Step into one of the most unique opportunities in Trumbull with this rare legal 2-family home in the highly sought-after Tashua neighborhood. This historic residence-originally constructed around 1840-was once home to the family of the namesake for Jane Ryan Elementary School, offering both charm and heritage. The side-by-side design provides true dual-occupancy flexibility, featuring one unit with 4 rooms, 2 bedrooms, 1.5 baths, and a full basement, and the other with 6 rooms, 3 bedrooms, 2 full baths, and a full basement. Both sides showcase hardwood and tile flooring throughout, complemented by modern updates including a one-year-old roof and a newer furnace and hot water heater on one side. A detached three-car garage adds valuable storage and convenience. Ideally situated near top-rated schools, parks, shopping, restaurants, and highways, this property is perfect for an owner-occupant seeking additional income or an investor looking for steady returns. Move-in ready, rich with history, and located in one of Trumbull's most desirable areas, 14-16 Gisella Road is a rare and exceptional find.