42 Prospect Ave + Part 23 Serpentine Drive, Shelter Island, NY 11964

Built in 2002, "Treetops" is an AIA Archi Award-winning modern classic that boasts some of the most sweeping and unobstructed views on Eastern Long Island-stretching across the North Fork, Peconic Bay, Long Island Sound, and reaching to Connecticut. Positioned at 162 feet above sea level on "Divinity Hill" in Shelter Island Heights, it sits at one of the island's highest natural elevations. The home is the result of a thoughtful evolution of an original design by Peter Schladermundt, renowned for his iconic structures at the 1964 New York World's Fair, brought to its current form by noted architect Frederick Stelle. The architectural concept centers around two clean-lined volumes joined by a glass pavilion, using a restrained palette of stone, steel, and glass, executed with clarity and elegance. On the view-facing side of the home, a dramatic pavilion wrapped in 9-foot floor-to-ceiling glass walls provides unobstructed vistas. These are framed with anodized aluminum windows, hand-laid aluminum inlay mouldings, and solid core doors that reflect the home's refined craftsmanship. The main living area is open, featuring a fireplace, radiant heat floors, a screened dining area, and access to two decks, one with a built-in barbecue. An elevated kitchen is outfitted with Poliform cabinetry, high-end appliances, and a butler's pantry. Additional spaces on this level include a family room with Scandinavian fireplace, powder room, laundry, office/library, and a first-floor en-suite guest bedroom. A sculptural bluestone staircase, with treads subtly suspended one inch from a glass wall, rises beside 19-foot acid-etched glass windows, filtering natural light through the space, offering a graceful ascent to the primary en-suite bedroom. An aerie above the canopy of treetops, this suite features a covered rooftop terrace, steam shower, soaking tub, and a Scandinavian propane stove, offering a serene and secluded experience. The at-grade lower level includes recently installed travertine flooring, a guest bedroom with direct access to the pool area, a mirrored gym/exercise studio, Finnleo sauna, full bath, second laundry area, walk-in cedar closet, Eurocave 150-bottle wine cooler, and a Sub-Zero side-by-side refrigerator and freezer. Outdoors, a 57-foot heated freeform Gunite pool is bordered by Arizona buff stone and surrounded by lush perennial gardens. Pathways lead to a separate garden with multilevel bluestone decking and grandfathered steel cord railings, blending natural and architectural elements. As Hamptons Cottages & Gardens once wrote: "This place is indeed divine... not only in the sense of 'oh how divine,' but also in its distinctive sense of other-worldliness. Here the air, the light, the very atmosphere, feels celestial. Clouds floating by overhead appear within reach, and the sunsets are cinematic events." A rare Shelter Island offering, "Treetops" is as much a sanctuary as it is a landmark, complete with a protective vegetative buffer and unmatched architectural pedigree.