Discover this beautifully renovated and updated Craftsman bungalow in the highly desirable Historic District of Downtown Winter Garden! Nestled on a sprawling 0.34-acre lot shaded by majestic grandfather oaks, this property combines timeless charm with modern amenities. Located just steps from vibrant shops, restaurants, local events, a community theater, and the popular splash pad, this home offers a quintessential Winter Garden lifestyle. Step through the leaded glass front door and be welcomed by the warm heart pine floors, soaring 9' ceilings, and elegant crown molding that set a storybook tone. The front living and dining area opens to a versatile bedroom (or office) with its own half bath. At the heart of the home, a spacious farmhouse-style kitchen boasts real wood cabinetry, granite countertops, and a side entry for easy grocery access. Adjacent is a convenient laundry room with storage. Down the hall, two generously-sized bedrooms share a charming subway-tiled bathroom. Upstairs, a versatile loft leads to the serene primary suite, tucked among the treetops, complete with an updated en-suite bath (2023), storage, and office nook. Outdoor enthusiasts will love the expansive backyard with a detached 25x25 garage/workshop featuring a separate 100-amp electric service – perfect for hobbyists or extra storage. A sturdy new roof (2023), low-maintenance turf, exterior paint (2024), and enchanting front yard lighting (2021) add to the appeal. With its unmatched character and prime location, this historic gem offers an inviting retreat in the heart of a growing, vibrant community. Don’t miss this rare opportunity to own a piece of Winter Garden history!