9 Margarets Dr, Shelter Island, NY 11964

An AIA Award-winning design by Lacuna Architecture Atelier, 9 Margarets Drive brings architecture, landscape, and natural light into remarkable harmony. Encompassing approximately 5,530 square feet, including a substantial finished lower level, the home offers four en-suite bedrooms, five full baths, and one half bath, with a design that creates a seamless connection between indoors and out. A soaring, light-filled great room unfolds beneath dramatic vaulted ceilings, where expansive walls of glass dissolve the boundary between interior and exterior spaces. A striking two-sided fireplace anchors the living areas, creating a natural dialogue between the home's architecture and surrounding landscape. At the heart of the residence, a chef's kitchen with top-tier appliances integrates beautifully with the living and dining spaces, equally suited to everyday living and entertaining. Custom white oak millwork and carefully selected finishes reflect the architectural vision of Gregory Thomas, known for exceptional craftsmanship and attention to detail, developed in collaboration with builder Sean Murphy. Each bedroom suite opens directly to the surrounding landscape, further reinforcing the home's connection to nature. Beyond the walls of glass, a 50' x 17' heated saltwater gunite pool anchors the outdoor setting, framed by expansive terraces and multiple lounge and dining areas. A beautifully appointed pool house with a full bath and outdoor shower, together with mature landscaping, creates exceptional privacy while preserving a sense of openness. The result is the ease and privacy of a refined private resort. Situated on a tree-lined street just moments from Shelter Island's beaches, marinas, and restaurants, 9 Margarets Drive offers a rare opportunity to own an architecturally significant residence defined by timeless design, natural beauty, and effortless indoor-outdoor living.