luxury real estate for sale Chatham, United States

If you love to drive long gravel roads through maplewood forests dotted with antique farmhouses and barns, we have this offering located in the corner of Columbia County that serves mountaintop views across the Hudson Valley. The impressive drive into the property through the gate is uphill past three meadows ablaze in native wildflowers across three seasons and through its own maple stock. The residence is a J.L. Ramirez, Architect PC (NYC) designed and built 4 bedroom 2.5 bathroom 3200 square foot center hall colonial with an open downstairs floor plan, high ceilings on both floors, grand porches on both front and back with sunlit, expressive Pella paned windows highlighting the Catskills to Berkshires views surrounding this tippy top sited spot. The estate, constructed in the year 2000, has 89 acres in total, with 20 acres mowed and lovingly maintained over 25 years to provide a lawn for lounging and entertaining. Afternoon breezes and birdwatching become the cocktail hour calling with a built in bar for service. The kitchen, with its bank of paned windows and buzzed by hummingbirds all day long, is adorned with heirloom custom cabinetry that is passed through the generations whether the countertop material de rigueur changes or not. A flock of turkeys wanders by and the yellow warbler works a tree branch while you stir bolognese for the evening supper and star gazing is absolutely magnificent from this spot. The house includes an office downstairs currently used as the media room, a mudroom with a floor of native stone off the kitchen, a wood burning fireplace and a barn. All of the bedrooms are off the center hall upstairs and all 4 enjoy good size proportions with the primary on the rear en suite. Situated in the quaint hamlet of East Chatham, this residence enjoys proximity to Chatham village and the Old Chatham Country Store with its delightful, local fare menu, the Massachusetts attractions of Stockbridge including the talent featured at Tanglewood and the convenience of I-90 to Boston or Maine at hand.

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.

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.

Originally built in the year 1800 on one the areas most historically significant roads lies this delightful antique farmhouse brimming with original details and charm. Perched above the road with its wrap around porch you are immediately transported to a simpler time where quality and beauty mattered. Further selling the vision, the periphery of your view is flanked with mature trees and one of two large barns providing a nostalgic aesthetic and endless opportunities. The barn closer to the home contains a garage for sheltered parking and the ability to create a guest house, work studio, private gym or anything you can dream up. In fact, there's room for all of those options within the same structure. A serene hilltop view in the distance beckons you to walk through the more than five and half acres of lawn, meadow and fruit trees to the second barn structure to continue dreaming up the possibilities. Currently this space is absolutely perfect to host outdoor dinner parties and gatherings with a bucolic view. The interior experience begins in the entry parlor, anchored by a traditional wood-burning stove. Original wide plank painted floors flow seamlessly into a spacious dining area bathed in natural light. Adjacent to this space, the modernized kitchen offers optimized storage solutions and updated appliances. The main level extends toward the rear of the residence, where the family room features stunning beamed ceilings that evoke a historical atmosphere. Completing this floor is a versatile adjoining room, ideally suited for guest accommodations or a home office and also conveniently hosts the laundry room. Up the wooden stairwell from the entry parlor three bedrooms and a bathroom surround the landing which has enough room to be its own library/reading space. The bedrooms are quite large for the era continuing this property's themes of charm, beauty and modern comfort. Just minutes away from Queechy Lake, where residents can enjoy access via an annual pass, its prime location offers easy reach to Chatham, Ghent, and Hudson on the New York side, while Great Barrington, West Stockbridge, and the Berkshires are equally accessible. Whether you are looking for a full-time residence or a perfect weekend retreat from NYC or Boston, this home serves as an ideal destination.

True quiet country roads are increasingly rare--and land offering this degree of privacy and seclusion is rarer still. This wooded, unimproved parcel, adjoining 171 Old Gale Hill Road in East Chatham, offers an estimated 1,186 feet of road frontage along an unpaved and quiet gravel road and an exceptional opportunity to claim a peaceful corner of Columbia County surrounded by nature. The gently rising terrain ranges in elevation from approximately 1,030 to 1,122 feet, creating natural contours, varied woodland scenery and intriguing possibilities for thoughtfully sited improvements. Explore the land's potential for responsible timber harvesting, hunting, camping and other recreational pursuits--or envision building the private country sanctuary you have always dreamed of. Although tucked away from traffic and noise, the property is conveniently located approximately 11 miles from Chatham Village, 10 miles from the hamlet of New Lebanon, 19 miles from Pittsfield, 26 miles from Hudson, 135 miles from New York City and 140 miles from Boston. This is land for those who value stillness, privacy and the freedom to create something entirely their own—a rare opportunity to enjoy an authentic country setting along a truly quiet road, within easy reach of the Hudson Valley and Berkshires.

Set on eight acres, between the Hudson Valley and the Berkshires, this idyllic, light-filled house offers ample opportunity for living, work, and entertaining. With three bedrooms, four full baths, and a recent addition, the property has stunning views of the surrounding hills, a large deck, a two-car garage, a creative studio, and a picturesque pond. Enter through a breezeway with floor-to-ceiling windows and a tiled floor. The foyer leads into the living room, with a wood burning fireplace, and a large dining area. The kitchen and the adjacent great room make it easy to host gatherings. Wide-board floors are throughout the house. French doors open from the great room to the large deck outside, overlooking the pond. The first floor bedroom, which is currently used as an office, has an ensuite full bath. Upstairs, comfort and convenience are a priority for both the primary bedroom and the guest bedroom, which have ensuite bathrooms and large walk-in closets. The primary bedroom looks out over the Berkshire hills, including views of Jiminy Peak. The recent two-story, 1,433 square-foot addition conveniently connects via the breezeway to the main section of the house. The first floor of the addition has a very large, flex room, which can be additional living or work space or as a place for entertaining. It opens to a separate area that is currently being used as an exercise room. Upstairs is a spectacular studio space with vaulted ceilings, walls of windows, and features a full bath that includes a Japanese style soaking tub. It has been used as an artist's studio, but could easily be repurposed for meditation, yoga, music--the possibilities are endless. Outside, you can relax on the deck, looking out at the pond, enjoying the hot tub or walking the trails on the property; a small bridge leads you to a gazebo. Just minutes away is the farm market store and The Blueberry Café for delicious breakfast, lunch and dinner. Chatham Village has restaurants, The Crandell movie theater, bookstore, along with many other shops. A short drive into The Berkshires for music and theater or head the other direction to Hudson for the vibrant scene on Warren Street and access to Amtrak. Only a two-and-a-half-hour car ride to NYC. This peaceful, scenic and spacious house offers so much for the next owner.

Welcome to Bons Reves House, a beautifully designed escape tucked away on nearly seven acres in the most desirable part of the Austerlitz hills. Built in 1985 and meticulously renovated and expanded by a top builder in 2012 and again in 2025, this 4-bedroom, 3.5-bath contemporary home feels like a luxury treehouse hidden among mature hardwoods and surrounded by large estates and high-end residences. Custom millwork, natural stone and wood surfaces, bespoke plaster treatments, and designer-chosen paint colors all speak to exceptional quality. The gracious, flowing layout offers plenty of room for gathering, and bedrooms tucked into separate wings create privacy and practicality. This is a home built as much for weekend entertaining as it is for quiet days spent resting and recharging.On the first floor, a renovated chef's kitchen with stone countertops, custom cabinetry, multiple prep areas, and an island breakfast bar make it a true country kitchen, with plenty of room for gatherings and holidays. It flows into a Thanksgiving-sized dining area and a large, inviting living room centered around a cozy wood burning fireplace. Just off the kitchen, a newly built four-season sunroom looks out through oversized windows onto treetops and the ridgeline beyond. A mudroom with laundry, a full bath, and a powder room round out this level.Up one set of stairs, the primary suite has vaulted ceiling, multiple closets, and a full bath with a dramatic architectural sensibility. A second staircase off the kitchen leads to two more bedrooms and a full bath. Down on the lower level, an additional bedroom joins a studio or work space, an exercise area, and a newly built window-lined sitting room, offering room to spread out or tuck away.Outside, the wraparound Trex deck, front porch, fenced garden, handbuilt stone walls, and professionally landscaped grounds create a storybook atmosphere for outdoor living. The wooded acreage surrounding the home creates a natural buffer for privacy and quiet. Recent upgrades reflect real investment in the property: new windows, six new heat pumps, a recently replaced roof, a generator, a new garage door, and a freshly painted interior and exterior.The location suits both a weekend retreat and a full-time home. Just 15 minutes from Chatham, 20 to Great Barrington, MA, 35 minutes to Hudson, 45 minutes to Albany, and two-and-a-half hours to New York City, Bons Reves House puts summer evenings at Tanglewood, a movie night in Chatham, dinner out, and gallery walks through Great Barrington and Hudson all within easy reach. Local golf courses and cycling routes round out the list of ways to spend a day here. Convenient to the region's best amenities and attractions, the home still feels hidden away from the world.

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.

OPEN HOUSE on Saturday, August 1 from 11-1 Built in 1739, this Kinderhook Village house is one of the oldest in Columbia County. It would be ideal as your upstate weekend retreat or a full-time home. Surrounded by lush vegetation, vines, and trees, the property has a private lawn suitable for a small garden. Additionally, there is a one-car garage with a gardening shed attached. The house retains most of its original wide-plank flooring, molding, cabinets, and many of its closets and doors. The galley kitchen area looks forward to your creativity and individual design. The first floor features two parlors (or a parlor and a bedroom) a freshly installed full bath, a dining area, a three-season porch and a galley kitchen. Upstairs are two more bedrooms, another full bath, and an area currently used as a laundry space. This charming hideaway is an easy five-minute walk to the Village of Kinderhook's Town Square with its coffee shops, 4 restaurants, book store, bagel shop, seasonal Farmer's Market and Post Office. The Kinderhook Memorial Library off the square is a wonderful meeting place for children and adults of all ages. Kinderhook is 2 -1/2 hours from NYC, 25 minutes from Albany, and 15 minutes to Hudson, NY. The Hudson Amtrak station has eight trains daily to/from NYC's Penn Station. Please come to Kinderhook and discover this charming getaway!

Don't miss an opportunity to own one of the most stately and desirable properties in the historic and charming Village of Kinderhook, the former hometown of Martin Van Buren, the Eighth President of the United States. Tucked in the center of the historic district, steps from the Village Square, sits a grand early Nineteenth Century colonial, on 1.3 private acres, which harkens back to a bygone era. The eighteen room home's distinctive features include a large front porch, nine over six windows, seven mantels, period moldings, vintage hardware, soaring ceilings, shiplap, built-in cabinets and bookshelves, and beautifully refinished classic wood floors. The owners have maintained the historic character of the home while updating the kitchen and baths to provide functionality and modern conveniences. The first floor is ideal for entertaining. Enter through the original eight panel front door to find the center hall complete with refinished narrow wood floors and a classic staircase with newel post. To the left of the entry hall is a huge parlor with large windows, hardwood floors, and beautiful woodwork. The hardwood floors, woodwork, and large windows continue into the adjacent formal dining room with original crystal chandelier. To the right of the entry hall is another large room with narrow board floors, vintage woodwork, and large windows, including a splendid bay window which floods the room with light. An impressive gathering room with architectural details, wide board floors and a crystal chandelier anchor the space at the rear of the entry hall. Also on the first floor is an eat in kitchen with vintage coffered ceiling, large pantry with hosier and open shelving, full laundry room with farm sink, half bath with classic tile floor, a spacious bedroom with period lighting and wide board floors, a separate dressing room with built-in cabinet, a mudroom, a heated screen porch, and an office with separate entrance. The second floor contains an immense primary bedroom with double closets, two additional large bedrooms with walk-in closets, and an ensuite bedroom with separate dressing room with vanity. A bath with a marble floor, updated shower, and period vanity service the three front bedrooms. The ensuite bedroom is serviced by a private bath with a marble floor, shower, and soaking tub. The ensuite can also be accessed by a private back staircase. There is a walk-up attic for ample storage, and a two-story mortise and tendon barn suitable for a workshop, additional storage or as a two-car garage. The private lot consists of 1.3 grassy acres of flat land with gardens, shade trees, and lots of wide-open spaces. There is ample room for a pool. The property is convenient to Hudson, Chatham, Albany, Troy, the Catskill Mountains and the Berkshires and easily accessible by car or train to New York City and Boston. It is a short walk to restaurants, coffee shops, a seasonal farmer's market, the post office, churches, art galleries, shops, parks, a museum, a garden center, an orchard, a yoga studio, the Kinderhook Creek boat launch, the Hudson River Valley Greenway, and all of the wonderful activities, concerts and events that make the Village of Kinderhook such a special place. Seize the opportunity to own a truly special property in a truly unique place before it is too late. Call to make an appointment for a private showing.

Spectacularly renovated and offered for the first time since its complete transformation, this exceptional pond front residence overlooking Maiden Lake is located within the highly sought-after Fern Hill community and offers refined design, privacy, and effortless indoor-outdoor living. The home is clad in warm natural cedar siding, lending timeless character while blending seamlessly with the surrounding landscape. Maiden Lake is a shared pond maintained by the Fern Hill HOA with private swimming access. Set on a quiet country road just outside the Hawthorne Valley hamlet, the property is minutes to Great Barrington, Massachusetts, close to respected private schools, and offers convenient access to the Taconic Parkway and Albany International Airport, allowing for easy travel from New York, Boston, and Connecticut. The thoughtfully designed home features multiple private bedroom suites, lofted ceilings, and expansive light-filled living spaces. Interior finishes highlight exceptional natural materials and craftsmanship, including white oak flooring in the main living areas, cherry cabinetry, soapstone kitchen countertops, French oak stairs, and a custom single-stringer stair with a black steel beam, black steel railing, and white oak banister. Bedroom suites feature maple flooring, while the upstairs loft, office, or studio includes wide-board pine floors. Custom wainscoting and a dedicated linen closet serve the bedroom suite hallway. The open main living area centers around a well-appointed chef's kitchen with an oversized dining island and additional dining space. Premium stainless steel appliances include a Bosch wall oven, Thermador gas cooktop, Fisher and Paykel refrigerator, KitchenAid dishwasher, and Zephyr range hood. Bathrooms feature white subway tile, marble sink countertops, rain and hand-shower fixtures, and wood-grained porcelain tile flooring. The home is filled with light and comfort through Marvin triple-pane windows and doors with built-in shades, automated skylights, and thermal skylight shades. Ceiling fans, insulated thermic shades, and remote-operated skylights enhance energy efficiency and airflow. Multiple dedicated home office areas support flexible modern living. Year-round comfort is provided by an energy-efficient heat pump system with heating and cooling, radiant heated floors in the main living areas and primary bathroom, and a separate gas furnace serving the rear portion of the home. A whole house backup generator provides added peace of mind. Additional upgrades include high-efficiency insulation, fully updated plumbing and electrical systems, a 400-amp electric service, and ethernet outlets. A gas fireplace adds warmth to the main living space. The laundry room includes cherry cabinetry and Bosch stackable washer and dryer units. The entry mudroom features a brick floor, bluestone bench seating, antique wood beams, a Buderus European-style radiator, abundant windows and skylights, and generous storage. The landscaped grounds include perennial gardens, bluestone walkways, copper gutters and drainspouts, selective fencing suitable for small livestock or chickens, and fenced raised-bed gardens. A charming barn includes a three-to-four-person luxury sauna with an Amerec SaunaLogic controller and Laava series heater. Outdoor living is exceptional, with an expansive wraparound Brazilian walnut deck, a spacious gazebo with sweeping pond views, an additional deck overlooking the water, and a dock. This rare offering blends natural beauty, modern comfort, and the coveted Fern Hill lifestyle in an ideal location. Cultural destinations like Hudson galleries, Art Omi, Tanglewood, and Jacob's Pillow are nearby, along with skiing at Catamount, Jiminy Peak, and Butternut. Best of all, Hawthorne Valley Waldorf School and the renowned Hawthorne Valley Farm Store—featuring the highest quality local, organic, and biodynamic food—are just moments away by foot or bicycle.

Welcome to DREAMLAND. Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow—perfectly oriented for southern exposure—creates an ideal setting for a modern country estate, while a network of winding, tree-lined trails invites exploration through a landscape of mature hardwoods, including striking 200-year-old oak trees and historic stone walls. The setting feels both expansive and intimate, a 5 acre building site offering the opportunity to design a home that fully captures the surrounding natural beauty. Located moments from the renowned Hawthorne Valley School and its celebrated farm store, and within easy reach of the cultural richness of the Berkshires, this property places you at the intersection of nature, design, and lifestyle. Skiing, art, and dining are all nearby, while the vibrant riverfront city of Hudson is just 20 minutes away. A rare opportunity to create a legacy property in one of the Hudson Valley’s most sought-after settings—where architecture, landscape, and lifestyle come together seamlessly. BOHA, Driveway permit, survey

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that caters to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 square foot heated indoor arena, which includes an owner's apartment and viewing area--and a professional-grade outdoor ring.

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.

This quintessential 19th century four bedroom farmhouse with a classic front porch, on over an acre of land, boasts impressive Catskill Mountain and sunset views. Only minutes from Hudson, the house, built in 1860, and now beautifully restored with wood floors throughout, has an expansive great room that includes the kitchen, a living area and a banquette for casual dining. The center island has a convenient prep sink and a breakfast bar for more seating. The room is perfect for cooking and entertaining with space for everyone. A wood stove warms the room and radiant heated floors in the banquette area keep feet warm in winter. Maple wood counter tops with mahogany trim are throughout the kitchen, a classic porcelain farm sink overlooks the garden, a subway tile backsplash and a high performance six burner gas stove for discerning cooks. Glass doors open to the bluestone patio and gardens, easily combining inside and out. A convenient pantry and laundry room off the kitchen offers ample storage. A separate dining room has space for formal dining and on the other side of the hallway, the light filled living room has a wood stove. The original staircase leads to the second floor with four bedrooms and two full baths. The primary bedroom has a vaulted ceiling, an office nook, a private dressing room and a wonderful en suite bathroom with a tiled walk-in shower and clawfoot soaking tub with views of the garden. A loft area can be opened in the primary bedroom creating an additional private space. Outside, the gardens have been meticulously tended with raised beds for vegetables, perennial plantings, native species, stunning gabion stone walls and a built-in fire pit for chilly evenings. An important historic heritage sugar maple tree graces the fenced back yard along with black walnut trees, ornamental cherry, hydrangea, forsythia, magnolia, mulberry, white pines and a lovely orchard of apples and peaches. The front porch wraps around the house and provides the ideal spot for relaxing with a summer breeze and wonderful distant views of the Catskills and vibrant sunsets. A vintage garage has space above that could be work or creative space. A well-maintained house with a standing seam metal roof on the main part of the house, new asphalt shingled roofs, a Buderus boiler, a new hot water heater, a water filtration system and an automatic generator for summer or winter storms. A beautiful country home in an ideal location on the historic Old Post Road that linked NYC to Albany. A short drive to historic Kinderhook Village, Art OMI sculpture park, Chatham Village, farmstands, restaurants, shops, Hudson and Amtrak. Just over two hours to NYC.

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.

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.

Rare opportunity to own an enchanting horse farm in the heart of Columbia County. A historic Hudson Valley 1840s center hall Colonial farmhouse sits on over 20 stunning acres of rolling fields, fenced paddocks with water troughs and run-in sheds, a horse barn with a large hay loft and 8 stalls + an additional 3-stall pony shed that could be used as a chicken coop, garden beds, mature trees, a supplementary living space above the garage with a full bathroom, and a charming wooden bridge over a clean spring-fed creek where wild watercress grows. Prime farmland with 3 fields on the property currently leased to neighboring Hawthorne Valley Farm. Step from the L-shaped porch into the bright house filled with character, featuring exposed wood beams, vaulted ceilings, original moldings and wood floors, 2 wood-burning fireplaces, 6 bedrooms including a spacious, first-floor primary bedroom with an en suite bath and a private entrance, 4.5 bathrooms, wet bar, 10' ceilings, plaster walls, window seats, flagstone patio, mudroom. Recent improvements include a brand-new generator, fresh paint, new laundry with a new LG clothes dryer, and recessed LED lighting. This equestrian property is in an idyllic countryside setting and mere minutes from everything one might need in terms of culture, social life, sports and schools for children. N earby Hudson and Rhinebeck offer fine shopping and dining. There's certainly no lack of things to do and places to eat! Take your pick of farm-to-table restaurants, farm stores, farmer's markets, bookstores, bars, cideries, distilleries, hikes, art galleries, antique stores, and more.

This stylish log home on 3+ acres is the complete Berkshire retreat. Recently updated and improved, the home pairs modern lodge character with resort-like amenities. A heated saltwater gunite pool and integrated hot tub anchor the beautifully landscaped grounds. A locust fence encloses the pool area, with bluestone patio, lush lawn, and a stunning renovated pool house designed for entertaining, dining, or remote work. Inside, the home is warm, open, and full of character, with the added benefit of true one-level living. The great room is the centerpiece, with soaring ceilings, exposed log beams, and a substantial stone fireplace. The adjoining kitchen and dining areas are designed for gathering, with cherry floors, custom pine cabinetry, a large island, and stainless appliances. A large screened porch and wraparound deck extend the living space outdoors and take in the wooded setting and ridge views. The luxurious first-floor primary suite offers private porch access and a spacious bath with soaking tub and separate shower. First-floor laundry completes the main-level living arrangement. Upstairs are three additional bedrooms and two full baths. The walk-out lower level includes a dedicated home gym and additional flexible space. Beyond the pool area are several other amenities, including a dramatic fire pit tucked into a natural rock outcropping, a children's playground, and open lawn for games and play. Private but not remote, the property is just minutes from downtown West Stockbridge, with Stockbridge, Lenox, Great Barrington, and Tanglewood all within easy reach.

Old Farm Lane, Lot #26 offers the perfect blend of wooded privacy and neighborhood community, while being tucked away on a quiet cul-de-sac. Utilities are in place with public sewer, private well, underground electric and gas. This lot borders the Pittsfield State Forest and offers close proximity to other year-round activities. It is also a short drive to the cultural hubs of Lenox, Williamstown, and North Adams. Privately located with access to everything.

This Woodmonte Estates lot offers a builder-ready parcel equipped with on-site utilities, including public sewer, a private well, and underground electric and gas. Tucked away in a premier luxury community, this location provides a serene, private setting while maintaining close proximity to year-round recreation. It is just a short drive to the renowned cultural hubs, skiing, lakes, and numerous outdoor activities of the Berkshires. Please note that home must be minimum 3000 sf, with design and construction of home subject to HOA approval. With additional adjacent lots available to create an expansive, custom estate, this location represents the ultimate destination—privately situated yet perfectly connected to everything the region has to offer.

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.

On one of the most scenic country roads in the County, Willow Branch Farm, a 19th century farmhouse on over 53 acres has been transformed by the noted architect owner into a stunning property with Catskill views and sunsets. The Italianate three bedroom house is surrounded by a traditional English style landscape with a picturesque pond that delights the eye. Inside, 10 foot tall ceilings, wood floors and large windows bring in light and views throughout the day. Enter through original 19th century carved doors into the foyer. To the right, the expansive living room has a bay window to take in the view, floor to ceiling windows and a gas fireplace with an exceptional 19th century French Portoro black marble mantel. French doors open to the north porch. The spacious kitchen and dining room combine for the perfect place for cooking and entertaining. Custom rift and quartered white oak cabinetry hides a convenient coffee area and pantry space. A walnut topped island contains an induction cooktop and ample storage underneath. Top of the line appliances include a Sub-Zero refrigerator, a Bosch dishwasher, refrigerated drink drawers in the coffee station and two full size, convection wall ovens hidden behind a custom designed cabinet. A wall of floor to ceiling glass doors open to the west porch with dramatic views and sunsets throughout the year. Grass cloth walls, an English Wilton carpet and a 1940's French chandelier make for a very cozy library or ''Snug.'' The back hall, with a black basalt stone floor from Waterworks and antique 1920's pendant lights, leads to a large pantry and a separate laundry room with storage and a sink. The mud room, with double closets, hooks for hanging and a convenient bench, has a side door for easy access to and from the outside. The screened porch at the end of the hallway, which overlooks the pond and property, is ideal for summer relaxing and dining. A custom-built staircase with walnut bannister spindles and a hand tufted wool runner leads to the second floor. The primary bedroom has spectacular views facing west, a walk-in closet and en suite marble tiled bathroom. Off the hallway are two guest rooms, each with their own bathroom. The tower room with 16' ceilings is the ideal office or workspace. Bespoke details are throughout the home including St. Jude and Christopher Farr wallpaper in the bedrooms and first-floor half bath, all bathroom and kitchen fixtures and tile from Waterworks, many Vaughan and antique lighting fixtures, and all custom cabinetry. Outside, the barn has been redone with a new roof, concrete floor, plumbed for a bathroom, space for cars or workshop on the first floor and an impressive, high ceiling space on the second floor that can become guest space, extra living, studio, or work space. Beautifully restored original columns and decorative brackets line the north and west porches. Modern improvements include a new standing seam metal roof, buried power lines, energy efficient geo-thermal heating and cooling, new insulation, full house generator, Lutron lighting, motorized window shades, irrigation, sound, and security systems. The property is on two parcels. There is a separate 4-acre parcel of vacant land can be built on for a guest house, an, investment property, or sold. Just a few miles from the Hudson River and only minutes to the historic Village of Kinderhook with restaurants, bookstore, wine shop, Jack Shainman gallery, library, orchard, and the Empire Trail for walking or biking. Twenty minutes to Chatham Village. Just 30 minutes to Hudson's vibrant Warren Street and Amtrak. An easy drive to Albany Airport. Willow Branch Farm is the perfect blend of location, history, elegant design, and modern updates.