Unique property with potential for a wide range of educational, recreational, residential or other potential re-development uses. Formerly part of an residential school facility, the property consists of over 11 acres with extensive road frontage on both sides of Route 23. The buildings include: 1) 10,560 sq. ft. gymnasium w/ levels of office/conference rooms, 750 lb elevator, 4 bathrooms, and extensive mechanical infrastructure. 2) Former administrative/dining hall/office building offering 7,597 sq. ft. of adaptable space over 3 levels. Located in Residential (R-2) zoning area. Priced well below assessed value. Virtual tour & floor plans available.

A charming historic home nestled in the heart of Great Barrington, moved to it's location from Main Street in 1858. This delightful detached residence boasts 2,060 square feet of living space across 10 rooms. The living area features a wood-burning fireplace and space for formal dining. The eat-in kitchen, complete with built-ins, adds character. With four bedrooms and two baths, there's ample space with natural light. Hardwood floors flow throughout the home. Outside, enjoy the tranquility of garden views from the covered side porch. There's a gazebo tucked privately in back and plenty of room for a pool. With its classic architectural elements, it's a true gem on beautiful South Street nearby other fine homes. Available fully furnished. Schedule your appointment today.

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.

Prime commercial frontage on Great Barringtons South Main Street. This Large building has been actively run as retail, manufacturing and residential housing for many years. This property is a perfect spot for a live/work scenario or to produce income.Currently this space has been used as two retail fronts, one space for manufacturing, one space for machine repair and two residential rental units on the second floor. With lots of parking the possibilities are endless!

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.

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.

OPEN HOUSE: Sat, May 3rd 11-1PMUnique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has its own kitchen and bath ideal for a business or potential third apartment conversion. Beautiful hardwood floors, original woodwork, high ceilings, and new double-pane windows throughout add timeless character.Located one block from the local tea shop with ample off-street parking and a one-car garage. Schedule you showing today!

OPEN HOUSE : Sat, May 3rd 11-1PMDon't miss this rare opportunity to own an iconic building in the heart of Housatonic. This versatile property features a thriving retail space on the first floor, currently an antique gift store, and two spacious residential apartments upstairs. Each apartment offers two bedrooms, a large kitchen, sitting area, enclosed porch, bathroom, and in-unit washer/dryer hookups--ideal for rental income. The commercial space includes its own kitchen and bathroom, offering the option to continue as a store or convert into another apartment. With hardwood floors, high ceilings, double-paned windows, and updated siding, this property is perfect for investors or those seeking to live and work in one space. Schedule your viewing today!

Nestled ''On the Hill'' in the heart of Great Barrington, this inviting 4-bedroom, 2.5-bath Colonial offers a perfect blend of comfort, style, and location. Just minutes to the tranquil Lake Mansfield, this home is ideal for those seeking both convenience and serenity.The generous living room is perfect for both family gatherings and quiet evenings, featuring a cozy pellet stove fireplace that creates a welcoming atmosphere.The eat-in kitchen offers ample space for cooking and entertaining, while the adjacent screened-in deck provides an ideal spot to relax and enjoy the outdoors, whether you're hosting friends or savoring a morning coffee. 4 bedrooms, including a primary suite with an ensuite bath. The additional bedrooms provide flexibility for family, guests, or a home office.

1880 4 Bedroom Colonial in a beautiful Pastoral setting. Open Living and Kitchen plan.Permitted wood burning stove in living room. Second floor has 3 bedrooms, one is a generously sized en-suite. Garage was converted partially for a perfect home office or 4th bedroom. Laundry facilities and half bath located on 1st floor. Outdoor space includes a deck, a partially fenced portion of yard for a dog or children, and lots more level ground for a future pool or recreation. Minutes to town of Great Barrington and all the Berkshires have to offer.

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.

Nestled ''On The Hill'' in one of Great Barrington's most sought-after neighborhoods, this well-built expanded Cape sits on 1.69 acres, offering the perfect blend of privacy, charm, and space. From the moment you arrive, the home's warmth and character welcome you in, promising both comfort and versatility for its next steward.

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.

A Contemporary Cape loaded with charm is beautifully upgraded. The front porch addition has added a welcoming first impression. The current owner has reimagined the flow and improved room utilization on the first floor to create an open concept living room and kitchen area with cathedral ceiling, wood fireplace and French doors leading to a large backyard deck. The separate dining space also has a fireplace that adds both warmth and charm to those winter evenings. Two flex spaces for Exercise/yoga and a bonus 4th bedroom/office with bathroom on the main level create options. A primary suite plus two more bedrooms and bath upstairs complete the inner living spaces. The backyard, while showcasing a hot tub is centrally located for easy living and entertaining.

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.

Positioned in the center of downtown Great Barrington, this stand-alone commercial building offers an opportunity for medical, professional, or retail use. Fully renovated in 2019, the property features modern systems and finishes while maintaining strong curb appeal along busy Rt 7. Inside, the space is clean and flexible - ideal for a medical office, wellness center, or customer-facing business. Large display windows, prominent signage, and dedicated off-street parking make this property stand out in a high-traffic area. The layout is efficient and adaptable, allowing for private offices, open work areas, or treatment rooms as needed. Surrounded by shops, restaurants, and other service-based businesses, this is a location that offers high visibility, accessibility, and long-term value.

New York style living in the Berkshires! This last unit available in this fabulous setting! Poised above Main Street Great Barrington, this Southworth Penthouse Condo offers 1,974 sq ft comprised of 2 bedrooms, 2 full 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.