplaces, two screened porches, an old tennis court and a stone wall between the dining and living rooms add to the story. Once a farm, now a home with history, land and possibility. The road ends here, but the rest is yours. The current owners weren't looking for this house. They were looking for a small lake cottage. Instead, they found something they hadn't expected. Twenty-six years later, it's easy to see why. You can even feel it when you're here. This became their place to gather. In summer, the back screened porch was their living room and dining room. In winter, they came together in front of the fireplace. Easy to get to from Boston and New York. Easy to get to great restaurants and farmers' markets, world-class dance and theater, skiing and lakes, and secret spots that are crazy beautiful. Life happened here. Memories were made here. This isn't a perfectly restored showpiece. It is a real old house, with history, quirks, and room for the next family to make it their own. That's good. You can move right in, live in it, and let the house help you figure out what you want to change, what you want to preserve, and how you want to live. Inherent to the home is the land. Like much of New England, what were once farm fields and pastures have gradually returned to forest. Old cart roads still wind through the woods, inviting exploration in every season. Follow them toward the remains of a small nineteenth-century quarry just beyond the northern property line. That is living history. Hike, mountain bike, cross-country ski, or just explore, right from your back door. Revive the gardens. Pick blueberries and apples. Spend the afternoon at the nearby beach. Bike to dinner. The house owes you nothing and you owe nothing to the house. The home is what it is, and no apologies are needed. A lovely old farmhouse, with 60 acres, at the end of a quiet country lane, where you can look up at night and the stars are so bright you can see the Milky Way, and hear the peepers and the owls, and that's it. Enjoy the uncommon peace that comes from knowing the road ends at your home. But the end of the road is really just the beginning. The best old houses don't ask to be admired. They ask to be lived in. Not everyone will understand this house. The right person will.

Quitessential 1831 side hall Colonial. Charming home located in the village of Interlaken in the town of Stockbridge, MA. Just minutes to Lenox, downtown Stockbridge, and the Berkshire Botanical Center. Listen to the babbling water from the Larrywaug Brook and visit the nearby town park. Sit on the deck or around the firepit to soak in the atmosphere of privacy and peace. This 3 bedroom, 1.5 bath house has been meticulously updated. These updates include: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer. Garage is partitioned for a workshop but can easily be converted to a one-car garage again.

Offered for the first time! Welcome home to this well-maintained split-level offering the perfect blend of comfort, convenience, and classic Berkshire charm! The bright and inviting layout features a spacious living area, eat-in kitchen, and a four-season sunroom. Upstairs flows into 3 bedrooms and a beautifully newly renovated full bathroom. The basement provides excellent storage space, workshop potential, or future expansion opportunities. The attached garage adds everyday convenience, and the nearly 1.5-acre lot offers plenty of room for gardening, outdoor entertaining, or enjoying the private yard. Additional recent improvements include a new 200-amp electrical service, fresh interior paint, and new carpeting. This cherished home is ready for its next owner to make it their own!

Perfectly-timed for summer in the Berkshires, this 1,320-square-foot contemporary retreat at 311 Tamarack Trail is refreshed and ready for immediate move-in. Tucked away in the private Otis Wood Lands community, the home borders protected state forest land, offering a serene and private wooded setting for your seasonal escape. The interior features a bright, open-concept layout with soaring vaulted ceilings, skylights, and expansive windows that bring the beauty of the forest indoors. For effortless year-round comfort, the home is equipped with a brand-new pellet stove and high-efficiency mini-split units in every room for customized heating and cooling. The kitchen has been thoughtfully refreshed for the modern cook, featuring a brand-new built-in oven and microwave alongside stainless steel appliances. The three-bedroom, two-bathroom floor plan is supported by a septic system installed just three years ago, providing peace of mind for the long term. Designed for summer enjoyment, the outdoor space includes a deck with a direct propane line for easy grilling and a large screened-in porch featuring a projector screen for cinematic movie nights. Residents also enjoy full access to premium community amenities, including a private lake, beach, pool, club house, and tennis courts. This turnkey property is the perfect low-maintenance opportunity to start enjoying the best of Berkshire living the moment you turn the key.