Great Barrington, MA Homes for Sale with Acreage

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

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

Lauren Molk ELYSE HARNEY REAL ESTATE

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming

Eric Steuernagle FAIRGROUND REAL ESTATE, INC

CLASSIC ARCHITECTURE WITH CONTEMPORARY ELEGANCE! A beautifully maintained home set back from the road. Exceptional landscaping embraces the property, offering a private sanctuary. A front porch welcomes you to the first floor. A light-filled,capacious living room, dining room with a fireplace opened to both main rooms, a primary suite with two walk-in closets, a 1/2 bath, and study open to a

Mandy Victor-pieczarka STONE HOUSE PROPERTIES, LLC

New Build Contemporary. Timbercraft Homes & Rosengren Architects collaborated to create this Contemporary 1584 square foot 2 bedroom home. Clean lines and simple one level living. Energy efficient Home with beautiful oak floors, custom kitchen open to dining and living room. Primary bedroom spacious and bright with well appointed bathroom and walk-in closet. Fireplace, dual fuel heating and AC. 1

Mark Rosengren LANCE VERMEULEN RE, INC

SWEEPING MOUNTAIN VIEWS less than 5 minutes to Main Street. Sited on 5+ acres, this stylish contemporary is located in the most desirable section of Great Barrington. The home has an open living/dining/kitchen floor plan with a gas fireplace and huge windows taking in the view. A screened porch is conveniently located off the kitchen. The first floor also has a primary bedroom suite with full

Tom Lynch COMPASS MASSACHUSETTS , LLC GB

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

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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

Claire Pollart LANCE VERMEULEN RE, INC

Artist Retreat / Family Compound! This very special property has a lot more to offer than anything on the market with three separate living/working spaces all thoughtfully designed for inspiration and comfort! Completely remodeled from top to bottom, the main house has three bedrooms, three bathrooms and featuring in-floor radiant heat under reclaimed ancient teak floors. There is a first floor

Ryan Lane Gilcrest Properties

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

Lawrence Reilly BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

1815 Antique Alford Colonial Beauty on 13.5 Acres! It has been over 25 years since this one of a kind property has been listed for sale. Not only does this home sport 4 bedrooms and 3 1/2 bathrooms, but it also has a fabulous two-story barn-like structure ready to be made into a terrific entertainment area for events large and small. Did you know that Alford was one of the first Berkshire

George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Welcome to this beautifully updated home with frontage on the serene Williams River, just a short drive from downtown Great Barrington. Renovated in 2017, this home boasts modern convenience with cozy charm. Step inside to a bright, open kitchen featuring granite countertops, stainless steel appliances, a farmhouse sink, and Kraftmaid cabinetry. The first-floor primary suite offers peaceful

Tony Segalla LANCE VERMEULEN RE, INC

Nestled on a quiet country road, this well-kept ranch offers the ease of single-level living with ample space to relax, entertain, and make your own. The home features an inviting floor plan with plenty of natural light and room for upgrades, allowing you to personalize each space to your taste.Enjoy seamless indoor-outdoor living with a large back deck--perfect for gatherings or quiet mornings

Tony Segalla LANCE VERMEULEN RE, INC

Nestled on 6.6 peaceful acres, this beautifully renovated country Cape offers exceptional privacy just minutes from town. Set well back from the road, the home enjoys a quiet, convenient location surrounded by mature trees and gardens.Inside, a spacious dining room features a striking stone fireplace, while the large living room showcases wood floors that extend throughout. Every detail has been

Allison Rada STONE HOUSE PROPERTIES, LLC

This rare find, located on the Great Barrington/Monterey line, offers the right buyer a unique opportunity to live, work, and play in the heart of the Berkshires. Situated on 4.32 acres, this 1958 ranch-style home has evolved over the years into a sprawling 5,200 square-foot property boasting endless potential. While it currently serves as an owner-operated wellness facility, an expansive

Cortney Dupont COHEN & WHITE ASSOCIATES

This historic 4-bedroom 3.5-bath home sits on a beautifully landscaped 1-acre lot surrounded by ornamental trees, vibrant flower gardens and mature plantings. Originally built around 1800, this comfortable well-maintained house features high ceilings, warm wood flooring, and plenty of period charm. The main level welcomes you with a spacious living room accented with Greek Revival moldings, an

Vashti Poor LANCE VERMEULEN RE, INC

First-time for this treasured dwelling to be available for purchase. This magical setting surrounded by lush gardens and plantings is just the beginning of the enchantment. Distant mountain views to the east brings your viewscape to Butternut Ski & beyond. Inside the dwelling is a large open living space & kitchen on the first floor. Separately, there is a first-floor Ensuite. Abutting the first

Thomas Doyle, Sr. BISHOP WEST REAL ESTATE

Two beautifully renovated duplexes within walking distance to the charming village of Housatonic. Enjoy scenic views of the Housatonic River from each unit. All utilities are separate, making this an ideal investment. All units are fully rented.

Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

HIDDEN GEM!!! Enjoy the best of both worlds with privacy in a country setting, only minutes from town. Thisbeautiful property is set back off the road in a lovely clearing, surrounded by 2 acres of woodsfor privacy. Mature perennial gardens enhance the natural beauty of this saltbox-style home.Solidly built in the 1980s with many upgrades including; A new kitchen (2021) with all newappliances,

Suzann Ward HOUSATONIC REAL ESTATE

Escape the expected and discover the art of effortless living on Terra Ferma Drive. Tucked away on a private dead-end road in coveted South Egremont, this nearly new (built within 5 years) residence redefines one-level luxury. Imagine a home where every detail is designed for comfort and ease - no steps, just seamless flow leading you first to a beautifully appointed kitchen, the true heart of

Tony Segalla LANCE VERMEULEN RE, INC

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

Mark Rosengren LANCE VERMEULEN RE, INC

THE GOAT......This exceptional Berkshire minimalistic sensation has been architecturally designed to maximize the open floor plan concept while being mindful of private work/play spaces. A showpiece with 12+ acres of privacy surrounds you while the panoramic western views in every season bring you peace and calmness. The walls of glass integrate nature and the tranquil spellbinding views with

Mary Jane White COHEN & WHITE ASSOCIATES

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,

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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

Katie Williams STONE HOUSE PROPERTIES, LLC

STUNNING LONG VIEWS, RARE 330+ ACRE PARCEL, ABUTS CONSERVATION LAND! Total seclusion and privacy, bucolic countryside with some open meadows and wooded hillside. Once a grand Berkshire estate, the property is comprised of the main Tudor style residence with indoor pool, shingled barn, Dutch colonial multi family dwelling, a guest house & several smaller sheds and workshop. The buildings are all

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

Alford Stunner! Exceptionally Designed Turnkey Home with Mountain Views!Completed in 2006, this 5200+ sq ft architect-designed home comes to the market for the first time. Meticulously curated materials, interior designer finishes, and a high-end build culminate in this showpiece home on 19.3 acres, with gunite pool and pool house.Upon entry, this home exudes warmth, style, and comfort - the

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

Moments to morning coffee at the iconic Southfield store, you'll find your private, yet accessible contemporary home completed in 2005.Set back from the road, the home offers a fantastic and sensible layout including a primary suite on the first floor as well as two bedrooms and shared bath. The spacious living, dining, kitchen (with fireplace and gathering space) all open to the west-facing

Freddy Friedman Birch Properties

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

Mark Rosengren LANCE VERMEULEN RE, INC

Classic family home in Great Barrington. 3 Bedroom 2 Bath on almost 2 acres. First floor large Primary bedroom, wrap around porch, deck and oversized heated garage with office space above. Enjoy the Berkshires with all it has to offer; Butternut ski area around the corner, schools, Tanglewood, theaters and restaurants all conveniently located nearby.

Mark Rosengren LANCE VERMEULEN RE, INC

Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/

Elvia Gignoux WILLIAM PITT SOTHEBY'S - SALISBURY

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

Tony Segalla LANCE VERMEULEN RE, INC

Embrace the epitome of Berkshires luxury in this newly constructed residence, poised on a serene cul-de-sac with community pool privileges. Spanning an impressive 4,200 square feet, this home is a stone's throw from the bustling heart of Great Barrington. Step under the elegant covered portico and into the grandeur of a cathedral great room, where a cascade of natural light streams through

Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON