4 Dawn Lane , Shelter Island, NY 11964 - Suffolk County

Designed by Norman Jaffe in 1971 and expanded by him in 1981, the Osofsky House is a rare waterfront estate that has been meticulously renovated while fully honoring Jaffe's original vision. All 6 bedrooms have ensuite bathrooms, with a total of 8 full baths and 2 half baths, the home comfortably accommodates up to 14. Set on 1.7 acres with 175 feet of frontage on Gardiners Bay, the property offers panoramic water views, cantilevered decks, an extra-deep heated gunite pool, an outdoor pergola with kitchen and fireplace, and a separate guest wing for added privacy. The beach-inspired landscape design shines in all seasons, with magical pollinator gardens and natural coastal plantings that complement the architecture. Additional amenities include a chef's kitchen, private gym, movie theater, tennis court with pickleball lines, and a detached two-car garage. Total living space is 6,715 sq. ft., including a fully finished 1,626 sq. ft. lower level. The renovation and design were overseen by the homeowner, a noted designer, ensuring that every update both respects and elevates this significant modernist home.