Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane fireplace, wide plank floors, large kitchen, first floor bedroom, office and a welcoming floorplan emanating warmth and comfort. Perfectly situated mere moments from Butternut Basin (one of the Berkshires top ski destinations) and a short drive from vibrant downtown Great Barrington, this charming sanctuary invites you to experience the best of Berkshire living.

Immaculate and sparkling home within walking distance to downtown. Easy care with 4 bedrooms, 2.5 baths, open plan, gleaming wood floors, high ceilings, loads of light, updated chef's kitchen with brand new appliances, fireplace in large living room, family room, first floor laundry, ensuite spacious primary. The walk out lower level has a work out room or office and a two car garage. Quiet neighborhood, sunny lot. Lovely home with town water, town sewer and natural gas. New washer, dryer, furnace and water heater.

Great New England farmhouse with really nice views. Common rooms are amply sized and the kitchen great room is perfect for many different activities. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many extras - structural renovations in 2004, central air, in line generator, in ground pool, screened porch and so much charm. Nice 3.89 acre parcel with detached garage.

This 1700s Dutch farmhouse is filled with history and was originally utilized for farming and wagon manufacturing. The residence boasts spacious, well-lit rooms with stunning wide plank wood flooring, offering a grand setting for gatherings and entertainment. The sizable kitchen and dining area, along with four bedrooms and two fully renovated bathrooms, provide ample living space. A highlight of the property is the beautiful sunroom that overlooks the backyard, complete with a heated gunite pool. Additional features include a workshop, seasonal living room, bonus room and studio within the carriage barn, offering potential for further customizable living spaces.

A must-see exceptional Egremont parcel on a coveted and beautiful country road. A gracious stone bridge leads into the heart of the property. Complete with an approved building permit for a primary residence on one of the parcels, the well & utilities are in place, and a driveway is already in, setting the stage for construction to begin on that parcel. With enough frontage & acreage for a guest house additionally on second approved building site. Embrace the chance to build your dream home in a location that offers both serene privacy & convenient access to New York & the Berkshires. With all building permitting completed, this is the time to build! There is a building plan available & can be built to suit. Intented as a one owner compound, must be kept as one property for 15 years.

WELL MAINTAINED FARM HOUSE WITH THE BONUS OF A SEPARATE APARTMENT! Ideal for friends, family, plus the benefit of rental income. The backyard is an oasis to find peace after a busy day. Extensive perennials, and a beautiful mountain and pasture view.. Simplicity defined when relaxing on the rocking chair front porch. Detached barn and workshop. Close proximity to the Waldorf School, Simon's Rock College, and Main Street Restaurants and Shops. So much potential and plenty of room for home office.

WELL MAINTAINED FARM HOUSE WITH THE BONUS OF A SEPARATE APARTMENT! Ideal for friends, family with the added benefit from rental income. The backyard is an oasis to find peace after a busy day. Extensive perennials, and a beautiful mountain and pasture view.. Simplicity defined when relaxing on the rocking chair front porch. Detached barn and workshop. Close proximity to the Waldorf School, Simon's Rock College, and Main Street Restaurants and Shops. So much potential and plenty of room for home office.

POOL COMMUNITY: BUILD YOUR DREAM HOME: Open plan living with, first floor master, fireplace, screened porch, high ceilings, two car garage, community pool. HOA covers all lawn maintenance, plowing, shoveling up to the front door. Quality New Construction. This price cannot be matched. 10 months to move into your beautiful new home. Photos are from a similar home with the same floor plan in the community, with upgrades. Build your dream home on one of the other beautiful lots. Single level with 2100 square feet or as large as 3800 square feet. 3-5 bedrooms with prices beginning at $689,000.

Residential development opportunity! This expansive parcel offers potential for 17 building sites, ideally located just minutes from downtown Great Barrington and Butternut Ski Area. The property abuts the iconic Appalachian Trail, offering tranquil access to nature and recreation. Build a cul-de-sac community where residents can experience the best of the Berkshires--hiking, skiing, and vibrant town life--all just moments away!

Embrace the extraordinary at 395 Park St. North, where history meets opportunity. This stunning red brick 6,833 sq.ft. warehouse, once a bustling trolley barn, boasts high ceilings and a rich industrial charm, with river views while exploring the spacious layout, featuring 3 updated bathrooms, a newer roof and building updates. It has versatile separate offices and garage/shop areas. With ample parking and loading docks, envision endless possibilities from manufacturing to art gallery or more. Conveniently located near dining, parks, and cultural attractions, this property invites you to re-imagine living or workspace with style and creativity. Total acreage and assessment include two lots.

New York style living in the Berkshires! Poised above Main Street Great Barrington, this Southworth Penthouse Condo offers 1,566 sq ft comprised of 2 bedrooms, 2 1/2 baths, kitchen, laundry, storage, dining and living rooms with high ceilings and, views to the West. 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! (#13)

Situated ''on the hill'' in Great Barrington, this sprawling ranch home offers the perfect combination of peace, privacy, and proximity to nature. Abutting McAllister Wildlife Refuge, you'll enjoy access to 94 acres of stunning conservation land and Green River access.The 5-bedroom, 2.5-bath single-level layout is filled with potential, whether you're looking to modernize or customize the space. With a solid foundation and prime location, this home offers a fantastic opportunity to enhance its value through thoughtful renovations.The quiet backyard, complete with a cozy patio, adds to the home's appeal, making it ideal for both relaxation and entertaining. A fantastic opportunity in an area where value endures.

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.

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.

A stylish four-bedroom, three-bath home located at the top of a sweeping drive. The traditional exterior gives way to a fresh, contemporary open floor plan, with a dedicated dining room that could also serve as a den or office. A large screened porch and sunny deck off the great room expand the living space, ideal for large gatherings and enjoying the landscaped five-acre property. All bedrooms are on the second floor, including an en-suite primary and three guest rooms, plus a renovated guest bathroom. The home also features an attached 2-car garage, powder room, ample closet space, and dry storage in the clean basement. One can hike their own property to higher elevations. Nearby Great Barrington center. Furnishings available outside 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.

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.

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.

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 !

Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond, just minutes away, this home is a haven for those who crave both serenity and adventure.Where Modern Elegance Meets Natural Beauty A Grand Welcome - A wraparound deck, inground pool, and upper balcony invite you to take in the forested surroundings, framed by black aluminum railings and Trex boards built for beauty and longevity.