Set among the beautiful rolling hills on 203 acres is this private estate that takes you back in time. The farm was built in 2008 around a c.1754 Dutch barn that was dismantled from upstate NY and transformed into an incredible great room with 34' soaring ceilings, a brick fireplace and two huge French doors to take in the view. Designed by Cynthia Filkoff with 6,340 square feet, the main house offers five bedrooms and three and one half baths. The home feels centuries old, with the wide board floors and plaster walls throughout, while providing the modern conveniences, like the geothermal heating and cooling system and the automatic generator. Every room is a piece of art and history; comfortable, primitive and functional. Adding to the list of amenities is a two-car garage with loft; three bedroom caretaker's house; and equestrian facilities including a five stall barn, equipment barn, outdoor riding ring and six paddocks. The expansive property has trails throughout and was placed in the Dutchess Land Conservancy for love of the land. A once in a lifetime opportunity to purchase this private country estate. Just minutes to Pine Plains, and two hours to NYC.

Set among the beautiful rolling hills on 203 acres is this private estate that takes you back in time. The farm was built in 2008 around a c.1754 Dutch barn that was dismantled from upstate NY and transformed into an incredible great room with 34' soaring ceilings, a brick fireplace and two huge French doors to take in the view. Designed by Cynthia Filkoff with 6,340 square feet, the main house offers five bedrooms and three and one half baths. The home feels centuries old, with the wide board floors and plaster walls throughout, while providing the modern conveniences, like the geothermal heating and cooling system and the automatic generator. Every room is a piece of art and history; comfortable, primitive and functional. Adding to the list of amenities is a two-car garage with loft; three bedroom caretaker’s house; and equestrian facilities including a five stall barn, equipment barn, outdoor riding ring and six paddocks. The expansive property has trails throughout and was placed in the Dutchess Land Conservancy for love of the land. A once in a lifetime opportunity to purchase this private country estate. Just minutes to Pine Plains, and two hours to NYC. Additional Information: Amenities:Soaking Tub,ParkingFeatures:2 Car Detached,

Ledgerock, the riverfront masterpiece by modern architect Lee Ledbetter is back on the market after undergoing significant infrastructure improvements. This one-of-a-kind estate offers the finest Hudson River and Catskill Mountain views on the market today and is set on 5 private acres. Constructed from the finest materials available, this gorgeous fossilized French limestone & glass compound boasts a 15,000+/- main residence offering 5 bedrooms and 7.5 bathroom plus a similarly styled guest house offering 3 bedrooms and 2 baths. Ledgerock is one of the very few properties built DIRECTLY on the Hudson River and can never be built again as current set-back laws prohibit building directly on the water’s edge. Modern lines combined with exotic wood & stone from around the world create a truly unique home designed to entertain both indoors and out. Interior features include a breathtaking, glass-walled great room with a fireplace, a formal dining room, library, billiard room, gym and & massive dine-in kitchen with separate butler’s pantry. The corner primary suite floats above the Hudson River like a houseboat and features an incomparable spa-like bathroom that includes two large dressing rooms and an office. Outside, there are two levels of travertine decks and terraces that extend from all major rooms offering jaw-dropping river and mountain views. Outdoor features include an infinity-edge saltwater pool, an elevated hot tub, fire-pit, an outdoor kitchen and a covered open-air living room. Updated mechanicals include geothermal heating/cooling, radiant heated stone floors, and state of the art security and ample indoor parking to satisfy a collector. Ledgerock is one of the most extraordinary homes available in the Hudson Valley.

Welcome to “Reveille”. Beautifully sited, turnkey hilltop estate in Garrison, New York, the centerpiece of this magnificent, gated 50+acre estate is a stunning, Loire Valley inspired stone chateau and five bedroom carriage house surrounded by formal gardens and protected woodlands. Constructed from 1927-29, this estate has remained in the same family for nearly a century and has recently undergone a significant restoration including the installation of top of the line mechanicals and HVAC systems. Upon entering the 6,200+ square foot, slate roofed main residence, one is greeted by a gracious rotunda with a winding 3-story staircase. Included in the main residence are 5 bedrooms (two with sleeping porches), 5.5 bathrooms, two ground floor porches. In addition to the main residence, the 4,000 square foot converted carriage house is on two levels encompassing 5 bedrooms, 5 full & 2 half bathrooms, an artist's studio with tower and attached two-car garage. The total bedroom and bath count are reflected in the main house and guest house. A billiards room/outbuilding with massive brick fireplace completes the compound. The breathtaking grounds have been meticulously maintained and feature a balustrade south terrace, a formal rose garden with pergola and fountain, a secret fire-pit area, a 44’ x 22’ gunite pool surrounded by stone terraces and flower beds - all offering pin-drop serenity and westerly views toward the neighboring acres of protected conservation land. Deeded recreational access to nearby Lake Alice is included. This is a rare opportunity to own the most recent addition of important restored estates in the Hudson Highlands region, all just fifty miles from Manhattan.

S3 Architecture, in collaboration with the Aston Martin Design Team proudly presents Sylvan Rock, one of the most exciting and sophisticated modernist estates to be built in the Hudson Valley. Reached via a 2,000 ft driveway winding through natural rock outcroppings and nestled on 55 private acres, the 5,983 SF main residence rises like a dramatic geological rock formation, perfectly blending a modern aesthetic with its rural location and connection to nature to create a uniquely harmonious, luxury experience. With its sense of tranquility combined with unparalleled design & craftsmanship, one is immediately struck by the jagged edges of the roofline, the black cedar facade, floor-to-ceiling glazing and the dramatic cantilevered owners' suite. The main residence offers 4 bedrooms, 4 bathrooms and 2 half baths, incredible volume and incomparable common space, including an executive office suite, a den, a lounge with bar and a custom wine cellar showcasing Aston Martin's signature cross-hatched lattice design. Included in the geothermal compound is a stunning pool with stone decking and outdoor kitchen, a 873 SF pool house / wellness pavilion with hot tub, sauna and two treatment rooms, 3 multi-functioning guest 'pods' to accommodate guests, remote office or home schooling, an architect-designed tree house and a dedicated agricultural food garden with a separate service entrance that can supply both the owner and regional farm markets - allowing for the luxury of true self-sufficient privacy. The total finished living space of this extraordinary sustainable estate will be 8,430 and anticipated completion is late 2021. Within 15 minutes to both Rhinebeck and Millbrook Villages, Sylvan Rock will be one of the most important modernist residences in the Hudson Valley and is the first single-family, residential collaboration by S3 Architecture and Aston Martin.,ExteriorFeatures:Cabana,Gazebo,Outside Lighting,FLOORING:Wood,Slate,Basement:Garage Access,EQUIPMENT:Water Filter,ROOF:Metal,InteriorFeatures:Gas Stove Connection,Walk-In Closets,OTHERROOMS:Formal Dining Room,Family Room,Foyer,Library/Study,Breezeway,Laundry/Util. Room,Office/Computer Room,Professional Suite,Rec/Play Room,AboveGrade:8430

Perched directly on the Hudson River offering breathtaking River views, this remarkable Catskill compound offer multiple buildings and stretches over 17+ acres with 1,400 linear feet of pristine Hudson River frontage. The waterfront compound is perfect for year-round entertaining and outdoor activities included boating and water-sports. Additional structures include a guest house with serene 25' pond, a 60' x 40' garage built as a helicopter hanger and a large renovated office building with separate entrance and parking. Enjoy unobstructed views of the River, Rogers Island Eagle Sanctuary and the surrounding landscape. The Rogers Island Wildlife Management Area ensures that these vistas remain preserved. The main house was built in the Jacobean style in 1903 and offers 29 rooms on 3 levels. The dramatic interior includes a glass-enclosed ''winter garden'' with custom, ventilated built-in grille and year-round breathtaking views. Also featured is a massive gourmet kitchen with central island and heated Himalayan Granite floors, six exquisite oversized bedrooms all featuring a unique European design offering breathtaking views of the Hudson River. The lower level includes a recreation room with a pool table, and an imported Bavarian pub with a full bar. The property is conveniently located just a mile from the charming village of Catskill, with its Victorian storefronts, eclectic dining, boutique shops, and a rich artistic history, and Hudson River Skywalk, a scenic route connecting the Thomas Cole Site and Frederic Church's Olana. The compound is also under 5 miles from the town of Hudson and Amtrak trains. This is a once-in-a-lifetime opportunity to own a piece of history and is one of the largest Hudson River-Front Estates currently on the market.

Nestled in the heart of Woodstock, this extraordinary 70+ acre estate is a rare offering of artistic heritage, architectural beauty, and serene natural surroundings. Known as The Stone House on Striebel Road, this iconic bluestone compound has stood at the crossroads of music, literature, and counterculture for over a century. Built in 1914 as a country retreat, the main Stone House features 4 bedrooms, 2 full baths, and 2 half baths, with rich period details throughout—including original carved woodwork, wide-plank floors, historic fireplaces, and Dutch doors that enhance both charm and function. One of the home's standout features is the spacious and inviting living area with brick flooring, original bluestone walls, and a dramatic wood-burning fireplace—perfect for cozy evenings or sophisticated entertaining. A gracious covered front porch offers a peaceful place to take in the natural landscape, while a deep soaking tub and light-filled meditation/yoga room provide quiet spaces for rest and renewal. In the 1920s and '30s, the home was owned by famed cartoonist John Striebel, creator of the Dixie Dugan comic strip. Over the years, its walls have echoed with the voices of Bob Dylan, Janis Joplin, Allen Ginsberg, George Harrison, and many other cultural legends. A true cornerstone of Woodstock's creative legacy, the estate was once owned by Albert Grossman, legendary music manager and founder of Bearsville Records and Studios. It was here, in 1965, that the iconic album cover for Bringing It All Back Home was photographed, capturing Bob Dylan and Sally Grossman in the home's elegant living room. Later, the home welcomed talents ranging from Johnny Cash and William Kennedy to Bjork and the Dave Matthews Band. Viking Hall, next door to the main house, offers an exceptional space designed to inspire. This stunning building features a bright and open studio area, ideal for artists, musicians, wellness practitioners, or remote work. With hand-hewn beams, loft space, French doors, and spa-like amenities—including a sauna, steam shower, and soaking tub—the space combines rustic elegance with modern comfort, perfect for creative retreats, workshops, or wellness sessions. Beyond Viking Hall, a private apartment with a stone fireplace, bedroom, and full bath once served as Albert Grossman's personal retreat, where he ran Bearsville Records. His legendary vinyl collection remains, and the lower level offers a gym area with ample storage. The estate includes the Farmhouse at Speare Road, a recently updated 4-bedroom, 2-bathroom residence. With its own private setting, this charming home is well-suited for guests, caretakers, or multi-generational living—offering flexibility for a variety of lifestyle needs. In the surrounding woods, discover a charming cabin complete with a bedroom, bathroom, and cozy kitchen. This private hideaway is ideal for long-term guests, studio rentals, or a secluded creative workspace. Both ready for a variety of uses, a spacious workshop building offers room for artistic or hands-on pursuits, while a classic barn adds rustic charm and versatile storage or studio space. Gardening enthusiasts will appreciate the sun-filled greenhouse, designed for year-round cultivation. A meditation gazebo—ideal for yoga, writing, or reflection in nature and an amphitheater complete with electricity, seating, and platform are among the estate's many distinctive features. Outdoor amenities include a heated, saline gunite pool, garden areas, spring-fed pond, seasonal mountain views, and woodland trails that offer total immersion in the natural beauty of the Catskills. This iconic Woodstock estate is two hours from NYC and in close proximity to the area's most beloved destinations. Whether inspired by its profound cultural roots or artisanal architecture, this property is a once-in-a-generation opportunity. This property is co-listed with Kathryn Johnson, William Pitt Sotheby's International Realty.

Nestled on top of Carpenter Hill, with unparalleled views of Stissing Mountain, the Catskills and the surrounding farmland, sits this country estate on 24.78 acres. The traditional, cedar shake 6,310 square foot home exudes elegance exhibited through the well proportioned rooms with 9’4” ceiling height, exceptional craftmanship and attention to detail found throughout the home. A dramatic double height foyer leads to the gracious living room which features a wood burning fireplace, built-ins, a cozy window seat and French doors that open to a covered porch. Lots of natural light floods into the family room through the walls of windows with western views. The chef’s kitchen boasts custom finishes, top of the line appliances, an impressive river stone matte finish granite island, pantry and opens to the spacious dining area. Three sets of French doors open to two covered porches, added in 2021, seamlessly blending indoor-outdoor living. The second floor provides the primary ensuite, two bedrooms and a full bath. Connecting the main house to the guest wing is an attractive, yet functional, mudroom with bluestone floors. The guest wing was added in 2001 and includes a foyer, kitchenette, first floor ensuite bedroom, and a second floor bedroom and bath. In 2015, a two car garage with studio above was added, creating a beautiful space for working from home, the possibilities are endless. The manicured property offers perennial gardens that bloom throughout the season. There is a gunite pool that is seamlessly blended into the landscape to embrace the surrounding vistas. Truly a remarkable property offering peace and privacy with spectacular views.

Sited on one of the most beautiful parcels in the Hudson Valley, this idyllic estate on a quiet country lane offers endless possibilities with the features of a mini-resort. Set on a knoll overlooking a gorgeous, spring-fed pond complete with gazebo, swing and swim-up dock, this historic country retreat includes the circa 1860 main house, a separate guest apartment with views of an additional pond, a gunite pool with pool house, a tennis court, golf green with three separate tee boxes, and a large sports barn which offers a fully equipped gym on the upper level and a first floor basketball court (and potential indoor pickle-ball court). The renovated vintage Colonial has five bedrooms, three and a half baths, a chef's kitchen with top of the line appliances (including three ovens and two dishwashers) perfect for cooking and gathering with an adjacent sitting room and fireplace; a spacious dining room with a delightful breakfast nook; a light-filled living room with a fireplace and hidden cabinets for storing wood, a family room/den with a fireplace, a wet bar and plenty of storage, as well as an all-season, window filled sunroom with radiant heated stone flooring and views to the back lawn and hot tub. The second floor offers four bedrooms, three newly done baths with linear drains, an office, a well appointed laundry room and a walk-up attic. There is a Sonos sound system with indoor and outdoor speakers, whole house generator and security system. Outdoors, incredible recreational options abound with two swimming ponds, sweeping lawns, a 50 ft. heated gunite pool and a pool house complete with kitchen, full bath, laundry, internet and Sonos sound (indoor and out), golf, tennis and sports barn. Additionally, there is a three-car garage and guest apartment with a full bath and kitchenette, a second barn for storage or workshop and a fully enclosed and irrigated vegetable garden. The grounds are magical and noteworthy, with lovely stone terraces, perennial gardens, a charming playhouse, specimen trees, rock walls, running brook and a waterfall. A superb location less than 2 hours from NYC, minutes to the Taconic State Parkway, 20 minutes to Millbrook and Rhinebeck Villages, and convenient to all the Hudson Valley has to offer.

Sited on one of the most beautiful parcels in the Hudson Valley, this idyllic estate on a quiet country lane offers endless possibilities with the features of a mini-resort. Set on a knoll overlooking a gorgeous, spring-fed pond complete with gazebo, swing and swim-up dock, this historic country retreat includes the circa 1860 main house, a separate guest apartment with views of an additional pond, a gunite pool with pool house, a tennis court, golf green with three separate tee boxes, and a large sports barn which offers a fully equipped gym on the upper level and a first floor basketball court (and potential indoor pickle-ball court). The renovated vintage Colonial has five bedrooms, three and a half baths, a chef's kitchen with top of the line appliances (including three ovens and two dishwashers) perfect for cooking and gathering with an adjacent sitting room and fireplace; a spacious dining room with a delightful breakfast nook; a light-filled living room with a fireplace and hidden cabinets for storing wood, a family room/den with a fireplace, a wet bar and plenty of storage, as well as an all-season, window filled sunroom with radiant heated stone flooring and views to the back lawn and hot tub. The second floor offers four bedrooms, three newly done baths with linear drains, an office, a well-appointed laundry room and a walk-up attic. There is a Sonos sound system with indoor and outdoor speakers, whole house generator and security system. Outdoors, incredible recreational options abound with two swimming ponds, sweeping lawns, a 50 ft. heated gunite pool and a pool house complete with kitchen, full bath, laundry, internet and Sonos sound (indoor and out), golf, tennis and sports barn. Additionally, there is a three-car garage and guest apartment with a full bath and kitchenette, a second barn for storage or workshop and a fully enclosed and irrigated vegetable garden. The grounds are magical and noteworthy, with lovely stone terraces, perennial gardens, a charming playhouse, specimen trees, rock walls, running brook and a waterfall. A superb location less than 2 hours from NYC, minutes to the Taconic State Parkway, 20 minutes to Millbrook and Rhinebeck Villages, and convenient to all the Hudson Valley has to offer. Additional Information: Amenities:Guest Quarters,Marble Bath,Steam Shower,Tennis,HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Detached,