One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated, or rendered. 5256 Estero Boulevard presents a rare and captivating Gulf-to-Boulevard assemblage on Fort Myers Beach. Spanning over ½ acre with approximately 90 feet of direct Gulf frontage and approximately 270 feet of depth, this exceptional offering provides a unique opportunity for investors, developers, or those seeking to create a legacy beachfront estate. The assemblage includes two Gulf-front properties 5266 Estero Boulevard (Pink House) and 5256 Estero Boulevard (Yellow House) plus the rear 5250 Estero Boulevard double lot, which can be legally divided into two separate single-family homesites. Together, the assemblage provides the potential for four individual single-family homesites extending from the Gulf of Mexico to Estero Boulevard. Each homesite offers the potential for a new elevated residence with approximately 2,250 square feet of living area across two living levels, with elevation and garage space on the ground level. This creates an exceptional opportunity to develop four luxury coastal residences within one Gulf-to-Boulevard assemblage. The existing Gulf-front residences at 5266 and 5256 Estero Boulevard offer a combined 8 bedrooms, 6.5 bathrooms, and more than 4,500 square feet of living space, providing immediate use while offering substantial future redevelopment potential. Zoned for weekly rentals, the property offers significant flexibility for luxury vacation homes, an exclusive residential compound, or income-producing investment properties. The combination of Gulf frontage, multiple potential homesites, weekly rental zoning, and future redevelopment potential creates a particularly compelling opportunity on Fort Myers Beach. For those seeking an even larger development footprint, the 5256 Estero Boulevard assemblage can be combined with the adjacent 5300 Estero Boulevard assemblage, which includes the Gulf-front 5268 Estero Boulevard lot and the rear 5300 Estero Boulevard and 5280 Estero Boulevard lots. Combining the two assemblages creates an extraordinary Gulf-to-Boulevard development opportunity with substantial Gulf frontage and exceptional flexibility for a larger-scale luxury residential or investment project. With extremely limited Gulf-front inventory and the continued redevelopment of Fort Myers Beach, this offering provides exceptional scale, flexibility, income potential, and long-term value in one of Southwest Florida's most desirable beachfront locations.