A once-in-a-lifetime opportunity to build your dream home on a large waterfront parcel in Lenox. This spectacular 14-acre property offers privacy, tranquility, and direct frontage on beautiful Laurel Lake while remaining just minutes from downtown Lenox, Tanglewood, shopping, dining, and all the Berkshires has to offer. Enter through the stone and metal electric gate, cross the stone bridge, and arrive at a cleared, manicured homesite ready for your custom estate or compound. A scenic boardwalk winds to your private dock and lakeside sitting area. Truly a rare Berkshire offering combining natural beauty, convenience, and waterfront living.

Entertainer's Delight! Tucked away in one of Sandisfield's most scenic settings, this quality-built log home offers over 4,600 sq.ft. of finished living space, plus an additional 2,000+ sq.ft. in the walkout basement ready for living, recreation, or storage. Crafted with exceptional materials, the home features soaring ceilings, expansive gathering spaces, and a warm, inviting atmosphere perfect for entertaining or everyday living. Multiple decks provide an ideal setting to dine, unwind, and enjoy the peaceful natural surroundings. Experience the perfect balance of privacy and convenience, just 20 minutes to Guido's and downtown Great Barrington, 30 minutes to Lenox and Tanglewood, and 15 minutes to Ski Butternut. A true Berkshire gem for year-round living, weekend retreat, or investment!

Discover a rare lakefront opportunity on Otis Reservoir with amenities seldom found in one property. Combined with the lower lot, enjoy 62 feet of direct waterfront, a grandfathered boathouse with electricity and electric lift, waterfront bathhouse with living room, heated garage, dedicated hot tub room with fireplace, and lake views from nearly every room. Perfect for entertaining with an updated kitchen, multiple living areas, separate driveways, ample parking, and two storage sheds. Remodeled in 2021 with new heating and cooling, on-demand hot water, quartz island, stacked cabinetry, stainless appliances, and gas range. Walk-out basement. Sold fully furnished and ready to enjoy.

Classic eyebrow colonial along the Roeliff Jansen Kill w/ renovated barn and large tillable field across the road. The home has been completely redone from the studs out. Exposed beams, vaulted ceilings, radiant heat, central air, new plumbing, new electrical yet so many original details were preserved. Kitchen is open to dining with wood stove and seating area making this the center of the home. Off the entry is the den (with laundry closet) and the living room with french doors to a patio. Upstairs there are three bedrooms, two with en suite baths. The barn is three stories of finished space with central air and heat. Lower level presently a wood shop, main floor is separated into two large studios; high ceilings, natural light. 2nd floor is a large space with full bath and kitchenette.

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.

Exceptional Commercial Investment Opportunity | 5.1 Acres | Multi-Tenant AssetPositioned along a high-visibility corridor on a major highway, this rare 5+ acre commercial offering features five well-maintained buildings with a diverse and fully occupied tenant mix. The property includes a popular restaurant, gift shop, coffee/breakfast cafe, hair salon, lively beer hall, medical office, and a dedicated maintenance building--providing stable, multiple income streams in a single, cohesive investment.The grounds and infrastructure have been meticulously cared for, with recent upgrades including newer septic systems and new boilers, ensuring operational efficiency and long-term reliability.

CONTEMPORARY FARMHOUSE! Sited on a knoll dotted with old apples trees overlooking scenic views all framed by a meandering fence. All you could ask for is in this well-built home, offering a first floor primary ensuite, library with fieldstone fireplace, A well appointed kitchen opens to both the dining and a living room with fireplace. A screen porch, 1/2 bath, laundry room/mudroom leading to a 2 car garage completes the first floor. The second floor offers 3 addition bedrooms, full bath, built-in bookcase with window seat. Kick back and relax on the front porch! A fabulous Berkshire house close to all Berkshire cultural venues, skiing, shopping, restaurants and, just plain fun!

Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes -one a four bedroom home and a 1000 sq ft guest house-both surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Spacious garage allows room for cars, hobbies and workshop, perfect pool site, and privacy ensured by abutting protected land. Generator for both houses.Access to town beach.

Nestled in the heart of Great Barrington, this spacious 4 bedroom, 4 bathroom residence offers the perfect blend of family-friendly comfort and private sophistication. The home greets you with gleaming wood floors and a stunning fieldstone fireplace that anchors the living spaces in warmth and character. Cook like a chef in the large open kitchen, where generous countertops, a welcoming island, and ample natural light inspire everyday gatherings. The first-floor primary suite provides convenience without sacrificing privacy, ideal for busy households seeking single-level living when desired. Step outside to your expansive outdoors: a grand deck that overlooks lush acreage, plus a screened-in porch and an oversized porch ideal for morning coffees, evening entertaining, and quiet

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.

Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a great room with woodstove and 3/4 bath. Upstairs there are two bedrooms, a hall bath and ample closet space. The lower level has a walkout section with a large bedroom, hall bath and a hall that takes you into the below grade finished area with office, play space and extra room. The screened porch off the entry foyer leads to a very large deck on the east side of the property angled southeast with views

Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout. The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's kitchen is thoughtfully designed with quartz countertops, custom cabinetry, and seamless flow into the dining and living spaces--perfect for both everyday living and entertaining. Custom built-ins add character and functionality, while an inviting den or home office on the main level provides flexible space for work or relaxation. Guests will appreciate the privacy of well-appointed en-suite bedrooms.

This Stockbridge home has it all...privacy, protected view, river frontage, plenty of room for all washed with natural light and location, location, location!! Down a town maintained country lane, this special property welcomes you to this spacious home with living rm, great room w/fp, den/office, open kitchen/dining w/wall of glass leading to the wonderful screened porch & spacious decking, mud room off 2 car garage, laundry & half bath complete the main level. Upper level has generous primary en suite with balcony overlooking the serene yard and two guest bedrooms and bath. Centrally located for easy access to restaurants, theater, shopping, museums, skiing, cultural venues and only ,minutes to the Village of Stockbridge!

Experience refined Berkshire living at Devon Meadows, one of the area's most desirable luxury condominium communities. This beautifully appointed residence offers the ease of a first-floor primary suite combined with sophisticated design and exceptional comfort throughout. The open-concept floor plan features soaring ceilings, abundant natural light, and elegant modern finishes. The chef's kitchen is thoughtfully designed with quartz countertops, custom cabinetry, and seamless flow into the dining and living spaces--perfect for both everyday living and entertaining. Custom built-ins add character and functionality, while an inviting den or home office on the main level provides flexible space for work or relaxation. Guests will appreciate the privacy of well-appointed en-suite bedrooms.

Just minutes from Tanglewood on the sunny side of Lenox Mountain, this lovely five-bedroom, five-bath home is privately set on almost eleven acres of rolling lawn and woodland. A welcoming foyer opens to a light-filled great room where a striking two-sided stone fireplace creates distinct living and dining spaces, all flowing to decks, a terrace and a screened porch. The main level also features a library/den, a primary suite, laundry room, powder room, and an attached two-car garage. Upstairs are three guest bedrooms and two full baths, one being en suite. The walk-out lower level offers a fully self-contained one-bedroom apartment along with extensive storage. Outside, the expansive pastoral grounds provide ample space for a pool, while Lenox Mountain Brook meanders through the propert

Views, privacy, and frontage on Mill Pond. This custom built classic Gilligan house is the perfect home for hosting family and friends with plenty of space both inside, and out. There are 4 plus bedrooms and 5 baths, including a generous primary suite on the first floor, a large den, and a bonus room above the 2 car garage. The property includes a fenced, in- ground pool, extensive flat lawn, perfect for soccer or croquet, and a private dock for paddle boats, fishing and watching out for the resident Bald Eagle! The house sits on 4.49 acres and also includes 4 additional lots for a total of almost 13 acres.

A significant price reduction has just been made on this terrific revenue opportunity property in Stockbridge. The 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. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. 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. Rental income? This property has a very nice history of rental income! Who could ask for anything more? Call for a showing today

Set on 21.5 acres at the end of a long, winding private drive, this extraordinary residence is a true architectural gem--where art, landscape, and modern living converge. Originally designed by Robert McMahon and built by Lou Boxer and later reimagined through a contemporary project by Deborah Reiser of the award-winning RUR Architecture with Hird Design and Construction as the builder, the home reflects a sophisticated, transitional approach to residential architecture and interior design. With five bedrooms and four baths, the home is defined by its dramatic walls of glass, seamlessly framing bucolic country views, a classic red barn, and thoughtfully designed gardens. Natural light pours into every space, creating an ever-changing connection to the surrounding landscape. The kitchen is

IMMACULATE, LIKE-NEW DESIGNER CONTEMPORARY HOME tucked away on a quiet country cul-de-sac just minutes from downtown Great Barrington. Thoughtfully planned for effortless luxury living, this exceptional residence is part of an HOA community that allows you to simply arrive, enjoy, and leave with peace of mind knowing your home will remain impeccably maintained. The open-concept floor plan is highlighted by soaring 12-foot tray ceilings, stunning wood floors, a dramatic linear fireplace, and beautifully designed living spaces filled with natural light. An oversized screened porch overlooks the lush green lawn, mature plantings, and serene backyard setting, creating the perfect extension of the home for relaxing or entertaining. A spectacular chef's kitchen: see supplement:

Step into a piece of history with the once Iconic Card Lake Inn Tavern, now transformed into a stunning residential haven in the heart of downtown West Stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully designed to meet the needs of modern living. These units feature elegant wood floors and come equipped with all necessary appliances, including dishwashers and in-unit laundry facilities. Central air conditioning ensures comfort year-round, while tiled double-sink bathrooms add a touch of luxury. Ample storage space is available in each unit, allowing residents to keep their living areas tidy.