Great Barrington Real Estate

Nestled in the heart of the picturesque Berkshires, Great Barrington, Massachusetts, is a charming town that effortlessly blends small-town warmth with a vibrant cultural scene. Known for its stunning natural beauty, Great Barrington offers residents and visitors alike the chance to embrace the great outdoors, with the majestic Berkshire Mountains providing a breathtaking backdrop for a variety of recreational activities. Whether you're hiking the trails of nearby Monument Mountain or enjoying a leisurely stroll along the banks of the Housatonic River, the area's natural splendor is truly captivating.

Great Barrington is also celebrated for its rich arts and culture. The town boasts a lively downtown area filled with unique boutiques, artisanal shops, and farm-to-table restaurants that showcase the region's culinary delights. The Mahaiwe Performing Arts Center, a beautifully restored theater, hosts an array of performances, from live music to film screenings, making it a cultural hub that draws in visitors from all over.

With a strong sense of community, Great Barrington is home to a diverse population that values both tradition and innovation. The town's commitment to sustainability and local initiatives fosters a welcoming atmosphere where neighbors know each other by name. Families will appreciate the highly-rated schools and the abundance of outdoor activities that promote a healthy, active lifestyle.

In Great Barrington, every season brings its own charm, from the vibrant colors of fall foliage to the winter wonderland perfect for skiing and snowboarding. With its idyllic setting, rich culture, and strong community spirit, Great Barrington is not just a place to live; it's a place to thrive. Come discover the magic of this Berkshire gem!

Newest Listings in Great Barrington

$3,695,000

4 Beds ⋅ 6 Baths ⋅ 73568631 MLS

STILL HOUSE brings a new level of contemporary design to the Berkshires—quietly luxurious, exquisitely detailed, and made to be lived in. Minutes from the center of Great Barrington, this newly completed 5,148-square-foot home pairs the distinctive vision of acclaimed Brooklyn studio Me & General Design with exceptional craftsmanship and materials throughout. Four bedrooms, five-and-a-half baths, a heated saltwater pool, bespoke spa and fitness spaces, solar energy and exceptional privacy make this as much a retreat as a home.Preserved stone walls from the original structure bring history, texture and a distinctly Berkshire character to the new architecture. The main living level opens into a dramatic kitchen, dining and living space with cathedral ceilings, two stories of glass and views into the surrounding landscape. The custom Porcelanosa kitchen features richly veined stone, a substantial island, induction cooking, double ovens, integrated refrigeration, microwave drawer, dedicated coffee station and breakfast nook. A separate stone-walled sitting room offers a restored wood-burning fireplace and a more intimate place to gather.The main-level primary suite makes true one-floor living possible, with direct deck access, a walk-in closet and private bath. Upstairs are two additional bedrooms and two full baths, plus a library/sitting area overlooking the great room. The light-filled lower level includes a private fourth bedroom suite, home cinema, office, yoga/Pilates studio, traditional Canadian red cedar sauna, full bath and laundry.High-efficiency multi-zone heat pumps, radiant lower-level heat and solar energy support year-round comfort. Outside, the heated saltwater pool is set against mature trees, with decks, paths, stonework and an outdoor fireplace creating places to gather throughout the seasons. Landscape design by Windy Hill Farm complements the natural setting.Lake Mansfield, Monument Mountain, Ski Butternut, Tanglewood, Jacob's Pillow and the restaurants, shops and cultural life of Great Barrington are all within easy reach.STILL HOUSE is the inaugural residence of NUESTRA Collection, a series of design-led Berkshire homes created around a simple idea: exceptional contemporary design should feel as good to live in as it is to look at.

114 Christian Hill Rd, Great Barrington

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.

$2,149,000

4 Beds ⋅ 5 Baths ⋅ 73558556 MLS

Luxurious, fully-modernized 1850s Victorian in the heart of Great Barrington. Elegant, four-story 3600 sq. ft. newly renovated clapboard and shingle house with covered porch. Meticulous renovation features chef's kitchen, 4+ bedrooms, 4.5 bath, second floor and basement laundry, walk-out finished basement with private entrance and bathroom, perfect for guest suite or professional office. High-end appliances, including 6-burner Wolf stove and Bosch French door refrigerator with two freezer drawers, Bosch dishwasher, wine cooler and microwave in the island. Full-size prep sink in the kitchen island, 36'' farmhouse sink in the main counter. Cabinets are all-wood with soft-close drawers and doors; vented whole-house A/C and heat pump with propane back-up; primary bath with heated floor gas grill. EV charging station in driveway. Walking distance to Lake Mansfield and Main Street shops, restaurants and theaters. House can be sold furnished.

10 Berkshire Heights, Great Barrington

Listing courtesy of Listing Agent: Suzann Ward from Listing Office: Housatonic Real Estate.

$1,200,000

73556496 MLS

Own a part of history..."Blue Stone Manor". Available for the first time in over twenty years. Create your own 'one of a kind' estate on a piece of the land houses the "Gilded Age Tudor" mansion that is associated with McKim, Mead & White. West Sheffield Road is one of Great Barrington's most picturesque country Road. Offering a quintessential Berskhires landscape of rolling meadows, mature woodland and sweeping mountain vistas. Enjoy privacy and yet all the conveniences of walking to acclaimed restaurants, cultural attractions, and the heart of Great Barrington. Easy access to Tanglewood, Butternut Mountain and the Appalachian Trail. This 3.69 acres is ready for a new steward with 300' of frontage on West Sheffield Road.

Lot 2 West Sheffield Road, Great Barrington

Listing courtesy of Listing Agent: Shelly Tretter Lynch from Listing Office: Kinlin Grover Compass.

$104,900

73553500 MLS

Come enjoy the outskirts of Great Barrington just 1 mile off of Rte23/7 intersection, this 7 acre lot on a dead end private way. Just off of Route 23 this land abuts a Commonly owned lot of the East Mountain Estates community adding a buffer between you and Route 23 also a view of a pond. Watch the area wildlife come to the pond while enjoying the outdoors on your future deck/patio area you are going to build. There is a downslope from the road but level when you get to the main portion of the lot. Drive would be cut in along the slope to have a more gentle access. Utilities are underground, HOA fees will apply to help with maintenance of the roadway and common areas.

5 East Mountain Rd, Great Barrington

Listing courtesy of Listing Agent: Susan Como from Listing Office: Buy Rite Home.

$1,995,000

73537817 MLS

Over 30,000 square feet of Commercial Property in the heart of Great Barrington. Ideal Route 23 location, adjacent to the retail-commercial district and CSX Freight Rail Line. Currently consisting of 5 Structures (13,233 sq.ft, 6,600 sq.ft,, 4,000 sq.ft., 5,000 sq.ft. & 1,554 sq.ft.) with ample on-site parking. Previously used by a major Plumbing Distribution and Warehouse Company. Use 'as is' or create new structures on this 1.63 Acre Parcel. Zoned B2 with Public Water & Sewer.

20 Maple, Great Barrington

Listing courtesy of Listing Agent: Steven Weisz from Listing Office: William Pitt Sotheby's International Realty.

$825,000

73531420 MLS

Lake Mansfield Lakefront Lot. Rare chance to live on a private road, on the prettiest of Lakes, minutes to downtown Great Barrington. Over 3 Acres with 175 feet of frontage in the most of bucolic settings. Make your dreams come true.

Lake Mansfield Rd, Great Barrington

Listing courtesy of Listing Agent: Steven Weisz from Listing Office: William Pitt Sotheby's International Realty.

$550,000

2 Baths ⋅ 73476339 MLS

An iconic Great Barrington landmark, the beloved “Little Store” presents a rare opportunity to own a high-visibility commercial property on Main Street in one of the Berkshires’ most vibrant downtown corridors. Just a short stroll to the center of town, the location offers steady foot traffic and excellent exposure surrounded by restaurants, boutiques, galleries, and year-round activity. Home to a well-established antique business for over 50 years, the space offers flexibility for retail, gallery, studio, office, specialty shop, or creative mixed-use potential (buyer to verify use). An upstairs apartment was previously owner-occupied, offering possible live/work or income potential. Business and inventory available separately and negotiable.

88-90 Main St, Great Barrington

Listing courtesy of Listing Agent: Freddy Friedman from Listing Office: Birch Properties.

$550,000

4 Beds ⋅ 2 Baths ⋅ 73475779 MLS

Building has been used as an antique business for the last 50 years. Seller had previously lived in the upstairs apartment. Located across the street from Mend and Calgary's and .5 miles from downtown Great Barrington. Selling as is, business and inventory for sale separately - negotiable with owner. Near all the cultural events specific to the Berkshires!

88-90 Main St, Great Barrington

Listing courtesy of Listing Agent: Freddy Friedman from Listing Office: Birch Properties.

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