Welcome to 2255 Trelain Dr S! This timeless 1928 two story Craftsman sits just three doors down from Al Capones storied Lake Maggiore residence. Nestled on a quiet, brick lined street in Lake Maggiore Shores, the 5 bedroom, 2 bath home spans 2,192 sq ft and showcases tile floors, tall ceilings, vintage hardware, and a decorative fireplace. The flexible floor plan offers space for dual home offices, a nursery, or creative pursuits. The kitchen and baths await your personal design, giving you the chance to blend modern updates with historic character. Energy conscious buyers will appreciate the paid off solar panels upon closing, while the accessory dwelling unit (ADU) with loft provides the perfect option for guests, rental income, or studio space. Currently, multiple long term tenants are in place on month to month leases, generating $3,515 in monthly rental income. Enjoy a landscaped lot with off street parking and a welcoming front porch, all just blocks from Dell Holmes Park, Lake Maggiores trails and splash pad, and less than 10 minutes to Tropicana Field, Central Ave, and vibrant downtown St. Pete. Located in Flood Zone X with no HOA. Priced under $400/sq ft with million dollar neighbors nearby, this is a rare opportunity to own a piece of St. Petersburgs history, enjoy immediate rental income, and build lasting equity in one of the citys most appreciating neighborhoods.