About 227 Homeport Dr
Well-Appointed Waterfront Home on 2.58 Acres with Spectacular Views
Private & exceptional design and craftsmanship define this magnificent custom-built waterfront residence, offering three finished levels of refined luxury and breathtaking water views from nearly every room. Perfectly sited on 2.58 acres along picturesque Winchester Creek and the Chester River, this home includes its own private sandy beach — a rare and unique offering.
Step through the welcoming 8-foot leaded glass double doors into a grand foyer where soaring ceilings, walls of glass, and wide-planked walnut floors create a sense of openness and light. The sun-drenched great room features an 18-foot custom fireplace and opens effortlessly to a fabulous heated screened porch and expansive decks overlooking the water—complete with remote-controlled shades and a retractable roof. This home is not only well maintained, also amazing up-dates throughout.
The gourmet kitchen is both beautiful and functional, designed for serious cooks and entertainers alike. It boasts high-end appliances, custom cabinetry, propane cooking, a walk-in pantry, double refrigerators, and a butler’s pantry for additional prep and storage. Recent updates include fresh paint and stunning new counters, giving the space a crisp, contemporary look.
The main-level primary suite serves as a luxurious retreat, featuring his-and-her walk-in closets, a beautifully refinished bath with dual vanities, and an oversized glass walk-in shower. Also on the first floor are a private library/office, a formal dining room, a breakfast room, and an attached two-car garage—creating the perfect, functional layout for everyday living.
Upstairs, the second level offers three spacious bedrooms, two full baths, a large family room with access to an upper deck, and a finished bonus room over the garage—ideal as a playroom, hobby space, or sixth bedroom. The third floor is a showstopper, featuring a stunning guest suite with a fully renovated bath and a private theater room with surround sound—perfect for movie nights or entertaining guests.
Outdoors, the setting is every bit as impressive as the home itself. Positioned on a point with sweeping views of the creek, river, and bay, this property includes beautifully landscaped grounds, irrigation systems, and a sandy beach with protected shoreline. Enjoy access to a dedicated boat slip (number 2) and jet ski lift at the nearby community marina, just steps from your door.
The 18.5’ Aqua Spa offers a heated 18’ lap pool with a four-seat jet spa—ideal for year-round relaxation. Additional highlights include a whole-house generator, propane heat (two underground tanks), four central HVAC units (three recently replaced), motorized Silhouette blinds, an attached storage shed, and meticulous attention to detail throughout. Every element of this home reflects thoughtful maintenance and superior quality.
Conveniently located near the Cross Island Trail, restaurants, shopping, gyms, golf courses, and the Bay Bridge, this extraordinary home combines elegance, comfort, and the best of Eastern Shore waterfront living.
Come experience it for yourself—create your own waterfront lifestyle.
