57 Dellenbaugh Road

Historic Artist’s Retreat in Cragsmoor Nestled atop the Shawangunk Ridge in the storied hamlet of Cragsmoor, this singular home was designed by painter, explorer and writer Frederick S. Dellenbaugh, and offers a rare opportunity to own a piece of American art history. Built circa 1907 and listed on the National Register of Historic Places, this 4BR/2BA home spans nearly 2,100 sq ft across three levels and sits on 4 acres of naturally sculpted land with old-growth sugar maples, striking glacial boulders, a stream and sweeping grassy knolls. Dellenbaugh, a founding member of Cragsmoor’s 19th-century artist colony, alongside notable painters like George Inness, created this residence as part of a larger vision, an enclave where creativity and landscape intertwined. The home retains its historic character with original woodwork, hand-crafted details and a sense of quiet elegance that unfolds room by room. Large windows frame ever-changing light and nature views, while a stone patio offers the perfect perch for morning coffee or an alfresco dinner party under the stars. The grounds feel timeless, part curated, part wild with the kind of privacy and serenity that’s increasingly rare. Whether you're wandering through the trees, lounging beside the stream or entertaining with friends on the lawn, the experience is immersive and deeply grounding. Just outside your door is direct access to Bear Hill Nature Preserve and just down the road is Sam's Point, where thousands of protected acres offer hiking, blueberry fields, waterfalls and dramatic cliffs. And while this mountaintop retreat feels worlds away, it’s only 90 minutes from the GWB. This is more than a home. It’s a legacy property in one of the Hudson Valley’s most magical and storied communities.