166 DUKE OF GLOUCESTER STREET Experience the perfect blend of historic charm and modern luxury in this circa 1885 end-unit brick townhome, ideally located in the heart of the Annapolis historic district. Thoughtfully renovated to the highest standards, this home seamlessly marries timeless elegance with contemporary amenities, offering a rare opportunity to own a piece of Annapolis history. Step inside to find a residence rich with exquisite features and fine craftsmanship. The original high ceilings, custom moldings, and heart pine flooring exude warmth and authenticity, while three wood-burning fireplaces, including the original kitchen hearth, serve as evocative focal points. The historic character is further enhanced by weathered exposed brick walls and floors in several interior rooms, creating a sense of history and comfort throughout. The main level welcomes you with a foyer showcasing original brick walls and flooring. The spacious living room features a brick fireplace with a Jotul-brand cast iron wood stove, complemented by white planked walls and dentil crown molding. The home is exceptionally quiet, even with its prime location, thanks to well-insulated windows. The dining room, accessible from both the living room and the kitchen, is perfect for entertaining. Completely remodeled in 2023, the kitchen is a chef's dream, featuring custom cabinetry, a stainless steel Bosch appliance suite, quartz countertops, and a dry bar with a 144-bottle wine refrigerator. The new tin kitchen ceiling adds character, while the original brick floors connect past and present. A Dutch door leads to a private courtyard, where a pergola draped in wisteria offers a serene setting for outdoor gatherings. The home’s main level also includes a secondary suite anchored by the original outdoor kitchen’s brick fireplace, featuring a Murphy bed and a design-inspired ensuite bathroom. A chic black-and-white hall powder room completes the main level. The upper level is home to the primary suite, where a fireplace with a second Jotul-brand cast iron wood stove, a custom walk-in closet, and a spa-inspired ensuite bathroom with heated floors, towel warmer, custom vintage vanity, and large shower create a sanctuary of comfort and style. A versatile guest suite with a spacious bedroom, a cozy den or office space, and a private en-suite bathroom. This area is ideal for guests, remote work, or as a private retreat within the home. A dedicated laundry room nearby adds to the convenience, ensuring effortless living with ample storage and functionality. Located just a block and a half from Main Street, this home offers the quintessential Annapolis lifestyle. Meticulously updated and exceptionally well-cared for, this property is a rare gem where every room tells a story and every detail speaks to an exceptional level of quality and care. Hillman parking garage conveniently located on Duke of Gloucester.