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.

Welcome to your dream investment opportunity or multi-generational living paradise! Nestled on a tranquil side street, this newly renovated two-family home offers the perfect blend of modern amenities and charming character. Located just minutes away from vibrant town parks, scenic hiking trails, the serene river walk, a local co-op, and a bustling shopping area, this property provides an ideal lifestyle for both relaxation and convenience. Enjoy your wrap-around front porch, a perfect spot for morning coffee or evening relaxation. The property boasts ample parking, ensuring convenience for all residents and guests. The lush surroundings include beautiful fruit trees, gardens, back patio and fire pit.

Welcome to your dream investment opportunity or multi-generational living paradise! Nestled on a tranquil side street, this newly renovated two-family home offers the perfect blend of modern amenities and charming character. Located just minutes away from vibrant town parks, scenic hiking trails, the serene river walk, a local co-op, and a bustling shopping area, this property provides an ideal lifestyle for both relaxation and convenience. Enjoy your wrap-around front porch, a perfect spot for morning coffee or evening relaxation. The property boasts ample parking, ensuring convenience for all residents and guests. The lush surroundings include beautiful fruit trees, gardens, back patio and fire pit.

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.

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.

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.

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 1,974 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.

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

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.

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.

CRISSEY FARM is available. Condo #5 is 6707 sq. ft., it is one of the largest Meeting/Event spaces in the Berkshires. Built in 2007 with large open plan with room for up to 200 seated patrons, 2 fireplaces, Bar and ADA Bathrooms. Fully sprinklered. Air Conditioned. Generous Parking for over 185 cars. High visibility on Route 7. Use the space as is or convert into Professional Office Suites, Performance/Educational space, or something new.**Crissey Farm receives the benefit of reduced electric and hot water costs, due to its inclusion in a power cooperative with its neighbor.****Acreage & Parking is for the entire Condo Association use.

122+ Acres of Land in Egremont & Sheffield Only. Over 700 feet of frontage on Sheffield-Egremont Rd on the Egremont / Sheffield Border. Former use as Golf Course for the Egremont Country Club. *Does not include any acreage in Great Barrington. See MLS # 241894 for the full parcel of 225 Acres.

The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved the property significantly to include: AC system, new kitchen, structural upgrades, new parking lot and landscaping. Solid income and occupancy history. Known for its beauty, the Inn features spacious public rooms with high ceilings, fireplaces and historical details intact, and large suites, each with a bathroom. A short walk to the many restaurants & shops of the town & minutes to Tanglewood.

The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved the property significantly to include: AC system, new kitchen, structural upgrades, new parking lot and landscaping. Solid income and occupancy history. Known for its beauty, the Inn features spacious public rooms with high ceilings, fireplaces and historical details intact, and large suites, each with a bathroom. A short walk to the many restaurants & shops of the town & minutes to Tanglewood.