5 Chesapeake Bay Waterfront Estates with Deep-Water Docks

Set on 350 acres in Easton, this estate unfolds across owner and guest wings, balancing privacy with an easy sense of togetherness. Inside, a gourmet kitchen anchors the living spaces, while soaring glass walls and heated limestone floors bring light and comfort into everyday routines. An elevator adds effortless flow between levels, and multiple decks extend living outdoors.

Size: 350 Acres

Along the water’s edge in Easton, Maryland, Ship’s Point unfolds across a completely private 13+/- acre setting at the confluence of Trippe’s Creek and the Tred Avon River. Nearly one-half mile of shoreline wraps the estate, creating 270-degree views that shift with the light and weather throughout the day. A deep water pier extends the waterfront lifestyle, offering direct access to the surrounding waterways. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction, preserving the sense of a true estate while elevating its day-to-day comfort. With privacy as a defining feature and water on all sides, the experience here is less about scale and more about the rare feeling of living within the view itself.

Along the water’s edge on the Sassafras River in Earleville, Cassidy Wharf Farm unfolds across 93 acres with 6,100 feet of waterfront and three additional waterfront lots. A deep water dock and expansive sandy beach set the tone for days spent boating, swimming, or simply watching the horizon shift. The six-bedroom primary residence is complemented by a three-bedroom guest house, creating an easy rhythm for hosting and retreating in equal measure. For leisure, a pool house includes a gym and steam room, while a two-story waterfront pavilion brings everyone together just steps from the shore. Beyond the shoreline, a private pond and exceptional hunting add to the sense of privacy and range. Detached garage, barn, and auxiliary buildings support life at every scale, from sunrise to moonrise over the water.

Along the water’s edge in Wittman, Maryland, this 86±-acre estate stretches across 1.5± miles of shoreline, with approximately 7′ MLW for boating and waterfront living. Two residences anchor the setting: a main house with five bedrooms and a separate guest house with three bedrooms, offering flexibility for extended stays and everyday privacy. Beyond the homes, two subdivided waterfront lots—each SDA approved for a four-bedroom home—invite future plans while preserving the land’s long horizons. A large barn with an attached hunting lodge adds a distinctly rural cadence, complementing the property’s 60± tillable acres. Here, days can move between open fields, the working landscape, and the steady presence of the shoreline—an expansive canvas for a life shaped by land and water.

Along the storied Chesapeake Bay on Gibson Island, this five-bedroom, five-and-a-half-bath waterfront residence unfolds across a rare double lot with beautiful landscaping and 180-degree views stretching to the Bay Bridge and the Magothy River shoreline. Bay windows span the width of the house, drawing light and water into daily life, while beautiful hardwood floors connect a mahogany-paneled screen porch, sun porch, richly fashioned library, and a spacious, thoughtfully designed kitchen. A first-floor bedroom suite with a separate entrance adds flexibility, and upstairs the primary suite includes a steam bath, gas fireplace, and doors to outer decks with crafted wooden railings; three additional bedrooms, two full baths, and a large cedar closet complete the level. Downstairs, a finished basement offers a pool table, weight and exercise room, and a fully equipped sauna—then outside, a 63-foot heated lap pool keeps the Bay close at hand.