1741 Holly Beach Farm Rd, Annapolis, MD 21409

A Rare Waterfront Legacy Property on the Chesapeake Bay: Along a quiet stretch of Annapolis shore, where the Chesapeake meets 232 acres of protected parkland, a singular offering emerges. Few properties in the region can claim its provenance, privacy, and position on the water. Set upon 3.5 acres overlooking Moss Pond, the farm commands 287 feet of private shoreline with sweeping, unobstructed vistas of the Bay beyond. Once part of a celebrated working thoroughbred operation, it carries forward a legacy deeply woven into Maryland's agricultural and maritime heritage. At the heart of the property stands a historic farmhouse of quiet distinction. Five well-appointed bedrooms each capture views of the water, and a series of gracious sitting rooms preserve the residence's original character. Heart pine floors, bespoke built-ins, and twin staircases speak to an era of craftsmanship rarely preserved so thoughtfully. A screened-and-glassed porch extends the season year-round, while a waterside patio invites summer dinners and sunset gatherings with the Bay as backdrop. Beyond the main house, a four-car carriage barn, a second barn with equestrian stalls, and a detached retreat suited to a study, studio, or guest quarters lend the property remarkable versatility. At the water's edge, a private pier offers immediate access to the boating and fishing traditions for which the Chesapeake is justly renowned. Bordered by parkland yet a short drive from Annapolis, the farm offers the increasingly uncommon pleasure of true seclusion without sacrifice, moments from the cultural and culinary life of Maryland's historic capital.