Cherokee Park was founded by James C. Brown, a Scotland-born silk manufacturer who came to Sarasota at the end of Florida's real estate boom and envisioned creating "Sarasota's most desirable community." As the earliest developments in Cherokee Park, master builder Leadley Ogden erected walls, gateposts, and corner markers in the Mediterranean Revival style using terra cotta block, completed in 1925. The community took its name from the Cherokee rose depicted on its gatepost mosaics, and Brown built the first home there for himself as a Mediterranean-style estate, intending it to be the first of many majestic homes for elite residents. To ensure an upscale neighborhood, he imposed strict deed restrictions, but after the Florida Land Boom collapsed and Cherokee Park failed to develop, he removed most of those restrictions in 1935. Most of the homes were not built until after World War II. In 1951, nearly 50 residents formed the Cherokee Park Association and began a long-range beautification and improvement program with the city of Sarasota, including plans for streetlights and plantings in the street medians. Over the next 43 years, brick streets were repaved, gas lanterns were added atop the gateposts, streetlights were installed in the medians, live oaks and crape myrtles were planted, and the wall was repaired several times. A history of Cherokee Park was published by residents in 1994. By 2021, the neighborhood had more than 90 homes, with many original houses replaced or redesigned, creating a vibrant community of diverse architectural styles and residents while maintaining its historic legacy.