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 porch—complete with new hardwood decking and twin ceiling fans—and 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 flexibility—ideal 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 café 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.