Welcome to 186 Flagg Place, a rare modern masterpiece perched high on Todt Hill, Staten Island's most exclusive and private enclave. Located next to the Richmond County Country Club, this residence delivers an unmatched blend of architectural drama, lifestyle comfort, and elevated living. This nearly 7,000 sq ft custom home spans four levels of thoughtfully designed spaces offering 5 bedrooms, 9 bathrooms, 3 balconies, and exceptional indoor-outdoor flow. Inside, you're greeted by a grand foyer with a sculptural circular staircase, soaring ceilings, and walls of glass that flood the home with natural light. The main level features expansive entertaining areas, a designer living room with a stone fireplace, and a sleek Italian-inspired chef's kitchen with premium finishes throughout. A true showstopper sits at the heart of the home: your own private indoor pool, complete with a waterfall feature, sauna, steam room, and full spa amenities; perfect for relaxation, wellness, and year-round enjoyment. The upper floors offer spacious bedroom suites, including a luxurious primary with a private terrace and dramatic views. There's also a separate guest/housekeeper suite for added convenience. An entire entertainment level includes a large den/billiards room, multiple lounge zones, radiant heat floors throughout, two laundry rooms, a gym area, and an elevator connecting all floors. Outside, enjoy multiple terraces, a private driveway, an oversized garage, and sunset views that elevate every moment. And when you want a change of scenery? Simply walk across the street to the country club and enjoy golf, dining, and events.