Originally constructed in 1970 and extensively renovated in 2018, the main residence embodies refined sophistication and modern comfort. The open-concept floor plan seamlessly connects living, dining, and kitchen spaces, highlighted by high-quality hardwood floors, custom built-ins, and shiplap detailing that harmonize timeless charm with contemporary luxury. A chef’s kitchen with premium custom cabinetry, upscale appliances, quartz countertops, and a striking center island flows effortlessly into the living room and casual dining space. Anchored by a double-sided wood-burning fireplace, these areas connect gracefully to a formal dining room. Expansive sliding glass doors and oversized windows frame tranquil water views of Gross Creek. The luxurious primary suite boasts panoramic waterfront vistas, an exceptional walk-in closet with sauna, and a spa-like en-suite bath featuring a freestanding soaking tub, expansive tiled shower, marble accents, and refined fixtures. Additional highlights include three guest suites with private baths, and a workshop within the oversized two-car garage. Outdoors, an inviting wraparound brick patio and covered porch provides serene space to relax, enjoying the waterfront views and lush landscape. The property's gentle elevation comfortably positions all structures above the floodplain, complementing its mature, peaceful setting. Two pastures, each approximately 3.5 ac, offer flexibility for livestock or natural habitat restoration. Mature Willow Oaks lining the paved driveway complete the property's picturesque Eastern Shore charm. The waterfront guest house offers both privacy and comfort, featuring a farmhouse-inspired kitchen with primary suite including private half bath. Sliding doors open onto a covered waterside porch and patio, ideal for tranquil mornings and scenic sunsets. Enhanced by modern HVAC, LVP flooring, and laundry, this residence is perfect for extended stays or guests desiring independent accommodations. The caretaker cottage is situated apart from the main residence and discreetly screened by farmland and mature greenery, including its own parking area and separate driveway. Fully renovated, it provides three bedrooms, two baths, efficient mini splits, and low-maintenance LVP flooring. The greenhouse and crafting workshop offers functionality and charm, delighting gardeners, crafters, and hobbyists alike. The greenhouse includes irrigation, raised beds, and a potting shed, while the adjacent crafting workshop provides a welcoming farmhouse aesthetic with ample workspace bordered by mature hydrangeas further enhancing this delightful space. The pole building provides extensive accommodations for woodworking, automotive projects, marine storage, or machinery. Equipped with three-phase power, 12-ft-tall garage doors, an automotive lift, durable interior finishes, and abundant workspace, it is ideal for hobbyists or professionals requiring a versatile, temperature controlled environment. Ideally located just 7 mi from Easton Airport (ESN), 9 mi from downtown Easton, and a leisurely seven-mile boat ride to St. Michaels, Court Road Farm represents an exceptional opportunity to acquire a distinctive waterfront estate.