luxury house for sale Canaan, United States

Set on 4.7 beautifully landscaped acres with distant views. This impeccably maintained home offers generous space, thoughtful craftsmanship, and remarkable indoor-outdoor living. Located just minutes from so many of the Berkshires' most beloved attractions, including only 15 minutes from the main gate at Tanglewood, this Richmond property also boasts easy access to major traffic routes connecting you conveniently to both New York and Boston. Your ability to enjoy the region's culture, adventure, and cuisine starts right here.

Commanding one of the highest residential elevations in the Hudson Valley, this extraordinary custom residence enjoys breathtaking, uninterrupted views across the Catskill Mountains and Hudson Valley, offering spectacular sunsets, endless skies, and extraordinary stargazing from the privacy of your own mountaintop retreat. Thoughtfully designed for luxurious everyday living and effortless entertaining, the home features a chef's kitchen appointed with premium Bosch, Sub-Zero, and other high-end stainless steel appliances, a gas cooktop, a handsome butler's bar, and exceptional custom cabinetry and built-ins handcrafted by renowned local artisan Vormer Cabinetry of Hillsdale. Superb craftsmanship is evident throughout, complemented by high-performance insulated Pella windows that enhance comfort and energy efficiency while framing the spectacular views. The dramatic great room is anchored by a striking stone fireplace with a reclaimed wood mantel, while a marble gas fireplace with a wood mantel creates an inviting atmosphere in the den. The spacious primary suite enjoys magnificent views and is complemented by an open spa-inspired bath, laundry, and generous closet space. The spacious two-car garage offers abundant storage for outdoor equipment, bicycles, paddleboards, and kayaks, perfectly complementing the property's proximity to Queechy Lake, Stockbridge Bowl, and the region's exceptional outdoor recreation. Modern conveniences include app-controlled security cameras and heating and cooling systems, allowing effortless remote management of the home. Outdoor living is equally impressive, with expansive decks and patios positioned to capture the extraordinary views, multiple barbecue and fire pit areas, and a heated saltwater swimming pool creating an exceptional setting for entertaining or quiet relaxation. A charming pool house with its own outdoor grilling patio extends the outdoor living experience, while the walkout lower level opens to an additional stone patio and fire pit--another spectacular vantage point from which to enjoy unforgettable Catskill sunsets beneath expansive evening skies. Raised garden beds, ornamental flower gardens, and fenced vegetable gardens with programmable drip irrigation provide an ideal setting for growing vegetables, herbs, and flowers. Flexible living space offers additional guest accommodations, while a backup generator provides year-round peace of mind. An additional five-acre parcel is included in the sale, presenting an exceptional opportunity to construct a guest house, studio, office, or other accessory structure, subject to approvals. Located within an exclusive community with privately maintained roads, the property offers exceptional privacy while remaining just minutes from Chatham, Hudson, and the Berkshires. Enjoy easy access to acclaimed dining, boutique shopping, yoga and Pilates studios, organic markets, farm stands, theater, antiquing, and renowned cultural destinations including Tanglewood, Jacob's Pillow, Stockbridge, Lenox, Egremont, Great Barrington, and the Shainman Gallery. Convenient to the Taconic State Parkway, Interstate 90, New York City, Boston, and Albany International Airport, this remarkable residence offers the very best of Hudson Valley luxury living.

This serene 5-acre property boasts open meadows and mature trees, offering a tranquil retreat that feels a world away, yet remains highly accessible to the best of the Hudson Valley and Berkshires. Its proximity to the Taconic State Parkway and Interstate 90 ensures an easy retreat from both New York City and Boston. Locally, you'll delight in the charming town of Chatham's cafes, restaurants, bars, and a burgeoning art museum scene, with Queechy Lake just a 10-minute drive away. Popular destinations like Hudson and Great Barrington are also easily reached in just 35 minutes. Inside, discover the ease of single-floor living, featuring a spacious living room with a high vaulted ceiling and a warming wood-burning fireplace. The perfectly updated kitchen is both tasteful and functional, complemented by three generously sized bedrooms and two full bathrooms. The full-footprint basement, partially finished, presents an excellent opportunity to create additional bedrooms, home theater or even a self contained inlaw suite. True to its agricultural surroundings, this perfect home is perched above grounds that are mostly flat and highly versatile for a variety of activities. A charming chicken coop is discreetly tucked behind a 1.5-car garage, inviting you to embrace the farm-to-table lifestyle of the area. A barn sits across the field behind the home providing a bucolic view and awaits your vision for an art studio, guest house or stable. Truly a fantastic value for those looking to find peace of mind in their own private Hudson Valley oasis.

Experience idyllic country life and the best this area has to offer in this charming wood shingled house. Situated on two acres, this three-bedroom cape has an updated kitchen with stone counters which opens into the dining room. The spacious living room has a brick fireplace, built-in shelves and lovely French doors that open into a four-season heated sunroom with a vaulted ceiling and large windows that look out onto the property. Glass doors open onto a small porch that leads to the backyard. Enjoy days and evenings relaxing or entertaining outdoors with the fire pit, stone patio and the clawfoot tub converted into an outdoor shower. Upstairs are three bedrooms and a full bath. The large primary bedroom has double closets. Additional finished space adjacent to one bedroom could be used as an office, playroom or studio space. Finished space in the basement contains a cozy den, an exercise area, the laundry with a utility sink and a separate storage room. Two car garage opens directly into the kitchen and a convenient first floor half bath. EV/RV chargers. Just minutes to Beebe and Harvey Mountain State Forests with thousands of acres for hiking, many local ski options, Tanglewood, Berkshires cultural offerings and Chatham Village restaurants, shops and movie theater. A short drive to Hudson and Amtrak. Come visit this charming home in an ideal location!

This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

Just around the corner from world-renowned Tanglewood, this exceptional Richmond property offers a truly prime Berkshires location-- where music, culture, and natural beauty meet. Set on just over five picturesque acres with shared ownership in a charming small pond, the setting is as special as the home itself. Beautiful open landscaping creates an inviting approach, with sweeping lawns and thoughtfully maintained grounds that enhance the sense of privacy and serenity. The home itself is bright and airy, filled with natural light and designed for both comfortable everyday living and gracious entertaining. The kitchen is the heart of the home, seamlessly open to a sunny breakfast nook and a sun-filled family room-- perfect for gathering with friends and family. A large pantry provides exceptional storage and functionality. For more formal occasions, enjoy a separate dining room, elegant sitting room, and formal living room. A heated sunroom offers year-round enjoyment, while a dedicated first-floor office/library provides ideal work-from-home flexibility. Upstairs, you'll find four spacious bedrooms and two full bathrooms, offering ample room for family and guests alike. Practicality meets versatility on the main level with a convenient laundry/mudroom and half bath located just off the garage. Above the garage, a finished bonus space with its own full bathroom presents endless possibilities-- whether as a private studio, guest suite, bedroom, or additional family room. In a highly desirable Richmond location near Lenox and all that the Berkshires have to offer, this property combines space, light, and flexibility with an unbeatable address close to Tanglewood. A rare opportunity to enjoy quintessential Berkshires living.

Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-study home features triple-glazed windows, super-insulated envelopes, and geothermal climate control.

Dating to around 1770, this pre-Revolutionary Dutch Colonial is among the oldest surviving homes in the historic hamlet of Old Chatham. Set on 8.5 beautifully restored acres, the property feels less like a single residence than a small historic compound, complete with a 19th-century barn and carriage house, an original ice house, a saltwater pool, and even a thoughtfully repurposed 1968 Airstream serving as its pool house. Beginning in 2017, the current owners—both architects—undertook an extraordinary restoration that respected the home's remarkable age while quietly transforming it into an exceptionally comfortable modern residence. Rather than reinventing the house, they carefully uncovered it. Original timber framing was revealed, wide-plank pine floors restored, and the proportions of the eighteenth-century rooms returned to their original clarity. A later addition now houses a beautifully understated kitchen anchored by Wolf, Sub-Zero, and Bosch appliances, along with a sitting room and mudroom that feel entirely in keeping with the home's evolution. Upstairs, two spacious bedrooms are complemented by beautifully renovated en-suite baths, while a library occupies what was once a 1930s porch addition. Every modern system has been thoughtfully addressed, including all new electrical and plumbing, ground-source geothermal heating and cooling, and a standing-seam Galvalume roof designed to last for generations. Even the carriage house has been outfitted with an EV charger. You'll find Marvin windows and sprayfoam insulation. Outside, the landscape has been reimagined with the same level of restraint and care. Dry-stacked stone walls, native plantings, meandering paths, and garden terraces recall the timeless character of an English country garden while framing the property's collection of historic buildings. What makes this home so compelling, however, isn't simply the caliber of the renovation—it's how little attention the renovation calls to itself. Every decision feels inevitable. Original beams, centuries-old brick fireplaces, luminous painted floors, and beautifully scaled rooms coexist naturally with contemporary comforts, creating a house that feels authentic rather than preserved. It is exceptionally rare to find an eighteenth-century home that has been restored with this level of architectural discipline while remaining so warm, livable, and unpretentious. Nearly 256 years after it was built, this remarkable Old Chatham property feels as relevant today as it ever has.

Welcome to Chicory Hill House, a unique designer home set at the end of a long private driveway on 20 beautiful acres located in Columbia County, prime Hudson Valley. The property features pastoral views, a year-round creek, and a small waterfall woven into the landscape.Following an extensive high-end renovation and infrastructure overhaul, the original 1985 contemporary has been transformed with remarkable artistry, craftsmanship, and thoughtfully integrated modern systems. Triple-paned Austrian-engineered windows and sliding doors flood the interiors with natural light while providing outstanding insulation and quiet, and looking out onto your own private field.Major upgrades include new James Hardie concrete siding, a new roof, updated electrical and plumbing systems, new water pump infrastructure, all new split-unit heating and cooling systems, and solar panels, creating a home that is both highly energy efficient and deeply considered.The main living spaces blend warmth, texture, and refined modern design. Wide plank white oak flooring runs throughout the upper levels, while the living room centers around a dramatic floor-to-ceiling fluted marble wood-burning fireplace. The adjacent dining area includes a built-in entertaining station with an ice maker and wine fridge, ideal for hosting gatherings large and small. Walls of glass open directly onto a generous new cedar deck designed for seamless indoor-outdoor living. Complete with a hot tub, outdoor shower, grilling area, and sunny lounging spaces, the private deck overlooks rolling pastoral fields, creating a private outdoor setting equally suited for entertaining, quiet mornings, or evenings spent soaking under the stars.The kitchen pairs clean contemporary lines with stone countertops, custom cabinetry, a walk-in pantry, handcrafted emerald green Zellige tile, and Fisher & Paykel appliances. Bathrooms continue the same elevated approach, featuring marble finishes, Zellige tilework, and spa-like details including heated floors and a heated towel rack. The primary en suite bedroom is a true retreat, complete with a lofted living space overlooking the main open floor plan living area, a double walk-in closet, and tranquil woodland outlooks.The walk-out on grade lower level offers substantial additional living space ready for customization, with architectural plans available for future completion. Anchored by a wood-burning stove, the space could easily accommodate additional bedrooms alongside media, guest, spa, or studio space.Outside, mature trees and wooded landscape, and the year-round creek create a peaceful and immersive setting. A garage with space for three vehicles adds practicality to the property's thoughtful design. Only five minutes from the village of Chatham, the property offers rare privacy and natural beauty without sacrificing access to the region's most beloved towns, restaurants, and cultural destinations. Hudson's celebrated Warren Street, with its restaurants, galleries, boutiques, and Amtrak station, is under twenty minutes away, while the Berkshires' cultural and outdoor destinations, including Great Barrington, Lenox, and Tanglewood, are all within easy reach. New York City is reachable in just over two hours by car or train. Chicory Hill House delivers sophisticated country living with privacy, design, and a high level of finish at every turn.

Experience the perfect blend of professional utility and luxurious comfort at 1 Almon Ave., a beautifully constructed and impeccably maintained retreat located in a BG-zoned area. This home offers an exceptional opportunity for those looking to operate a business or maintain a home-office setup without sacrificing lifestyle quality. The main residence provides four spacious bedrooms, including a convenient first-floor bedroom w/ a walk-in closet, complemented by four full bathrooms. At the heart of the home, the gourmet kitchen showcases custom hickory cabinetry paired with solid granite countertops. The second floor--which, along with the stairs, will feature new carpet--includes three additional bedrooms, a family room, a full bath with laundry, and a massive storage closet. Versatility Versatility defines the living space, further highlighted by a finished third floor that includes an additional full bath, perfect for a primary or guest suite, studio, or recreation area. The lower level offers even more flexibility, featuring its own separate entrance and ample space that can be utilized for business needs. Comfort is prioritized year-round with a wood stove that adds warmth to the home. The exterior is equally impressive, featuring meticulously landscaped grounds, a welcoming front porch, and a rear Trex deck ideal for outdoor entertaining. Car enthusiasts and hobbyists will appreciate the standout garage setup, which includes electricity and heated bays fully equipped with a steel beam, as well as a separate, heated, three-bay garage with electricity. Sustainability is a significant benefit here, as the home comes equipped with owned solar panels that have allowed the current owners to eliminate electric bills for the past seven years. Adding to its local charm, this property is famously known as the premier holiday light display destination in the Berkshires.

Set along one of the most beautiful roads in Columbia County, this extraordinary country property offers a rare convergence of architecture, design, and landscape. Surrounded by 13 gorgeous acres of rolling hillside and forest, the setting feels both cinematic and deeply peaceful. Just beyond, the road is famously home to the Chatham Sheepherding Company's iconic complex of vernacular barns and agricultural buildings, lending the area a distinctly historic and pastoral character that is increasingly difficult to find. This is a home with true soul--restored and refined with remarkable sensitivity. The interiors were led by a House & Garden UK 100 designer, and that level of design fluency is immediately apparent. Every decision feels intentional, creating spaces that are quietly luxurious, deeply livable, and impossible to replicate. Throughout the home, original character is honored and elevated through exceptional materials and thoughtful detailing. Wide-board antique pine floors run throughout, grounding each room with warmth and patina. Even the smallest elements were considered: Forbes & Lomax brass switches punctuate the walls like jewelry--subtle yet unmistakably luxurious. Lighting by Workstead brings sculptural warmth to the interiors, while Lefroy Brooks bathroom fittings introduce a quietly classic sensibility rooted in craftsmanship and timeless design. The living spaces unfold with intimacy and grace. A richly layered library wrapped in custom shelving invites slow mornings and long evenings. A stunning music room, anchored by a grand piano and bathed in soft natural light, feels both elegant and welcoming. The kitchen and dining spaces are especially compelling--bright, beautifully composed, and effortlessly functional, with bespoke cabinetry, marble surfaces, and seamless connection to the outdoors for summer dinners and quiet morning coffee. The home offers three bedrooms plus a flex space, allowing for a variety of uses--guest quarters, office, studio, or media room. Each space has been designed with extraordinary sensitivity to proportion, light, and texture, resulting in interiors that feel collected over time yet perfectly resolved. What makes this property so exceptional is not simply its beauty, but its atmosphere. It possesses that elusive quality of the very best country houses: sophistication without formality, design without excess, and luxury rooted in authenticity. A truly rare offering--an extraordinary design-forward retreat on one of the county's most storied roads, immersed in the timeless beauty of the Hudson Valley.

Escape the hustle of city life and discover Bellavista Country Estate, a grand 12,000-square-foot Georgian brick residence set on over 25 private acres in the foothills of the Berkshires, ideally situated between the Hudson River Valley and the Berkshires. Offering 6 to 9 beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, and both a fully stocked eat-in kitchen and a formal dining room, the estate blends elegance and comfort with ease. Recreation and relaxation abound, with a spacious in-ground pool, a serene pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, guests enjoy a full gym, a game and entertainment room with arcade favorites, a home theater, a library of hundreds of books, and a finished attic, while a 4,500-square-foot barn with foosball, ping pong, and bar space provides additional room for gatherings and events. Perfect for weddings, anniversaries, family celebrations, and private retreats, Bellavista also offers access to private chefs, caterers, and event planning support, with every detail—from fiber-optic internet and full-house generators to weekly pool and grounds maintenance—thoughtfully attended to. Since 2011, the estate has been a successful luxury rental for vacations and retreats, equally suited to private full- or part-time residence, a hybrid work-from-home escape, or an unforgettable destination getaway. Just minutes from Chatham, Hudson, and Kinderhook, and a short drive to Lenox, Stockbridge, and Great Barrington, the estate is surrounded by farm-to-table dining, art galleries, organic markets, and the renowned Crandell Theater, with easy access via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, or Albany International Airport.

Experience the perfect balance of grand-scale architecture and tranquil nature in this stunning 6,000+ sq. ft. modern Colonial. Nestled on 3.42 manageable acres within a private enclave near Onota Lake, this 5-bedroom, 5.5-bath estate offers sweeping meadow views just minutes from the world-class arts of Tanglewood and The Clark. The entry is marked by dramatic dry-laid stonework, leading into an interior defined by soaring heights. The heart of the home is a two-story living room featuring vaulted ceilings and a floor-to-ceiling stone fireplace. The expansive living space of the great room flows effortlessly into a gourmet chef's kitchen equipped for high-end entertaining with dual refrigerators, double wall ovens, and a center island cooktop with a built-in griddle. High-top island seating allows for social cooking and a sizable breakfast area flanked by a wall-to-wall credenza—ideal for buffet-style hosting. The home's floor plan thoughtfully blends communal areas with distinct privacy across three levels. The main level is designed for complete convenience and the primary suite is a true sanctuary. It features a private egress to the pool and a hidden back staircase leading to a secluded loft—perfect for a library or reading nook overlooking the suite. The upper level offers a sweeping gallery balcony overlooking the great room, leading to four spacious bedrooms. This includes two private ensuites and two additional bedrooms serviced by a full bath and a dedicated laundry room. The lower level is an entertainment hub featuring a home theater, gaming space, gym, full bath, and a secondary egress for easy garage access. The fully-fenced backyard makes for a resort-style oasis. Host movie nights on the expansive deck, or relax by the heated inground pool and custom-finished patio. The designer firepit is anchored by a unique stone compass inlay, and a poolside full bathroom ensures guests never need to track water through the main house. For the automotive hobbyist or enthusiast, a high-end, three-bay attached garage is professionally finished with epoxy floors, industrial-style metal cabinets, and an EV charger. You will also find a massive, 50x40 detached shop with four bays and oversized doors. Whether for housing a car collection, an RV, or a professional art studio, the possibilities of this space are endless. Embrace the Berkshire landscape in a home where every detail has been considered. Whether you are heading out for fine dining or staying in to enjoy your private oasis, Blythewood Estates offers a lifestyle of unparalleled peace and sophistication.

Set on six picturesque acres in Stockbridge, this beautiful contemporary home offers privacy, comfort and stunning views. The thoughtfully designed layout features five bedrooms and 4.5 baths, including a spacious main-level primary suite with a luxurious en-suite bath. The chef's kitchen is equipped with premium Wolf and Sub-Zero appliances, perfect for entertaining or everyday living. An oversized three-car garage and finished lower level provide ample storage, while expansive windows showcase the surrounding landscape. Available furnished. This exceptional property is move-in ready and an ideal Berkshire retreat.

Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living experience unlike anything else on the market. The first floor features an impressive great room with soaring timber beams, an elevated Malm fireplace, and floor-to-ceiling glass that captures the surrounding vistas. A gourmet kitchen imported in its entirety from Germany anchors the main living space with exceptional craftsmanship and modern sophistication. Radiant heat throughout the main floor for year round comfort. The first-floor primary suite offers a private retreat with a spacious spa-like bath, featuring a large shower, soaking tub, and generous walk-in closet. An impressive entry foyer sets the tone with a sleek architectural staircase, powder room, and coat closet. A two-car attached garage provides ease and convenience. Upstairs, a dramatic loft overlooks the great room and sits adjacent to a second bedroom suite, perfect for guests or family. Separate from the two main suites, a private guest wing includes two additional bedrooms, a large sitting room, and a shared full bath, offering a comfortable and flexible space for visitors. Despite its very quiet mountain-top privacy, the property is ideally situated just 10 minutes from Tanglewood and downtown Lenox. Enjoy effortless access to I-90, making trips to Boston or New York City remarkably convenient. Nearby West Stockbridge offers a charming village atmosphere with boutique shops, a local marketplace, wine store, café, inviting restaurants, and even an old-fashioned hardware store—everything you need within a short and scenic drive.

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room.Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional guest bedrooms share a Jack and Jill bathroom, providing comfort and privacy for friends.The finished lower level is dedicated to leisure and repose, crafted with the ultimate goal of relaxation in mind. Here, in this tranquil setting, you'll find the peace and privacy you desire, all within a home that exudes charm and character.

Beautifully renovated historic farm house available in Lenox, Massachusetts. A charming 1840s clapboard house located on the estate of ''Brookhurst,'' one of the famed Berkshire ''cottages,'' this former guest house has 3 or 4 bedrooms and 2 full baths spread over three floors (primary bedroom and bath on main floor). It has a private gated driveway and an attached 2-car garage. Luxurious traditional decor throughout the home but with all the modern conveniences including AC, wifi, whole house generator and more. A flagstone terrace overlooks the lush backyard and fully planted walled garden. The house benefits from the rolling landscaped vistas of the beautifully maintained estate property it abuts. Minutes to the town of Lenox and to Tanglewood!

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

Have you been dreaming of year round fun on Stockbridge Bowl? The time is now! Built in 2011, this lovely home is directly across the street from the beloved town beach and affords water views from most windows. Offering single-level living, 3 BR, 1 full BA, a well appointed kitchen and gracious living spaces. The unfinished walk-out lower level is the perfect place to store your kayaks, and could be finished to offer more living space. There is plenty of off-street parking above and below the home. You are mere moments to Tanglewood's Lions Gate and the very best of the Berkshires. Would make a great rental, or a wonderful family retreat to make memories for years to come. Town sewer, private well, radiant heat, and energy efficient construction, all in a location that can't be be beat!

Embrace effortless seasonal living in this beautifully maintained, vintage three-season cottage. Nestled on a quiet, unpaved lane in the desirable Mahkeenac Heights community, this two-bedroom home offers the quintessential Berkshires getaway. Recent thoughtful updates include fresh flooring and an opened-up floor plan that maximizes natural light and flow. Step outside onto expansive decking designed for alfresco dining. Whether you are spending your mornings at the local lake beach or your evenings taking in world-class music at nearby Tanglewood, this private haven offers prime proximity to the best of Lenox and Stockbridge.

Just 3 miles from Tanglewood and moments from the heart of Lenox, this 36+ acre estate offers rare scale, privacy, and flexibility in one of the Berkshires' most sought-after settings. A long, tree-lined driveway creates a strong sense of arrival, unfolding into two separate residences surrounded by woods, open land, and long-range possibility. The acreage offers both seclusion and the ability to selectively open views toward October Mountain State Forest. The main residence is thoughtfully configured for multi-generational living. The first floor centers around a large living and dining room anchored by an oversized stone fireplace, an eat-in kitchen with oak cabinetry and granite counters, and multiple access points to the outdoors. A heated sunroom and screened porch extend the living experience across seasons. The primary suite includes an en-suite bath, and this level is further enhanced by a second kitchen and laundry hookups, creating true independence within the home. The second floor functions as its own private level, featuring three bedrooms and two full baths. The guest house feels like a second home entirely. With two bedrooms, two full baths, a dramatic stone fireplace, and a kitchen finished with Caesarstone quartz, it offers independence without compromise. Mini-split systems provide year-round comfort, while a private laundry and generous scale make it equally suited for extended stays or full-time living. Both residences feature claw-foot tubs and roofs replaced within the past three years. A two-car garage at both houses, potting shed, fire pit ring, and expansive grounds complete the offering. This is a property defined by flexibility and scale--where multiple generations can live together while maintaining independence, and where land, light, and structure align to create lasting possibility.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

Quitessential 1831 side hall Colonial. Charming home located in the village of Interlaken in the town of Stockbridge, MA. Just minutes to Lenox, downtown Stockbridge, and the Berkshire Botanical Center. Listen to the babbling water from the Larrywaug Brook and visit the nearby town park. Sit on the deck or around the firepit to soak in the atmosphere of privacy and peace. This 3 bedroom, 1.5 bath house has been meticulously updated. These updates include: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer. Garage is partitioned for a workshop but can easily be converted to a one-car garage again.

Elegance meets history on 1 Eaton Lane! Tucked away on a quiet, sought-after street just minutes from the Country Club of Pittsfield and only 10 minutes to vibrant downtown Lenox, this remarkable Colonial seamlessly blends timeless character with extraordinary versatility. Offering just under 5,000 square feet of living space, this historic estate presents a rare opportunity for those seeking a home with a story. The main house is a masterclass in classic architecture, featuring period details enhanced by thoughtful modern updates. High ceilings, gleaming hardwood floors, and charming front and back staircases ground the home in history, while the spacious layout provides endless room to breathe. The heart of the home is a sophisticated kitchen, featuring rich cherry cabinetry, new stainless appliances, brand-new quartz countertops, and a dedicated coffee bar. The living room is a large inviting retreat, anchored by a wood burning fireplace and striking exposed joist-and-beam ceilings. The dining room has been beautifully refreshed with crisp finishes and refined crown molding, offering a bright, modern aesthetic while honoring the home's traditional roots. With five bedrooms, two full baths in the main house, a convenient first-floor laundry, and a newly constructed one-car garage every detail has been attended to. Other recent upgrades include a new 200 AMP electrical panel, a newly installed water meter, and a renovated upstairs full bath. Connected to the main residence is a captivating guest house with a unique pedigree--originally purchased from Berkshire Life for $1 and relocated to this site. This versatile space is perfect for multi-generational living, an in-law suite, or a private studio. It is defined by soaring cathedral ceilings, rustic barnwood doors, and an expansive loft bedroom, all echoing the property's rich history. The Grounds , Situated on a beautifully manicured half-acre lot, the property offers a serene outdoor escape. Whether you are enjoying a morning coffee on the tranquil front porch or hosting an evening on the new composite deck overlooking the grounds, the curated landscape provides the perfect backdrop for gracious living. This historic estate is not just a home--it is an incredible collection of possibilities for its new successor. Viewings scheduled exclusively by appointment.