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!

FANTASTIC, UNUSUAL AND UNIQUE WATERFRONT OFFERING: THREE PROPERTIES ON OTIS RESERVOIR, the largest recreational lake in the state at 1085 acres. The three separately deeded properties included are: 183 Pine Road, a charming 4 bedroom cottage located 20 feet from the water's edge with a swimming area and three docks - lots of space for water toys; 185 Pine Road, a 2 bedroom contemporary cabin featuring a delightful covered deck overlooking the long lawn leading to the lake and the fourth dock; and finally 0 Pine Road, a vacant lot abutting both house lots with multiple potential uses - future guest house, garage and more. The combined properties offer 150 feet of beautiful lakefront and a total of 1.5 acres.

Handsomely built with modern comfort and amenities. Meet Guests on the covered porch and welcome them into the first floor open kitchen and great room with stone fireplace. On the first floor is also the dining room, office, den, mudroom and breezy screened porch for summer drinks. First floor primary suite with sparkling ensuite bathroom and sitting room with fireplace is its own hideaway. Upstairs, three more large ensuite bedrooms for the crew. One-car garage located off the first floor for easy access to the kitchen, two oversized garages below. Located at the end of a shared private drive with similar homes, and maybe some new friends, this retreat will be home base for all of your Berkshire adventures.

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...

Nestled three miles from the heart of downtown Great Barrington, this contemporary oasis offers a designer details and breathtaking 360-degree views. A wood burning stove invites warmth and comfort, beamed ceilings, designer lighting, and wide plank wood floors add a touch of elegance. Chefs kitchen and soaking tub beckon for indulgence, while the main floor primary bedroom with a wraparound deck offers a private retreat. A second primary bedroom on the second floor provides additional luxury.

Exceptional custom-built contemporary home with magnificent views. Featuring multi-level living including a beautiful great room/living room with floor-to-ceiling stone wood burning fireplace, expansive well-appointed kitchen with large breakfast area and walk-in pantry, and a formal dining room. The first floor also offers a primary suite with walk-in closets, an office with laundry room, a mudroom, and a half bath. The second floor has two bedrooms, one bathroom and an office overlooking the great room. The lower level offers a large family room, bedroom (currently used as an exercise room) a bath, and a two-room workshop. There is a separate screened porch on the wraparound porch and a hot tub to take in all the amazing views.

Discover unparalleled sophistication and privacy with this magnificent estate, introduced to the market for the very first time. Situated on more than 17 acres of pristine land, this gorgeous home is enveloped by a magical outdoor sanctuary featuring a crystal clear swim pond and intricately designed gardens bursting with a variety of plantings and flowers. Enjoy peaceful moments wandering through these stunning gardens or lounging on the sophisticated bluestone patio, a perfect spot for soaking in the tranquil surroundings or gathering fresh flowers for your home.This expansive home includes four bedrooms and 3.5 baths, providing ample space for family and guests. The kitchen features rich Cherry cabinetry with matching hardwood floors and a welcoming wood burning fireplace,

Contemporary lakeside living on nearly five acres with just over 270 ft of water frontage on desirable Stevens Lake. This non motorized lake is perfect for the nature lover who dreams of quiet days swimming, kayaking or paddle boarding on a private lake only used by the neighboring lake homes. With mature landscaping, the home is situated a short stroll up from the water and has a tree house feel with nearly 3600 Sq ft of living space. Views from every window, ensuite bedrooms and social spaces on each level, with a wine room and sauna on the lower level. A newly updated septic system, 50 yr roof and whole house generator are just some of the most recent updates. Six minutes to Great Barrington and five to Ski Butternut, this is the perfect location for year round fun and activities!

An unusual and wonderful early barn conversion, originally built in the 1700s and converted to a house around 1910. The current owner has renovated and added onto it thoughtfully and completely. A large open space with lots of windows, a huge stone fireplace and a cathedral ceiling define the living a dining rooms. The kitchen was enlarged and remodeled in 2012 with Wolf and SubZero appliances, and Cherry cabinets. With five bedrooms and four and a half baths on two levels, all but one of the bedrooms are ensuite. The very creative and bright primary bedroom, up a few steps from the second floor, also has a cathedral ceiling and gorgeous built-ins. This romantic property contains a large field, lawns, woodland and huge ponds; a virtual national geographic display of bird and animal life.

A peaceful waterfront home situated on the pristine Highland Lake; this beautiful family compound offers a rare opportunity to enjoy lakefront living on a private waterfront lot. The 4000 sq ft renovated home offers lake views from most rooms, including the primary suite that opens to a screened-in porch. There is plenty of room to stretch out with 5 bedrooms and several large open rooms. Complete with an oversized workspace and ample parking. Included in the home are 3 fully furnished cottages and a walkout basement apartment for your guests or extra income throughout the year. There is a recently installed solar array, a Tesla charging station, and a backup generator. Paradise found! 20 min. to Northampton, less than 1 hour to the Berkshires. 3 1/2 hrs. from NYC and 2 hrs. from Boston.

Step into the charm of history with this renovated exceptional property nestled in the picturesque town of Stockbridge, just off Main Street. A meticulously renovated 4-bedroom, 4-bath historic home offers elegant living spaces with the convenience of modern amenities such a solar array providing all electricity, a car charger and central air. The new eat-in kitchen offers SubZero, BlueStar, Vent-A-Hood and Bosch appliances, while overlooking the Kampoosa Brook and a private swimming hole. The Millhouse, as it's known, one of the first in Stockbridge is a 3-bedroom, 3-bath guest house with a great summer rental history. There's also a two-car garage and a fruit orchard. Enjoy the sound of the rushing brook from almost any window along with walking to town for an espresso, food or theater.

Built in 1904 this historic home sits on a beautiful 1.4-acre lot, which offers privacy while being in the most coveted and accessible neighborhood of Great Barrington. High ceilings and adorned with oak and mahogany woodwork throughout, this home has been tastefully renovated while retaining its period charm. The spacious layout, with 4 bedrooms, 31/2 bathrooms and an expansive porch provide comfort and grace. A fully updated kitchen, new windows, central air and natural gas enhance the living experience with modern ease. The surrounding landscape is adorned with perennial beds, and mature specimen trees. Walkable to town's restaurants, shops and farmers market, this property offers laid-back charm along with convenience and high style.

Set amidst 250-acres of wide open meadow and pristine woodland you'll find your dream, Berkshires oasis. Breath-taking views, a just-completed light-filled 4-bedroom contemporary home (fully furnished) , a nearly 1-acre swimming pond, tennis, miles of trails for hiking and skiing, and massive barn offering a multiplicity of opportunities: entertaining? Guest space? Store your toys? KEY DATA POINTSSolar and Tesla PowerwallsHighest standard (R-70) insulation and Zander Air Exchange | Air filtrationRadiant heat and ACFiber internetTennis Court - synthetic turf60 x 40 newly built barn - fully insulatedFrom Boston - 2 hrsFrom Bradley Airport (Hartford,CT) - 1 hrFrom New York City - 3 hrsTo Jacobs Pillow Dance Festival - 15 minTo Lee, MA - 20 min

A setting surrounded by classic Columbia County views of rolling hills and bucolic farmland, smack in the middle of Old Chatham hunt country is the ideal location for this grand, turn of the century five bedroom farmhouse with a in-law suite, guest cottage, in-ground stone pool, pedigree three story barn, a studio outbuilding, and three car garage. A traditional layout prevails throughout with a gracious entrance complete with dutch door, stone flooring and a wood burning fireplace. The large, light filled country kitchen is the heart of the home with expansive views and doors leading to a deck and sublime stone patio, making it ideal for entertaining. The first floor is complete with three more fireplaces and many more rooms for dining, gathering, studying, reading and creating.

HISTORIC BERKSHIRE FARM Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

Escape to the serene countryside, where this stunning New England farmhouse beckons with its picturesque setting on 10 acres. This property boasts a pool, pool house, garage and barn, offering endless possibilities for enjoyment and relaxation. Step inside this beautifully renovated home, where modern amenities blend seamlessly with classic charm. The 4 bedrooms and 3.5 baths provide ample space for comfortable living. This home is sure to impress with its impeccable design and attention to detail. Outdoor living is a true delight at this property, with plenty of space to roam and explore. The in-ground pool is a refreshing spot to cool off, while the pool house provides a convenient place to relax and unwind. The garage and barn offer storage space for all of your outdoor essentials.

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

Possibly the best waterfront location on Lake Garfield, this 1935 cottage was completely renovated, added to and winterized in 1997/98, with further recent renovations including a new metal roof and HVAC. A quintessential lake house with fresh and modern amenities, fixtures and appliances. Although one would want to spend all their time on the wraparound porches and decks, the bright interior offers a living room with a stone fireplace, a first floor primary suite, three second floor guest bedrooms and a large overflow family room, all with water views. Hardscape, including stone retaining walls, patio and fire pit lead to a long dock. There's a beach for pulling up kayaks and jet skis, with easy swimming off the dock. Offered mostly furnished. Water water everywhere!

Welcome to The Factory - a gorgeous three bedroom, three bath loft that comes with a rather large 10,000 foot manufacturing or studio space, along with an executive office with its own bedroom, another full bath and a service kitchen. Essentially two separate living spaces within the commercial space. The loft space is extraordinary, featuring a huge common area with a glass garage door to a large screened porch and deck, and a Malm 360 fireplace. All bedrooms and baths are generous. The commercial space includes two offices and other ancillary rooms with lots of storage on the second level. Enjoy the one year old in-ground lounge pool, newer barn with a corral and the neighboring Appalachian Trail. Located in the Housatonic Valley with views of neighboring protected cornfields.

Blue Hill Farm: an 1820 Center Hall Colonial farm and farmhouse in excellent condition on 249 high acres with organic hay meadows and pastureland, an apple orchard, woodlands, gardens, tennis court, a 1970's caretaker/farmer's house and multiple barns. The main house has 6/7 bedrooms and three baths, along with a three-car attached garage. The property consists of seven parcels of contiguous land surrounded by the Umpachene River on three sides. There are long views to the west of the Taconic Range from inside and outside of the home, and a grouping of supportive barns to the south across a very rarely traveled, narrow dirt road. Offered for the first time since 1967, this is truly an unusual and rare offering with development possibilities featuring extraordinary views.