Rare Intracoastal waterfront investment opportunity on nearly one acre with 158 feet of direct waterfront, multiple existing structures, private dock, boat lift, guest cottages, and exceptional income-producing potential! Offering a combination rarely found in Port Orange, this distinctive property presents an exciting opportunity for investors, multigenerational living, a private waterfront compound, or buyers looking for a property with multiple living spaces and future possibilities. Additional residential or rental uses may be possible subject to zoning, permitting, and governmental approval; buyers are encouraged to verify intended use with the City of Port Orange. Originally built in 1920 from beautiful coquina stone, the main residence is filled with historic Old Florida character and craftsmanship, enhanced by custom Western and California redwood finishes throughout. The property offers incredible Intracoastal views along with direct boating access from a private boat lift. An impressive two-story dock spans approximately 900 square feet and extends nearly 100 feet into the water, providing an incredible setting for boating, fishing, entertaining, and enjoying panoramic river views. The nearly one-acre, fully fenced property feels like a private Florida retreat. A spectacular 50-foot solar-heated swimming pool with a decorative bridge is surrounded by winding garden pathways, peaceful courtyards, mature landscaping, and multiple fruit trees. Two gated entrances and a wraparound driveway provide abundant space for boats, RVs, trailers, guests, and additional vehicles. The property includes a 2-bedroom, 2-bath main residence along with three detached 1-bedroom, 1-bath guest cottages, creating tremendous flexibility for extended family, multigenerational living, private guest accommodations, home office or creative spaces, and potential income-producing uses subject to applicable zoning and approvals. For investors and buyers searching for an Intracoastal waterfront property, riverfront investment opportunity, multi-generational estate, waterfront compound, property with guest cottages, or Florida home with a private dock and boat lift, this estate offers a truly unique combination of land, location, amenities, and versatility. With approximately 158 feet of direct Intracoastal frontage, nearly one acre of land, multiple existing structures, resort-style outdoor amenities, private boating access, and potential for additional uses subject to governmental approval, the possibilities here are compelling. Buyers interested in rental, redevelopment, or additional dwelling opportunities should independently verify permitted uses and development potential with the appropriate governmental authorities. Whether envisioned as a private waterfront retreat, multigenerational family compound, vacation property, or investment opportunity, 5202 Riverside Drive offers a level of character, flexibility, and waterfront lifestyle that is increasingly difficult to find. Schedule your private showing today and explore the possibilities of this extraordinary Port Orange Intracoastal property.