A private waterfront retreat designed for entertaining, multigenerational living, and the classic Chesapeake Bay lifestyle. With 4 bedrooms, 3.5 baths, and panoramic water and woodland views, 771 Macsherry Drive offers a lifestyle that feels both private and inspiring. Inside, rich hardwood floors and walls of elegant windows create a light-filled atmosphere designed to bring the outdoors in. The thoughtfully designed floorplan showcases sweeping water views while offering comfortable spaces for entertaining flow and relaxing alike. The stunning primary suite is a true sanctuary, featuring oversized closets, private balcony access, and a renovated spa-inspired luxury bath with an expansive walk-in shower. Outdoor living takes center stage with expansive decks, two private balconies, and a beautifully updated dock ready for boating, kayaking, or simply enjoying peaceful waterfront sunsets. These spaces are designed to delight you and your guests in every way. From an afternoon nap in the hammock, to a waterfront BBQ for your whole crew, this home has spaces to accommodate every activity. And when you're ready to relax, a separate cottage with a brand-new hot tub (2023) creates the perfect getaway space. Ideal for multigenerational living, the home also features a true in-law suite updated in 2021, with its own private entrance, full kitchen, and separate laundry. Additional highlights include durable HardiPlank siding (2024), a spacious two-car garage, and the peace of mind of a 17kW Generac whole-house backup generator. This is a rare opportunity to own a sophisticated waterfront home that seamlessly combines architectural beauty, flexible living spaces, and resort-style amenities in one of the region's most tranquil settings.