Timeless Old Florida charm defines this ideally located residence, positioned between the 3rd Street South and 5th Avenue South entertainment districts and just three blocks from iconic 5th Avenue South. This enchanting four bedroom plus den residence offers 2,909 square feet of living space, three full and one half baths, and a welcoming wraparound porch that sets the tone for relaxed coastal living. Tucked just off Cambier Park, the property features a thoughtfully connected two-story guest house with living space on the lower level and a private bedroom above—ideal as a primary suite, guest quarters, extended-family accommodation, or a private office retreat. The upper level of the main home showcases two bedrooms and a loft beneath a vintage tongue-and-groove wood-plank ceiling, with both bedrooms opening to private balconies that capture gentle coastal breezes. The main floor includes the kitchen and great room, along with a fourth bedroom or den with en-suite bath. Classic Old Florida storm shutters add both character and function. The generous backyard offers ample room for a pool and outdoor entertaining, while a rear-entry two-car garage off the paved alley provides convenience and additional parking. Private front and rear yards are framed by mature hedging, with a charming archway entry, quaint wooden gate, and parking for two vehicles off 8th Avenue South, plus additional parking in the rear. A 2019 metal roof adds peace of mind. Located directly across from Cambier Park, offering a competitive tennis program, shuffleboard courts and bocce, covered pavilion, band shell, and expansive green space. Close to everything, welcoming, and rich in character—this is a rare opportunity to own a true downtown Old Florida cottage.