A premier street offering a perfect walkable lifestyle to Maitland's vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater, and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. 5 bedrooms, 4 baths stretching across 4,814 sf with bonus space there is many ways to make it your own. Inspired by Classic Charleston architecture with a Florida influences, the exterior features French doors across both the front and rear elevations, lantern-style lighting, and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters & upper-level balconies at both sides of home complete the design. Step inside to a sweeping staircase with elegant iron details, with neutral travertine flooring flows throughout the main level & finished with volume ceilings. The kitchen, living, and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink, and high-end stainless-steel appliances. Generous laundry and pantry storage are a bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround sound speakers, and direct access to the outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms and the spacious primary retreat opens to a private balcony spanning across back of home and with pool views. the rear of the home. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating, and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light and great closet storage and additional loft is a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining, or a private workspace. Outdoor speaker system add to the ambience. Additional improvements and features include a newer metal roof (2020), 2 HVAC's (2021), water heater (tankless Rinnai installed by Maitalnd/winter park plumbing) plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings, and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and master suite both have ceiling installed concert speakers & outdoor speakers, Lower floor speakers have individual room controls and are served by pantry stereo system. This exceptional home offers a highly desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School, and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a true standout in one of Maitland's most special neighborhoods.