Located just one block from Oxford's scenic waterfront, 105 Jefferson Street offers a rare opportunity to own a beautifully updated home in the heart of historic Oxford, Maryland. With a fully operational elevator, full service off-street parking, a detached two-car garage, and a finished studio apartment above the garage, and a dedicated home-office, this property combines the charm of one of the Eastern Shore's most beloved waterfront towns with the convenience and flexibility today's buyers are searching for. Designed for entertaining, the floor plan features multiple gathering spaces, including a family room, formal living room, dedicated recreation/game room with a newly installed wood-burning fireplace, additional den, and a separate home office, making it ideal for hosting family and friends, working remotely, or accommodating multi-generational living. The home offers four bedrooms and flows effortlessly to a private backyard retreat featuring a gunite swimming pool and expansive newly installed composite deck. Recent exterior improvements include premium composite siding, new composite exterior doors, and durable metal roofing on the bump-outs. A new gas range adds another thoughtful update to the home's well-appointed kitchen. Whether you're searching for a full-time residence, second home, or Eastern Shore retreat, this exceptional Oxford property places you just moments from marinas, public waterfront parks, local restaurants, the Oxford Community Center, the Oxford Museum, and the iconic Oxford-Bellevue Ferry. Combining timeless coastal charm with modern updates, versatile living spaces, and outstanding outdoor amenities, 105 Jefferson Street is a place to gather, entertain, and enjoy the best of waterfront town living.