Situated in the premier waterfront neighborhood of Painter Pointe, this stunning property offers an unparalleled lifestyle on the Chesapeake Bay. Breathtaking views of Fleets Bay from nearly every room, this home is a serene retreat designed for both relaxation and entertaining. Private, sandy beach just steps from the expansive waterside deck. The grounds create a sense of privacy and tranquility, w/ ample room for additional features such as a pool, thanks to the remote septic drainfield. Step inside to discover a light-filled great room with soaring vaulted ceilings, dining area, and a cozy gas fireplace. The adjoining dining area makes this space perfect for hosting family and friends. The well-equipped kitchen features an island, providing extra counter space for cooking or casual dining. The first-floor primary suite offers luxury and convenience, complete with two spacious walk-in closets and a private ensuite bath. This level also includes a dedicated office, a den, and a charming screened porch that opens to the wraparound deck—ideal for soaking in panoramic waterfront views. Upstairs, two generously sized bedrooms share a full bath, providing comfort and privacy for guests. Above the two-bay side-load garage, you'll find a bedroom w/ ensuite bath. A separate workshop off the garage adds to the functionality of this remarkable home. Just minutes from fine dining, boutique shopping, and Indian Creek Yacht and Country Club, 286 Waterbury Road is a rare opportunity to own a private oasis in one of the Chesapeake Bay's most desirable neighborhoods.