4910 gregory road

Step into the elegance of a 50-acre waterfront estate steeped in timeless charm. Built in 1920, this Neo-Classical Eastern Shore property offers the perfect combination of sophistication and natural beauty. The property is awaiting the perfect buyer who can transform it back to the style and charisma of it's earlier days. Enjoy a bright, welcoming interior. The main house features a large center hall foyer that leads to a stunning living room with a brick fireplace, custom-built shelving, and dual French doors opening into a sunroom. Bask in serene waterfront views from the sunroom, complete with hardwood flooring and another brick fireplace—a space designed for entertaining or quiet retreats. Create unforgettable dining experiences in a formal dining room highlighted by Black Walnut paneling, tasteful wall sconces, and a custom-built wine glass cabinet. The enclosed side porch, fitted with vintage touches like brick flooring, laundry amenities, and the original farmhouse enamel sink, doubles as a mudroom. Meanwhile, the waterside screened porch invites al fresco dining with picturesque views of Church Creek. The second floor offers practicality and comfort with four bedrooms and two bathrooms, accommodating family and guests with ease. A walk-in cedar lined closet and another walk-in attic closet offer a surprising amount of storage. Enhance your lifestyle with additional perks. A thoughtfully updated guest cottage (2019) offers two bedrooms, one bathroom, a kitchen, a living room, a dining area, and laundry facilities—currently enjoyed as a vacation rental. Wildlife thrives here: expect visits from ospreys, bald eagles, and white-tail deer in an atmosphere guests rave about. Relax poolside with a redesigned in-ground pool (2022) boasting a paver deck, modern landscaping, and fencing—all with views of Church Creek. A 28 x 42 wooden barn with concrete flooring, with space sufficient for garage/vehicle or boat storage, and an upper story is complemented by a four-stall stable and additional sheds. The barn built in 1960 was built using reclaimed wood from old chicken houses. Environmental stewardship defines this property. Placed in an Environmental Trust, the land remains protected, ensuring its use promotes nature and agriculture. Boating lovers will appreciate the creek’s access to the Chesapeake Bay, renowned for crabbing, fishing, kayaking, and paddle boarding. Let your vision breathe life into this stunning space. This estate pairs historical allure with limitless possibilities for those ready to turn dreams into reality.