luxury houses 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.

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 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.

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?

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.

Charming 1930 Stockbridge home perfectly located just minutes from the iconic Red Lion Inn, dining, and shopping in town. This spacious 4-bedroom, 2.5-bath residence features a large enclosed front sun porch, offering a bright and inviting space to relax. The home retains original character and details throughout with gorgeous hardwood floors throughout and generous living and dining rooms ideal for gatherings. The large kitchen and barn garage add to the property's potential. Enjoy the spacious rear deck and backyard, perfect for outdoor activities and entertaining. This sunlit home is ready for its next chapter and your vision, offering plenty of opportunity for a full renovation to create your dream residence in a coveted location.

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.

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.

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.

Rare, renovated Berkshire investment compound on 0.59 acres in pedestrian-friendly Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Moments from Berkshire Mountain Bakery; minutes to downtown Great Barrington and Tanglewood. A rare, turnkey find!

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

Charming home brimming with character and far more space than meets the eye! A lovely front porch with mahogany floors welcomes you to gracious living and dining spaces, wood floors throughout, and a stately fireplaced living room. The updated kitchen features an abundance of cherry cabinetry, plus a first-floor laundry, half-bath, den, and a useful office addition. Upstairs offers three ample bedrooms--including a primary with his/hers closets--and an updated bathroom with a walk-in shower. The walk-up attic provides additional storage or could easily be finished. Outside, find a detached one-car garage, large back deck and a great fenced-in back yard perfect for pets and fun. Sidewalks to town; minutes to Laurel Lake and Lenox. A well loved and cared for home, ready for its next chapter!

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

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.

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room.Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional guest bedrooms share a Jack and Jill bathroom, providing comfort and privacy for friends.The finished lower level is dedicated to leisure and repose, crafted with the ultimate goal of relaxation in mind. Here, in this tranquil setting, you'll find the peace and privacy you desire, all within a home that exudes charm and character.

Imagine owning 10 private acres in low-tax Alford, MA with beautiful seasonal views! Included are two buildings, a small Chalet style home (1,500 sq ft) with living/dining room, kitchen, laundry, three bedrooms, a full bath, and a deck for entertaining or relaxing. Utilities are electric heat and electric hot water heater in partial basement. The Studio building has two rooms, a half bath, electric heat, and a separate hot water heater. Fiber Connect for internet. Both buildings are in need of some love and attention but are absolute gems on a private lot in a highly desirable location.

Originally built in the year 1800 on one the areas most historically significant roads lies this delightful antique farmhouse brimming with original details and charm. Perched above the road with its wrap around porch you are immediately transported to a simpler time where quality and beauty mattered. Further selling the vision, the periphery of your view is flanked with mature trees and one of two large barns providing a nostalgic aesthetic and endless opportunities. The barn closer to the home contains a garage for sheltered parking and the ability to create a guest house, work studio, private gym or anything you can dream up. In fact, there's room for all of those options within the same structure. A serene hilltop view in the distance beckons you to walk through the more than five and half acres of lawn, meadow and fruit trees to the second barn structure to continue dreaming up the possibilities. Currently this space is absolutely perfect to host outdoor dinner parties and gatherings with a bucolic view. The interior experience begins in the entry parlor, anchored by a traditional wood-burning stove. Original wide plank painted floors flow seamlessly into a spacious dining area bathed in natural light. Adjacent to this space, the modernized kitchen offers optimized storage solutions and updated appliances. The main level extends toward the rear of the residence, where the family room features stunning beamed ceilings that evoke a historical atmosphere. Completing this floor is a versatile adjoining room, ideally suited for guest accommodations or a home office and also conveniently hosts the laundry room. Up the wooden stairwell from the entry parlor three bedrooms and a bathroom surround the landing which has enough room to be its own library/reading space. The bedrooms are quite large for the era continuing this property's themes of charm, beauty and modern comfort. Just minutes away from Queechy Lake, where residents can enjoy access via an annual pass, its prime location offers easy reach to Chatham, Ghent, and Hudson on the New York side, while Great Barrington, West Stockbridge, and the Berkshires are equally accessible. Whether you are looking for a full-time residence or a perfect weekend retreat from NYC or Boston, this home serves as an ideal destination.