Rare South Fort Myers Waterfront Compound – No HOA – Direct Gulf Access A one-of-a-kind waterfront retreat in highly sought-after South Fort Myers. With no HOA fees, two separate homes, and three private living spaces, this exceptional property is ideal for multigenerational living, a private family compound, or a proven income-producing vacation rental. Situated on Hendry Creek with direct Gulf access, you'll enjoy a short 20-minute boat ride to Lovers Key and Dog Beach and a 5-minute walk to Lakes Park. Conveniently located just minutes from HealthPark, Gulf Coast Medical Center, shopping, dining, and RSW International Airport. The elevated saltwater resort-style pool is the centerpiece of the property, designed so you can simply step out of the cottages directly into the pool. Features include a swim-up bar, sun shelf, oversized electric heater, swim jet, lazy river feature, and durable Jewelscape glass finish. The outdoor entertaining area offers a summer kitchen with a built-in gas grill, wood-fired pizza oven, seafood burner, and stainless-steel sink with hot and cold water. Boaters will appreciate the private dock featuring a 500-square-foot boathouse, 10,000-pound boat lift, and full RV hookup. The oversized lot offers exceptional privacy, generous parking, and access from three driveways on two separate streets. Cypress Cottage features 1 bedroom, 2 bathrooms, a library loft, elevator, and a lower-level mother-in-law studio with a full bath, kitchen, and private garage. Built with premium materials including a commercial standing-seam metal roof, James Hardie concrete siding, foam insulation, impact windows and doors, and beautiful sinker pecky cypress timber-frame ceilings. Interior upgrades include granite countertops, KitchenAid stainless appliances, custom copper Bevolo gas lanterns, porcelain tile, live-edge burled cypress table, walk-in pantry, spacious laundry room, and a luxurious primary suite with a hammered copper soaking tub and dual walk-in closets. Creekside Cottage offers 2 bedrooms, 1 bathroom, a full kitchen, laundry, and an oversized two-car garage. A large unfinished attic provides excellent potential for an additional bedroom and bath. Both cottages feature commercial-grade construction, Carrier mini-split A/C systems, LP tankless water heaters, and Trex composite decking throughout the pool deck, patios, and dock. Surrounded by protected state preserves and waterways that limit future development, this is a truly rare waterfront opportunity offering privacy, flexibility, and exceptional investment potential in one of South Fort Myers' most desirable locations.