8163 Bayside Drive, PASADENA

Perched above the Chesapeake Bay, this exceptional coastal residence offers breathtaking panoramic views, an extraordinarily wide private sandy beach, and multiple waterfront decks in one of Maryland’s most coveted locations along the upper Western Shore. Thoughtfully and comprehensively renovated in 2003, the home features an expansive, open main level and a wall of floor-to-ceiling windows and doors framing approximately nine miles of sweeping water views east toward Kent Island.

The main level encompasses a spacious waterfront great room, a classically styled kitchen, dining area, office (formerly a fourth bedroom), and full bath. High ceilings and wide-plank hardwood floors lend warmth and character throughout. Upstairs, the primary suite is enveloped in windows, capturing spectacular Chesapeake Bay vistas. Vaulted ceilings, a private owner’s deck, walk-in closet, and an ensuite bath featuring distinctive, richly veined earth-toned marble complete this inviting retreat. Two additional bedrooms and a third full bath are also located on the upper level.

Exceptionally well-crafted, the detached two-car garage complements the residence with timeless East Coast architectural detailing, additional space above, and ample driveway parking.

Beyond the extraordinary views and peaceful waterfront setting, this property is ideally suited for entertaining, with a generous waterside deck, an expansive private beach, and open, inviting interiors that encourage effortless gathering and a natural flow between indoor and outdoor living.

Here, the Chesapeake Bay becomes part of everyday life. Spend summer days lounging on your own remarkable stretch of sandy beach and wading in the water, then settle into Adirondack chairs around a beachside fire as the evening air cools. With Downs Park nearby and charming local dining options and an independently owned grocery market just a short drive away, this rare waterfront retreat offers the best of coastal living without sacrificing convenience. A truly special opportunity to experience the Chesapeake Bay lifestyle at its finest.