luxury real estate for sale Stockbridge, United States

Experience elevated wellness living in this exceptional Canyon Ranch penthouse in Lenox. This 3,300+ sq. ft. residence offers three spacious ensuite bedrooms, a powder room, an expansive great room, a chef's kitchen and three fireplaces that create a warm, inviting atmosphere. A private patio provides the perfect retreat to relax and enjoy the natural beauty of the Berkshires. Ownership includes a requisite annual resort membership with full access to Canyon Ranch's world-renowned wellness amenities. Just minutes from the Berkshires' acclaimed cultural attractions, fine dining and outdoor recreation, this is a rare opportunity to enjoy luxury, wellness and timeless design in one extraordinary home.

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.

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.

Stone steps rise through a hillside of pachysandra to a midcentury modern home nestled among the trees. Inside, the living room pairs high ceilings and warm wood paneling with beautiful ceramic tile floors and a wood-burning fireplace. Wide windows look into the surrounding branches, bringing the landscape into view. The living room opens to the kitchen and dining area, giving the main spaces an easy flow. A hallway leads to one bedroom with a full bath across from it. The bedroom at the back of the house has its own en suite bath, and a stackable washer and dryer are tucked into the layout. Outside, a slate patio offers a place to gather, while a one-car garage and off-street parking add convenience. For anyone looking to scale down and simplify, this home offers a distinctive place to do it. Laurel Lake is nearby for summer swimming, Miraval Berkshires is right around the corner, and downtown Lenox is just minutes away.

Tucked beside the renowned Miraval Berkshires resort and the historic Wyndhurst estate, this beautifully updated townhouse-style condo offers refined Berkshire living with resort amenities right next door. Step out to a back screened porch and adjoining deck that overlook the golf course—the perfect setting for summer cookouts, easy entertaining, or a well-earned drink after a round. Inside, an open, airy floor plan flows effortlessly beneath soaring vaulted ceilings, filling the home with light and space. The first floor features two generous bedrooms, each with its own en suite. The primary suite is a true retreat, with a spa-like bath boasting a double vanity, radiant heated floors, and an elegant walk-in shower, plus a large walk-in closet and a cozy reading nook. Upstairs, a catwalk leads to two more spacious bedrooms sharing a full bath, with ample closet space throughout— including a walk-in. At the heart of the home, a stunning, thoughtfully updated kitchen offers an abundance of cabinetry and storage and opens seamlessly into the living room, making the space ideal for gathering and entertaining. With Miraval's world-class spa, dining, and wellness offerings and the Wyndhurst golf course just steps away, this is a rare opportunity to enjoy luxury, comfort, and an unbeatable Lenox location.

Crosby House, a property with a storied Lenox history and a location second to none, presents a rare opportunity to own a residence of remarkable character, scale, and flexibility in the heart of the village. Currently configured as two spacious residences, this distinctive multifamily property offers an exceptional array of possibilities. Subject to applicable zoning, permitting, and approvals, the existing configuration may offer the potential to be thoughtfully combined into one extraordinary single-family residence or could provide the foundation for two highly distinctive condominium residences. Each residence offers two plus bedrooms and two full baths, along with generous kitchens featuring high-end Bosch appliances, hardwood floors, tiled baths, in-unit laundry, central air, natural gas heat, and an abundance of windows. All major systems have been updated, providing modern comfort and efficiency while complementing the property's historic character. Both primary bedrooms feature adjoining flexible spaces ideally suited to an office, nursery, sitting room, dressing room, or private retreat. The first-floor residence features a magnificent screened porch opening to the front porch, as well as a separate rear deck; wonderful spaces for outdoor dining, entertaining, and enjoying the seasons. The upper residence offers its own private deck, while cathedral ceilings and both front and rear landings add architectural interest and a wonderful sense of space. The property is further enhanced by an oversized two-car garage with an attached greenhouse, ample parking, owned solar, and separate utilities. These thoughtful amenities, together with the updated systems and generous living spaces, create an exceptional blend of historic character and contemporary convenience. With its storied past, substantial proportions, versatile configuration, and enviable in-town setting, Crosby House represents a truly rare Lenox offering. Just minutes from the heart of the village, the property combines the best of location and lifestyle with the opportunity to shape a residence, or residences, of exceptional distinction. Subject to zoning and required approvals, its possibilities are extraordinary; its location is simply second to none.

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.

Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An oversized three-car garage and finished lower level provide ample storage, while expansive windows showcase the surrounding landscape. Available furnished. This exceptional property is move-in ready and an ideal Berkshire retreat.

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.

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!

Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-study home features triple-glazed windows, super-insulated envelopes, and geothermal climate control.

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location-- where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room-- perfect for gathering with friends and family. A large pantry provides exceptional storage and functionality. For more formal occasions, enjoy a separate dining room, elegant sitting room, and formal living room. A heated sunroom offers year-round enjoyment, while a dedicated first-floor office/library provides ideal work-from-home flexibility. Upstairs, you'll find four spacious bedrooms and two full bathrooms, offering ample room for family and guests alike. Practicality meets versatility on the main level with a convenient laundry/mudroom and half bath located just off the garage. Above the garage, a finished bonus space with its own full bathroom presents endless possibilities-- whether as a private studio, guest suite, bedroom, or additional family room. In a highly desirable Richmond location near Lenox and all that the Berkshires have to offer, this property combines space, light, and flexibility with an unbeatable address close to Tanglewood. A rare opportunity to enjoy quintessential Berkshires living.

Welcome to this wonderful Colonial in a quiet, sought after neighborhood in Lee, MA. 3 bedrooms, 2.5 baths, and a finished lower level. Enjoy an expansive deck overlooking the rear yard; providing plenty of outdoor living space. Amenities include vinyl siding, gas heat, hardwood floors, eat-in kitchen, dog fence, and a two car attached garage.

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.

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 out your back door and onto the mountain! This unique slopeside condo offers direct access to skiing and hiking trails right from your backyard. Offering 2,750 sq. ft., this beautifully updated 3-bedroom, 2½-bath home features a gas fireplace and refreshed kitchen with quartz countertops, subway tile backsplash, and GE Profile appliances. Updates include newer carpeting and paint, California Closets, and USB-A/USB-C outlets. The unfinished basement offers generous storage, home gym or future living space and is stubbed for plumbing. Enjoy peaceful mountain surroundings and a community pool in warmer months. Just a short drive from Lenox and Tanglewood, with easy access to dining, shopping and the best of the Berkshires.

Gracefully situated on a gentle sloping hillside street this distinctively designed multi-level home offers distant and seasonal Berkshire mountain views. Abutting the rolling meadows of Arrowhead, Melville's historic home and grounds, you can embrace the vast privacy, open land and natural beauty much like the famed author. Surrounded by artfully designed gardens, this architecturally refined residence is a private enclave offering 4-5 bedrooms, 3 full bath, masterfully landscaped set on 1.5 acres with unique tree selection, blooming shrubs and pollinator flowering perrenials. Just 10 minutes to the culture, cuisine and art offerings of Lenox especially the sounds of Tanglewood. Minutes to all that is Berkshire while being immersed in renowned peacefulness. Follow the gently curved stone stairway to the covered front porch and enter into an open and spacious entry with an intriguing glimpse of flowers exquisitely private. Be welcomed into a graciously sized formal living and dining rooms ideal for entertainment, memories and laughs to be shared. Relax in comfort and warmth of the brick fireplace fully framed with wall to wall windows balancing light while inviting the outdoors in. Adjoined to the expansive cooks kitchen topped with granite countertops, triple windows for full backyard viewing, and spacious everyday dining which leads to a private and expansive rear deck and screened sunroom. Step inside and ascend a half flight of stairs to the bedroom level, where four generously sized bedrooms offer both comfort and ample space. These rooms share a spacious full hall bath. The private, king-sized primary suite welcomes you each morning with cheerful and soothing sunrise views over the October Mountain ridgeline. Descend to the walk-out entry level, which features a versatile home office or guest suite, a third full bath, and a convenient shared laundry area all situated on the lower entry level close to the oversized two-car garage. The next lowest level remains unfinished, providing an excellent opportunity for large-scale storage, a workshop, or additional creative uses. This is a unique opportunity in this glorious Berkshire Summer market, situated close to Lenox for enriched entertainment, Pittsfield's Guido's Fresh Marketplace for gourmet, farm-fresh foods. Enjoy lake activities at Pontoosuc or Onota Lake within 20 minutes or indulge in hiking and mountain biking at October Mountain and kayaking or hunting at Canoe Meadows Wildlife Sanctuary. With incredible views at home and endless outdoor adventures nearby, this residence offers the best of Berkshire 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.

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main floor for year round comfort. The first-floor primary suite offers a private retreat with a spacious spa-like bath, featuring a large shower, soaking tub, and generous walk-in closet. An impressive entry foyer sets the tone with a sleek architectural staircase, powder room, and coat closet. A two-car attached garage provides ease and convenience. Upstairs, a dramatic loft overlooks the great room and sits adjacent to a second bedroom suite, perfect for guests or family. Separate from the two main suites, a private guest wing includes two additional bedrooms, a large sitting room, and a shared full bath, offering a comfortable and flexible space for visitors. Despite its very quiet mountain-top privacy, the property is ideally situated just 10 minutes from Tanglewood and downtown Lenox. Enjoy effortless access to I-90, making trips to Boston or New York City remarkably convenient. Nearby West Stockbridge offers a charming village atmosphere with boutique shops, a local marketplace, wine store, café, inviting restaurants, and even an old-fashioned hardware store—everything you need within a short and scenic drive.

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that caters to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 square foot heated indoor arena, which includes an owner's apartment and viewing area--and a professional-grade outdoor ring.

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.