This bucolic destination offers no shortage of outdoor activities, epicurean delights and an unmatched arts and culture vibe.


If you’re looking for the perfect escape from it all, look no further than Great Barrington, Massachusetts. With its sprawling, green hills, the breathtaking Berkshire Mountains, and vibrant downtown shopping and dining, it’s easy to get lost in the peace and tranquility of this charming town. Take a drive up East Street, lined with beautiful Victorian houses and framed by tall, old trees. Let your worries melt away as you marvel at the lush gardens and flowering landscapes in every yard. As you move further away from town, the roads lead you deep into the wooded hills. Enjoy a leisurely hike and spot birds singing from high above or meander through quaint back roads, taking time to pause and explore their charming and picturesque New England charm. After an outdoor adventure, venture into downtown Great Barrington and peruse the selection of local, independent shops, savor delectable treats at the bakeries and eateries, or enjoy an art walk on Main Street and view sculptures, pottery, and photographs created by talented local artisans. On warm summer days, treat yourself to a cool drink at a local pub and enjoy the musical accompaniment of live performances. With its unparalleled beauty, charming attractions, and warm and welcoming people, it’s no wonder why so many are seeking the perfect escape from it all and calling Great Barrington their home away from home.


Exploring the beautiful outdoors of Great Barrington, Massachusetts is an amazing experience. Whether you’re looking to bike, hike, fish, raft, ski, or snowboard, you’ll find the perfect activity for all skill levels and ages. Start by exploring the hills and valleys of the Berkshires, taking in the spectacular views as you pedal through winding roads. Head to Lake Buel, a popular spot for fishing with lots of great catches. For those who want to stay closer to land, you can take a rafting trip down the Housatonic River. For those looking to tackle the snow, hop on your skis and hit the slopes at Ski Butternut or even go snowboarding at Bousquet Ski Area. So make the most of the outdoors and experience all Great Barrington has to offer.


The town of Great Barrington, Massachusetts is full of delicious, locally-sourced food and dining options! From mom-and-pop restaurants serving up family-favorite dishes, to upscale bistros featuring farm-to-table ingredients, there’s something for everyone to enjoy. Enjoy a wood-fired pizza and fresh, house-made pastas at Uno Trattoria, savor seafood dishes with views of Monument Mountain at Allium, or snack on home-baked pies at Sugarsnap. Enjoy a truly unique meal at Bueno Y Sano, with burritos and quesadillas made from freshly-grilled veggies. Try a craft brew from Big Elm Brewing and indulge in a chocolate cake from Samuel’s Sweet Shop for a delightful local dining experience.


Great Barrington, a quaint New England town in western Massachusetts, is renowned for its commitment to the arts and culture. Every weekend, locals and tourists alike gather to admire and support the creative works of local and visiting artists in the galleries of Railroad Street, located at the heart of town. Throughout the year, a variety of events are held for locals to participate in and celebrate the arts, including theatrical performances, musical concerts, film screenings, and public readings. For those wishing to take their appreciation of the arts to the next level, The Mahaiwe Performing Arts Center in Great Barrington offers a wide range of live performances of all genres. The renowned non-profit has welcomed artists from all over the world to the stage and proudly presents Broadway hits, comedians, rock bands, classical orchestras, dance ensembles, and family friendly programming. There’s something for everyone in Great Barrington.


As you step into Great Barrington, your heart fluttering with anticipation. You meander through the vibrant, colorful stores and retail spots, delighting in the selection of locally influenced and sourced products, bright new fashions, and other Berkshire lifestyle necessities. Everything here is calling to you, and you find yourself pausing in every store, unable to resist the temptation to shop. You’ll easily admire each piece, eagerly searching for something that fits you just right for any Berkshire season. It is hard to choose when everything looks so beautiful, but eventually, you find something that catches your eye and make it your own. It is amazing how much joy shopping in Great Barrington can bring!


The little town of Great Barrington, Massachusetts, is the perfect destination for a relaxing spa getaway. With its small-town charm and spectacular scenery, it is a haven for those seeking an escape from their everyday routine. Spend a day enjoying a full range of treatments, such as a Swedish massage, facial, or seaweed wrap, in one of the many spa locations around town. Afterwards, take a leisurely stroll through the town’s quaint downtown streets, lined with antique shops, cafes, and art galleries. Whether you’re in search of relaxation, adventure, or some time to reflect, a spa getaway in Great Barrington is the perfect way to treat yourself.


Great Barrington is the perfect family fun destination. Whether it’s exploring beautiful Berkshire Mountain scenery, hiking the lush trails, or visiting historic landmarks, there’s something for everyone to enjoy! Take a drive up Route 7 for some window shopping in downtown, visit Monument Mountain for some fresh air, or explore The Bousquet Ski Resort for some skiing and tubing fun. Visit The Berkshire Scenic Railway for an exciting train ride and then enjoy the fresh made-from-scratch Italian ice from White Wheel Ice Cream Co. Great Barrington has something for everyone! Come experience the amazing activities and attractions of Great Barrington!


Whether renting or buying a Great Barrington home or condo, Great Barrington real estate has it all. Great Barrington is an ideal location for those seeking the perfect balance between small town charm and city amenities. The town offers a range of housing options, from modern condos and townhomes to older homes with plenty of charm. With an array of top-notch schools and nearby activities, the community is great for growing families. Plus, with nearby recreational attractions and plenty of shopping, Great Barrington is an excellent option for those looking for an escape from the city hustle. Whether you’re a first-time buyer or seasoned real estate investor, Great Barrington offers a safe and exciting investment opportunity.


For more information regarding Great Barrington homes for sale or to list your home with a premier Great Barrington real estate agent, contact Alexis Prisendorf and his team today  via phone or email.


Discover the available Great Barrington properties below.

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Great Barrington MA

Great Barrington, Massachusetts 01236

CONTEMPORARY COUNTRY HOME AND A BARN WITH OFFICE ABOVE! A rare combination of attributes are found in this thoughtfully sited home. Open sunny grounds bordered by woods and trails, with a lovely view to Flag Rock off your rocking chair front porch. Open plan living with fireplace in LR, a practical layout for both family living and entertaining.
MLS Number 240506

Great Barrington MA

12, 16, 18 Rosseter St, Great Barrington, Massachusetts 01230

A rare opportunity to acquire 3 duplex's in the bustling downtown of Great Barrington! These 3 houses are all next to each other and surrounded by very popular businesses and restaurants. Close to anywhere in downtown with ease. They have a very long established rental history. With the popularity and growth of Great Barrington the potential is endless.
MLS Number 240509

Great Barrington MA

1 Deer Trail, Great Barrington, Massachusetts 01230

Stunning, turnkey home situated on 1.6 acres, nestled within a peaceful cul-de-sac. Exceptional residence renovated by an architect and a designer. Features 4 bedrooms plus office/den, 3 full bathrooms, soaring ceilings with skylights and a wood-burning fireplace.
MLS Number 240426

Great Barrington MA

29 Church St, Great Barrington, Massachusetts 01230

Elegant older Greek Revival Victorian located just one block off of Main Street in Great Barrington. Barn to the back of the property. Has three units currently (all are vacant), was in use as a dental office and two rental apartments. Main Floor (dental office area) has no kitchen. Could be converted back to single family and would be a wonderful large home for a growing family.
MLS Number 240531

Great Barrington MA

29 Church St, Great Barrington, Massachusetts 01230

Elegant older Greek Revival Victorian located just one block off of Main Street in Great Barrington. Barn to the back of the property. Has three units currently (all are vacant), was in use as a dental office and two rental apartments. Could be converted back to single family and would be a wonderful large home for a growing family.
MLS Number 240409

Great Barrington MA

22 Monument Valley Rd, Great Barrington, Massachusetts 01230

Easy living in this open plan three bedroom two bath home on Monument Valley Road near Ski Butternut. Sited on over an acre, the house is sited nicely off the road with a long driveway to the house with plenty of paved parking for guests. Off the great room is a three-season porch overlooking the very private backyard with two sheds and hot tub.
MLS Number 240380
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