luxury properties for sale Pittsfield, United States

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The second floor functions as its own private level, featuring three bedrooms and two full baths. The guest house feels like a second home entirely. With two bedrooms, two full baths, a dramatic stone fireplace, and a kitchen finished with Caesarstone quartz, it offers independence without compromise. Mini-split systems provide year-round comfort, while a private laundry and generous scale make it equally suited for extended stays or full-time living. Both residences feature claw-foot tubs and roofs replaced within the past three years. A two-car garage at both houses, potting shed, fire pit ring, and expansive grounds complete the offering. This is a property defined by flexibility and scale--where multiple generations can live together while maintaining independence, and where land, light, and structure align to create lasting possibility.

Beautifully maintained home set on a private one-acre lot on a quiet cul-de-sac in one of Lenox's most desirable neighborhoods. This thoughtfully designed residence offers four bedrooms and 5.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The inviting floor plan is ideal for both everyday living and entertaining. Step outside to a beautifully landscaped backyard featuring a built-in grill, hot tub and plenty of space to relax or gather with family and friends. A rare opportunity to enjoy privacy, comfort, and an exceptional Lenox location.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

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.

Welcome home! This magnificent 13.3-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. A low-maintenance wild garden of perennial flowers and shrubs produces a kaleidoscope of colors during the spring and summer seasons. A large, private office area with high-speed internet provides a productive ''work from home'' environment. The first floor features an eat-in country kitchen with an antique Glenwood stove. The formal living room, with its wood-burning fireplace, is ideal for cozy evenings. The sitting room, complete with built-in bookshelves, is perfect for a home library or study. A large addition boasts vaulted ceilings, adding grandeur and space to the home with versatility for a home office, first-floor primary bedroom, family room or guest quarters. The formal dining room, featuring built-in cabinetry, is perfect for hosting dinner parties. The sunroom, featuring a fountain pond, is bathed in natural light and offers a serene setting. Additionally, the first floor includes a laundry room and a full bathroom, as well as an enclosed four-season porch. The second floor includes four bedrooms, offering peaceful retreats for family members or guests. A full bathroom serves the upstairs bedrooms, and a hobby room provides an ideal space for crafts, projects, or as an additional study area. The large barn is perfect for storage, farming, hobbies, or even transforming into a creative space. The two-car detached garage includes a finished space above, providing a perfect spot for a potential home office, studio, or guest accommodations. Further enhancing the property is a brand-new heating system, new septic and a whole-house generator. Steeped in history and surrounded by beautiful gardens and pastoral views, this property is more than just a home--it's a lifestyle.

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?

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.

The one you've been waiting for...a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley.

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.

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!

Perfectly poised and priced! This immaculately maintained four-bedroom residence, set on an acre of land, delivers three levels of sophisticated living space designed for both effortless entertaining and quiet sanctuary. The property balances a serene, retreat-like setting with beautiful mountain views and unparalleled convenience to local amenities and top-tier Great Barrington schools. The home is enveloped by a lush and mature landscape, offering a changing tapestry of flowering color and seasonal interest throughout the year. Cross the welcoming mahogany front porch an ideal vignette for morning coffee or evening relaxation into the expansive main level. The heart of the home is an open-concept great room featuring beautiful cherry wood floors, anchored by a warm fireplace, built-in surround sound, and a chef-inspired kitchen with a built-in wine refrigerator. A large Carrara marble island serves as the ultimate gathering point, transitioning seamlessly into the living and dining spaces. This floor is thoughtfully completed with a versatile guest bedroom or home office, mudroom, pristine powder room, and direct access to the two-car garage. There is an additional Trex deck perfect for an afternoon BBQ, overlooking the grounds. Ascend the staircase to the private quarters on the second floor, featuring a luxurious primary suite--a peaceful haven with its own ambient gas fireplace, a custom cabinetry walk-in closet, and an ensuite bath complete with a custom steam shower. Two additional generously sized bedrooms share a beautifully appointed full bath, offering exceptional comfort for family or visitors. The finished lower level further expands the home's well-designed footprint. A freshly renovated recreation room, outfitted with a custom bar featuring a solid white oak countertop and an additional half bath, serves as an ideal space for game days, a home theater, or a private lounge.

Timeless farmhouse charm meets modern luxury in the heart of Old Chatham. Set on 1.4 picturesque acres, this beautifully renovated 1875 home has been thoughtfully restored from top to bottom, blending historic character with contemporary comfort. Inside, you’ll find sun-filled living spaces, gleaming hardwood floors, a gourmet kitchen featuring a Wolf range, Bosch appliances, quartz countertops, and custom solid wood cabinetry, plus three spacious bedrooms, 2.5 designer baths, and an oversized dressing room. Outside, enjoy a brand-new wraparound porch overlooking peaceful grounds that invite morning coffee, evening cocktails, and everything in between. Whether you’re searching for a full-time residence or the perfect Hudson Valley weekend escape, this move-in-ready home offers the rare combination of classic farmhouse warmth, exceptional craftsmanship, and effortless living in one of Columbia County’s most charming villages.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury. The main level of the home includes a generous living room, a formal dining room featuring a custom four-wall mural by noted (formerly local) artist Laurel Tewes, a cozy library or den, a well-appointed kitchen with three refrigeration units including a side-by-side Sub-Zero, two Miele dishwashers, a six-burner Viking range with double ovens, and two large pantries. There are two screened porches: one informal and accessible from the living room, and a larger one off the kitchen vestibule, currently used for outdoor dining. A guest powder room completes the main level. The second floor includes a second primary suite, along with three additional spacious guest bedrooms, each with its own private bathroom to ensure comfort and privacy for family and visitors alike. A well-equipped gym provides a dedicated space for fitness and wellness, while a large laundry room with two washers and dryers adds everyday convenience. A generous corner office, with windows facing east, south, and west, offers a quiet and functional workspace, complete with a dumbwaiter to easily transfer items between floors. The grounds are a nature lover's retreat, featuring a network of walking trails, including approximately half a mile of cut grass perimeter paths, and strategically located perennial gardens. A fenced backyard encloses roughly three-quarters of an acre, perfect for pets or recreation. Along the southern side of the home, a slightly elevated patio spans the kitchen, dining room, and living room, with direct access from French doors and a single kitchen entry. Part of the patio is shaded by mature, 20+ year-old wisteria growing over a trellis, while another section is covered by a motorized awning, creating an ideal setting for outdoor dining and entertaining. Throughout the home you will find six functioning fireplaces, wide-plank wood flooring, oversized windows, and exceptional craftsmanship in every detail. An oversized three-car garage adds functionality to the home's many luxury features. Ideally located just minutes from the vibrant center of Great Barrington, the property also offers quick and scenic back-road access to Taft Farm, Catamount, Tanglewood, and the surrounding cultural and recreational attractions that make the Berkshires so desirable. This is a rare opportunity to own a one of a kind estate in the region's most sought-after settings, where refined living meets timeless natural beauty.

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.

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound.