255 Flagg Place

Commanding one of Todt Hill's most elevated and scenic settings, 255 Flagg Place is a truly special home designed by renowned architect Robert A.M. Stern, inspired by the neighboring historic Ernest Flagg estate. With sweeping views overlooking New York's Lower Bay, the home combines timeless architecture with comfortable luxury living. Spanning nearly 7,000 square feet across four finished levels, the home was designed to take full advantage of its incredible setting. An elevator services three levels for added convenience, while large windows and multiple terraces bring in natural light and water views throughout nearly every room, creating a feeling of openness and connection to the outdoors. The main level offers a beautiful flow for both entertaining and everyday living, featuring a formal living room, formal dining room, elegant sitting parlor, and a cozy den with fireplace and powder room. Several rooms open directly onto wraparound terraces overlooking the bay, while a covered and enclosed outdoor patio creates an additional space to relax or entertain year-round. As you enter the home, a grand entry hall with detailed woodwork and a fireplace immediately sets the tone. The eat-in kitchen is equipped with Wolf and Sub-Zero appliances and includes a bright breakfast area perfectly positioned to enjoy the surrounding views. The home features five bedrooms and seven bathrooms, including a private guest suite on the ground level complete with its own living room, kitchen, and bath—ideal for extended family or guests. The primary suite feels like its own private retreat, offering a sitting room with fireplace, dual bathrooms, three walk-in closets, and two private terraces overlooking the water. Three additional en-suite bedrooms each include walk-in closets, with one also featuring its own private terrace. A finished fourth level provides flexible space for a home office, gym, playroom, studio, or recreation area. Outdoor living is a major part of the experience at 255 Flagg Place, with multiple terraces and gathering spaces designed to take in the views, fresh air, and sunsets over the bay. Built with high-quality materials including real stone, a slate roof, and copper gutters, 255 Flagg Place is a rare opportunity to own one of Staten Island's most architecturally significant and beautifully positioned luxury homes.