8974 S Bayview Drive

Chestertown, MD 21620

Built on a 40-foot bluff overlooking the Chesapeake Bay facing west for nightly sunsets, this is a tour-de-force of design and luxury on the Eastern Shore of Maryland, with truly stunning views from every room. Follow your dreams with this resort-like property as a primary or secondary home. Drive along the maple-lined lighted drive to 1.5 acres of award-winning, irrigated, landscaped grounds designed by South Fork Studio. Walk through the mahogany gate into the courtyard with fountain along the bluestone path around the Gunite pool. The main house on the water (c. 2011 and updated in 2018) has 3 bedrooms and 2 and 1/2 baths, and a wall of large windows with an automatic shade system that follows the sun's path. Open floor plan living with private first-floor owner's suite (double shower, Toto washlet, and custom walk-in closet). Wake up to views of the Bay and Bald Eagles fishing. Custom hand-crafted hardwood flooring, millwork, cabinetry, and New Zealand wool carpeting. Built-in Sub-Zero and Wolf appliances and top-of-the line luxury materials throughout. Automated control for whole-home media and sound, lighting, HVAC, irrigation, swimming pool, alarm system, and window shades. Gas-started wood-burning fireplace in the living room. Ipe decking, 3 outdoor showers, and numerous spaces to entertain friends and family. A custom-lighted staircase and brand-new dock (2023) with boat lift and large Ipe dining table sit above the rip-wrapped shoreline. The guest house and three-car garage, designed by Purple Cherry Architects and built by the acclaimed Taylor-Loughry partnership in 2019, cleverly create the privacy, mystery and architectural stature of the entire four-parcel domain. Currently, the guest house presents 1 bedroom, 1 full bathroom with laundry, a kitchenette and a very large multi-purpose room with cathedral ceiling that overlooks the center core of the gardens, saltwater and heated pool, custom cedar pergola, and Chesapeake Bay.The pool building contains the latest technology in pool filtration, whole-property water filtration system, well pump, irrigation system, pool heater, and storage. There is also on-demand hot water throughout the property and radiant heated flooring in all full bathrooms.This property awaits a most discerning and capable buyer yearning for a discreet and well-designed lifestyle. Only 15 minutes from historic downtown Chestertown.