luxury houses for sale Great Barrington, United States

A true diamond in the rough and priced to sell! One of the most requested towns in the Berkshires and the lowest tax rate in South County all on 31 private acres. Live in your own guest cottage while you complete the build out on a custom and gorgeous timber frame home! Enjoy the beautiful views of Tom Ball mountain and the relaxing sounds of a babbling brook in the front of the property. There are also apple trees, grape vines, hiking trails and a small pond adding to its appeal. The cottage has a recent renovation that's 95% completed. It has vaulted ceilings, soapstone counter tops, butcher block island and stainless appliances just waiting for your finishing touch. Don't let this unbelievable opportunity pass you by!

Welcome to a slice of New England charm known for its rich history, scenic beauty, and vibrant community, Sheffield offers a quintessential Berkshires lifestyle with easy access to cultural attractions, outdoor recreation, and everyday conveniences associated with in-town living. Enjoy a picturesque setting offering a unique blend of historic elegance and modern comfort. Imbued with the timeless allure of Greek Revival architecture, this home boasts classic columns, symmetrical proportions, and refined details that evoke a sense of grandeur and sophistication. The heart of the home is the gourmet kitchen, equipped with top-of-the-line appliances and custom cabinetry making it a chef's delight and the perfect space for culinary creations and gatherings. With three spacious bedrooms, including a luxurious primary suite, there is ample room for relaxation and rejuvenation. Featuring two and a half baths, each meticulously designed with modern fixtures and elegant finishes. Large windows bathe the interiors in natural light, creating a bright and inviting ambiance throughout the home. Enjoy the cozy fireplace in the spacious living room, perfect for chilly evenings with friends. From gleaming hardwood floors to crown moldings and designer lighting fixtures, every detail exudes quality craftsmanship and refined taste. Above the oversized 2 car garage, a beautifully finished loft awaits, offering endless possibilities as a home office, studio, or guest quarters. Adding to the versatility of this property is an unfinished outbuilding with electric and plumbing , ideal for either residential or commercial use. Whether you envision a charming guest cottage, a home gym, or a boutique storefront, the potential is limitless. Close to the library, bank,Town Hall, Post Office and the many local eateries makes Sheffield the perfect location.

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.

River Road, set amongst the rolling hills of picturesque Hillsdale you’ll find this turn of the century farmhouse set on 20 acres of sprawling meadows and wildflower fields. The storybook approach follows River Road alongside the rushing Green River and up a private drive overlooking mountain ridges and whimsical tall pines. The c1890 farmhouse welcomes you with its wraparound porch and fieldstone front steps. Inside the rooms are large, the living room and master bedroom are both anchored by a magnificent stacked stone fireplace, recently restored and in use. The dining room opens to the wrap around porch through french doors, and when opened the sound of the rushing Green River flows through the house. Tucked around a corner you’ll find an outdoor shower overlooking the water. The kitchen is recently redone with brand new appliances and herringbone countertops, and the ground floor features an office and a full bath, which could be used as a fourth bedroom. Upstairs, all three bedrooms have ensuite baths with wonderfully deep soaking tubs, each with beautiful views of forest, pond and river. Windows, siding, roof, insulation, HVAC and floors are all brand new, allowing the next owner to own a beautiful antique farmhouse with little to no maintenance. A separate studio lies up the hill, used for creative projects by the current owners but open for future possibilities. This incredibly charming property is just 10m to the village of Hillsdale, 15m to Great Barrington and 2h to NYC.

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?

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.

Masterfully imagined, minimally modern take on an elegant post and beam country home. A playful, warm, inviting vibe will fill you with joy, while the architect's use of light, space, and flow will captivate. The combination of high end materials and mechanicals, quality construction methods and owners who have properly maintained this jewel, will make you feel like you are purchasing a brand new home. Recent upgrades include a whole house generator, under counter kitchen cabinets, California Closet systems, plus the finishing off of the basement for added spaces for work, play, and storage. A few highlights include a back deck with a wood burning fireplace, a telescoping sliding door to said deck which brings the outside in and a voluminous main living space for you to spread out. A property as outstanding as this needs an equally impressive location. Positioned in a community of high end homes, close to the Massachusetts border, creates a jumping off point to thoroughly enjoy this very special and unique region. Your go to town for shopping, dining, movies, books and more will be Chatham and Lenox with Tanglewood and more culture is a short drive away.

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.

A remarkable opportunity to combine residencial on the second floor with commercial on the main floor in an excellent location with plenty of private parking. The kitchen is set up for the discerning chef , a large dining room, a bedroom/office and living room with a propane fireplace completes the first floor. The gorgeous hardwood floors throughout the house have just been finished and the house is in pristine shape for the next owner. Finally, there is central air on the second floor to complete the full package!

An early Hudson Valley farmhouse, this c1840 eyebrow colonial sits on two and a half acres with a guest house. There are plenty of period details to fall in love with like wide, old growth pine floorboards and classic farmhouse two-over-two windows. Comfortable, approachable, and built with function in mind like all great northeastern cottages, the rooms are nicely sized and flow easily into one another. The country kitchen is simple, sweet and sunny with classic bead board cupboards and a farmhouse sink, and there’s a mudroom leading outside into the lawn. There is a first floor bedroom & full bath, and on the second level, along with two additional bedrooms you'll find a large, central seating area & another full bath. Across the lawn and past the firepit, French doors lead you into a streamlined, new build guesthouse. There is a spacious living room with a vaulted ceiling & Noguchi pendant. The large bedroom has a new ensuite bath with a beautiful marble shower. There is a 1 car garage attached. Updated, high end mechanicals in both homes. 720 Center Hill Road is very much the quintessential Hudson Valley farmhouse, charming and sweet. 2h to NYC and 20m to Amtrak.

Towards the end of Sky Top Road and tucked away at the end of a long driveway sits The Nine-Square House. A modernist masterpiece, the home is perched amidst dramatic natural topography with magnificent views of the Taconic Hills. The Nine-Square House was born of a several-year-long collaboration between a multi-disciplinary artist/designer and an esteemed architect. The result is an immensely livable and sustainable 3,900 square-foot home that carefully balances the relationship between its well thought out interiors and the surrounding wooded landscapes and impressive open views of multiple mountain ranges. Every feature of the home was conceived to be both functional and pleasing to the eye; after all, the team behind the house spent more than two years planning a design that addressed every conceivable ergonomic and environmental question. The nine-square philosophy of living is very much felt in the distribution of spaces - on the main floor, the double living room, dining area, and kitchen all flow into each other and are anchored by a marble fireplace and three large glass doors opening to the exterior terrace with a breathtaking view. The kitchen features Danish-designed Reform cabinetry, Bardiglio marble, and Fisher Paykel appliances. An office, a washroom, a dry bar, and a generously proportioned laundry room complete the main level. The central architectural piece of the home is the solid white oak staircase leading up to the second floor. The four bedrooms upstairs, though spacious, are much more private and intimate, each with large windows on two sides, communing with the serene and quiet landscape outside. The two sizable bathrooms have dedicated shower rooms and freestanding soaking tubs with panoramic views. The expansive landing of this level has a reading room at one end and a sitting area at the other. Distinguishing features of the Nine-Square House include high energy efficiency due to insulation exceeding all current standards, multi-zone central AC, radiant heated floors, solid 200 lb interior doors, satin nickel Kohler fixtures, cast iron sinks, and solid forged and machined brass and satin nickel door hardware. An expansive floor plan and extensive technical solutions are met with human-scale rooms, creating an abundantly peaceful and welcoming environment. The land around the house, perfect as it is, has been touched as little as possible. There are wooded and open areas, with meandering walking paths trailing through the property. The minimal clearing around the house has been planted with native plants, allowing ferns and forest growth to come back up to the building over time. The Nine-Square House is just 20 minutes from Hudson, Great Barrington, and Millerton and two hours from New York City. Offered with all the furniture curated specifically for the home.

Lovely North Canaan CT colonial home nestled on about one acre of land. This comfortable home offers 3 bedrooms and 2.5 baths. The main level is comprised of an expansive living room with warming gas fireplace and an adjoining office. From the country kitchen one can enter the formal dining room or carry along down the hall which has a full bath and then leads out to a spacious private deck. There is also a bonus room with a half bath awaiting ideas of the new owners. The upper level has 3 bedrooms and a full bath. The large primary bedroom has access to its own private outdoor balcony. Newer thermopane windows allow great natural light. Enter the full basement, with workshop, through the one car garage and then on to the kitchen. The home comes equipped with a propane fueled full house generator and utility shed. This property is ready for you.

Nestled on one of Lenox's most desired streets, 48 Cliffwood St exudes classic colonial charm and modern elegance. Just steps away from the vibrant village center with its array of shops and restaurants, this pristine home offers the perfect blend of convenience and tranquility. Boasting 3/4 bedrooms and 3 baths, this residence is move-in ready, inviting you to experience a lifestyle of comfort and sophistication. The kitchen is a chef's dream, featuring high-end Viking appliances and a wine cooler, making it a delightful space for culinary creations. A recent addition includes a spacious family room with a dining area, a cozy gas fireplace, a full bath, as well as a pantry and laundry room, ensuring both practicality and luxury. The full basement with a wine cellar adds an extra touch of refinement to this already impressive property. With its easy-care yards, this home even presents itself as a compelling condo alternative, catering to a variety of lifestyle preferences. Stepping inside, you are greeted by a harmonious blend of traditional elements and contemporary comforts. The interior exudes warmth and sophistication, with wood flooring adding a touch of elegance to the living spaces. The layout is thoughtfully designed to offer both intimate spaces for relaxation and open areas for entertaining guests. The two fireplaces create cozy focal points, perfect for unwinding on chilly evenings. Natural light floods the rooms, creating a welcoming ambiance that invites you to make yourself at home. Every detail in this residence has been carefully curated to provide a harmonious living experience that caters to both style and functionality. Architecturally designed in the colonial style, this home showcases timeless appeal and enduring quality. The attached garage ensures convenience and security, while the central air cooling system guarantees year-round comfort. The property's thoughtful layout allows for seamless indoor-outdoor living, with a deck providing the perfect spot for al fresco dining or relaxing in the sun. The therapeutic whirlpool adds a touch of luxury, offering a private oasis for relaxation and rejuvenation. The property's asphalt roof and public sewer system add to the overall ease of maintenance, allowing you to focus on enjoying the beauty and comfort of your surroundings. Situated in the heart of Lenox, this home not only offers a serene retreat but also provides easy access to the town's amenities and attractions. With Morris Elementary School and Lenox Memorial High School in close proximity, you will appreciate the convenience of nearby educational facilities. The vibrant community is known for its cultural events, outdoor recreation opportunities, and historic charm, ensuring there is always something to explore and enjoy. Whether you're strolling through the picturesque streets or dining at one of the local eateries, living in this home offers a lifestyle of comfort, convenience, and endless possibilities.