Welcome to this exceptional Kruzel Built custom residence, where timeless craftsmanship meets thoughtful modern design. Perfectly appointed and meticulously maintained, this stunning home offers luxurious living with every detail carefully curated for comfort, style, and functionality. Step inside to discover an expansive open floor plan filled with natural light, elegant finishes, and seamless flow throughout the main living spaces. The beautifully designed great room features a cozy gas fireplace, creating a warm and inviting atmosphere ideal for both everyday living and entertaining. The kitchen opens effortlessly to the dining and living areas, making gatherings feel both intimate and spacious. The first-floor primary suite serves as a private retreat, complete with a generous wa

Situated at the top of vibrant Railroad Street, this property offers exceptional visibility in a bustling location, making it an ideal spot for retail stores, restaurants, cafes, or office spaces. The building features two spacious stories and a full basement, providing ample room for various business operations. With high ceilings that create an airy atmosphere and windows on three sides that flood the interiors with natural light, the space feels open and inviting. This is a remarkable opportunity to establish your business in the heart of Great Barrington, surrounded by the excitement and energy of a thriving community.

Some spaces change the way you imagine living. Loft 306 is one of them. 1,985 SF inside. Another 1,615 SF of private terrace outside. South-facing Berkshire mountain views. Suddenly there is room for long summer dinners, a garden in pots, friends for the weekend, morning coffee in the sun--and an entire outdoor room under a very big Berkshire sky. Conceived by celebrated architects LATENT Productions, Greylock WORKS is a highly considered transformation of a historic Berkshire mill, respecting what was here rather than erasing it.

Step into luxury and comfort in this stunning, 1-of-a-kind custom-built home--where natural light pours through expansive windows framing serene views of your private outdoor oasis. The beautifully landscaped backyard features an inground pool, elegant gazebo, multiple decks, patios, and balconies-perfect for relaxing/entertaining in style. Inside, you will find exquisite craftsmanship & thoughtfully designed spaces, including high-end gas fireplaces, custom built-in storage, and en-suite bathrooms for every bedroom. Enjoy the convenience of a new outdoor shower, whole-house generator, Rinnai tankless wh, slate walkways, and a sophisticated irrigation system that nurtures a variety of mature, professionally placed trees. Though nestled in a quiet, secluded setting, this home is just minute

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26.

Welcome to 9 October Hill, a refined Berkshires retreat set within the coveted Twelve Oaks Village in Lenox. Elevated by serene views and a peaceful, wooded backdrop, this residence features an expansive screened-in porch, ideal for quiet mornings or sunset entertaining. The first-floor primary suite offers effortless living, while the beautifully finished lower level with fireplace creates a warm and inviting escape. Two additional en-suite guest bedrooms occupy the second floor with sitting area between. Residents enjoy exclusive access to a resort-inspired amenity suite—pool, fitness center, clubhouse, and tennis—all just minutes from the cultural and culinary heart of Lenox. A rare blend of privacy, comfort, and sophistication. This is a truly outstanding home, must see.

Nestled on 5.6 private acres across the street from Catamount Mountain Resort, this updated contemporary home offers the quintessential Berkshires escape. Sunlight fills the living area, framed by vaulted ceilings, hardwood floors, and a cozy fireplace made for crisp mountain evenings. Each level flows effortlessly towards spa-like features including an expansive deck and 3 season porch from main living level. Access to the heated fiberglass pool and hot tub from the ground level rooms makes this a private sanctuary for all season entertaining against scenic mountain views. Bonus flex room for a home gym, media room, or extra guest sleeping space. This retreat balances privacy with effortless access to skiing, hiking, dining, and the vibrant town of Great Barrington just minutes aw

This iconic building has been home to one of the Berkshires most beloved businesses for over 50 years. Built in 1731 as the Egremont Tavern stage coach stop, it was expanded in the 1960s. The 2.2 acre lot provides substantial parking. The historic front section offers unique features like stone floors and exposed beams and fireplaces. The rest of the building consists of a series of lovely rambling spaces with rustic elements on the main and lower levels, and two rental apartments upstairs (one 3/1, one 1/1). This property offers a buyer an extraordinary opportunity: own an incredible income producing property in the bustling town of South Egremont.

A rare opportunity to experience a lakefront living on beautiful Lake Buel. This distinctive log cabin captures breathtaking water views from nearly every room and is filled with natural light. The dramatic great room features a soaring cathedral ceiling with exposed beams, rich wood floors, and a handsome fireplace, creating an inviting setting for both intimate gatherings and grand entertaining. Designed for effortless one-level living, the home offers four bedrooms and three full baths, including a private primary suite with en-suite bath, plus a dedicated office. A generous deck overlooks mature landscaping, the lake and private waterfront with dock which is an idyllic setting for morning coffee, and summer gatherings. A truly exceptional Berkshire lake retreat. A must see!

Rare opportunity to own a commercial store front on the iconic Railroad Street in downtown Great Barrington. Great investment property with two filled store fronts. Options available to increase a larger footprint.

Nestled among spectacular rhododendrons and mature landscaping, this architect-designed contemporary home offers a seamless blend of natural beauty and timeless mid-century modern inspiration. Designed by architect Andrew Daland, the residence features expansive windows that frame peaceful pastoral views and fill the home with natural light. Designed for comfortable one-level living, the main floor includes the primary living spaces, while the lower level provides exceptional accommodations for family and guests with two bedrooms each with ensuite full baths, and a spacious family room. The open-concept great room boasts a cathedral ceiling, a fireplace, built-in bookcases, and flows seamlessly into the kitchen. Additional highlights include a screened gazebo, attached two-car garage.

Jaw-dropping water and sunset views from every room define this beautiful contemporary overlooking Lake Garfield. Offered fully furnished, this Berkshire retreat features a chef's kitchen flowing into a light-filled great room and screened porch. Four bedrooms -- including an ensuite primary -- plus a spacious family room offers plenty of room to gather. Linger on the screened porch, entertain on 2 decks, or unwind in the hot tub as the sun sets over the water. Privately sited on 2.5 acres, this is refined Berkshire living -- a truly magical place to escape, gather and enjoy.

Fabulous historic church. Located in the Stockbridge hamlet of Interlaken. Quiet and exclusive neighborhood just off Rt.183. Stylishly decorated by a renowned architect and designer. High ceilings, huge windows, and mahogany fittings. Beautifully restored kitchen with many original details. Marble topped sink/counter. Walk through to the magnificent living area to step back in time to an earlier era. Then on to the nave to enjoy soaring ceilings, oversized windows and room for entertaining. Enjoy this 'party space.' Or use for an artist studio, recording studio or any pastime that needs space. Minutes to Berkshire Botanical Garden, Tanglewood and the center of Historic Stockbridge.

Exceptional Federal style reproduction farmhouse located in a peaceful setting on a scenic country road. Offering 3-4 bedrooms, 3.5 bathrooms, beautiful hardwood and marble floors. The kitchen with Viking range, custom cherry cabinets, granite countertops and walk-in pantry opens to a family room with a brick Rumford fireplace. The formal dining room opens into the living room. There are French doors to a heated sunroom that connects to a barn/garage with 2nd floor great room and full bathroom. The grounds include a bluestone patio and Goshen steps to the home. Property setting has mature landscaping and perennial gardens. Adjacent undeveloped 2.5 acre lot included.

Historic 9-Unit Bed & Breakfast | ±10,560 SF on ±0.33 Acres Exceptional opportunity to own a beautifully maintained three-story historic bed & breakfast offering approximately 10,560 square feet on a ±⅓-acre lot. Within walking distance to the downtown theater/business district. This well-appointed property features nine unique guest suites, each with private baths and kitchenettes, blending classic charm with modern amenities. Large parking lot in the rear of the property also offers a separate right of way directly onto East Housatonic St. Guests are welcomed through an elegant entry foyer, leading to inviting common spaces including a parlor, formal dining room, and fully equipped common kitchen. The first floor also includes two spacious guest suites.

Imagine owning your own secluded sanctuary, where total privacy and tranquility are yours for the taking. This extraordinary property offers the rare opportunity to build your dream retreat on a breathtaking piece of land, untouched by the outside world. With 20-foot-tall mountain laurel trails leading to the top of a mountain with stunning views right at your doorstep, you'll have endless access to nature's beauty, all while remaining completely secluded. The land consists of 6 separate parcels, all being sold together, creating the perfect canvas for whatever you envision. Don't miss out on staking your claim to this hidden gem, an unparalleled escape !

Discover this sleek 2022 contemporary set on a beautifully landscaped parcel of just over 2 acres. Thoughtfully designed for low-maintenance, efficient living, this home offers 3 bedrooms, 3 bathrooms, and approximately 2,400 square feet, with every detail crafted for both beauty and everyday convenience.

Tucked away at the end of a private cul-de-sac on 1.22 acres, this 4-bedroom, 4-bathroom contemporary home delivers sophisticated Berkshire living just minutes from downtown Great Barrington. Offering the perfect footprint for full-time remote professionals, weekend escapees, or downsizers, this property pairs a spacious layout with the effortless lifestyle of a premier community association. The heart of the home is a dramatic, light-filled great room anchored by soaring cathedral ceilings and a brick fireplace paired with charming built-ins. The main level is designed for entertainment and ease, featuring a lavish first-floor primary suite with walk-in closets and a spacious ensuite bath. Upstairs, three additional guest bedrooms are complemented by a private, separate bonus studio

Elevated Living - Inside and Out! Exceptional design and craftsmanship distinguish this stunning home. The single-level interior is warm, sophisticated and filled with natural light, with the kitchen, dining and living areas flowing together in one open space surrounded by specialty windows and French doors. Set on four private acres amid the highest peaks in South County, the home offers immediate access to premier hiking and protected lands. Locally sourced Massachusetts walnut floors, Scavolini cabinetry, Miele and Sub-Zero appliances, extensive custom woodwork, shoji-inspired glass sliding doors, and a dramatic stone fireplace wall speak to the quality and attention to detail throughout.

A DRILLED WELL, A COMPLETE 6 BEDROOM SEPTIC SYSTEM, A HORSE BARN AND A SHED COMES WITH THIS FABULOUS 42 PLUS ACRE PARCEL. BEAUTIFUL STONE WALLS SURROUND THE BUILDING SITE AND ACROSS FROM PROTECTED LAND