Welcome to 400 S Main St, a versatile and well-located 4 bedroom, 2 full bath detached home in the heart of historic Woodsboro. The current layout and use offer the unique ability to function as a single-family residence or convert back to be utilized/rented as a 2 unit multi-family, providing excellent flexibility for owner-occupants or investors alike. Inside, the home offers light-filled living areas with a practical floor plan that easily accommodates multi-generational living or separate living spaces. Each level features comfortable bedrooms and renovated full bath access, allowing for privacy and functional separation if needed. Outside, enjoy a manageable yard, off-street driveway with a 6+car parking lot, and a convenient Main Street location just steps from local shops, dining, parks, and community amenities. With close proximity to major commuter routes while maintaining a small-town feel, this property presents a rare opportunity for flexible living, rental income potential, or long-term investment in a sought-after Woodsboro location. 2026 UPGRADES: structural repairs to foundation, side porch concrete being redone, painted metal roof, new LVP flooring throughout upper and lower level, fresh paint throughout, bathrooms renovated, turn key move in ready!