586 houses for sale in Great Barrington

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90+/- acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams and Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with appro

HOME BEING SOLD AS IS NO NEGOTIATION ON INSPECTION ISSUES. THE PRICE IS NOT NEGOTIABLE. Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom, 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer

Sited down a long shared drive this lovely contemporary colonial style home is incredibly private. Circular drive brings you around the front entry, the current owner extended the house to give it a proper entry and created a lovely front porch. The living space is flanked with windows to the private backyard and open to the kitchen and dining area. A large great room sits on the south side of the home and the soaring ceilings and multiple skylights give it a solarium feel flooding it with light. Kitchen is large with good working space, a pantry closet, counter seating and french doors to the screened porch and patio. The side entry brings you from the 3 car detached garage through the coveted boot room into the kitchen with laundry tucked away. Upstairs there are 3 guest rooms, a hall bath and a primary suite. The primary has a working fireplace, a balcony over the great room with a sauna and potential office space. A truly private setting yet close to all the Berkshires has to offer

Newly constructed and thoughtfully designed, this home is ideally located within the Copake Lake community-Columbia County's only high-speed motorboat lake-and built by one of the area's most respected contractors. The property reflects quality craftsmanship throughout. The home offers 3 bedrooms and 3 full bathrooms, including two primary suites on the main level. The third bedroom is on the lower level currently used as additional living space. The open-concept great room combines the living area with a gas fireplace, ample space for dining, and kitchen with custom cabinetry and stainless steel appliances that includes double ovens. There is also a large full basement with potential for future expansion. Additional features include a heated two-car garage, an attached carport, an in-ground pool, and a beautifully maintained lawn with a protected vegetable garden with raised planting beds. The property is privately set among the trees while remaining close to lake access and activitie

Set on just under 4 acres along County Route 7, this property offers a farmhouse ready for restoration and a straightforward starting point for creating something of your own. The house is ready for updating and restoration, with a well and septic system already in place. With the subdivision currently in process, the property offers a manageable amount of land and plenty of room to shape the setting around the existing farmhouse. The location puts you minutes from Copake Lake and approximately 12 minutes from the Taconic State Parkway, with Hudson and Great Barrington both within easy reach. Surrounded by the landscape and amenities of the Hudson Valley and Berkshires, this is a property with a solid foundation and a blank slate for its next chapter

'A Perfect Place Farm' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for. a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26

Perched on a hill overlooking a scenic valley road, this 4-bedroom Dutch Gambrell offers a secluded country setting just a few minutes from town. This vibrantly-designed home opens into a handsome petrol-green kitchen with polished concrete floors and an ample dining area framed by French doors. The kitchen/dining area flows into an inviting living room anchored by a herringbone tile propane fireplace, a warm gathering space for family and friends. Just off the living room the 1st floor primary suite is a cheerful retreat with it's own striking classic black-and-white tiled bath with glass shower surround. Upstairs 3 guest bedrooms, a full bath and an upstairs playroom/lounge offer plenty of room for guests to relax. On the basement level there are two unheated semi-finished spaces for exercise and Media viewing. The lush back yard features a beautiful stone patio and hot tub. An attached 2-car garage with EV charging completes the package. Easy access to hiking, swimming, and everythi

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90+/- acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams and Warren in an Elizabethan/Jacobean Revival style. The original mansion remains at the heart of the property, surrounded by broad lawns and a collection of buildings added during its later evolution into an educational campus. Despite decades of institutional use, much of the character of the original country house remains. Handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom recall Overlee's Gilded Age origins. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors, creating an intriguing foundation for its return to residential use. Beyond the main house, the campus includes two dormitory residences with appro

HOME BEING SOLD AS IS NO NEGOTIATION ON INSPECTION ISSUES. THE PRICE IS NOT NEGOTIABLE. Two family minutes from downtown Lenox. First floor unit has 2 bedrooms with spacious living area and kitchen. Upstairs unit is a 1 bedroom, 1 bath with fireplace and back deck. Roof replaced in 2021, natural gas, town water and sewer

Welcome to this beautiful home dead end location AND is the QUEEN OF THE LAKE on Robinsons Pond! Amazing 101' of water frontage! Situated high on the property this one of a kind home enjoys incredible, beautiful waterfront views. The exterior stone walls give this home unprecedented distinction. 3 Full levels of outdoor living and possible entertaining space. The first floor features a Trek Deck with clear railings to sit and enjoy a cup of coffee or'whatever' lol while the sun sets or rises. The lower level enjoys a slate patio with 2 magnificent curved granite staircases on either side of the property to the yard/grass level. There is a totally separate private section/area that was built and is ready and waiting for your Hot Tub to be installed! What an unbelievable setting for any event, wedding, or just enjoying life in this fabulous property. The mid section of the yard is totally flat, completely fenced in with rod iron pretty fencing and can host any type of any party you can i

Terrific opportunity to own a piece of Historic Lenox. Set back from the road, secluded by deciduous shade tree. Spacious front lawn and close to village This is a diamond in the rough and with some sweat equity could be a shining star. Original wood floors throughout. One car garage and garden shed in backyard which is very private. HW heater 1 yr old. Enclosed Porch has new footings and roof is about 8 years old. Call today for your private viewing. Won't last long

CLASSIC VILLAGE CENTER HOME WITH OFFICE - Graciously restored vintage home. Ideal in town location. Residential/Commercial zone. Private Office/Studio. High ceilings, wonderful light. Large modern Kitchen. Filled with period detail alongside modern updates. Radiant heat in baths. Spacious Primary Bedroom Suite. Wood burning fireplace in Living Room. 1st floor Laundry Room. New 4 bedroom septic 2023. 1,000 square foot outbuilding with water, electric service, and unlimited possibilities. This is a property with a long, rich history. It feels like home. Come see for yourself!

Experience refined Berkshire living at Coldbrooke East, where timeless elegance meets exceptional privacy. Perfectly sited at the end of a quiet cul-de-sac and abutting the golf course, this extraordinary six-bedroom, 5.5-bath residence offers luxurious single-level living with a thoughtfully designed 1,000-square-foot addition. Custom designer finishes, exceptional craftsmanship, and substantial built-ins create a sophisticated yet comfortable totally renovated interior. Outside, magnificent perennial gardens, privacy, outdoor showers, and courtyard provides a serene retreat. Enjoy access to the nearby Wyndhurst Club and Manor pool, tennis courts, reduced-rate fitness membership, and more. A rare offering combining luxury, lifestyle, and one of Lenox's most coveted settings

Upper Rhoda Pond in Copake, New York (Southern Columbia County) is a very special place. About 2 hours from New York City, it is a private body of water with no public access. The waterfront area includes docks and a kayak to row out to your exclusive floating raft. This 3 bedrooms (plus office) has 3 bathrooms and is approximately 1944 square feet. The open floor plans lends itself to family, friends and entertaining. Wood-burning fireplace to warm up on those cool nights. Fiber-optic is on premises. The screened porch has panels, so that you can take in the country location and water views all year round. There is even a heater out there. The lower level has a sizeable family room and includes a pool table and ping-pong table. Storage has been very well organized and there is plenty of it. All this is sited on over 2.5 acres. There is a detached two-car garage and gardens. This central location makes it so convenient to so many cultural activities (Tanglewood, Catamount Adventure Mou

Location, location, location! Ideally situated within easy walking distance of the village, elementary school, and Tanglewood, this charming ranch offers comfortable single-level living in a quiet, desirable neighborhood. The large, level and semi-private backyard provides plenty of room to relax, entertain, garden, or enjoy the above-ground pool. Inside, the home features a spacious open living area currently used as a dining and family room, separate living room, eat-in kitchen, three bedrooms, and a full bath with tub. Step directly from the kitchen onto the deck overlooking the pool and expansive backyard. Additional highlights include an attached two-car garage, full basement with four versatile rooms, and a designated laundry space complete with a laundry chute!

'A Perfect Place Farm' - a Berkshires Masterpiece on 17+ Acres The one you've been waiting for. a preeminent build in a premier location. 37 Main Rd checks off the wish list: sweeping views, modern comforts, privacy, location, and colonial era character, but in an immaculately kept turnkey 2002 home. Located in Tyringham valley, one of the Berkshires' most majestic locations, 37 Main Rd is idyllically sited on the northern slope of Tyringham valley, and faces to the southwest. The expansive front porch, sunroom, and living and sleeping quarters all are positioned to track the sun's daily arc across this picturesque east-west valley

Single level living with room for everyone. This well loved Ranch House sits in a quiet park like neighborhood on a cul-de-sac. Livingroom with Fireplace, Eat-in Kitchen, 3 Bedrooms + a Bonus Bedroom that may double as an ADU (accessory dwelling unit), Rental or In-law suite. Large yard. Private Deck. Well located near shopping and schools. Truly a special home

Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two spacious levels. Natural light fills the interior, highlighting beautiful wood floors throughout and adding to the warm, inviting atmosphere. Skylights bring even more light into the home, while the oversized deck provides an ideal setting for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. An oversized two-car garage offers generous parking and storage. Tucked away in a completely private setting yet just minutes from town, this exceptional property is approximately two minutes from Sheffield's Cobble and the Appalachian Trail, offering easy access to hiking, nature, an

73 Birch Road on Robinson Pond in Copake, New York. This wonderful retreat is situated on one of the largest parcels in the private Taconic Shores Property Owners Association (lots 648, 649, and 650.5), a private lake community, 2 beaches, shared community areas, multiple boat launching areas. Built in 1960 and remodeled over the years, this 3-bedroom, 2-bath ranch home (noted in public records as 2-bedroom, 1-bath) features an open-concept with Great Room with a wood stove. It includes an attached four-season enclosed sunroom with a glass ceiling, tiled floors, laundry facilities, and ample storage. The first floor offers two bedrooms and a bathroom, while the walkout basement includes a living room with another woodstove, an office or additional bedroom, another two rooms for storage or additional living areas, a 3/4 bath, and a mechanical room. The exterior is equally impressive, featuring manicured gardens, a handmade stone water fountain, and a large deck off the dining area. Addi

Some homes are purchased. Others become part of a family's legacy. Welcome to 109 Under Mountain Road. There is something unmistakably special about a Berkshire summer- evening stroll to Tanglewood, morning coffee overlooking protected meadows, or relaxing on the patio as the music of the Boston Symphony Orchestra drifts softly through the evening air. Bathed in extraordinary natural light, this architect-designed home embraces its breathtaking setting with soaring walls of glass, vaulted ceilings, exposed beams, skylights, and exquisite gardens. Thoughtfully designed for gracious entertaining and comfortable everyday living, the spacious first-floor primary suite allows you to enjoy the home with ease for years to come, while family and friends gather in beautifully appointed guest rooms

Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while maintaining the cozy charm expected from a lakeside retreat. French doors open to a spacious deck overlooking the water, creating a seamless connection between indoor living and the peaceful lake views beyond. Just steps from the deck, enjoy your private shoreline and dock-perfect for swimming, boating, and relaxing by the water. Copake Lake is one of the area's only fully motorized lakes, ideal for water sports, fishing, and sunset cruises. Conveniently located near Copake Country Club and Catamount Mountain Resort, and under 30 minutes to both Amtrak and Metro-North rail service, as well as the vi

Terrific opportunity to own a piece of Historic Lenox. Set back from the road, secluded by deciduous shade tree. Spacious front lawn and close to village This is a diamond in the rough and with some sweat equity could be a shining star. Original wood floors throughout. One car garage and garden shed in backyard which is very private. HW heater 1 yr old. Enclosed Porch has new footings and roof is about 8 years old. Call today for your private viewing. Won't last long

Set on a large, private lot with scenic views in beautiful Copake, NY. This inviting Ranch offers two bedrooms and a full bath on the main level, while the private primary bedroom is located on the second floor, complete with its own bathroom creating a peaceful retreat with added privacy. The open concept dining and kitchen area create a great space for entertaining. The spacious light filled living room leads to the partially finished basement, offering flexible space for a home office, recreation room or additional living. Step out onto the spacious deck and enjoy the large fenced in private yard, perfect for relaxing, entertaining, or simply taking in the peaceful Hudson Valley setting. A one car garage provides plenty of room for your vehicle and additional storage. Just a short distance to the Copake town park, center of town, Copake Lake and Bash Bish Falls. Only 25 minutes to vibrant Hudson and Great Barrington for shopping and dining

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the 2-car garage is a sunny space for all of your seasonal gear. Upstairs, the large primary bedroom includes a 2nd wood-burning fireplace and en suite bath, while two additional bedrooms share a full bath. Main floor office and a finished lower level currently serves as guest accommodations, media room, fitness, laundry, and a variety of additional uses. New landscaping! 4 bed Title V, completed 4/26

Welcome to this inviting Raised Ranch set in the private Taconic Shores community. Offering 2 bedrooms, 2 full bathrooms, a spacious living room with vaulted ceilings and open-concept kitchen and dining area that create a bright, airy feel ideal for everyday living and entertaining. The office provides the perfect space to work from home or as an additional bedroom. Hangout and relax on the wraparound deck while taking in the mountain views and stunning sunsets. The spacious basement has endless potential with ample storage, finishable living space, and a cozy wood-burning stove. Whether you're looking for a weekend escape or a full-time residence, this home delivers a relaxed lifestyle in a sought-after lake community. Enjoy exclusive Taconic Shores lake perks with a short stroll to the beach area for swimming, fishing, and boating. Just minutes from the center of Copake and the town park, local golf courses, Bash Bish Falls, and Catamount Ski Resort. Centrally located between Hudson,

It's MAGIC at the TOP This extraordinary private and peaceful retreat rises into its living landscape with forever views across the Taconic Range to the Catskills-some of the most magical in the Hudson Valley. Set on 19 serene acres at the base of Mount Washington, the morning light rises over the Taconic Range, and by evening, the sun slips behind the Catskills, transforming the sky into a constantly changing display of gold, rose and crimson. And then there is the house. Architecturally refined, this deeply comfortable 5,540-square-foot residence was redesigned and renovated beginning in 2020. Modern living meets mountain majesty, with soaring spaces, dramatic natural light and endless walls of glass that bring the landscape into every room. The living room is a breathtaking space, with soaring ceilings and a wall of windows framing the Catskills panorama, anchored by a carved limestone fireplace. The effect is dramatic, yet the house remains warm, comfortable and wonderfully livable

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals-just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train

Crosby House, a property with a storied Lenox history and a location second to none, presents a rare opportunity to own a residence of remarkable character, scale, and flexibility in the heart of the village. Currently configured as two spacious residences, this distinctive multifamily property offers an exceptional array of possibilities. Subject to applicable zoning, permitting, and approvals, the existing configuration may offer the potential to be thoughtfully combined into one extraordinary single-family residence or could provide the foundation for two highly distinctive condominium residences. Each residence offers two plus bedrooms and two full baths, along with generous kitchens featuring high-end Bosch appliances, hardwood floors, tiled baths, in-unit laundry, central air, natural gas heat, and an abundance of windows. All major systems have been updated, providing modern comfort and efficiency while complementing the property's historic character. Both primary bedrooms featu

Mixed use property located just 7 miles south of Gt Barrington on Route 7. Two commercial units and two residential units. Solar on roof and in back of property bring in additional lease revenue. Long term tenants in each apartment. Anchor commercial tenant, Berkshire Fence and Accessories, to sign long term lease with new owner. Second commercial unit vacant, perfect for owner occupied buyer