A Rare Craftsman Gem in the Heart of Colonial Town North! Welcome to 21st century living wrapped in timeless 20th century charm. Nestled on an oversized corner lot along a quiet, brick lined street, this beautifully maintained Craftsman style property is just a short stroll from Lake Highland Prep and the vibrant dining, shopping, and cultural experiences of the Mills/50 District. Step onto the wide, covered front porchcomplete with new hardwood decking and twin ceiling fansand into a home where character meets comfort. Inside the 3/1 main residence, newly refinished hardwood floors flow throughout a warm, light filled interior featuring two spacious bedrooms and a smaller third bedroom perfect for a home office or nursery. The inviting living room centers around a cozy wood burning fireplace, while the generous dining room sets the stage for memorable gatherings. The updated kitchen includes a charming eat in booth, new refrigerator and dishwasher, and plenty of room for culinary creativity. Outside, the magic continues. Nestled at the back of the property a private entrance to a beautifully designed 1 bed/1 bath guest home offers exceptional flexibilityideal as an income producing ADU, private MIL suite, or additional space for entertaining. Thoughtfully designed to maximize every inch, it boasts a full kitchen, in unit washer/dryer, sleek under/over cabinet lighting, and includes all appliances. This property has an expansive, fully irrigated yard shaded by majestic oak trees, lush landscaping, mature avocado trees and a brand new, show stopping deck. This outdoor sanctuary features automatic low voltage lighting, built in underlit bench seating, and caf lights that transform the backyard into an enchanting evening retreat. With a new roof (2021), two newer water heaters, updated appliances, and a large storage shed, this is a move in ready opportunity that rarely comes along. Whether you're looking for multi generational living, income potential, or simply a unique slice of Orlando history with all the right updates, this home truly has it all.