luxury houses for sale Austerlitz, United States

Rare waterfront opportunity on the Roeliff Jansen Kill / Green River! This prime .58-acre parcel in Hillsdale is the ultimate head-start for your dream home or weekend escape. Save thousands in development, the essential infrastructure is already completely in place, including an existing septic system, well, electric hookup, and a cleared house foundation ready for your vision. Imagine stepping out of your future back door right onto the water's edge. The property also features a detached one-car garage perfect for vehicle parking or secure storage, perennials throughout, and a charming, well-maintained gazebo for relaxing by the river. Located just minutes from Catamount Mountain Resort, Great Barrington, and the heart of Hillsdale, you get the perfect blend of tranquil waterfront living and Berkshire/Hudson Valley convenience.

Welcome to 13149 NY 22, Canaan, NY 12029—a beautifully updated 3-bedroom, 1.5-bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient single-level layout provides comfortable flow between the bright living spaces and the three well-sized bedrooms. Recent improvements include a brand-new roof, ensuring years of worry-free ownership. An attached two-car garage adds convenience and storage, while the expansive yard gives you plenty of room to garden, relax, or simply enjoy the quiet surroundings. Whether you're downsizing, seeking a weekend retreat, or looking for a low-maintenance full-time home, this ranch delivers a perfect blend of comfort, style, and practicality.

Light-filled contemporary Cape built in 2020, this Stockbridge home features an open floor plan anchored by a great room with a gourmet kitchen, dining area, and living room. Two spacious first-floor bedrooms share a full bath, while the expansive second-floor primary suite offers a luxurious spa bathroom and a balcony overlooking the living area. The four-season sunroom (heated and cooled for year-round use) opens to the level backyard. Lovely front entrance with Bluestone steps into an ample mudroom. Enjoy year-round comfort with zone-controlled mini-splits. Close to vibrant Great Barrington, Stockbridge, and Lenox. A quick drive to Tanglewood, cultural venues, and abundant outdoor recreation including hiking and lakes, this modern retreat blends style, comfort, and an exceptional Berkshires location.

Welcome home! This magnificent 13.3-acre estate is rich in history and brimming with enchanting features. Nestled in a county setting, this property offers a connection with the outdoors for nature lovers and recreational activities. A low-maintenance wild garden of perennial flowers and shrubs produces a kaleidoscope of colors during the spring and summer seasons. A large, private office area with high-speed internet provides a productive ''work from home'' environment. The first floor features an eat-in country kitchen with an antique Glenwood stove. The formal living room, with its wood-burning fireplace, is ideal for cozy evenings. The sitting room, complete with built-in bookshelves, is perfect for a home library or study. A large addition boasts vaulted ceilings, adding grandeur and space to the home with versatility for a home office, first-floor primary bedroom, family room or guest quarters. The formal dining room, featuring built-in cabinetry, is perfect for hosting dinner parties. The sunroom, featuring a fountain pond, is bathed in natural light and offers a serene setting. Additionally, the first floor includes a laundry room and a full bathroom, as well as an enclosed four-season porch. The second floor includes four bedrooms, offering peaceful retreats for family members or guests. A full bathroom serves the upstairs bedrooms, and a hobby room provides an ideal space for crafts, projects, or as an additional study area. The large barn is perfect for storage, farming, hobbies, or even transforming into a creative space. The two-car detached garage includes a finished space above, providing a perfect spot for a potential home office, studio, or guest accommodations. Further enhancing the property is a brand-new heating system, new septic and a whole-house generator. Steeped in history and surrounded by beautiful gardens and pastoral views, this property is more than just a home--it's a lifestyle.

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.

Perfectly poised and priced! This immaculately maintained four-bedroom residence, set on an acre of land, delivers three levels of sophisticated living space designed for both effortless entertaining and quiet sanctuary. The property balances a serene, retreat-like setting with beautiful mountain views and unparalleled convenience to local amenities and top-tier Great Barrington schools. The home is enveloped by a lush and mature landscape, offering a changing tapestry of flowering color and seasonal interest throughout the year. Cross the welcoming mahogany front porch an ideal vignette for morning coffee or evening relaxation into the expansive main level. The heart of the home is an open-concept great room featuring beautiful cherry wood floors, anchored by a warm fireplace, built-in surround sound, and a chef-inspired kitchen with a built-in wine refrigerator. A large Carrara marble island serves as the ultimate gathering point, transitioning seamlessly into the living and dining spaces. This floor is thoughtfully completed with a versatile guest bedroom or home office, mudroom, pristine powder room, and direct access to the two-car garage. There is an additional Trex deck perfect for an afternoon BBQ, overlooking the grounds. Ascend the staircase to the private quarters on the second floor, featuring a luxurious primary suite--a peaceful haven with its own ambient gas fireplace, a custom cabinetry walk-in closet, and an ensuite bath complete with a custom steam shower. Two additional generously sized bedrooms share a beautifully appointed full bath, offering exceptional comfort for family or visitors. The finished lower level further expands the home's well-designed footprint. A freshly renovated recreation room, outfitted with a custom bar featuring a solid white oak countertop and an additional half bath, serves as an ideal space for game days, a home theater, or a private lounge.

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.

Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region’s best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique. Plans are available for a one or two bedroom addition.

Comfort, privacy, and easy Berkshire charm on nearly four acres, just five minutes from downtown Great Barrington. Set well back from Division Street on a quiet road, this inviting home feels tucked away but not remote. A tree-lined drive winds through the property to a home surrounded by colorful gardens and mature trees. Inside, the house opens up and keeps surprising. A thoughtful expansion by noted Berkshire architect John James added volume, light, and a more contemporary flow while still feeling connected to the original home. The living room, with its wood-burning fireplace, connects to an updated kitchen, dining room, and sunken great room. With oversized windows and views into the trees, the great room gives the home a bright, open feel while still keeping a sense of definition between spaces. The large vaulted screened porch may be the best room in the house. Surrounded by trees and birdsong, it feels peaceful and immersed in nature -- easy to imagine using all summer. Just beyond, a stone patio overlooks the backyard and offers a great spot for outdoor dining and relaxing. The flexible floor plan includes a first-floor bedroom and full bath, offering the option for one-level living. Upstairs, the large primary suite includes generous closet space and a private bath with soaking tub and separate shower. Two additional bedrooms share a third full bath. A detached two-stall barn/garage with overhead storage provides useful space for vehicles, tools, garden equipment, hobbies, or recreational gear. Close to downtown Great Barrington, but with the feel of a country setting, this is a comfortable, open, good-feeling home in one of the Berkshires' most convenient locations.

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.

Welcome to Wolverton Creative Compound, a storied 119-acre estate set within a hidden valley offering complete seclusion, integrated creative workspaces, and timeless beauty. The original 1830s farmhouse is tucked away at the end of a private lane in Claverack, NY, where the road terminates in a round gravel driveway anchored by the property's original stone well. Two large ponds grace the land, including an aerated, swimmable pond directly in front of the house. Sited among meadows and mature woodlands, the main house, upgraded studio barn, and charming studio shed are framed by terraced stonework, a network of trails, and thoughtfully designed gardens. The setting is peaceful, restorative, and deeply connected to the land, yet only a short drive to both Hudson and Great Barrington.The antique farmhouse offers four bedrooms and two bathrooms across 2,825 square feet, where original details like moldings, wood floors, and Dutch doors preserve its old-world charm. A generous double living room and a Vitsoe-outfitted studio lead to a bright dining area and kitchen, each with direct access to patios and gardens. The layout supports an easy indoor-outdoor rhythm, with covered porches and multiple terraces for lounging, cooking, or gathering. Two staircases rise to the upper-level bedrooms, where southern exposure fills each room with light, and the insulated attic improves year-round comfort. Throughout the home, an intentional color palette lends softness and cohesion. The design brings together European sensibility and Hudson Valley character, creating a live-work compound that balances utility with ease, warmth, and quiet sophistication.Across the garden sits a fully insulated 1,900-square-foot historic barn transformed into a large-scale creative studio, complete with bathroom and clawfoot tub, kitchenette, updated electrical, and HVAC. The studio is wired for photography, cinematography, sound, editing, and workshop use, with fiber-optic service and an underground data connection linking house and studio. The compound has a full HUE lighting system with states created by a film lighting designer. A detached potting shed offers another versatile space, ideal as a garden studio, writer's nook, or future guest cottage, and connects to an outdoor bath deck that invites restorative soaks beneath the stars with its fireplace, clawfoot tub, and outdoor shower. A carport at the barn with EV charging and a full-property generator ensure comfort and continuity year-round, whether for everyday living or on-site production. A whole-house water filtration system adds another layer of comfort.The primary pond is the centerpiece of the property. This aerated, swimmable pond, bordered by a pebble beach and firepit, is ideal for swimming or evening gatherings after a day in the studio. Terraced gardens by The Secret Gardener surround the home with a cottage-style blend of flowering plants, herbs, and vegetables. Rewilded fields and meadows lead to two miles of maintained trails through native grasses and towering trees. The land qualifies for a forestry exemption and includes multiple cleared areas, offering potential for a guest house, additional studios, horses, or even a helipad. Whether hosting music on the lawn, staging a shoot, convening a creative team, or watching the changing sky reflect in the pond, Wolverton Creative Compound is a rare legacy estate and true sanctuary for creative work and retreat.

A modern country home inspired by the farmhouses of the Hudson Valley. Taconic Creek Road is tucked away amongst rolling hills and large surrounding parcels, on a beautiful dead end road with just a few lovely houses. The palette is restrained but luxurious with a thoughtful layout and custom design details. Spanning 2,100 square feet, you’ll find lime washed walls with stunning depth of color, custom millwork and wideboard wood flooring that adds warmth to the space. The main living area is anchored by the open kitchen, with Tundra Gray marble counters, an English farmhouse sink, custom inset cabinetry and paneled appliances. A deVOL pendant hangs over the kitchen table. The sitting area is lined with custom built bookshelves and there are large, deep windows lining the room. They face out into the garden, and french doors at the center take you onto the patio. There is storage and a built in bench at the entry for your boots and bags, and a lovely bath on the main level with Noguchi pendant lights. Upstairs, a light filled sitting room walks out to a screened in porch, and there are three bedrooms spread out across the floor. The primary suite is large with a stunning picture window, an office/walk-in closet and a gorgeous bathroom. You’ll find a walk-in-shower and soaking tub with views of the surrounding treetops. Two other bedrooms share the third bathroom off the hall. There is an extensive list of upgrades that includes a new roof, HVAC and septic, and the current owners buried the electrical lines to the house. A large pool is surrounded by lilacs and hedges, private and peaceful, and there is a garage for parking. Taconic Creek Road offers a rare level of calm and sophistication just 15m to Hudson and Amtrak and under 2.5h north of NYC.

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.

Welcome to Cricket Hill Farm-a circa 1949 country home set against sweeping Catskill Mountain views, this home offers the rare opportunity to create your own Hudson Valley retreat. Privately sited with a beautiful front lawn, mature trees, and a gorgeous bluestone patio designed for outdoor dining and summer evenings, the setting alone is worth the drive. Inside, the three-bedroom, two-bath home is filled with character, including hardwood floors throughout and a wood-burning fireplace that anchors the living space. The seller has already gutted the kitchen, opening the space and creating a true blank canvas for the next owner to design and renovate to their taste. The bathrooms are also ready for updating, making this an ideal opportunity for someone with vision looking to bring new life to a well-loved home. A detached one-car garage adds convenience, while the mountain views and established landscape create the kind of setting that's hard to replicate. An authentic Hudson Valley fixer with soul, views, and endless possibility.

Newly completed and set on 11.7 private acres in the heart of Hillsdale, this architect-designed 4-bedroom, 4-bath modernist residence combines striking contemporary architecture with sweeping pastoral and mountain views in every direction. Arriving via a long private driveway, rolling lawns and open fields unfold toward a home defined by bold geometric forms, expansive walls of glass, and a seamless connection to the surrounding landscape. Just minutes from the Hamlet of Hillsdale, Catamount Mountain Resort, Great Barrington, and Hudson, the property offers a rare balance of architectural refinement, privacy, and access to the region’s most desirable destinations. The residence is centered around a dramatic great room with a soaring 20-foot vaulted ceiling and a wood-burning fireplace clad in richly toned chestnut marble. Floor-to-ceiling glass and oversized Arcadia sliding doors dissolve the boundary between interior and exterior, opening onto more than 540 square feet of covered outdoor living space designed for year-round entertaining and relaxed outdoor living. Throughout the home, natural light shifts across clean architectural lines and warm materiality, reinforcing a strong connection between structure and landscape. The kitchen serves as both a design centerpiece and functional workspace, featuring custom walnut cabinetry crafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A fully equipped butler’s pantry and bar area provides additional prep space, storage, second dishwasher, and additional refrigeration, allowing the main kitchen to remain clean and open for entertaining. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble, featuring a soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second ensuite bedroom offers its own walk-in closet and marble-appointed bath, complemented by an additional guest bedroom suite. A versatile fourth bedroom on the main level provides flexible use as a guest suite, office, media room, or wellness space with direct access to the outdoor terrace. Designed for high-performance modern living, the home includes spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a detached heated 26' x 26' two-car garage. Located just minutes from Catamount Mountain Resort and within easy reach of Great Barrington and Hudson, the home places owners at the center of the Hudson Valley and Berkshires lifestyle. Days might begin with coffee overlooking the fields, followed by a visit to the Saturday farmers market, skiing at Catamount, or hiking nearby trails. Afternoons can be spent browsing Hudson’s celebrated design and antique shops or exploring the galleries, bookstores, and restaurants of Great Barrington. Evenings bring performances at local theaters and live music venues, or a quiet return home as the light settles across the landscape. The setting balances architectural refinement, outdoor recreation, and cultural depth in equal measure. A rare expression of contemporary Hudson Valley living, where architecture, light, and landscape are held in perfect balance. An adjoining 6.73-acre parcel is also available for purchase, offering the opportunity to expand the estate or create a private family compound. (listing agent has a financial interest in the property)

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.

Enchanting Egremont! Positioned on a beautiful 5.3 acre lot in Egremont, this solidly built home offers a rare combination of privacy and accessibility. A tree lined driveway leads to this peaceful Berkshire retreat, conveniently located with quick access to the Taconic State Parkway. Inside, you'll find over 2,500 square feet of living space highlighted by a dramatic living and dining room featuring a soaring two-story ceiling, skylights, an interior balcony, and a wonderful wood-burning fireplace. The spacious kitchen is complemented by a separate breakfast room with slider access to the outdoors, offering an ideal setting for everyday dining and entertaining. The home offers three spacious bedrooms and two full bathrooms, along with a versatile first floor den that can easily serve as a home office, guest room, or potential fourth bedroom. All three bedrooms feature slider access to the rear deck, creating a seamless connection to the surrounding landscape. Generous closet space throughout adds to the home's functionality. Enjoy front and rear decks, a beautiful natural setting, and seasonal mountain views. The property provides exceptional privacy while remaining close to Great Barrington and the area's amenities, recreation, dining and cultural attractions. A rare opportunity to own a private Berkshire retreat in one of Southern Berkshire County's most desirable locations.

Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining. A tranquil sun-room provides a versatile space, ideal for a home office or a quiet retreat. Down a private hall, the sleeping wing awaits. The primary suite is a true haven, featuring a second fireplace, a charming window seat for reading, a large walk-in closet, and an en-suite bath. Two additional well-proportioned bedrooms with ample closet space share a pristine hall bathroom. A generous two-car attached garage and a full basement offer abundant storage and convenience right off the main entry.Outside, the 8.3-acre grounds are a serene blend of manicured lawn, wild meadow, and mature plantings. The location is truly stellar: less than five minutes to Catamount Mountain Resort for year-round adventure, and just moments from

Set on just under an acre along one of Lee's most desirable roads, this beautifully maintained home combines timeless design, quality craftsmanship, and exceptional outdoor living. Overlooking peaceful meadows with stunning sunset views, the setting offers the perfect balance of privacy and natural beauty. Designed for both entertaining and everyday living, the backyard is truly the centerpiece of the property. A tiered bluestone patio creates multiple spaces to gather and relax, featuring a built-in outdoor kitchen, gas fire pit, and a heated saltwater plunge pool by Soake Pools. Mature landscaping, professionally designed landscape lighting, and a charming storage building complete the outdoor space, creating a backyard that feels like your own private retreat. Inside, the home is warm, inviting, and thoughtfully designed. The eat-in kitchen is the heart of the home with a large center island, custom cabinetry, premium JennAir appliances, and direct access to the patio for seamless indoor-outdoor living. Just off the kitchen, the family room offers a comfortable place to unwind, while the formal living and dining rooms provide the perfect setting for holidays and entertaining. A powder room and first-floor laundry add convenience to the main level. Upstairs, the spacious primary suite offers a walk-in closet and a beautifully appointed en-suite bathroom featuring a soaking tub and walk-in shower. Two additional bedrooms share a full bath, while the oversized bonus room provides incredible flexibility. Filled with natural light from a dramatic picture window overlooking the backyard and rolling meadows with distant mountain views, it's the perfect space for a media room, playroom, home office, or fourth bedroom/guest suite. A second staircase offers easy access and enhances the home's thoughtful layout. Additional features include a new roof in 2022, an attached two-car garage and a full basement with radiant heat, providing ample storage and endless potential for future finishing. From the quality craftsmanship and thoughtfully designed floor plan to the incredible outdoor spaces and picturesque setting, this is a home that has been exceptionally cared for and is ready to be enjoyed for years to come.

For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is experiencing a renaissance and is dotted with new restorations of gorgeous farmhouses and new builds, adding a fresh dynamic to the area. This site is perfect for any health and wellness guru looking to recreate life on a farm for the benefit of the community, for an hotelier or hospitality group to develop an Upstate experience compound or simply to restore a piece of American architectural history to become a beautiful 4 bedroom 2 bathroom residence in the heart of the Craryville to Hillsdale corridor and all the conveniences that entails. The house sits high on a bluff overlooking West End Road and below the dale is a large former dairy barn with a metal roof and cattle stalls. There is a detached garage with an efficiency apartment over it behind the house with the opportunity to plant a crop in an adjacent waiting field. Three large parcels make up this offering and the residence has the opportunity to sell the remaining two while maintaining 100 acres for an impressive estate.

Step back in time and discover the timeless charm of this classic 19th-century New England home, ideally situated on a generous .66-acre corner lot on a quiet street just minutes from the heart of downtown Great Barrington. Rich in character, this antique home retains many of its original architectural details, offering an exceptional opportunity for restoration and reimagination.The inviting, old-fashioned front porch welcomes you to a home filled with history and potential. A classic barn adds versatility for storage, hobbies, or future creative use, while recent updates--including a new boiler and barn roof in 2025 and the convenience of natural gas--provide a solid foundation for your vision. Whether you're looking to restore a beloved antique or create your dream Berkshire retreat, this property offers endless possibilities in an unbeatable in-town location. Bring your imagination and breathe new life into this historic gem. Property is being sold as is.

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot with almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen and bathrooms, as well as the furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for its next owners to create their own Berkshire journey and memories. Replaced/Updated Within the Last 3 Years: furnace, central AC, kitchen, bathrooms, all exterior doors, basement improvements Community Details: -8 homes in the community -$1,500 transfer fee due at closing from buyers to the Association -HOA dues will decrease to $900 per quarter ($300 per month) after two loans are paid off in July and October 2027 Rental Policy: -First rental term has a 28-day minimum -Second rental term has a 7-day minimum -Maximum rental term is 1 year -Lease extensions must be approved by the Association