For the first time ever, two contiguous bayfront parcels are being offered together to create an extraordinary 5-acre waterfront compound along the coveted Roosevelt Channel on Captiva Island. Boasting nearly 350 feet of water frontage, three private docks, direct Gulf access, and exceptional privacy, this is one of the largest and most significant residential offerings to come to market on Captiva Island in generations. Set behind a gated entrance and surrounded by unspoiled island beauty, the custom-built residence, recently freshly painted, captures the warmth and character of refined island living. Soaring beamed ceilings, rich wood flooring, and a dramatic beacon tower fill the great room with natural light, while thoughtfully designed living spaces create an atmosphere equally suited for elegant entertaining and relaxed waterfront living. The home features an inviting kitchen designed for gathering and entertaining, a formal dining room, private study, flexible guest accommodations, and two expansive ensuite retreats. A dedicated wellness wing elevates the lifestyle experience with a travertine-lined indoor pool, fitness room, and sauna. Outdoors, the estate unfolds into a truly resort-inspired setting with three private docks, direct Gulf access, a tennis court, bocce court, rooftop hot tub, bayfront firepit, and expansive tropical grounds designed for recreation, privacy, and connection to the water. A spacious three-car air-conditioned garage with workshop provides ample room for vehicles, storage, and waterfront essentials. Included in the offering is the adjacent 1.5-acre bayfront parcel, bringing the total property size to nearly 5 contiguous acres and creating a rare opportunity to enjoy the estate as it exists today or further elevate the property into a truly world-class legacy compound. Concept plans by MHK Architecture have already been prepared, presenting the opportunity to thoughtfully expand the existing residence or design an entirely new architectural estate. In addition to the plans, recent surveys have been completed along with an updated elevation certificate for the residence, located in desirable Flood Zone X. The property has never flooded, enhancing peace of mind while offering meaningful time and cost savings throughout the planning and design process. With no HOA restrictions, extraordinary scale, direct Gulf access, and unmatched privacy, this is a truly irreplaceable Captiva Island estate offering.