Welcome to 1292 Alabama Drive! This beautifully maintained home sits on a .42-acre corner lot in one of “Olde” Winter Park premier neighborhoods, and directly across from Lake Maitland. The home boasts an impressive blend of classic charm and modern design, with the original design by James Gamble Rogers and renovations by Phil Kean Design Group. As you walk up the custom paved walkway, you’ll be greeted by an expansive front porch perfect for enjoying beautiful sunset views. Formal spaces greet you as you enter the home, with the formal dining room to the right, and the formal living room to the left, showcasing a wood-burning fireplace. The adjacent sunroom is covered in natural light and provides gorgeous lake views. As you make your way to the back of the house, prepare to be wowed by the light and bright gourmet kitchen boasting solid wood custom cabinetry, honed granite counter tops, stainless-steel appliances, and a vast, walk-in, hidden pantry. The open floor plan adds an informal dining area, with expansive windows and French doors - providing an abundance of natural light, as well as the oversized family room, which features a wood-burning fireplace, custom full wet bar, and another set of French doors, leading to the covered patio and well-manicured backyard. One of the oversized primary bedrooms is located downstairs, and offers an en-suite marble bathroom, a huge walk-in closet, and a wonderful seating area. Next door is the downstairs flex room, which can be used as a gym, additional office space, or nursery. The main upstairs wing is home to two generously-sized bedrooms, a full bathroom, and another enormous primary bedroom with a wood-burning fireplace, a large walk-in closet, stunning marble bathroom, and French doors to a balcony overlooking the private backyard. A separate upstairs wing offers an immense room with an en-suite marble bathroom and large walk-in closet, which could be used as a private guest room or mother-in-law suite. The exclusive boat house across the street is the jewel of this property, with two electric lifts, ample storage, a cozy, built-in sitting area, and breathtaking sunset views of Lake Maitland, which connects to the sought-after Winter Park Chain of Lakes. Other highlights include a three-car garage, plantation shutters, built-in cabinetry, and a large utility room. Recent updates include a new roof and architectural gutters (2023), all new siding (2023), regraded new pavers (2023), dock lift new cables (2022), all new Anderson windows (2019), two electric water heaters (2019), detached three-car garage and expanded driveway (2019). This home is truly one-of-a-kind!