Centrally located to everything Key West has to offer, and tucked behind a concrete privacy wall on a lush, tropical corner lot, this Midtown Key West property makes a statement the moment you step through the gate. A private courtyard filled with vibrant flowers and mature landscaping immediately sets the tone, leading you to a spacious home full of character and personality! Built with a metal roof, hurricane impact windows and doors, and thoughtfully updated throughout. The functional layout prides itself on easy indoor-outdoor living, effortlessly flowing from the living areas and out to the pool, patios, and guest cottage. The kitchen and dining area are truly made for entertaining, mimicking a chef's kitchen offering generous counter space, ample storage, a bar setup, and abundant natural light pouring in. Step outside to a sunny patio and resort-style pool, perfect for lounging or hosting. Alongside, you'll find a separate guest cottage offering a perfect multi-purpose space. Each bedroom features its own en suite bath, including a spacious primary suite with a walk-in closet, custom built-ins, and your very own private treetop balcony. Additional guest suites are thoughtfully positioned on both levels, including one with its own private entrance. Rich details set this home apart, including Dade County Pine accent walls, stone flooring and bathrooms, multiple balconies, patios, and an outdoor shower. Can be offered turnkey and fully furnished. Additional upgrades include new central AC, high-quality custom awnings, shade sails, a heavy duty storage shed, irrigation system, gutters, and new kitchen appliances.