Welcome to 1710 Oregon Street, where classic Orlando character meets exceptional versatility in the heart of Colonialtown. This charming bungalow features solid hardwood floors throughout, an updated kitchen with quartz countertops and stainless steel appliances, a spacious living room, an enclosed breezeway ideal for dining or additional living space, a Florida sunroom, and a generous primary bedroom with an en-suite half bath. A major highlight of the property is the detached guest cottage built in 2013, offering a full kitchen, full bathroom with a large walk-in shower, washer and dryer, brand-new mini-split AC, private entrance, and its own outdoor patio, providing an excellent setup for guests, extended family, a home office, or flexible additional living space. Outside, the fully fenced backyard features tropical landscaping and an irrigation system, creating a private setting with plenty of room to enjoy the Florida lifestyle. Additional features include a tankless gas water heater and stainless steel appliances. Ideally located just minutes from Leu Gardens, Mills 50, Audubon Park, Winter Park, Downtown Orlando, local restaurants, shopping, and entertainment, this property offers a hard-to-find combination of character, location, and flexible living space in one of Orlando's most sought-after neighborhoods.