luxury house for sale West Stockbridge, United States

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.

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.

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.

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.

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.

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!

A Home like no other in the Berkshires. You will simply not find a Property like PIERCE PEAK, anywhere. Award Winning Architectural Design by Burr & McCallum, crested upon the summit of Cunningham Hill. Cleared for HELIPAD . Open plan living with Indoor and Outdoor Living Rooms. Gourmet Kitchen, 2 Primary and 2 connected Loft spaces. 2 Bedroom Guest Quarters. Gym. Infinity Pool w/Bar, Fireplace and Outdoor Shower. 360 Degree views of NY and Mass. 6 Acre Equestrian / Hobby Farm included with this 31 acre Estate. State-of-the-art Mechanicals include the efficiency of Geo-Thermal Heating & Cooling. On-site Generator, Security Gate and Privacy galore. On the NY and Massachusetts border. Close to all Berkshire and Hudson Valley attractions. For those who seek the extraordinary... (see Video)

Pine Needles--Built circa 1900 as a Berkshire ''cottage'' in the era of grand summer estates, this historic property blends the dignity of Colonial Revival architecture with the relaxed elegance of an Italian villa and the artisanal detail of the Arts & Crafts movement. Sited on 80 private acres just minutes from the heart of Lenox, the estate offers breathtaking southern views, rolling forest, and a rare level of privacy and provenance. Arrival. Approached via a long private drive, the property unfolds gradually—passing a sun-kissed meadow, through a grove of majestic pines, past a stunning carriage house, before arriving at an inviting courtyard. The house itself is beautifully sited to capture natural light and frame the sweeping mountain and pastoral views. Entry--A double-door entry opens to a gracious reception hall with original tile flooring and sightlines through French doors to the central living room and terrace beyond. Just off the entry is a coat room with period hooks and hardware, as well as a cozy sitting room with fireplace and built-in shelves. The central living room, paneled in rich wood, is anchored by a fireplace and opens to the view through a wide picture window and two sets of French doors leading to a stone terrace. West Wing--Formal and informal rooms radiate from the center of the home. The western wing includes a spacious living room, a library tucked beneath a vaulted studio, and a striking Persian-themed room adorned with carved woodwork, decorative tile, and intricate architectural details, providing an atmospheric space for reading, conversation, or quiet escape. Above, the vaulted studio with exposed beams and skylights offers an inspiring space for art, music, or quiet retreat. East Wing--The east wing centers around a chef's dream kitchen, thoughtfully tucked to one side for privacy, with direct access to a classic butler's pantry. The pantry connects to the kitchen, the formal dining room, and an airy summer dining space that opens to a loggia, offering an elegant progression for entertaining that bridges indoors and out. Sleeping Quarters--The second and third floors are devoted primarily to bedrooms, retaining the character of the original layout. Two sleeping porches, both located on the upper levels of the west wing, provide a nostalgic and tranquil way to enjoy the Berkshire air. Some of the bedrooms were originally designed for staff, while others, particularly those with the best views, served as guest or family quarters. Grounds and Outbuildings--Outdoor spaces are equally compelling, with lawns and mature plantings surrounding the home. A wide open meadow along the drive amplifies the sense of arrival and serenity. A pool built into the natural bedrock and fed by a spring provides a private and picturesque place to swim, echoing the home's seamless blend with the surrounding landscape. Additional structures include a striking two-story carriage house, distinguished by its dramatic arched entry and distinctive proportions. The lower level retains original horse stalls, a nod to the estate's equestrian past, while the upper level features a character-rich apartment offering opportunity for personalization. A detached garage with another apartment offers further accommodations for extended family, guests, or staff. The estate is well suited for a private compound or multi-generational retreat. Legacy--This is a rare opportunity to own one of Lenox's great legacy properties--where natural beauty, architectural significance, and enduring charm come together just minutes from the cultural heart of the Berkshires.

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.

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

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Who could ask for anything more?

Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor pools. Outdoor highlights include a hot tub, pool house with bathroom, pavilion, garden, and a fully enclosed treehouse for summer overnights, along with deeded Queechy Lake rights for swimming and kayaking.The main wing of the home features a dramatic triple-height great room with a fieldstone fireplace, flanked by a wraparound deck. The stunning southeast-facing views of the Taconic and Berkshire Hills turn every sunrise and sunset into a cherished ritual. A large kitchen is designed for the serious home cook, with Sub-Zero refrigerator, professional hood, and dual pantries. The breakfast bar opens directly to a cozy living space with its own fireplace, dining area, and mountain views. Custom built-ins for books and LPs encourage everyone to slow down and savor life's quiet moments. On the second level are three bedrooms, including a primary suite with fireplace, walk-in closet, and private balcony, plus a solarium and office nook. A breezeway connects to the north wing, where an indoor lap pool provides a year-round spa-like retreat. This section offers four additional bedrooms, three bathrooms, a kitchenette, loft-like studio, workshop, and attached three-car garage. Recent upgrades include a new geothermal heating system, refinished decks, new flooring throughout the main wing of the house, fresh exterior paint, and a new roof on all structures. The property sits on one of the largest lots in the sought-after community of Shaker Ridge, whose residents enjoy private tennis courts and a peaceful, well-maintained community setting. Minutes from Chatham, PS21 Arts Center, the Berkshires, and within easy reach of Hudson, Albany, western Massachusetts, and five ski resorts, this is a rare opportunity to own a one-of-a-kind Hudson Valley estate with total privacy, inspiring architecture, and unmatched versatility for entertaining or multigenerational living.

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.

Convenient one-level ranch in a prime location close to town. This well-maintained home offers four bedrooms and two full bathrooms, ideal for comfortable living. The updated kitchen features modern finishes and plenty of workspace. Enjoy energy efficiency with owned solar panels that significantly reduce utility costs, plus a pellet stove for supplemental heating. A generator ensures uninterrupted power during outages--peace of mind year-round. Situated on a private road, the property provides tranquility while remaining minutes from shopping and dining. Additional highlights include ample storage, a functional layout and move-in-ready condition. Whether you're downsizing, seeking your first home, or looking for a smart investment, this turnkey property delivers.

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 just over seven acres between Lee and Stockbridge, this c.1850 Greek Revival delivers classic Berkshire character with real scale. Nearly 4,700 square feet with a gracious flow, tall windows, and preserved period details. Every bedroom offers an en suite, creating an easy setup for hosting family and friends. Common spaces include a welcoming foyer, two living rooms, a formal dining room, a library, and a large cook's kitchen with eat-in area and pantry. Three period fireplaces add warmth and charm. Outside, mature trees frame open meadow, with room for gardens, games, and long summer evenings. The setting is remarkably convenient. Tanglewood, Lenox, Stockbridge, and downtown Lee are a short drive, and access to Route 7 and the Mass Pike keeps weekend trips simple.

Tucked away on 4 acres of wooded and partially cleared land, this lovingly maintained 1960 cape-style home offers the perfect blend of privacy, character, and opportunity. Set back from the road by a long driveway, the property creates a peaceful retreat just minutes from the heart of Lenox and outdoor destinations like October Mountain State Forest and Kennedy Park. Inside, the home is ready for its next chapter with spacious and inviting living areas including a formal living room, dining room, kitchen, and a cozy family room with gas fireplace and slider access to the private backyard. A sunroom off the kitchen is perfect for seasonal enjoyment. The first-floor primary bedroom features a connected full bath with convenient hall access, while upstairs offers two additional bedrooms, an office space, and another full bathroom. A two-car garage located under the home provides direct access to the basement and additional storage or workshop potential. Full of warmth and well cared for through the years, this property is ready for its next owners to reimagine and make it their own.

Set just moments from downtown Lenox, this charming New England farmhouse blends classic character with thoughtful modern updates. From the moment you arrive, the home's inviting presence and timeless appeal set the tone for what's inside. The recently renovated kitchen serves as the centerpiece of the home, beautifully designed with quartz countertops and all new appliances--perfectly opened to the dining area to create a seamless and functional space for everyday living and entertaining. A cozy living room is adjacent to the dining room. On the other side of the kitchen, a thoughtfully-designed mudroom and bonus space offers the ideal work-from-home office, complete with a half bathroom, laundry, and direct access to the backyard and patio. Upstairs, you'll find three comfortable bedrooms along with a full bathroom, offering a practical and well-balanced layout. Outside, the fully fenced yard provides a private retreat, enhanced by a newly-installed patio--perfect for gatherings or quiet evenings. A standout feature is the custom treehouse, complete with electricity, creating a truly special space for play or creativity. Additional highlights include a one-car detached garage and close proximity to Lenox's vibrant downtown, known for its shops, dining, and cultural attractions. A rare opportunity to own a move-in ready home that effortlessly combines charm, convenience, and modern living in one of the Berkshires' most desirable locations.

Tucked at the end of a peaceful cul-de-sac, this 3,300+ sq ft Cape is a rarity in today's market--a sprawling main home with the addition of a separate in-law/guest apartment. The main wing shines with refinished wide-plank wood floors, gas fireplace, and premium renovations, including a new chef's kitchen and bathrooms. Upstairs features three gracious bedrooms, including a primary suite with massive walk-in closets, en-suite full bath, and secret bonus room awaiting your imagination. The private in-law apartment--with its own entrance, full kitchen, and 2 bedrooms--boasts a proven rental history, ideal for guests or income. Enjoy close proximity to downtown Lee's dining and golf, all while being under 10 minutes to downtown Lenox and Stockbridge. A multi-generational gem in a prime locale!

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.

Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom guest house offers beamed ceilings and full amenities. Manicured grounds include an infinity pool, hot tub, pool house with full bath, tennis and pickleball courts, 7 garage bays, and a barn. State-of-the-art lighting, whole-house generator, smart tech, and security. Fully furnished and ready to enjoy.

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.

Spacious and adaptable, this Pittsfield home offers exceptional flexibility for today's lifestyle. The first floor features a sun-filled living room with hardwood floors and a bay window, a generous kitchen with an island and large dining area, and a mudroom with convenient first-floor laundry. A full bath and two bonus rooms on the main level provide versatile options for home offices, guest space, or additional bedrooms, allowing for the ease of one-level living if desired. Upstairs, a large landing creates the perfect spot for a home office or play area, while the primary bedroom boasts a walk-in closet and private exterior balcony. Three additional bedrooms and a full bath complete the second floor. Outside, enjoy a fenced-in backyard, one-car garage, solar panels, and a location just minutes from parks, shopping, and dining.