Under contract-accepting backup offers. Tucked away on a picturesque cobbled street just off Virginia Drive, this stunningly updated two-storey DUPLEX is bursting with character, charm, and modern appeal. Built in the 1920s and beautifully restored, it offers the perfect fusion of historic soul and contemporary style in one of Orlando’s most walkable, vibrant neighborhoods. Each of the two 1-bedroom, 1-bathroom units—one upstairs, one downstairs—has its own full kitchen and living space, making this property a dream for both investors and owner-occupants. The original hardwood floors gleam like new, and the bright, modern interiors feel effortlessly fresh and inviting. Updated features include mini-split A/C systems, separate electric meters, a shared laundry room, a ROOF replaced just THREE years ago, and a termite bond. Insurance has been easy to obtain and affordably priced—another bonus for buyers. This property offers serious income potential, with each unit previously leased at $1,700/month, bringing in $40,800 annually. Flexible setup allows you to live in one unit and lease the other—or rent both for maximum return. The generous 7,676 square foot lot even provides the opportunity to add a third unit or accessory structure (buyer to verify). And the LOCATION? Truly unbeatable. You’re just minutes from Ivanhoe Village, Mills 50, College Park, and Audubon Park, surrounded by award-winning restaurants, local coffee shops, breweries, and indie boutiques. Lake Highland Prep and the Orlando Urban Trail are nearby, and downtown Orlando is only 10 minutes away. Commuting is a breeze with close proximity to AdventHealth, Orlando Health, UCF Downtown, and Orlando International Airport (just 20 minutes away). This is a rare find, income-producing property in the heart of the city with room to grow. Walkable, rentable, and undeniably charming. Schedule your private showing today.