Welcome to your four-door ticket to flexibility, style, and serious income potential in one of St. Pete's most beloved and walkable neighborhoods. Tucked beneath the oaks of Historic Uptown, this rare setup offers multiple ways to live, host, and earn, whether you're house hacking, investing in STRs, or building a long-term rental portfolio. The main home is a charming 2 bed / 1.5 bath perched above a 3-car garage, featuring hardwood floors, an updated kitchen, central AC, and private fenced yard. Up front, a detached triplex offers a sunlit 2 bed / 1 bath unit with updated kitchen and central AC, a 1 bed / 1 bath unit with vaulted ceilings and updated systems, and a stylish studio with a renovated kitchen, tankless water heater, and modern finishes. The property has over $100k in recent updates, including landscaping, fresh paint in and out, plumbing and electrical upgrades (all on individual meters), new AC units, windows, and so much more! Outside, you'll find a 2-car carport, green space with dog-friendly turf, and alley access perfect for tenants and guests. Whether you live in the main house and rent the rest, lease all four, or mix it up with short- and long-term stays, the layout offers total flexibility and privacy. Vintage charm meets modern ease throughout, and the location supports your vision. You're just blocks from Central Ave, Round Lake, Crescent Lake Park, and local favorites like Black Crow Coffee, Craft Kafe, Uptown Eats, and everything downtown St Pete has to offer. You're close to the water, close to the action, and tucked away just enough. This is not your average multifamily, it's a vibe. A compound. It's an income-producing compound with heart, soul, and a story. Book a showing and make it yours.