1500 E Jackson St Discover a rare East Hill dual-residence property featuring two independent homes on a prominent corner lot, where historic Craftsman charm meets extensive modern upgrades. Built in 1918, the primary residence offers approximately 2, 000 sq ft of living space, classic architectural character, and a welcoming full-length front porch surrounded by mature live oaks, native landscaping, fruit trees, and a timeless white picket fence. The property also includes a fully independent ~700 sq ft second residence with a private driveway, new metal roof, new HVAC and ductwork, EV charger, and updated flooring. With documented rental history available, this second home provides exceptional flexibility for income generation, guest accommodations, multigenerational living, or a private studio/workspace-a rare opportunity in sought-after East Hill. Significant system upgrades to the primary residence enhance comfort, efficiency, and long-term value, including new HVAC (2024), updated ductwork (2024), interior and exterior paint (2024), insulated attic (2024), whole-house dehumidifier (2024), ridge vent attic fan (2024), metal roof (2018), foam-insulated crawl space, updated plumbing, whole-house electrical updates, and hurricane-impact windows. The kitchen is currently equipped with an electric range and is plumbed for an easy gas conversion. Outdoor living is equally inviting, featuring the expansive front porch, backyard patio, outdoor shower, and on-demand gas hot water heater, creating a relaxed coastal lifestyle setting. Properties offering a true two-home compound with proven income potential are exceptionally uncommon in East Hill, making this a distinctive opportunity for homeowners and investors alike.