luxury houses for sale Stockbridge, United States

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!

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.

Envision waking up in this beautifully renovated New England farmhouse in quaint Lenoxdale Village. Enjoy morning sunrises on the front patio and quiet evening dinners on the terrace, all just minutes from the world-class culture of Tanglewood and the iconic downtowns of Lenox and Stockbridge. Inside, original hardwood floors flow throughout a versatile layout featuring 3-4 bedrooms, a cozy office space, and a spacious, freshly updated kitchen with a breakfast nook and extra pantry space. Outside, the large open yard is anchored by a charming car barn--ideal for summer projects, kayaks, bicycles, and flexible loft space. Come make this home your Berkshire dream!

Tucked away in one of Lenox's most desirable neighborhoods, this contemporary ranch has been completely renovated with no expense spared, offering effortless single-level living and a seamless connection to the outdoors. Vaulted ceilings, walls of glass, and an abundance of natural light create an open, inviting atmosphere, while nearly every room overlooks the beautifully landscaped, private backyard. Designed for both everyday living and entertaining, the thoughtfully planned floor plan centers around a stunning eat-in kitchen featuring quartz countertops, premium Thermador appliances and custom floor to ceiling millwork with an easy flow into the spacious living room with a gas fireplace, formal dining area, and an expansive sunroom with electric heat for extended seasonal enjoyment. A beautifully renovated full bathroom is conveniently located off the main hallway, while central air and a whole-home sound system provide comfort and convenience throughout. The primary suite is a true retreat, complete with direct access to the deck, a custom walk-in closet, and a spa-inspired bath featuring radiant heated floors, a soaking tub, and a walk-in shower. A second bedroom also opens to the outdoor living space, while the third generously sized bedroom offers flexibility for guests, family, or a dedicated home office. Step outside to a backyard designed for making the most of every season. The heated in-ground pool is surrounded by expansive bluestone patios, composite decking, mature landscaping, and multiple areas for dining, relaxing, and entertaining. Beyond the pool, the level lawn extends to a wooded backdrop, creating exceptional privacy and a peaceful Berkshire setting. Three outbuildings provide abundant storage and endless possibilities for a workshop, gardening shed, art studio, or hobby space. An attached two-car garage with epoxy floors and an oversized driveway complete this exceptional property. Recent capital improvements provide additional peace of mind and reflect the exceptional care this home has received. Upgrades include a Generac emergency generator, tankless hot water heater, security system, newer pool heater and brand-new pool liner, as well as front and rear composite decking. Ideally located just minutes from Tanglewood, Shakespeare and Company, The Mount, and the shops and restaurants of downtown Lenox, this turnkey home offers the perfect combination of thoughtful design, modern updates, and exceptional outdoor living in one of the Berkshires' most sought-after locations. Simply unpack and start enjoying everything this remarkable property has to offer.

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 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.

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.

Welcome to 140 Orchard Street, an inviting three-bedroom, one-bathroom Lee home that effortlessly combines everyday convenience with a warm, relaxed atmosphere. Bathed in natural sunlight, the cozy interior features an easy-flowing floor plan anchored by a desirable first-floor bedroom and full bathroom, creating a comfortable and welcoming layout the moment you step through the front door and offering a wonderfully bright canvas ready for your personal touch. The home's exterior is an outdoor lover's delight, featuring an expansive, partially fenced yard that provides a serene setting for summer barbecues, lawn games, or simply relaxing in the fresh Berkshire air. An attached one-car garage offers convenient shelter from New England winter weather along with extra storage space. Ideally situated within easy walking distance of Lee's charming storefronts, local dining, and everyday essentials, this sweet property also offers quick access to Route 20 and the Turnpike, making commuting and weekend exploring a breeze. Property is subject to a 72-hour (3-day) Right of First Refusal (ROFR) by designated party.

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.

Located in Lee, MA is a waterfront property built in 1880 and renovated in 1987. A bucolic location with views of rushing water and mountains. A perfect home for a variety of birds and established gardens. This 3500 sq. ft home offers an open floor plan that includes living room with fireplace, cooks kitchen with island and dining area. Main level includes a private bedroom and bath; screen porch, deck, laundry room/office, powder room, attached one car garage and office with separate entrance. The second floor offers 2 guest bedroom with private baths and primary with walk in closet, access to a Juliet deck and private studio space. Free standing single garage located at the rear of the property. This property has multiple uses!

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.

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.

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.

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.

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.