Two homes, one property, endless possibilities - and NO HOA. Located in FLOOD ZONE X where flood insurance is not required, 370 E Fray St is the kind of opportunity that rarely hits the market in Englewood's highly loved Dearborn area. Designed for flexibility, this property lives like two separate homes connected by a shared lanai. The main residence features a comfortable 2-bedroom, 2-bath split floor plan with its own private entrance, while the attached studio suite offers a full kitchen, bathroom, and separate entrance of its own - ideal for multigenerational living, guests, seasonal visitors, or creating income without sacrificing privacy. And the best part? The income potential here is already proven. The front residence has earned 25+ five-star Airbnb reviews, while the studio suite has a successful history as a long-term rental. Whether you're looking for a primary home with supplemental income, an investment property, or a setup that allows family to stay close while maintaining independence, this property adapts to your lifestyle. Major updates provide peace of mind from day one, including new windows in 2024, a fully fenced yard added in 2024, newer A/C in 2023, and a roof replaced in 2020. Outside, the property continues to impress with shelled parking for boats, trailers, RVs, and multiple vehicles, storage sheds, a paved side walkway, and outdoor spaces designed for true Florida living. Prefer a traditional layout? The property can easily function as a 3-bedroom, 3-bath single-family home as well. Just minutes from Dearborn Street, local restaurants, shopping, farmers markets, and Gulf beaches, this is more than just a property - it's a rare chance to own a versatile piece of Englewood in one of the area's most charming locations. Schedule your private showing today and come experience why this one stands out from everything else on the market.