In the Berkshires, the rarest luxury isn't simply a beautiful home--it's finding a place that makes you want to stay a little longer. Welcome to 130 East Dugway Road. As you arrive, the pace of life begins to slow. Morning coffee lasts a little longer, evenings linger beneath Berkshire skies, and weekends become treasured family traditions. Thoughtfully designed for both elegant entertaining and quiet retreat, this exceptional home blends timeless architecture, refined craftsmanship, and inviting living spaces that feel as welcoming as they are beautiful. Just minutes from Lenox, Tanglewood, and the region's finest cultural attractions, this is more than a remarkable residence--it is the place where generations gather, memories are made, and the Berkshires truly feel like home.

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings.

Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive building materials. Distinctive circular towers, curved walls, arched windows and premium natural finishes harmonize with the surrounding natural landscape. The grand foyer opens to an expansive kitchen, living, & dining space anchored by a striking Finnish soapstone wood stove and marble fireplace. A sun-filled breakfast room leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment.

Welcome to this Berkshire Waterfront Paradise! With amazing lake and sunset views this home has it all. Five bedrooms all with lake views. Your family and friends will find the total relaxation the Berkshires can offer. Whether it's a swim, paddle, fishing or a water ski on the lake it's all just steps out the door. The beautiful stone fireplace sores to compliment this open space and provides a warm cozy touch. Come and start to relax as you enter into paradise.

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. There's an impressive architect-designed guest house with 2 ensuite bedrooms, balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place for rentals, or hosting family and friends both winter and summer.The main house is 3-4 bed, 2 1/2 bath, views of Tom Ball mountain, the property is a combination of gardens, fields, forest, and offers several outdoor living spaces, including a stone patio off the kitchen. A short jaunt to No. Six Depot, The Foundry performing arts, and Tanglewood. Central to Gt. Barrington, Lenox and Stockbridge for theatres, boutiques, skiing, golfing, museums and so much more at your fingertips

Tucked at the end of a long, winding drive, where nearly twenty acres of woodland create an exceptional sense of privacy, this expansive contemporary residence feels quietly removed from everything--yet remains just minutes from the cultural and recreational treasures that define the Berkshires. The house reveals itself gradually. Cathedral ceilings lend a grand sense of arrival to the entry and living room, where expansive windows fill the home with natural light and frame changing views of the surrounding landscape. From there, the home's scale shifts naturally to spaces that feel warm, comfortable, and inviting.

Expertly crafted by Gregg Wellenkamp, this stunning property pairs everyday wellness with sweeping views. Begin your morning in the private fitness and pilates studio, complete with steam shower. The primary suite is a retreat unto itself, with two separate sleeping spaces, a spacious walk in closet, and two private bathrooms. Three additional en-suite bathrooms round out the home, each framing its own sweeping view. Entertain on the oversized deck, where sunsets are the main event. Inside, the chef's kitchen anchors the home with custom hardwood cabinetry, recycled glass countertops and high end appliances, while a custom fireplace brings warmth to the main living area. Mature, professionally landscaped grounds frame the home. Enjoy nearby Lake Garfield from this Berkshire masterpiece.

EXPANDED CONTEMPORARY CAPE Appointed with elegant detail, masterfully crafted, this stunning home is nestled on over 9 private acres offering 9 rooms, 4 bedrooms, 3 full and 2 half baths. An open floor plan flows seamlessly from the generous living room, featuring a striking coffered ceiling and a fireplace surrounded by natural raw granite, into a large kitchen and dining area perfect for entertaining. A stunning wrought iron detail by Ivan Bailey enhances the staircase.. A media room with glass-paned sliders and built-in bookcases completes the exceptional living space. The first floor primary ensuite is a true retreat, boasting a soaring vaulted ceiling and two large walk-in closets. The second floor offers three additional bed rooms, and two full baths.

Brookside Acres awaits your arrival, privately sited on 15 + acres, on one of the most scenic country roads in Richmond. This exquisitely renovated Contemporary offers a plethora of amenities for the person looking for a private retreat for a few or someone that likes to entertain and gather with a crowd. From the moment you enter your monitored driveway you realize Brookside Acres has it all; beautiful woodlands, acres of groomed lawn, established flower gardens, mature landscaping and the private stone pathway to the running stream side patio. Owned solar system, a whole house generator, a lighting system that lights up the house with an evening arrival, in ceiling sound speakers on the main level and pool area...no detail has been left undone.The interior of this 5 br, 5 bth

Set along the shores of beautiful Pontoosuc Lake, this extraordinary private estate captures the very best of Berkshire waterfront living. Enjoy sweeping lake and mountain views, a private dock, heated pool, outdoor kitchen and fire pits designed for unforgettable entertaining. Inside, open-concept living showcases the views, while a chef's kitchen with Wolf and Sub-Zero appliances anchors the home. Multiple private living quarters, a game room, loft and home office offer exceptional flexibility. Extensive garage and parking space provides room for cars, boats and recreational toys, while gated and fenced grounds offer privacy. Come for the views. Stay for the lifestyle. Make Pontoosuc Lake home.

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires.

Come relax amid sweeping pastoral and mountain views in this exceptional retreat designed for both entertaining and everyday comfort. The impressive great room, anchored by a massive stone fireplace, offers a welcoming focal point and flows into a spacious well-designed kitchen/dining area. A screened porch with fireplace overlooks the pool and rolling landscape, creating a seamless indoor-outdoor experience. The first-floor primary suite features a luxurious bath and tranquil views. An exceptional cinema room includes theater-style reclining seats and a half bath. Generous guest accommodations throughout. A private office suite with full bath. Outdoors, enjoy an infinity pool, bluestone patios, lush gardens, a charming pool house — all just three miles from downtown Great Barrington.

Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a tennis court, guest house, swimming pool, gazebo, and gym shed to a three-level modern house evoking the New England barn. From the third-floor master loft suite with private terrace and kitchenette, a skylit central stair leads to the mid-level kitchen/dining room with fireplace nook, between stone patio and screened porch. An atrium living room includes cozy coffered-ceiling seating by a fireplace. A cherry-walled study with private porch, pass-through full bathroom, and family room complete the floor. Family or guests on the lower floor enjoy four bedrooms and three bathrooms, as well as laundry room and two-car internal garage.