Some properties come along once in a generation. This is one of them. Tucked within the coveted Holland Point community of North Beach, Maryland, this rare and expansive waterfront compound offers something the Chesapeake Bay area simply does not produce anymore - significant water frontage, a grandfathered private dock that is the longest in North Beach, and the kind of breathing room and flexibility that coastal dreamers spend a lifetime searching for. From sunrise to sunset, the views across the bay are nothing short of extraordinary. Whether you're casting a line off the dock, pulling in with your boat after a day on the water, or simply sitting on the porch watching the last light melt into the Chesapeake, this property delivers the full Bay experience in a way few others can. The main waterfront residence has been thoughtfully updated where it counts - featuring a refreshed kitchen, dining area, and bath - and opens into a generously scaled living area designed for effortless entertaining. Multiple bedrooms, each with its own in-room sink, offer a charming nod to a bygone era of gracious hosting, while a spacious family room positioned closest to the water keeps you connected to the views at every turn. Step outside to a lovely enclosed wraparound patio that flows naturally to the oversized dock - the perfect perch for avid boaters and sunset watchers alike. What truly sets this compound apart is what's included beyond the main house. A second improved waterfront property, directly adjacent, comes with the sale - featuring a substantial garage base suitable for boats and vehicles, and an upper level that opens into a bright, airy great room with a full bath and flexible space ideal for guests, a studio, or a private home office. Completely self-contained, it functions as its own retreat while remaining part of your larger compound. Together, these two properties create something genuinely rare on the Chesapeake - a compound with room to spread out, house your toys, welcome your people, and savor coastal living exactly on your own terms. Whether your vision is multigenerational living, a boater's paradise, a creative haven, or simply an extraordinary primary or vacation retreat, this Holland Point compound has the bones, the footprint, and the waterfront to make it all possible. Opportunities like this do not come twice.