14 Wyndclyffe Court, Rhinebeck, NY

About 14 Wyndclyffe Court

Tucked at the end of a quiet private road and set behind a long, tree-lined drive, the gated Wyndclyffe River Estate is a storied Hudson Valley sanctuary offering over 8 acres of privacy, beauty, and light. Overlooking a quiet cove and more than 450 feet of Hudson River frontage, this majestic estate is both a celebration of history and a modern refuge for inspired living. The main residence is a masterclass in estate living, effortlessly blending traditional form with a flowing, contemporary layout. Natural light pours through expansive windows, and nearly every room opens to views of the river or to serene outdoor living spaces. Sprawling in scale yet welcoming in feel, the home offers 4 bedrooms—including a private one-bedroom in-law suite—and an elevator that connects the levels for ease and comfort. Anchored by three wood-burning fireplaces, the main floor unfolds with a grand great room, vaulted-ceiling family room, formal dining area, and an eat-in kitchen—all designed with warmth, gathering, and flow in mind. The primary suite is a retreat unto itself, featuring dual en-suite bathrooms, a generous walk-in closet, and panoramic views of the Hudson. A luminous attached greenhouse creates a four-season connection to the land Downstairs, you’ll find a home gym, sauna, family room, and guest suite with its own kitchenette and private deck—perfect for extended stays or multigenerational living. Outdoors, the pool and hot tub are poised for relaxation with unforgettable sunsets and river breezes as your backdrop. A crown jewel of the estate is the historic guest house, originally the carriage house of the famed Wyndclyffe Castle. Carefully restored to honor its 19th-century roots, it still features striking architectural elements from its days as horse stalls—offering a rare and soulful blend of past and present. The grounds are rich with mature gardens, stone paths, and sculpted terraces, all unfolding toward dramatic river vistas. Nestled on a peaceful cove and surrounded by established landscape, the property feels worlds away—yet is just 10 minutes from Rhinebeck Village and Amtrak. Wyndclyffe River Estate is more than a home and could easily be fabulous family compound. It’s a place where history, modern living, and nature meet—and where every day feels like a quiet return to something rare and beautiful.

Listing Map