A classic Main St Stockbridge residence on a remarkable 4.3 acres. Walk to shops, restaurants, town tennis courts, the library, the Stockbridge Golf Club, the Berkshire Theatre Festival and more. The David Dudley Field house c.1824 is steeped in history remaining in the Field family until 1984. The current owners have lovingly maintained and cherished this exceptional property for 40 yrs. The gracious interior is bathed in natural light and full of beautiful period details. Front and back staircases, pocket doors, built-in shelving, exceptional fireplace mantels, beautiful floors, etc. The carriage barn is a delight. An exceptional property perfectly located in the center of Berkshire activities. Lenox and Great Barrington are only a quick 10 minutes away.

Successful, turnkey inn located in the picturesque village of West Stockbridge, walking distance to shops, restaurants, and galleries. This unique property boasts nine spacious, well-appointed guest rooms, most with private outdoor entrances. Each room has a kitchenette and ensuite bathroom. Most rooms have gas fireplaces and private balconies, overlooking the manicured grounds. The Greylock suite is perfectly set up for long term stays, with a full kitchen, living room, and separate bedroom. For the innkeeper, there is a spacious owner's quarters, privately located on the top level of the inn, with its own separate entrance, full kitchen, laundry, and lots of charm.Close to all that the Berkshires have to offer, this is a great live/work opportunity in a highly desirable area.

Sited on the Housatonic River in Gt Barrington built in 2005/2014 the Barn exterior belies the contemporary interior w/ floor to ceiling windows overlooking the River; a seamless open floor plan on the main floor includes living/dining/ kitchen/fireplace/office/powder room/stairs to 422 sq.ft. loft & hallway to primary bedroom suite. Entire house has central ac. Two bedrooms on the ground floor share a stunning Alford marble bathroom. The entire lower level has radiant floor heat. One of the bedrooms serving as both office & sleeping accommodations w/ a sliding barn door opening to the one of a kind marble terrace overlooking the River. The ground floor is capped off by a laundry room, & all purpose gym/sauna/storage/extra sleeping. Two car garage w/ direct access to River Barn.

Own a piece of history in this pristine setting. Charming 4 BR 3 BA home, situated on 11.95 acres adjacent to hundreds of preserved land on one of Southern Berkshires most revered scenic roads. The current owners have updated the property preserving the integrity by installing Marvin triple-glaze windows, cotton insulation, energy efficient heat pumps & 2-zone forced air furnace. The exterior has new cedar clapboard siding & metal roofs. The home includes a 4-car heated garage with ample space above, an in-ground salt water swimming pool, & custom post & beam barn. A stunning 2-story 1800 sq. ft. converted timber-frame barn/studio sits across the road, a perfect place to set up an art studio, or perfect for extended guests. With pastoral views to protected lands. SF includes house & barn.

Executive colonial sited on over 1.3 acres bordering 17 acres of conservation lands. Hike off your property on Parsons Brook Conservation area or relax in your professionally landscaped backyard with fire pit, waterfalls, 35/70 yd tee boxes w/ synthetic putting greens and 18x36 inground saltwater pool and pool house w/ kitchen. The expansive main residence offers a balance between open concept entertaining, yet offering quiet, cozy areas when needed. Bonus spaces include a 4-season sunroom, home gym, media room and for the ultimate in game day gatherings, the third floor has an expansive entertainment room with custom 8-person wet bar, three tv's, and pool table. High level technology with Solar, 17kw backup generator, 52 speakers in/out Sonos system and whole property security system

At the end of a long tree lined driveway, you'll find a fabulous 4 bedroom, 5 bath Dutch Gambrel with detached garage only minutes to Great Barrington. This spacious home is set on almost 5 sunny acres, which include a possible abutting building lot. This place has it all - great entertaining spaces, perfect cook's kitchen, fireplaces and private and peaceful outdoor gardens, along with a lovely screened-in porch to take in the gorgeous landscaping. Home built in 1989 with 2004 and 2019 renovations. A luscious hi-beamed master suite is on the first floor. Meticulously maintained so you can move right in!

Escape to tranquility in the Berkshires with this stunning 4000+ square foot residence boasting an open floor plan, 2 fireplaces, large sunroom, 2-car garage, formal dining and wrap-around front porch, offering both luxury and privacy. Featuring four bedrooms including a lavish primary suite with a fireplace, this home is designed for relaxation. Outside, a gunite pool and expansive stone patio create an idyllic retreat, complemented by a wall of glass overlooking the pool from the living space. Additional features include a finished basement and a third floor living room complete with a full bathroom and private office space, both providing additional space for recreation or relaxation. This is the perfect spot to embrace the epitome of New England living in this exquisite property.

Poised proudly on Main Street, Great Barrington, a few blocks from eateries, shops, and performance venues, this marvelous place affords an unparalleled residential and income opportunity. Purpose-built as an inn, its main house features nine bedrooms and a studio suite, while its carriage house contains two apartments. The sellers have rebuilt porches and staircases, added AC, installed insulation, refreshed cosmetics, remodeled the kitchen and public spaces, and added parking and gardens. Gracious spaces, high ceilings, light-welcoming windows, fireplaces, and architectural details create the ideal setting for a new owner's tastes and ideas. As a residence, this property in the heart of the Berkshires has the potential to support itself!

Poised proudly on the vibrant Main Street of Great Barrington, a few blocks from eateries, shops, and performance venues, the Wainwright Inn affords an unparalleled lifestyle and income opportunity. Purpose-built as an inn, its Victorian main house features nine guest rooms with baths en suite and an owners' suite, while its carriage house contains an apartment plus two guest rooms with baths en suite. The sellers have completed significant updates and improvements including AC, structural and cosmetic work, remodeling the kitchen, and adding parking and gardens (See Documents). Gracious spaces, high ceilings, light-welcoming windows, fireplaces, and historic architectural details create the ideal setting for a new owner's tastes and ideas. Strong financials, available upon request.

Poised proudly on the vibrant Main Street of Great Barrington, a few blocks from eateries, shops, and performance venues, the Wainwright Inn affords an unparalleled lifestyle and income opportunity. Purpose-built as an inn, its Victorian main house features nine guest rooms with baths en suite and an owners' suite, while its carriage house contains an apartment plus two guest rooms with baths en suite. The sellers have completed significant updates and improvements including AC, structural and cosmetic work, remodeling the kitchen, and adding parking and gardens (See Documents). Gracious spaces, high ceilings, light-welcoming windows, fireplaces, and historic architectural details create the ideal setting for a new owner's ideas. Financials available upon request. 2024 Taxes = $13,737.

WEST STOCKBRIDGE.....The location you've been waiting for!! Minutes from the Main Gate of Tanglewood, this mid century Contemporary has it all just waiting for you to put your personal touches on it. Main four bedroom residence with walls ofglass taking in the sweeping view, separate guest cottage, in-ground pool w/pool house all surrounded by 18+ private acres on both sides of the country lane!

Discover a lucrative investment opportunity with this contemporary 8000+ square foot dental building boasting two long-term leased suites and a strong cap rate. Equipped with an elevator and situated in a high-traffic commercial district, this property ensures stable rental income and convenient accessibility. With modern amenities, including fully equipped operatories, waiting rooms, reception stations, offices and ample parking, this building has it all. Secure this asset for a promising return on investment and future growth potential.

Maya Lin Masterpiece. Evoking the serenity and simplicity of the Japanese courtyard aesthetic, this extraordinary home, Maya Lin's first residential conception, stuns in the purity of its design and materials, in the singular curvilinear articulation of its roofline, and in the liberal use of fieldstone, slate, cherry, maple and ash in restrained architectural elements yielding a rich yet exquisitely understated ambience. The graceful rooflines reflect the swells and hollows of the distant hills, and define as well the interior spatial configuration and elevations. Upon entering through the front door a glimpse of the lovely central courtyard hosting Japanese maples and koi pond lies ahead. The main living area opens both to this intimate courtyard and to a deck with the inspiring view.

Just a very special property. Located between the Rockwell Museum and the Botanical Garden. You are moments from Tanglewood. Equidistant from Lenox and Great Barrington so it's easy to access the Berkshires wonderful restaurants. The main house has three bedrooms and two baths , while the guest cottage adds another bedroom, bath, and large living room. Gracious grounds are well landscaped. Adorable play house for little ones. Several various outbuildings. Garages for at least 5 cars.

A Magnificent 6 bedroom stucco residence less than a mile to the center of Stockbridge. Enjoy views of the golf course and mountains in the distance. Five fireplaces, a beautiful eat in kitchen, stunning butlers pantry with a cozy nook to sit in, and a sun filled spacious dining room. Read a good book in the beautiful library next to one of the five fire places throughout the house. Step out beautiful French doors to your screened in patio which leads to a well lit and heated pool. A 20 ft hallway wall of built in cabinets and closets leading to the primary bedroom. Three en suite bedroom areas for guests and family. Electric car charger in the heated garage. Majestic stonewalls. Not far to all attractions Tanglewood, Norman Rockwell, ski areas etc. A must see!

Classic American Farmhouse With Epic Views - Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views. Step inside to discover an extra-large chef's kitchen seamlessly connected to a delightful breakfast room, sunroom, and screened porch, each offering tranquil views of the pool and raised garden beds. The inviting living room, complete with a cozy fireplace, flows effortlessly into the dining area, creating an ideal space for entertaining.

FOUR BROOKS FARM, owned by the De Kay Gilder Palmer Family since 1898, is now available. This exceptional property embodies idyllic country living in the heart of The Berkshires. This historic property consists of the Main House, Guest Wing, Barn with Tack Room, Roman Walled Garden with Sunrise/Sunset window, Stonewalls, Pastures, Trails & Views . Ready for restoration to former glory, many recent improvements have been completed.Some lots may be sold separately. Rolling meadows, gardens, stone walls and views! Rich in history, with so much potential to be a cherished Berkshire retreat. Close proximity to notable area cultural attractions . Reportedly visited by notables such as Mark Twain and Grover Cleveland...

An outstanding rarity in Northampton - an exquisitely designed and built Contemporary hilltop residence with sweeping southeasterly views. With over 6000 sq. ft, 6+ acres of land with trails abutting 17 acres of conserved land, this property has it all - from a luxurious 1st floor primary bedroom suite with 2 walk in closets, jacuzzi tub and private deck overlooking the vista, to the gourmet kitchen that opens to the living room & masonry fireplace. Other features include a 2nd en-suite bedroom on the main level, a sun room and private office plus a loft used as an artist's studio. Downstairs there are 2 bedrooms with a bathroom suite, media room, game room, indoor Endless lap pool with state of the art ventilation system. The 3-car garage has an exercise room above. Outside you'll find

Pristine, custom-built home in a lovely Lenox neighborhood. Close to downtown, this beautiful one-owner home on a corner lot has plenty of space to relax and enjoy the peaceful setting. Three beautifully appointed levels, with high-end finishes throughout, are thoughtfully laid out to include five bedrooms and four full baths. A true primary suite, with a luxurious soaking tub and expansive walk-in closet add to the comfort and convenience of the home, while the soaring ceilings and light-flooded rooms provide the wow factor. This home makes quite an impression the moment you walk in. A chef's kitchen overlooks a beautiful family room, with a gas fireplace and picture windows framing the view of the partially wooded lot. The dining room is also open to the kitchen, giving

High Mowing, is a magical Williamstown estate spread over fifteen glorious acres, and nestled in the hills less than 5 minutes from Williams College. This exquisitely welcoming home is different from any other property in the Berkshires, and it seamlessly integrates beautiful nature and sophisticated culture in an incomparable and eclectic way. The property has been meticulously developed with an artist's eye and a craftsman's hand to blend perfectly with its environment, complementing the colors and textures of surrounding fields, woods, and mountains, exposed under the huge open sky of day and starry nights.