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.

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.

Look out over pristine Windemere Lake from this exceptional 6.25-acre waterfront parcel. With 300 feet of lake frontage and a westerly orientation, the site offers stunning sunsets, exceptional privacy, and a peaceful connection to nature. Windemere Lake is a private, non-motorized lake--ideal for paddling, swimming, and fishing on long summer evenings. This rare opportunity in a quiet, well-maintained community invites you to create your Berkshire dream retreat: build at the water's edge, moor your boat, string up a hammock, and let the serenity settle in.

Look out over pristine Windemere Lake from this exceptional 10.35-acre waterfront parcel. With 250 feet of lake frontage and a westerly orientation, the site offers stunning sunsets, exceptional privacy, and a peaceful connection to nature. Windemere Lake is a private, non-motorized lake--ideal for paddling, swimming, and fishing on long summer evenings. This rare opportunity in a quiet, well-maintained community invites you to create your Berkshire dream retreat: build at the water's edge, moor your boat, string up a hammock, and let the serenity settle in.

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.

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.

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.

Experience the epitome of luxury and leisure in this exceptional custom-built contemporary home, nestled within a prestigious lakefront community. Sited on over four acres, this property offers exclusive access to a private beach and tennis courts, ensuring a lifestyle of both privacy and recreation. Boasting a sun-filled open floor plan, this residence features three well-appointed bedrooms and two full and one half baths, including a convenient first-floor primary suite. The heart of the home is the updated kitchen, complete with new appliances, which flows seamlessly into the living spaces, perfect for entertaining and everyday living.Relax in the comfort of your screened-in porch or gather around the warmth of the wood-burning fireplace. Close to Butternut and Great Barrington.

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.

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!

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.

Classic turn-of-the-century Berkshire residence on the Hill. Rich w/ history & ready for new memories, this home is a rare gem in an ideal location. Lovingly maintained by the same family for over 60 yrs. Nestled on 1.6 acres, this 4,000 SF residence offers 5 BRs, 3.5 BAs & an abundance of historic charm. Original wood floors, high ceilings & period details fill the home, while the grand staircase & 3-season porch add an air of elegance. The spacious kitchen, butler's pantry, oversized living room & large formal dining room are ideal for entertaining. Attached greenhouse & beautifully fenced garden with a shed, detached three-car garage, and expansive basement complete this remarkable property, just moments from town yet a world of its own!

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!

Nestled in East Mountain State Forest on a private road yet minutes from downtown and Ski Butternut, this meticulously maintained home is move-in ready. A heated sidewalk leads to a foyer mudroom with radiant heat. Cathedral ceilings with a wood-burning fireplace and large windows in the living room, overlooking a wonderful patio with a fire pit. An open kitchen with eat-in granite counter, formal dining room, screened porch with additional gas fireplace; powder room, two ensuite bedrooms plus an additional bedroom upstairs; another ensuite bedroom at garage level, with a laundry room and huge basement storage space. Two-car attached garage, HVAC system plumbed for oil, propane, or solar. Hike miles of wooded trails accessible from the back yard. Some furnishings are available separately.

Luxury Living in the Heart of the Berkshiresnestled on a picturesque cul-de-sac with access to community pool, this stunning new construction spans 4200 sf, located less than a mile from downtown Great Barrington. The home welcomes you through a covered portico into a soaring cathedral great room, bathed in natural light from a wall of windows overlooking lush woodlands and a screened porch. The open-concept layout seamlessly connects the living, dining, and kitchen areas, perfect for both entertaining and everyday living. The gourmet kitchen features top-of-the-line appliances, quartz counters, a spacious island. A split-bedroom design ensures privacy, with a luxurious primary suite offering a spa-inspired bath. HOA for lawn and snow removal for easy care living. See supplement

The Woodlands, A RARE OPPORTUNITY TO OWN YOUR OWN 74-ACRE PRIVATE SANCTUARY IN THE HEART OF GREAT BARRINGTON.This property abuts the Thomas & Palmer Brook preserve on three sides, is a two-minute drive to Ski Butternut and five minutes to dining and shopping in downtown Great Barrington. A picturesque pond flows into a babbling brook right outside of the large cathedral-ceiling primary suite's windows. Big open lawns, a hayfield and an orchard surround the five bedroom three bath house, along with pristine woodlands that rises to the top of Three Mile Hill ridge. Hike and snowshoe throughout with private points of access into an additional 267 acres of protected Berkshire Natural Resources Council land trust.