1305 Church Ave Chipley, FL 32428

Welcome to a truly one-of-a-kind historic home, currently known as the The Sullivan House Bed & Breakfast--originally the Alford House--where timeless character meets modern comfort. Established in the 1880s and thoughtfully rebuilt after a fire, this remarkable residence has been cherished by four generations and stands as a meaningful piece of local history. Spanning nearly 6,000 square feet, the main home features 6 spacious bedrooms and 3.5 bathrooms, offering ample space for everyday living, hosting guests, or multi-generational use. Inside, you'll find cedar-lined closets and six fireplaces (four coal-burning and two wood-burning), creating a warm and inviting atmosphere throughout. The expansive downstairs living areas provide a natural flow for entertaining, with room to comfortably host large gatherings. This home has been well maintained with key updates to include a new roof in 2025, central HVAC installed in 2023, a hot water heater replaced in 2023, and electrical and plumbing upgrades completed between 2023-2025. Outside, the property continues to impress with a 5-car garage and a charming carriage house above, complete with its own 1 bedroom and 1 bathroom--perfect for guests, extended family, or private living space. Modern conveniences such as a 50-amp RV hookup, Level 1 and Level 2 electric vehicle charging stations, and a five-car garage enhance both guest experience and owner flexibility. Additional highlights include a basement ideal for storage or flexible use, a separate outdoor wash house for added convenience, and a rare outdoor concrete block safe--providing a unique and secure solution for storing valuables. Modeled after a South Florida home inspired by Cuban architecture observed in the 1920s, the former Alford House is rich in history, craftsmanship, and character. Whether you're looking for a distinctive primary residence or a private retreat with room to grow, this exceptional property offers a rare opportunity to own something truly special.