New York style living in the Berkshires! Poised above Main Street Great Barrington, this Southworth Penthouse Condo offers 1,974 sq ft comprised of 2 bedrooms, 2 1/2 baths, kitchen, laundry, storage, dining and living rooms with high ceilings and, views of East Mt. Walk to the heart of town, shopping, Coop market, restaurants, movie theater and, The Mahaiwe Performing Arts Center and more! Elevator access. Interior will be newly constructed beginning in Fall 2024! Proposed finished interiors included in photos.

Classic Colonial transformed for today's living and entertainment. Excellent location just down from Butternut and 3 miles into the center of Great Barrington. House borders conservation land and boasts beautiful gardens, stone walls, fruit tree Orchard. This move in condition home features three en suite bedrooms and baths with radiant heat. Central A/C, spacious great room, Viking range, Sub Zero refrigerator, new dishwasher. Concrete pool, sun room with cathedral ceiling and skylights.

Solid investment opportunity. The owner has just put the underlying real estate on the market. Currently leased to ''Rebelle'' Cannabis Dispensary until 11/2029 with an additional ten year renewal option. Property boasts a superb, high profile location directly across from Guido's. Completely renovated inside and out with mature landscaping, large parking area and located on busy highway. Great long term income opportunity and a chance to own an incredible building that meets current energy construction codes as well as cannabis related build out requirements such as high security, upgraded electric and plumbing systems and handicap accessibility. Rare, true triple-net lease. Property is in excellent condition. Financials provided with completed NDA on request.

A stylish and bright 4 bedroom, 3 bath private yet convenient home, located at the top of a sweeping drive. The traditional exterior belies a fresh, contemporary, open first floor while retaining a dedicated dining room that would also make a terrific den or office. A very large screened porch and a sunny deck reached from the great room expands the summer footprint to allow for large gatherings and appreciation of the landscaped property of over five acres. All bedrooms are located on the second floor - an en-suite primary, three guest bedrooms and a renovated bath. An attached two-car garage is nearby a powder room. There's loads of closet space and dry storage in the clean, full basement. Just a five minute drive into the center of town. Furnishings are available outside of escrow.

The owners are retiring so this is an opportunity for a new generation to take over this 3 acre parcel with a two large buildings, Was a winery. One building is a beautiful tasting room with a kitchen and two half baths. The other is a heated and air conditioned storage room. See the grapevines and the beautiful scenery. Bring your friends, sit in the gazebo and enjoy the local wine . Minutes to town, Stockbridge and Lenox. Around the corner from Butternut Ski area. Could easily be a full fledged winery again or there are so many possibilities.

Immaculate Victorian on ''The Hill'' with stunning hardwood floors and abundant natural light from its many large windows. This versatile three-level property is currently enjoyed as a stately single-family residence, but can seamlessly be divided into two separate apartments, offering a range of layout options and rental income potential. The ground floor features a bright, modern kitchen, a spacious living & dining area, a bedroom and a den/office. The 2nd floor boasts stylish bedrooms, newly renovated bathrooms and a 2nd updated kitchen. The 3rd floor provides a 2nd living/dining area and another bedroom. Enjoy the prime location, placing you at the heart of all Berkshire attractions and just a short walk to downtown Great Barrington shops & restaurants and the superb Lake Mansfield.

Newly renovated family compound offers an abundance of living spaces across 2 distinct houses. The main house impresses with 6 en suite bedrooms, a grand living room with a fireplace and an ambiance steeped in 1800s charm. The revamped kitchen & large dining room provide a perfect setting for cooking and gathering. Beautiful wide plank, vintage wood floors throughout main & cottage houses. The main house has a first floor primary & office area. Upstairs there are 5 more ensuite bedrooms & an additional sitting area. Connected by a stone courtyard with trellis, the separate cottage has a mudroom entry with half bath & laundry. Step into a sweet kitchen with stylish breakfast nook. The back of the cottage has a sizable area for lounging & dining. Upstairs are 2 bedrooms & 1 shared bath.

Open, light airy 5BR contemporary & only a 5 minute drive to downtown Great Barrington! Loads of sunlight throughout with open floor plan. Floor to ceiling windows & cathedral ceiling in kitchen & great room. The main bedroom also has floor to ceiling windows & cathedral ceiling. State-of-the-art chef's kitchen opens to a huge deck overlooking the beautifully landscaped, level property. Home also features a den, living room, family room plus a lower level recreation room. Property is surrounded by majestic hardwoods & evergreens, with fenced dog run, creating serenity & privacy. Perfect for entertaining also has an outstanding short term rental history. Recently added generac full generator with 1000 gl propane tank. NEW Mitsubishi HVAC Splits. Sq ft includes 756 sq ft basement spac

Discover modern comfort in this stylish Contemporary retreat! The heart of this exquisite home is the open plan, integrating the Chef's dream kitchen complete with Bertazzoni 6 burner range, granite counters & SS appliances, into the easy flowing Living and Dining spaces. The upper level hosts a grand primary suite, totally renovated, with a dedicated office space and seating area, AND its own screened porch. The primary bath is pure luxury! Two additional Bedrooms and full Bath provide total comfort for family and guests. The expanded deck is an entertainer's delight offering a serene backdrop for gatherings or simply to unwind after a busy day. Quality and care throughout. Two car attached garage, Generator, and meticulously maintained grounds. Embrace the Berkshire lifestyle,

This NEWLY BUILT LAKE HOUSE has 4 bedrooms, 4 full baths which includes a main floor bedroom with full bath (walk in shower) just across the hall. This light-filled Contemporary, with deeded access to Round Pond, has shimmery water views from nearly every room. With a chef's kitchen, huge kitchen island, all stainless appliances, and large dining room, this open floor plan also provides direct access, through two sliding doors, to the full length mahogany deck with sparkling water views! This fresh offering has thoughtful details which include: high vaulted ceilings, shiplap walls, new propane furnace, a walk-in cedar closet and a remote controlled deck awning. The semi-finished basement offers a potential bonus room. All this, just 8 minutes to downtown Great Barrington. Easy to show

Contemporary home totally renovated and ready for your enjoyment or incredible income potential through short term rental market when you are not in the Berkshires. Main living/dining space is open and bright with soaring two-story ceilings and a wall of glass on the southwest side, a fireplace keeps a cozy feeling. Brand new kitchen, seller moved to the front of the house with a slider to the new deck. Upstairs there are 4 bedrooms and two full baths with an interior balcony over the great room. Primary has its own balcony and ensuite. Pool mechanicals have been overhauled and heater converted to propane.

A thoughtfully renovated former farmhouse on The Hill, within walking distance of Lake Mansfield and the town center. Flooded with light, the home features an eat-in kitchen with marble counters and Liebherr and Bosch appliances, open to a fully glassed family room and second dining area overlooking the backyard. With four bedrooms, two full baths, and the possibility for a first-floor primary suite, this charming home is located in a friendly and coveted neighborhood. Enjoy the backyard four-season studio with French doors leading to a patio. It could be a home office or guest space, as well. The property includes AC and new metal roofs on both buildings. Furnishings are available. Please call us to view this special property.

Carefully Renovated in 2019, this +/- 7200 sqft Main Street Commercial property is currently being utilized as an office building and is fully occupied. The building offers a large conference room, 2 kitchens, 8 second floor offices, 6 offices on the 1st floor, 1 Full bath, 4 1/2 baths

Fully leased with long term tenants! One of a kind location right in the heart of Downtown Great Barrington. Take advantage of this rare investment opportunity. Turnkey property with excellent tenants, updated utilities and well-kept building. This prominent location greets all downtown visitors with outstanding signage, well appointed landscaping and plenty of off-street, private parking for employees and clients. Office suites are clean and bright with high ceilings, wood, tile and carpet floors and exposed beams in the upper units. Within walking distance of everything downtown Barrington has to offer.

Discover a beautifully renovated contemporary home nestled on 4 serene acres, offering you unparalleled privacy.This expansive residence boasts 6 bedrooms and 3 full baths, including a sauna in the first-floor guest bathroom. The primary suite features a spa-like bathroom complete with a soaking tub, while two additional spacious bedrooms upstairs are perfect for guests, complete with skylights for nighttime star gazing.Cozy up by the wood-burning fireplace in the expansive living room, where sliders invite you to the large wrap-around Trex deck--ideal for sipping morning coffee or enjoying sunset cocktails. The open flow from the living room to the dining area and kitchen makes entertaining a breeze.

Experience modern sophistication in this uniquely designed home featuring large, unadorned windows that fill the space with abundant natural sunlight. The open floor plan and expansive outdoor deck create a perfect flow for entertaining. Situated on 10 private acres in low-tax Egremont, this property offers an ideal location with easy access to Egremont, Great Barrington, Hillsdale and the Taconic Parkway. The home boasts a maintenance-free exterior with a durable corrugated aluminum roof, radiant and hydronic heating, central A/C, a new state-of-the-art kitchen, new first floor tile, four bedrooms, 2.5 baths, an art studio with a dedicated sink, and a bonus third floor playroom and gym. Tucked among verdant deciduous trees with an expansive open sky, this home is a tranquil retreat.

FOUR WAYS FARM Set at the corners of Baldwin Hill Rd and Townhouse Hill Rd lies the original farmhouse of Four Ways Farm. With a long history of farming and community, the home, dating to 1850, evokes warmth and charm while being recently updated to serve the modern owner. This Center Hall Colonial features newly refinished wood flooring, an updated kitchen, 2 large primary suites both with newly renovated en suite baths and walk-in closets, a spacious 1st floor bedroom and option for 4th, fresh interior + exterior paint and incredible mature landscaping. At the center of the home lies the original wood burning fireplace in the Family Room open to the Kitchen making a wonderful transition for entertaining. 10 acres of land provides wonderful views from the large sunny deck and lots of

This home has just about everything you're looking for and more!A 4.62 acre private setting, just 5 minutes into Great Barrington and low Egremont taxes! 4 Beds & 4.5 baths with an in law loft apartment. Wide open back yard with plenty of room for a pool if you dont feel like cooling off in the crisp & refreshing Green River at the rear end of the property. First level of home has a primary suite with large jet tub and separate shower. Open the slider and slip onto your screened in porch. Washer dryer on first level as well as den/0ffice. Seperate dining room with open concept living room /kitchen that leads out to the rear deck or screened in porch. Attached over size 3 car garage. Enormous basement. additional barn and plenty of storage wherever you look! Freshly painted and updated!

INCREDIBLE OPPORTUNITY TO FINISH A 3-LEVEL, 6,000 SQUARE FOOT BERKSHIRE DREAM HOME ON 16 PRIVATE ACRES AND A TWO-BEDROOM GUEST HOUSE. ** DESIGN BY Woodhouse Timber Frame Company. ***CONSTRUCTION IN PROGRESS*** Completed: Surveys, land clearing, driveway installed, underground utilities, well, septic, house plans, building permits, privacy berm, foundation, framing, roughed-in plumbing, electric and propane heat, inground pool foundation, floor plans for 3 bedrooms, 4 baths, 2 kitchens, 2 family rooms, attached 2-car garage. GUEST HOUSE: Interior plans for 2 bedrooms, LR, kitchen, and bath over 2-bay garage.

Come see a unique investment opportunity with this charming mixed-use building in the heart of Great Barrington. Ideal for both residential and commercial purposes, it features a versatile ground floor for retail or office space, and a well-maintained upper level with comfortable apartments. The property boasts high visibility, 8 off-street parking spaces, and a vibrant local community. Perfect for entrepreneurs and investors seeking a blend of business and residential potential. Don't miss out on this rare gem in a growing small town!