Dating back more than two centuries, 403 South Fairfax Street is a remarkable historic flounder house with an unmistakable presence in Old Town. Its architecture, proportions, and beautifully preserved original details speak to another era, while thoughtful updates and an unusually compelling relationship between the interior spaces and private courtyards make the home feel entirely of its place and time. The main level makes a memorable first impression, with a gracious front living room that draws you into the home and a handsome drawing room with a wood-burning fireplace just beyond. A natural gathering space, the drawing room is equally suited to cocktails before dinner, an evening of games, or lingering conversation. A guest bedroom and full bath complete this level. The entertaining spaces continue below. The chef's kitchen, outfitted with Miele, Sub-Zero, and Viking appliances, opens to a comfortable family room with exposed wood beams. Just beyond, the elegant dining room is anchored by a gas fireplace and complemented by a built-in wine refrigerator beneath the staircase and adjacent dry bar. French doors open directly to a lower courtyard, creating an effortless extension of the home's dining and living spaces for grilling, outdoor dining, and lounging. From here, outdoor stairs lead up to the home's main street-level courtyard, an expansive garden completely enclosed by historic brick walls. Exceptionally private and rare in the heart of Old Town, the upper courtyard is enhanced by a custom water feature and offers a beautiful setting for entertaining or simply enjoying the outdoors. The second floor is devoted to the home's private quarters. The primary suite features an ensuite bath and a tucked-away staircase leading to a finished, temperature-controlled storage space, an especially rare amenity in a historic Old Town residence. Across the hall, a separate guest suite or office with its own full bath offers flexibility for guests, work, or additional living space. Throughout the home, original architectural details have been carefully preserved and enhanced. Beautifully restored wide-plank floors, custom crown molding and wainscoting, six fireplaces, coordinated custom brass light switches and dimmers, and exposed structural beams reflect the level of thought given to every detail. A distinctive copper roof completes the home's architectural presence. Set just moments from King Street, the waterfront, neighborhood parks, restaurants, and shops, the home offers an unusually private setting in the heart of Old Town. With its exceptional two-level courtyard, beautifully considered interiors, and spaces designed as much for gathering as for everyday living, 403 South Fairfax Street is a rare historic residence that has been thoughtfully shaped for life today.