New York’s Hudson Valley and Catskill regions offer a trove of secluded estates where luxury meets nature in captivating fashion. From Tudor-style grandeur with historic cobblestone drives to country estates once owned by renowned composers, these homes unfold across acres of gardens, private lakes, and mountain-view trails.
Whether it’s an 18th-century Canadian barn transformed into a majestic lodge or a Millbrook manse built for entertaining, each estate is a private retreat steeped in elegance and character. Here are three extraordinary New York properties that showcase the state’s most refined and secluded living.
1. Tudor-Style Estate in Hudson Valley
Located in Hudson Valley and built in 1932, this Tudor-style estate spans 9,481 square feet with 11 bedrooms and 7 bathrooms, and is listed for $6,400,000.
Set on 50 acres, the property features a 3-acre lake with a boathouse, a pool, tennis court, Japanese garden, guest house, and cobbled drive using stones from old Bronx streets. Interior highlights include a vaulted 40-foot oak-beamed great room, oak library, multiple dining spaces, and a renovated primary suite with an office and den.
Where is Ossining, NY?
Ossining is a village and town in Westchester County, New York, situated along the eastern shore of the Hudson River. It includes the Sing Sing Correctional Facility, one of the most well-known prisons in the United States. Ossining has a Metro-North station, making it a commuter hub for travel to New York City. The village features historic sites, riverfront parks, and a diverse residential community.
Living Room
Cathedral ceilings with exposed beams crown the expansive living room, where arched windows and chandeliers establish a grand atmosphere. Two seating areas, each with upholstered chairs, sofas, and rugs, break up the space and face toward a central wall of windows. A dark wood staircase and assorted classical artworks fill out the sides of the room.
Kitchen
Skylights bring natural light into the spacious kitchen, which features a large central island with black countertops and white cabinetry. In the middle of the layout, the cooking area stands out with a double oven, gas range, and a backsplash decorated with plant-themed tiles. Surrounding walls are lined with glass-front cabinets, and a bay window over the sink faces the outdoor greenery.
Dining Room
Framed by dark wood ceiling beams, the dining room centers around a glass-topped table with eight high-back chairs and a patterned area rug. Along the back wall, tall paned glass doors open to a shaded terrace that links the space to the outdoors. A fireplace, flanked by a small painting and topped with a green glass pendant light, adds warmth to the room.
Bedroom
Near wide windows with red drapes, the primary bedroom anchors its layout around a large wooden-framed bed with white linens on a soft cream rug. Opposite the bed, a fireplace and mounted TV sit beside a rustic set of tools and woven baskets. A work table and chair rest in the far corner, next to French doors leading to a balcony or patio.
Pool Area
Lounge chairs and dining sets with bold yellow-and-white umbrellas surround the kidney-shaped swimming pool. At the center of the backyard, the pool is bordered by gray stone paving and edged with a diving board and stainless steel ladder. To the side, striped outdoor rugs and low tables form a casual seating zone framed by lush bushes.
Listing agent: Dalia H. Valdes of Julia B Fee Sothebys Int. Rlty, info provided by Coldwell Banker Realty
2. Millbrook Country Estate
This 8,117 square-foot estate in Millbrook, built in 1900 and listed for $6,750,000, features 6 bedrooms and 9 bathrooms, set on 40 acres of scenic land.
The historic main house, once owned by Marvin Hamlisch, blends 19th-century architecture with modern updates, complemented by four distinct barns, a gunite pool, organic gardens, and fruit trees. Designed for entertaining, the home includes 2 kitchens, 5 fireplaces, and expansive light-filled rooms, all located minutes from the village and under two hours from New York City.
Where is Millbrook, NY?
Millbrook is a village in Dutchess County, New York, located in the Hudson Valley east of Poughkeepsie. It is part of the town of Washington and is known for its rural setting and large estates. The village has a small downtown with shops, cafes, and cultural spots like the Millbrook Vineyards & Winery. Millbrook also hosts the Cary Institute of Ecosystem Studies and is near several nature preserves.
Living Room
Positioned around a black fireplace insert with white trim, the sitting room includes a sofa, striped armchairs, and a glass coffee table on a faded area rug. Wood floors and wall sconces match the classic style, with wide windows on two walls bringing in soft daylight. A mix of modern and antique furniture lines the perimeter, including a spindle-back chair and a wood stump side table.
Dining Room
Stonework surrounds the fireplace in the library dining room, which features a round table with leather chairs under a black and gold chandelier. Built-in shelves line one wall, filled with neutral-toned ceramics and books. Across from the shelves, tall windows and a bench seat provide natural light and a view of the outside.
TV Lounge
Bookshelves built into the wall surround the television setup in the TV room, which includes a dark fireplace and a central coffee table. Upholstered seating faces the media wall, with a blue and white rug grounding the space. Windows and white trim reflect daylight, while a door opens to a darker wood-paneled room beyond.
Media Lounge
Wooden ceiling beams and planked walls wrap the media lounge, where a large sectional sofa runs along one side facing a wall-mounted television. In the center, a game ottoman and rug break up the space, with a game table and chairs at the back wall. Small windows and horse artwork complete the cabin-like atmosphere.
Bedroom
Ceiling beams stretch above the bed in the bedroom, where dark-toned wallpaper and drapes create a cozy enclosure. At the foot of the bed, a leather chaise lounge sits atop a hide rug near the windows. A wood dresser with matching lamps and a framed landscape print finishes the layout along the side wall.
Listing agents: Karolina Czekaj, Kyle Irwin of Corcoran Country Living, info provided by Coldwell Banker Realty
3. Birchwood Estate in the Catskills
Built in 2003 and priced at $9,950,000, The Birchwood Estate spans 8,600 square feet with 6 bedrooms and 5 bathrooms on 77 secluded acres in the Catskills. The main residence is a 6,000-square-foot Adirondack-style home reconstructed from an 18th-century Canadian barn, complemented by four additional structures including a Japanese tea house, a guest tower, and a horse barn with a greenhouse garden.
Set along nearly a mile of Schoharie Creek, the property features mountain views, a swimming pond, yoga pavilion, and wraparound trails, just 20 minutes from Woodstock and two hours from Manhattan.
Where is Hunter, NY?
Hunter is a town in Greene County, New York, located in the northern Catskill Mountains. It includes the village of Hunter and the nearby community of Tannersville. The town is home to Hunter Mountain, a major ski resort and year-round recreation area. Hunter also hosts seasonal events and concerts, drawing visitors for both outdoor activities and cultural experiences.
Great Room
Rustic timbers support the vaulted ceiling in the great room, where a stone fireplace anchors the main wall flanked by open doors. Leather armchairs and a wooden coffee table face the hearth, and a small upright piano adds a musical element in the corner. Natural wood finishes continue across the ceiling and floor, echoing the mountain lodge style.
Kitchen and Dining Area
Framed by heavy beams and natural textures, the kitchen and dining area opens fully to the deck through folding glass doors. A stone-topped island with wood cabinetry separates the kitchen from the long dining table placed under square pendant lights. Surrounding windows and doorways draw in uninterrupted views of the mountain range.
Covered Dining Porch
Set beneath an overhang with exposed beams, the covered dining porch holds a round table and wooden chairs in view of a wildflower meadow and distant peaks. Foldable glass panels slide open to the main house, integrating the porch with the indoor spaces. A mix of open sky and wood framing creates an outdoor room with panoramic surroundings.
Deck
Stretching alongside the house, the upper deck overlooks expansive views of tree-covered hills and distant ridges. Planters, deck chairs, and glass doors connect the space to the indoor areas, while a hot tub sits just below near the garden. A separate structure with a wood-shingled roof stands nearby, partially visible beyond the railing.
Listing agent: Philippe Uhrik of Win Morrison Realty – Catskill, info provided by Coldwell Banker Realty
