Chesapeake Bay Views Along Crab Alley Creek on the Eastern Shore

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330 Serenity Lane, Chester, MD 

Set along Crab Alley Creek with open views stretching toward the Chesapeake Bay, this waterfront estate delivers scale, privacy, and a level of execution rarely offered on the Eastern Shore.

The outdoor spaces set the tone. Expansive patios, balconies, and a waterside screened porch extend directly to the shoreline, with a private beach and long water views that define the property. From early morning light to sunset, the setting stays front and center.

The newly expanded 260-foot pier is designed for serious boating, with protected deep water, multiple lifts, and full-service capability for larger vessels. Direct access to the Chesapeake Bay puts Annapolis, St. Michaels, and beyond within easy reach.

Inside, the home reflects a builder’s own standard. A two-story foyer opens to light-filled interiors anchored by a wall of glass overlooking the water. The kitchen is equipped with Wolf and Sub-Zero appliances, custom cabinetry, and multiple areas for both everyday use and larger gatherings.

The primary suite is positioned as a private waterfront retreat, complete with fireplace and a spa-level bath with heated floors and soaking tub. Additional spaces include a waterfront game room, private theater, and five bedrooms upstairs, each with distinct architectural character and access to outdoor spaces.

A separate guest wing offers full independence with its own entrance, kitchen, and living area. Dual garages provide flexibility for cars, storage, or lifestyle use.

Tucked within a quiet enclave with convenient access to the Bay Bridge, Annapolis, and Washington, D.C., this is a rare combination of protected shoreline, deep-water dockage, and a property that supports life on the water at a high level.

Make Your Move with Maryland’s #1 Waterfront Team.

Brad Kappel | 410.279.9476