Situated on the South River with sweeping water views all the way to the Chesapeake Bay, this Nantucket-inspired waterfront home presents a rare opportunity to create something truly special in one of Annapolis' most coveted waterfront settings. Set on approximately 0.43 acres with more than 5,000 square feet of living space, the home offers 6 bedrooms and 3.5 baths across two levels. The size of the home provides generous scale and flexibility for a future renovation or reimagined coastal retreat. The gracious foyer is flanked by the primary staircase and opens into the large waterside living room. Adjacent to the living room is a more casual entertaining area, dining room and kitchen. The main level bedroom and full bath could be reconfigured into a lovely suite. There is a main level powder room, laundry and additional flex space. The secondary staircase provides convenient accessibility. Upstairs, three bedrooms overlook the water with panoramic views. The primary suite has an ensuite bathroom and waterside deck. The additional bedrooms are generously sized with lots of closet space. The unfinished attic has a full stairwell and offers tremendous storage possibilities. The waterfront setting is truly special. A gentle slope leads down to a beautiful sandy beach, creating an ideal place to launch a kayak, paddleboard, or simply enjoy the shoreline. While the home reflects a classic coastal aesthetic, it is ready for a refreshed vision. This is an exceptional opportunity for buyers seeking to renovate, expand, or create a custom waterfront residence in a premier location. Located in the sought-after community of Hillsmere, residents enjoy access to a community beach, pool, marina, playground, and waterfront pavilion. Quiet Waters Park, Downtown Annapolis, and major commuter routes to Washington, D.C. and Baltimore are all just minutes away.