Charming home in the heart of Rose Isle. Step into a piece of history with this architecturally timeless two-story home, one of the first to be built in the sought-after Rose Isle community. Nestled on a spacious 16,500-square-foot lot with a sprawling front yard, this residence boasts incredible curb appeal, shaded by magnificent Oak trees that enhance its timeless beauty. Offering over 4,200 square feet of living space, this home presents a wonderful opportunity to create your dream residence tailored to your tastes and needs. The main level features a first-floor primary suite, providing comfort and convenience. The expansive 34-foot-long Florida room overlooks a large pool, offering the perfect space for relaxation or entertaining with natural light streaming through the vast windows. Additional features include a grand formal living room with a wood-burning fireplace, a formal dining room ideal for hosting gatherings, and an open family room with a charming brick fireplace adjacent to a cozy dinette for casual meals. The second floor houses four generously-sized bedrooms, three of which include walk-in closets, offering ample storage and comfort. Located in the tranquil and picturesque Rose Isle neighborhood, which borders both Winter Park and Orlando, this home is less than a five-minute drive to Advent Health and the Orlando Museum of Art, a ten-minute drive to the vibrant shopping and dining scene of downtown Winter Park, and only 15 minutes to downtown Orlando. The home is zoned for top-rated schools: K-8 Audubon Park and Winter Park High School. Experience the charm, comfort, and convenience of life in Rose Isle. Don't miss this rare opportunity to own a piece of history and make it your own.