A rare multi-property investment opportunity in the heart of Key West. Offered together at a discounted price, 1217 Johnson Street and 1224 Flagler Avenue sit back-to-back and provide exceptional flexibility, rental income, and the potential to create a private compound or multi-generational retreat. 1217 Johnson Street is a newly built 5BD/6BA luxury home elevated above floodwaters and constructed with Category 5 hurricane protection, impact windows/doors, Hardie siding, and a generator. Located just steps from Higgs Beach, this 3,600+ sq ft residence blends modern design and island charm. A dramatic two-story foyer opens to the saltwater pool and waterfall, with glass doors that merge indoor and outdoor living. Enjoy a gazebo, lush landscaping, and a poolside cabana with bath. The chef's kitchen features quartz counters, shaker cabinets, a waterfall island, and Viking appliances. Upstairs are two primary suites with Juliet balconies, plus additional bedrooms and a flexible bonus room. Gated parking for two vehicles completes this private oasis. 1224 Flagler Avenue is a legal duplex with a separate 1BD/1BA private suite, offering multiple revenue streams. Unit B is a turnkey 2BD/1BA with updated flooring, renovated kitchen, stainless appliances, laundry, and shared backyard. The detached suite provides its own entrance for guests or added income. Unit A is a 2BD/2BA with tile floors, island kitchen, laundry, and a private fenced yard, easily enhanced with a light refresh. Together, these properties deliver versatility, income potential, and a unique chance to own two desirable Key West homes in a premium location.