luxury houses for sale Great Barrington, United States

Set on 36 acres in the Berkshires' most coveted town, this stunning 8600 sq ft home is completely turnkey, tastefully designed, and a mere 12 years old. Turning off of bucolic West Rd, a gently winding driveway brings you past two beautiful ponds, through the woods, and arrives on a sunny plateau - nicknamed ''Ebbets Field'' and the site of this spectacular retreat. Abutting 899 acre Alford Springs Reserve, this custom-built home was thoughtfully designed to host guests across multiple discrete living areas. Main House. A striking glass walkway leads from the three-car garage to the vaulted-ceiling kitchen, which boasts a double-oven Wolf range and plenty of space for cooking and gathering. A light-filled dining area adjoins the kitchen, along with a large living room with fireplaces on opposite ends. The primary bedroom suite is highlighted by a private covered porch, a large bathroom with soaking tub and views, and two walk-in closets. Two additional en-suite bedrooms complete the interior of the first floor, and three en-suite bedrooms and a central living area are found upstairs. The awesome walk-out lower level was created with entertainment in mind, featuring high ceilings, a two-sided fireplace, movie viewing room, en suite bedroom, gym, and wine cellar. Guest Quarters. Accessed via the glass walkway, the guest quarters are defined by its dramatic high ceilings and a long covered porch with views. The quarters include a spacious en suite bedroom, two guest bedrooms with shared bath, and a cozy and bright living area. Outdoors. The interior seamlessly connects to multiple outdoor spaces, including a beautiful patio with fireplace, a large screened porch, covered porches, and a large deck that steps down to the expansive green lawn, bordered by rock walls made from property-sourced stones. Just a short distance down from the lawn, a symphony of spring peepers awaits at the property's 5+ acre pond, a peaceful escape for nature watching and kayaking. This lightly-lived in 2012 home is the ultimate Berkshires escape, blending today's design with the natural surroundings. Situated in low-tax Alford, 139 West Rd is a prime location for those seeking tranquility a short stone's throw from the Berkshires lively shopping and eating centers and multitude of recreational and cultural attractions. Fiber Internet, iPad-controlled lighting system, Sonos hard-wired sound system, and multiple heating and cooling zones. 10 minutes to Great Barrington and 20 minutes to Lenox. Additional 20 acre lot is also available.

49 Bow Wow - A Gilligan Brothers Masterpiece on 30+ Acres! Set on over 30 acres of stunning meadows, mountain, pond access, and forest, the Gilligan family home at 49 Bow Wow Rd comes to the market for the first time. In the second half of the 20th century, the Gilligan Brothers name was synonymous in southern Berkshire County with a quality built home. Founded by three brothers - Matthew, William, and Earl - in the 1940s, Gilligan Brothers homes were often a showcase for the ingenuity and craftsmanship of their founders. And perhaps no home better illustrates their innovative streak than Matthew's family home at 49 Bow Wow Road. Built in 1941 for his family - and retained by them to this day - 49 Bow Wow was stylistically and functionally ahead of its time. Take, for example, the massive stone fireplace and exposed beams in the family room - built with materials reclaimed from a nearby mill. Or, for instance, the sliding wall that opens (still to this day) the family room to the expansive porch with westerly views. Equally impressive, however, is the 30+ acre parcel of land Matthew Gilligan chose for his home. It includes two multi-acre meadows, woodlands, pond access, and the western side and top of Little Johnny Mountain. From the front to the rear meadow, observing huge 20+ ft boulders seemingly dropped from the heavens, one imagines a glacier carving through this little valley thousands of years ago. The rear meadow sits next to Little Johnny, and could be a spectacular second home site accessed by an existing farm road. The scramble up the side of Little Johnny brings you to a table top mountain with awe-inspiring view potential of Mount Everett and the valley below. From there, one can descend the southern slope to Sheffield's Town Park, which has a frisbee golf course, playground, and ball field. Or cross the meadow and return home via a trail system passing through the forest and a small brook. Kayak and water lovers can cross the road and have rights to the small beach on Mill Pond. The home's first floor features two beautiful living spaces, a kitchen with vintage custom cabinetry, a wood-paneled dining room, a bedroom and full bath. The upstairs includes three more bedrooms and a full bath divided into two sections. A cedar closet could be repurposed into an en-suite bath for the primary bedroom. The basement shows off the home's quality build, with high ceilings, updated systems, and a spot for a future wine cellar. Perfectly functional now, but also ready for its second-ever owner to update the bathrooms and kitchen to their personal preference. The home's bones and spectacular property will amply reward future investment. Two-car garage, high-speed Internet, several hobby farm outbuildings, updated electric panel, Buderus hot water heating system.

Originally constructed in 1875, the house was owned by local church for Pastor Andrus, a name still prevalent in the Berkshires. A subsequent cast of owners included the Town Physician, Dr. Roberts and later Sheffield's Chief of Police. The previous owner bought the property as a two-family home which it remained until 2002 when the current owners purchased the property and converted it back to a one family home. The transformation of this property has been meticulously executed in four distinct phases, each enhancing the home's charm and functionality. Phase 1 focused on reinforcing the front portico and constructing a new porch, setting a welcoming tone. Inside, the main house saw extensive upgrades: wallpaper removal, floor refinishing, fresh paint, and ceiling repairs breathed new life into the rooms. A clever conversion of a large closet into a half-bath improved the foyer, while strategic window closures on the northwest side increased wall space without sacrificing natural light. The second floor underwent a significant reconfiguration, reducing the number of bedrooms from four to three to create a luxurious walk-in closet and an expanded bathroom with a large tub, and new fixtures. The living room's fireplace was serviced, ensuring cozy gatherings. Phase 2's rear section saw the transformation of a den/kitchen into a primary bedroom with cathedral ceilings and a primary bath/shower combo. A discovered chimney was restored, adding character, while new fixtures, windows, and a zoned baseboard heating system modernized the space. The side porch was enclosed to create a functional mudroom, and the groundwork for a future garage was laid. The third bedroom transitioned into a den, complete with new closets. Phase 3's kitchen expansion was remarkable, featuring new appliances, cabinetry, and soapstone countertops repurposed from a high school lab. The removal of old linoleum revealed original floors with historic markings, preserved for their character. A new laundry chute, plumbing for washer/dryer, and the elimination of an unnecessary bathroom streamlined the home's functionality. In the basement, a new oil tank, electrical upgrades, a water softener, and organized storage solutions were implemented. The garage, a proud addition, offers ample space, electrical outlets, and an ingenious heat transfer system from the bulkhead, keeping vehicles warm in winter. Above the oversized attached two car garage, a versatile room serves as an office or potential yoga/exercise space, complete with a propane heater, window A/C, and engineered wood floors. The property's exterior boasts a brand-new septic system and a detached building with commercial potential, complete with its own electric meter and plumbing linked to the septic system. Zoned for multi-purpose use, this property offers flexibility for residential or commercial aspirations, with an existing exterior sign to streamline the permitting process for business use. Each phase of renovation has been thoughtfully designed to enhance the home's historic charm while providing modern comforts and conveniences.

Ideally situated in the heart of downtown Stockbridge, this 1860 colonial home has been stylishly updated and is move-in ready. The stunning first floor has three spacious adjoining living areas, including a central dining area and a family room with fireplace. The renovated kitchen has a chef's range and a large island perfect for gathering around. In the rear of the first floor is one of the home's two primary en-suite bedrooms, both with gas fireplaces. Take the back or front staircase to the second floor, which has the second primary en-suite bedroom, a central sitting area, and three more bedrooms, each with their own bathroom. A light filled loft/office and a vaulted-ceiling media room are found at the rear of the second floor - a perfect place for work or entertainment. Outside, this property features all of the Berkshire outdoor essentials. Enjoy summers on the large screened porch, eat al fresco on a lovely patio, and hold summer soirées or pursue one's creative pursuits in the charming two-story timber frame barn. With 5 bedrooms, 6 bathrooms, and multiple living and creative/work areas - indoors and out - this 4,900 sq ft home welcomes the possibilities of today's lifestyles while captivating the heritage of this classic colonial. A short stroll to eateries, groceries, and entertainment, and just minutes to Lenox and Great Barrington. See it now and be in before the summer!

One of the Berkshires' finest residences, basking in the idyllic mountain scenery. Designed and crafted to meticulous standards, this distinguished 6.2 acre compound is surrounded by captivating, protected vistas far and wide. In the enduring tradition of the regions iconic estates, this extraordinary residence is a place for life to the fullest, providing an endless source of enjoyment in exquisite indoor /outdoor spaces. Fine millwork and 9 fireplaces underscore the comfortably elegant environment. Lower-level entertainment (media) room, wine cellar, fitness studio. elevator, computerized systems. 9,339 SF with 5 bedrooms,6 full/3half baths. Wraparound tiered terraces feature pool with pool house. Glorious terraced gardens and formal gardens with fountain. Separate 3 bedroom guest house

Nestled between the iconic Rockwell Museum and the serene Botanical Garden, 5 Glendale Rd in Stockbridge, MA, is a truly special property that offers a unique blend of charm and convenience. Situated just moments away from the renowned Tanglewood, this picturesque NE Farmhouse-style single-family residence embodies the quintessential Berkshires lifestyle. Boasting a main house with three bedrooms and two baths, complemented by a guest cottage featuring an additional bedroom, bath, and spacious living room, this home is perfect for those seeking a peaceful retreat with modern amenities. The well-manicured grounds feature an adorable playhouse for little ones and several outbuildings, including garages for at least 5 cars, providing ample space for storage and recreational activities. Stepping inside, the interior exudes warmth and character creating a cozy and inviting atmosphere. The floorplan offers flexibility and privacy, ideal for hosting guests or accommodating multigenerational living arrangements. A central fireplace adds a touch of elegance to the living space, while the abundance of natural light enhances the overall ambiance of the home. The partially finished full basement provides additional living space and storage options, catering to various needs and preferences. In addition to the property's charming interiors, residents can enjoy a range of modern conveniences, including central air cooling, a security system, and public sewer access. The expansive lot size of 3.6 Acres offers plenty of outdoor space for relaxation and recreation, with a patio perfect for al fresco dining and entertaining. Surrounded by lush landscaping and mature flowering trees, the property provides a peaceful oasis away from the hustle and bustle of city life. Whether you're unwinding in the tranquility of the backyard or exploring the vibrant local community, 5 Glendale Rd presents a rare opportunity to experience the best of Berkshires living in a truly enchanting setting. Ideally located between the charming towns of Lenox and Great Barrington, residents have easy access to a variety of dining, shopping, and entertainment options, making it a desirable destination for both full-time living and vacation retreats. With its convenient proximity to major attractions and amenities, this property offers the perfect balance of seclusion and accessibility, allowing residents to savor the beauty of the Berkshires while still being just a short drive away from all the wonders this region has to offer.

Imagine your own private getaway. Noble Lodge is a playground for nature walks, all-terrain vehicle and snow mobile adventures, swimming and paddleboarding, and hosting the grandest of parties. Have it all, on almost 300 acres in one of the prettiest places in the Hudson Valley and have the rare opportunity to design and develop your own perfect farmhouse or modern marvel. You will be enchanted with the charm of this highly sought-after hamlet and the close-knit community of Hillsdale, nestled in the hills near the Massachusetts boarder. All the locals meet up at Roe Jan Brewery, a wonderful brew pub located in a restored mercantile building that dates to 1850, and shop at the Hillsdale Country Store, an old-time country emporium. The focal points of Noble Lodge are the pond with its own little island where mallard ducks relax, and the creek that runs through the property. Cross the bridge and find the perfect site to build your dream home. The property includes a nicely appointed, 4-bedroom ranch, that is the perfect place to congregate with friends to plan your day of fun. Noble Lodge is only 15 minutes from Great Barrington and 35 minutes from Hudson, offering the best of everything. 300 acres in the Hudson Valley is an exceptional opportunity.

This charming mountain house is the perfect retreat for nature, lovers and outdoor enthusiasts. With easy access to hiking trails skiing, fishing you can enjoy all that Berkshire Mountain Washington Life has to offer right from your doorstep. Inside the open concept, living area is perfect for entertaining guests or simply relaxing by the stone fireplace. The large bay windows let in plenty of natural light and offer stunning views of the surrounding mountains. The kitchen is fully equipped and there is plenty of counter space for preparing meals. There is a first floor primary with an en suite bath and a wraparound deck. The additional two bedrooms upstairs are perfect for guests or home office.The peaceful surroundings and Mountain View make this an ideal setting for a weekend getaway. Don't miss your chance to own this unique mountain home or start living the ultimate lifestyle today 2.5 hours from New York City 30 minutes from all Berkshire attractions. Minutes from Guilder Pond. Can you smell the Mountain Laurel?

Prime Location in Lovely Lee! This beautiful and newly refreshed Colonial is ideally situated on a very desirable and quiet cul-de-sac. Behind its charming picket fence, discover a spacious sanctuary of five bedrooms and five full and one half bathrooms. The main level welcomes you with lofty ceilings, a living room adorned with built-ins, generous dining areas, and a sumptuous primary bedroom complete with a walk-in closet and luxurious en-suite. An absolutely beautiful and newly remodeled kitchen showcases sleek quartz and walnut countertops, stainless steel appliances, pantry, and island, seamlessly connecting to an attached sunroom, while the dining room offers direct access to the deck. Enjoy the serene outdoors from these inviting spaces which also offer a panoramic view of the lush, fenced-in backyard. Ideal for both intimate gatherings and grand affairs, the open-plan kitchen, living, and dining areas exude comfort and style. Upstairs, discover four generously proportioned bedrooms and three full baths, all elegantly tiled. The walk-out lower level unveils an exercise room, additional dining space, two expansive, yet combined, entertaining/play/work areas, and a spa-like bath, complemented by patio access. Additional features include a welcoming farmers porch, town services, solar enhancements, and an attached two-car garage with automatic openers. Bask in the meticulously maintained mature landscaping and embrace the lifestyle you deserve. This offering presents an unparalleled opportunity to immerse yourself in the natural beauty, cultural richness, culinary delights, and adventurous spirit of the Berkshires. With convenient access to Tanglewood, Mass MoCA, and a myriad of other captivating Berkshire attractions, seize the chance to call this haven your home.

At the crossroads of the Hudson Valley's most desirable locations lies the charming Hamlet of Hillsdale. The quaint town's architectural star-of-the-show is this fully restored Masonic Temple that offers its new owners a long list of options to maximize their enjoyment and use of the property. Zoned for both commercial and residential opportunities the Temple can easily be your architectural design dream home, your business' new headquarters, a premiere shopping destination or all of the above and more. Rarely is a space of such beauty and square footage offered to the market in pristine condition. Boasting impressive 14ft tin ceilings throughout and an abundance of large steel casement windows, the expansive space is illuminated with natural light throughout the entire day. The majestic scale of the building is a delight to take in and can be attributed to the Masons who built it with their understanding of mathematical precision, geometry and the power of form and proportion. Two bedrooms, 3 Bathrooms and a streamlined kitchen create a move-in ready residence while views of the surrounding hills from this gated, hedged and private property make you feel worlds away while still having the ease and accessibility of a village location. The temple is perfectly placed between popular local businesses such as Roe Jan Brewing Co, The Hillsdale General Store, Tiny Hearts Flower Shop and Cook & Larder offering a sweet walkable lifestyle as a residential property or the perfect business opportunity as commercial. The hamlet's bounds to the north and east is the intersection of NY-23 and NY-22. These roads connect the Catskills to the Berkshires West-to-East and offer easy access to Rensselaer and Dutchess County North-to-South. The connection to these areas creates a vibrant community of creatives, nature enthusiasts and culinary connoisseurs. The museum quality of this property offers an overwhelming amount of unique opportunities and must be seen in person to fully appreciate.

Escape to the serene countryside of New Marlborough, MA, where this stunning New England farmhouse beckons with its picturesque setting on 10 acres of land. A true oasis, this property boasts a pool, pool house, garage, and barn, offering endless possibilities for outdoor enjoyment and relaxation. Step inside this beautifully renovated home, where modern amenities blend seamlessly with classic charm. The 4 bedrooms and 3.5 baths provide ample space for comfortable living, while the kitchen is a chef's dream come true. Whether you're hosting a gathering or simply enjoying a quiet evening in, this home is sure to impress with its impeccable design and attention to detail. As you explore the interior of this farmhouse, you'll be greeted by a sense of warmth and elegance. The open layout creates a seamless flow between the living spaces, perfect for both daily living and entertaining. Natural light floods the home, highlighting the custom finishes and high-end features throughout. From the cozy bedrooms to the luxurious bathrooms, every corner of this home exudes comfort and style. Imagine waking up to the stunning views of the surrounding mountains and countryside, or relaxing by the fireplace on a chilly evening. This is more than a home; it's a retreat from the ordinary, offering a lifestyle of luxury and tranquility. Outdoor living is a true delight at this property, with a beautifully landscaped yard and plenty of space to roam and explore. The in-ground pool is a refreshing spot to cool off on hot summer days, while the pool house provides a convenient place to relax and unwind. The garage and barn offer ample storage space for all of your outdoor essentials, whether you're a hobbyist, a gardener, or simply enjoy the rural lifestyle. Surrounded by nature and beauty, this home is a private sanctuary where you can escape the hustle and bustle of city life and embrace the peace and quiet of country living. Located in the charming town of New Marlborough, this property offers a unique opportunity to experience the best of both worlds: a tranquil rural setting with easy access to modern conveniences. With top-rated schools, shopping, dining, and outdoor recreation just a short drive away, you'll have everything you need right at your fingertips. Whether you're seeking a year-round residence or a weekend retreat, this home is a rare find that combines comfort, luxury, and the beauty of nature in one exquisite package.

Mount Washington serves as the magnificent backdrop to the serene garden paradise that is The Mountain View Farmhouse. Set on a quiet dead end road in the hamlet of Copake Falls this double lot property has been sweetly manicured and set up for your calm enjoyment of the beautiful views. Time stops once you enter the grounds of this precious farmhouse expertly renovated to bring all the modern conveniences to a charming and character filled home. Upon entering the front door you and your guests will be greeted by the warmth only exposed beams and original wide plank wood flooring can evoke. The first floor has an open layout often desired but rarely achieved in homes of this era. The living room effortlessly flows into the dining room and beautiful kitchen that puts the Mt Washington views on display as you prepare your flowers and vegetables from your very own garden. A guest bathroom and side entrance complete the first floor. Upstairs 3 perfectly sized bedrooms (One used as an office currently) and a full bathroom offer comfortable stays for you and your guests. A large portion of the property is fenced in and filled with beautiful plantings, trees and enough tulips to keep every room of your home and your friends home filled all spring. Another area of the yard contains an expert's raised bed garden to grow your own fresh herbs and vegetables all summer long. Set in a peaceful and quaint neighborhood you are just moments away from a hike to Bash Bish Falls, a day on Copake Lake and skiing down the slopes of Catamount in the winters. Hudson, NY and Great Barrington, MA are both a 15-20 minutes drive away where you'll find the best shopping, restaurants & social events the Hudson Valley has to offer.

Great Stockbridge Location with Pool and a Wonderful Backyard! Calling all Tanglewood and Stockbridge Bowl fans! Stroll to the Music Shed at Tanglewood in just 8 minutes, or 10 minutes to Stockbridge Bowl for picnics or kayaking! Drinks or dinner at Wheatleigh is just a 5 minute amble away - AND the back yard is your own summer resort. This 2,829 sq ft home has been substantially renovated and improved since it was purchased in 2018. It now features all the coveted features one seeks in a Berkshires getaway: in-ground pool (with new liner and systems); beautifully landscaped backyard with patio, fire pit, hot tub and space for outdoor games; screened porch; 1st floor primary suite; renovated kitchen and new great room with fireplace; 4 bedrooms and 5 bathrooms; and a bonus basement rec room. Renovated and ready to go! Perfect for year round or seasonal use, and a great rental property. Move in and enjoy this special property! Just minutes without a car needed to Tanglewood, Stockbridge Bowl, Camp Mahkeenac, Wheatleigh, Kripalu, and Bullard Woods! Downtown Lenox, and The Mount mere minutes away and an easy, drive to Stockbridge, Great Barrington and Lee

On over eight acres of woodlands in the hills of Austerlitz sits this picturesque cabin down a long, private drive. Connected to hundreds of acres of state land, you can hike Harvey Mountain right out your front door. The recent renovations make this light & bright home a completely move-in-ready proposition. The original beams have been left untouched throughout and create warmth in tone, while the rest of the home has been finished with a clean, neutral palette. The kitchen has an English style range, marble countertops and lovely deep red cabinetry, and a farmhouse sink looks out over the property. The adjacent living area is anchored by a wood stove. There are two bedrooms and two baths on the main floor, one is ensuite and the other, with an antique clawfoot tub, is shared. Both are finished with beautiful Moroccan zellige tile. Upstairs, there is a cozy, private living space and a large light filled third bedroom. You’ll find a large two car garage outside for parking & hobbies. The home borders the Hudson Valley/Berkshire border and is equidistant to both Chatham and West Stockbridge and just over 2h to NYC.

New Connecticut Country Your new dream home TO BE BUILT perched above Twin Lakes on 6+ acres in quaint Salisbury, Litchfield County. Featured in Architectural Digest Summer 2020. Built by design driven, eco conscience architects, StoneFox who focus on contemporary architecture with a strong sense of emplacement with a clean simple design with a sensitive approach to nature and the environment. If you've been waiting for the perfect home, it has arrived. You head up the sinuous driveway to an auto court. The house is sited to face the southwest to take in views of the Taconic range and winter and summer sunsets. The home features an open plan with a central room to gather yet also has cosy private areas to tuck away. No detail has been overlooked and the design combines luxury with an ease for comfortable living. This home is well designed, thoughtful and encompasses all you could want in a stunning country retreat. The main living space features the kitchen, dining and living room with multi slide glass doors that pocket into the wall on either side of an expansive opening that invites you to walk outside to enjoy nature and the view. On the first floor there is also a library and a guest bedroom with full bath, mudroom and powder room. Upstairs you will find the primary bedroom and bath plus two more bedrooms each with their own bath. The lower level offers more space for a gym and bathroom plus a laundry room.

Down a long country drive off picturesque Center Hill Road sits this incredibly private modernist home on over forty acres of rolling pastoral fields and long ranging views. The approach curves through the landscape to expose a jaw dropping view of the Bash Bish gap and Taconic Mountain Range to the East. Serene, quiet and private, the property embodies the agrarian landscape the region is known for and the home was thoughtfully designed to frame the view. It is modern living at its best with soaring ceilings, walls of windows, and exterior decks that bring the outside in. The home has a central living room on the main level with a double-height ceiling & wood burning fireplace connecting to a light filled chef’s kitchen complete with a Wolf range, high end appliances & plenty of storage.The dining room has three walls of glass that allow you to “eat outside” all year round, and a screened-in porch and open air deck off the kitchen/dining area provide the same luxury throughout the warmer months. You’ll find two primary suites, one on the main level with a large bath, a walk-in closet and private outdoor balcony, and the other on the second floor with some of the best views the house has to offer. Two additional bedrooms upstairs share a bath and complete the second floor. The lower level walk out is anchored by a wood-burning fireplace and features radiant concrete floors. You’ll find a central downstairs living room with sliding doors out into the yard, an adjacent fifth bedroom with a full bath, and a home gym with beautiful views of the hills through large windows. A state-of-the-art Geothermal heating & cooling system has been installed. This turnkey modern home offers some of the most beautiful views the Hudson Valley has to offer. It is truly turnkey and just 2h to NYC and central to Hudson, Hillsdale and Millerton.