24318 Oakwood Park Rd, Saint Michaels, MD 21663

Welcome to Old House Cove Waterfront Retreat in St. Michaels, MD Nestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of Maryland’s most beloved waterfront towns. Formerly owned by the poet and author Gilbert Byron who was often called “the Chesapeake Thoreau,” it is easy to see how the tranquil setting on Old House Cove inspired much of his writing. Originally built in 1965, the main house has been thoughtfully updated to blend classic Eastern Shore style with relaxed modern comfort. The open-concept kitchen, dining, and living area centers around a gas fireplace - all with sweeping water views. Added in 1993, the spacious primary suite features a walk-in closet and en-suite bath. The waterside screened porch is the perfect place to unwind, enjoy the gentle breeze off the water and watch sailboats glide across the cove toward San Domingo Creek. Connected to the main home by a charming pergola walkway, the large carriage house and garage—also constructed in 1993 —includes two bays, one with double doors for boat access. The upper-level guest suite feels like a private treehouse retreat, complete with its own deck and sweeping views of the cove. Together, the main residence and guest suite create an ideal opportunity to expand the property and craft the waterfront home of your dreams—offering privacy, flexibility, and direct access to the property’s stunning setting. Outdoor living is a true highlight of this property. A generous brick terrace provides the perfect space for alfresco dining or entertaining just steps from the water’s edge. The property features approximately 130 feet of rip-rapped shoreline, a sandy kayak launch area, and a private pier equipped with one slip and 2.5’ MLW—ideal easy access to the Bay. Beautiful mature trees, lush landscaping, and a circular drive create an estate-like approach. The property is served by two wells and two septic systems, and sits comfortably in Flood Zone X (no flood insurance required). The area has been approved for public sewer hookup, offering excellent potential for future expansion or reconfiguration to suit your vision. This is a rare opportunity to own a timeless waterfront retreat—where Eastern Shore charm, literary heritage, and modern comfort come together just minutes from the world-class dining, sailing, and small-town allure of St. Michaels, Maryland.