Historic character, a complete renovation, and a newly built detached guest residence come together in Orlando’s desirable Lake Eola Heights Historic District. Selected to receive the Historic Preservation Board’s Rehabilitation Award, this distinctive property celebrates the preservation of its architectural heritage while offering modern comfort and the versatility of two residences. Set along downtown Orlando’s charming brick streets, 809 E Harwood Street features a 2,746-square-foot main home with four bedrooms, three bathrooms, and two primary bedrooms—one upstairs and one on the first floor. The separate 600-square-foot residence at 811 E Harwood Street adds flexibility for extended family, guests, or potential rental income. A new wood front deck and double glass entry doors welcome you into light-filled interiors, where restored historic windows and an original, restored wood-burning fireplace preserve the home’s character. The kitchen showcases Calacatta countertops and a custom seven-foot waterfall island with an integrated wine refrigerator and built-in microwave. A coordinating backsplash, stainless steel appliances, breakfast nook, and walk-in pantry with a frosted glass door and custom California Closets cabinetry complete the space. The dining area features a paneled accent wall, while glass French doors open to the rear porch and new wood deck with a ceiling fan. Three first-floor bedrooms include the downstairs primary bedroom. Upstairs, the main primary suite enjoys its own level, double entry doors, and a private balcony with weather-resistant composite decking. Its retreat-style bathroom features a spacious glass-enclosed walk-in shower and dual vanities, complemented by separate closets. Custom California Closets built-ins throughout provide thoughtful organization, while a versatile loft accommodates an office, den, or storage. The newly built detached residence offers its own address, one bedroom, one bathroom, living room, and kitchen, with estimated rental income potential of up to $2,000 per month to help offset ownership expenses. Exterior improvements include a new irrigation system, new ProVista sod, new fencing, and a new paver driveway with parking for approximately seven vehicles. An oversized approximately 600-square-foot garage adds convenience. Cedar siding accents the front of the main home, with durable Hardie board siding at the rear and throughout the detached residence. Lake Eola Heights offers historic architecture, tree-lined brick streets, and a neighborhood connected to downtown’s energy. Walk to nearby Lake Eola Park for lakeside paths and swan boats, or explore dining around Thornton Park and downtown Orlando. Assigned schools include Lake Como School for elementary and middle grades and Edgewater High School. AdventHealth Orlando and Orlando Health’s downtown medical campus—including Orlando Regional Medical Center, Arnold Palmer Hospital for Children, and Winnie Palmer Hospital for Women & Babies—are conveniently accessible by car. Recognized rehabilitation, two primary bedrooms, and an independent guest residence distinguish this versatile property in one of downtown Orlando’s most distinctive neighborhoods.