**Price Improvement!! OPEN Saturday 5/16 2-4pm!** 527 Shepherd Street NW is a rare Petworth offering that combines authentic architectural character, exceptional flexibility, and generous outdoor space on one of the neighborhood's most coveted blocks. With 4 bedrooms and 2 full bathrooms, this is a home of warmth, substance, and versatility - one that offers a layout and lot size increasingly hard to find in the city. A standout feature is the way the home lives almost like two separate residences. The upper two levels function as a classic 3-bedroom, 1-bath home filled with charm, natural light, and preserved period detail, while the lower level provides a self-contained 1-bedroom, 1-bath space complete with its own kitchen, living area, and separate laundry closet. Whether for extended family, guests, work-from-home flexibility, or supplemental living needs, the configuration offers rare practicality and long-term value. Throughout the main and upper levels, original character has been beautifully preserved. Original floors run throughout nearly every room outside of the kitchen, bath, and lower level, while transoms above every bedroom, original doors and hardware, and working pocket doors to the dining room reflect a level of craftsmanship and authenticity that is increasingly rare. These details give the home a warmth and sense of permanence that cannot be replicated. The main level is bright and inviting, with well-proportioned living spaces and a gracious formal dining room that support both comfortable daily living and easy entertaining. The lower level adds even more utility, with an open layout and a full-sized kitchen that make the home feel larger and more adaptable than expected. Outside, the rare double-deep lot creates exceptional space and possibility, with a large fenced yard, substantial patio space for outdoor dining and entertaining, and room for play, gardening, or pets. Rear alley access and off-street parking for two cars potential add even more everyday convenience. Set in the heart of Petworth, 527 Shepherd Street NW is moments from the Metro, the Upshur Street corridor, neighborhood markets, restaurants, community centers, and major commuter routes. A home with character, flexibility, and unusual outdoor scale, it is a distinctive opportunity in one of Northwest DC's most beloved residential neighborhoods.