Rich in history and timeless in appeal, the Parran House dates back to circa 1792 and showcases a seamless blend of early American character and thoughtfully executed modern updates. Nestled in Shepherdstown, the state’s oldest and most charming small town, the property beautifully captures its colonial heritage while also reflecting the rich Civil War history that shaped the region. This extraordinary property offers a rare fusion of historic charm and modern versatility, featuring an original main residence alongside two fully renovated private apartments, an ideal setup for both living and reliable income generation. Across the entire property, five bedrooms, four full bathrooms, and three fully equipped kitchens provide exceptional flexibility for a variety of residential and rental configurations. Offered with flexibility, the home may be conveyed largely turnkey with an acceptable offer, presenting a rare opportunity for a seamless transition. Perfectly positioned in the heart of town, it offers effortless access to acclaimed restaurants, curated boutiques, and the vibrant campus of Shepherd University. This highly desirable location not only enhances everyday convenience but also supports strong, consistent demand for long-term rentals, making it as compelling an investment as it is a home. Inside, the home’s historic character is exquisitely preserved, with original heart pine floors, windows, and detailed millwork creating a warm and authentic backdrop. Multiple fireplaces add charm and timeless elegance throughout. Soaring ceilings and a gracious, sun-filled foyer set an inviting tone, while the living and dining rooms sit on either side. The main level is completed by a well-appointed kitchen and a full bath. Upstairs, the second floor features three generously sized bedrooms along with the added convenience of a dedicated laundry area. Above it all, a spacious attic provides excellent storage or presents an exciting opportunity for expansion or customization. Along with the main residence are two self-contained one-bedroom apartments, each featuring a full bath, a fully appointed kitchen, and an open-concept living and dining area. Each unit, including the main home, offers its own private entrance, separate utilities, and individual addresses, ensuring complete privacy and independence. The apartments showcase exposed and restored stone and brick walls and fireplaces that add authentic historic character, while the upper unit is distinguished by a striking beamed ceiling. Every detail has been updated for both comfort and style: hardwood floors, modern plumbing, separate HVAC systems, and individual water heaters ensure convenience and efficiency. Contemporary kitchens, equipped with stainless steel appliances and designer finishes, create inviting spaces for cooking and entertaining, while carefully positioned lighting enhances both ambiance and functionality. These apartments offer a seamless blend of historic charm and modern luxury, making them perfect for long-term rentals or extended family living. Outside, the property continues to impress. A brick driveway and detached two-car garage includes a versatile second-story space, perfect for a home office, art studio, or creative retreat. The grounds are thoughtfully landscaped, with inviting flagstone patios and charming brick pathways winding through the tiered backyard. Enclosed with fencing, the outdoor space is designed for both privacy and enjoyment, offering cozy, intimate nooks perfect for entertaining or quiet relaxation, all while savoring the serene beauty of this historic town. Beyond its exceptional features, the Parran House enjoys a prime location in Shepherdstown, offering easy access to Shepherd University’s cultural events, the C&O Canal towpath, and a private boat dock. Nearby highlights include Antietam National Battlefield, Harpers Ferry’s outdoor recreation, Washington, D.C. commuting, and Loudoun County wineries.