luxury real estate for sale West Stockbridge, United States

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.

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.

Embrace effortless seasonal living in this beautifully maintained, vintage three-season cottage. Nestled on a quiet, unpaved lane in the desirable Mahkeenac Heights community, this two-bedroom home offers the quintessential Berkshires getaway. Recent thoughtful updates include fresh flooring and an opened-up floor plan that maximizes natural light and flow. Step outside onto expansive decking designed for alfresco dining. Whether you are spending your mornings at the local lake beach or your evenings taking in world-class music at nearby Tanglewood, this private haven offers prime proximity to the best of Lenox and Stockbridge.

Experience idyllic country life and the best this area has to offer in this charming wood shingled house. Situated on two acres, this three-bedroom cape has an updated kitchen with stone counters which opens into the dining room. The spacious living room has a brick fireplace, built-in shelves and lovely French doors that open into a four-season heated sunroom with a vaulted ceiling and large windows that look out onto the property. Glass doors open onto a small porch that leads to the backyard. Enjoy days and evenings relaxing or entertaining outdoors with the fire pit, stone patio and the clawfoot tub converted into an outdoor shower. Upstairs are three bedrooms and a full bath. The large primary bedroom has double closets. Additional finished space adjacent to one bedroom could be used as an office, playroom or studio space. Finished space in the basement contains a cozy den, an exercise area, the laundry with a utility sink and a separate storage room. Two car garage opens directly into the kitchen and a convenient first floor half bath. EV/RV chargers. Just minutes to Beebe and Harvey Mountain State Forests with thousands of acres for hiking, many local ski options, Tanglewood, Berkshires cultural offerings and Chatham Village restaurants, shops and movie theater. A short drive to Hudson and Amtrak. Come visit this charming home in an ideal location!

Welcome to Bons Reves House, a beautifully designed escape tucked away on nearly seven acres in the most desirable part of the Austerlitz hills. Built in 1985 and meticulously renovated and expanded by a top builder in 2012 and again in 2025, this 4-bedroom, 3.5-bath contemporary home feels like a luxury treehouse hidden among mature hardwoods and surrounded by large estates and high-end residences. Custom millwork, natural stone and wood surfaces, bespoke plaster treatments, and designer-chosen paint colors all speak to exceptional quality. The gracious, flowing layout offers plenty of room for gathering, and bedrooms tucked into separate wings create privacy and practicality. This is a home built as much for weekend entertaining as it is for quiet days spent resting and recharging.On the first floor, a renovated chef's kitchen with stone countertops, custom cabinetry, multiple prep areas, and an island breakfast bar make it a true country kitchen, with plenty of room for gatherings and holidays. It flows into a Thanksgiving-sized dining area and a large, inviting living room centered around a cozy wood burning fireplace. Just off the kitchen, a newly built four-season sunroom looks out through oversized windows onto treetops and the ridgeline beyond. A mudroom with laundry, a full bath, and a powder room round out this level.Up one set of stairs, the primary suite has vaulted ceiling, multiple closets, and a full bath with a dramatic architectural sensibility. A second staircase off the kitchen leads to two more bedrooms and a full bath. Down on the lower level, an additional bedroom joins a studio or work space, an exercise area, and a newly built window-lined sitting room, offering room to spread out or tuck away.Outside, the wraparound Trex deck, front porch, fenced garden, handbuilt stone walls, and professionally landscaped grounds create a storybook atmosphere for outdoor living. The wooded acreage surrounding the home creates a natural buffer for privacy and quiet. Recent upgrades reflect real investment in the property: new windows, six new heat pumps, a recently replaced roof, a generator, a new garage door, and a freshly painted interior and exterior.The location suits both a weekend retreat and a full-time home. Just 15 minutes from Chatham, 20 to Great Barrington, MA, 35 minutes to Hudson, 45 minutes to Albany, and two-and-a-half hours to New York City, Bons Reves House puts summer evenings at Tanglewood, a movie night in Chatham, dinner out, and gallery walks through Great Barrington and Hudson all within easy reach. Local golf courses and cycling routes round out the list of ways to spend a day here. Convenient to the region's best amenities and attractions, the home still feels hidden away from the world.

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.

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.

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.

Welcome to 13149 NY 22, Canaan, NY 12029—a beautifully updated 3-bedroom, 1.5-bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient single-level layout provides comfortable flow between the bright living spaces and the three well-sized bedrooms. Recent improvements include a brand-new roof, ensuring years of worry-free ownership. An attached two-car garage adds convenience and storage, while the expansive yard gives you plenty of room to garden, relax, or simply enjoy the quiet surroundings. Whether you're downsizing, seeking a weekend retreat, or looking for a low-maintenance full-time home, this ranch delivers a perfect blend of comfort, style, and practicality.

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.

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.

Adorable and full of character, 22 Franklin Street is a charming cottage-style property with the potential to become something truly special. Offering two bedrooms and one-and-a-half baths, the home features an inviting enclosed front porch and an enclosed rear porch finished in warm knotty pine, adding character and flexible space. The property will require some work and updating, but for the right buyer, that is precisely where the opportunity lies. Bring your vision and transform this cottage into a wonderful Lenox retreat, residence, investment property, or potentially a commercial venture. The property is commercially zoned, offering added flexibility for future use, subject to town approval. Additional features include natural gas, town water and sewer, and some replacement windows. The location offers the convenience and appeal of being in Lenox, with the village, shops, restaurants, and cultural attractions close at hand. An especially compelling opportunity for those looking to acquire multiple properties, 22 Franklin Street may also be purchased as part of a package with 24 Franklin Street and 85 Church Street. There is tremendous potential here to create something special in one of the Berkshires' most desirable communities.

Charming and ideally located in the heart of Lenox, 24 Franklin Street offers an inviting open-concept layout with two bedrooms and one and a half baths. An open front porch welcomes you into a comfortable home where the kitchen, dining, and living spaces flow naturally together. The generously sized kitchen is equipped with a range, refrigerator, and dishwasher, making it both functional and ready for everyday living. Electric heat with individual room controls provides flexibility and efficiency, while town water and sewer add to the ease of ownership. The open front porch offers a welcoming spot to relax and enjoy this quintessential Lenox setting. With an amazing location near the village, restaurants, shops, and everything that makes Lenox such a special destination, this is an appealing opportunity for a full-time residence, weekend getaway, or investment property. 24 Franklin Street may also be purchased as part of a package with 22 Franklin Street and 85 Church Street, offering an exceptional opportunity to acquire multiple properties in this prime Lenox location.

In the heart of historic downtown Lenox, 85 Church Street presents an exciting opportunity to own a versatile two-family property in one of the Berkshires' most desirable villages. Zoned commercial and delivered vacant, the property offers an unusual degree of flexibility for an owner-occupant, investor, or buyer seeking income-producing potential in the center of Lenox. The property features two two-bedroom, one-bath units, each with natural wood details and its own separate natural gas heating system. Both units are equipped with a refrigerator, dishwasher, and range. Refreshed bathrooms, some replacement windows, and a second-floor rear landing/mudroom add to the comfort and functionality. The first floor also enjoys an enclosed rear porch, while open porches provide additional outdoor space. Town water and sewer add to the convenience. Delivered vacant, 85 Church Street allows a new owner to immediately determine how best to utilize the property--live in one unit and rent the other, lease both units, or explore the possibilities afforded by its commercial zoning. Just steps from Lenox's renowned restaurants, shops, galleries, and cultural attractions, the location is truly exceptional. For an even more compelling opportunity, 85 Church Street may also be purchased as part of a package with 22 and 24 Franklin Street, creating the potential to acquire multiple properties in the heart of downtown Lenox. A rare combination of location, flexibility, and opportunity, 85 Church Street offers an exciting chance to own in the center of it all.

Don't miss this hard to find single floor living opportunity in the highly sought after town of Stockbridge. Offering nearly 2500 sq ft of thoughtful living space, this 3 bedroom, 2 full bath home blends main level convenience and genuine rustic warmth and modern versatility. Inside the home features multiple cozy heat sources for New England winters, including a classic wood burning fireplace as well as two separate wood stoves. Outside, the property sits on almost 6 acres of private land just 3 minutes from downtown Stockbridge. Open lawn areas offer plenty of room for vibrant flower beds, rich vegetable gardens, or custom outdoor entertaining spaces. Complete with an oversized garage providing ample room for vehicles, storage or workshop. Close to everything the Berkshires offer.

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.

Embrace classic New England living in this 3-bedroom, 2-bathroom home boasting 1,664 square feet of old-world charm, warmth, and character. Ideally located along East Main Street, this residence offers an unbeatable, close-to-everything village lifestyle while maintaining a remarkably quiet, private sanctuary indoors and out. Inside, a bright and open floor plan is filled with natural light, highlighted by rich hardwood floors, exposed timber beams, and thoughtful architectural details. The inviting main level features a cozy living room, a dedicated library nook with built-in shelving, and a sunlit dining area wrapped in oversized glass panels. The well-appointed kitchen includes a stylish SMEG refrigerator, a Bosch dishwasher, and gas cooking. The home's two full bathrooms blend distinct charm and functionality, featuring an updated downstairs bath alongside an upstairs bath complete with a classic clawfoot tub. Outside, the fully fenced backyard serves as a serene retreat complete with peaceful mountain views--the perfect backdrop for morning coffee or casual entertaining. Quintessential Berkshires living is right at your doorstep, with iconic village favorites like the Red Lion Inn, The Lost Lamb, Stockbridge Coffee, the local library, tennis courts, scenic hiking trails, and the Berkshire Theatre Festival all within easy reach. Futhermore, this property has a successful short-term rental history. All-around, a must see!

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.

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.

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.