A popular vacation spot, Winter park has attracted money, the majority of the time in the hands of white industrialists historically. With community planning in place, these wealthy New Englanders took over and developed the east side of Winter Park, forcing African Americans to reside to the west unless they were needed. Naturally, this physical division led to cultural differences in the communities despite their close proximity, and racism, as it is always the historical case, gave less priority to practical additions and upkeep in the black community. The west community consequently became dilapidated when compared to the ritzy white neighborhood just a railroad track away, and all eyes turned to focus on the east community, leaving the black community in its ruins.
Winter Park became associated with its better-conditioned rich white community thus, leaving lesser care for Hannibal Square and the rest of the black community by passers-by. The feedback loop of lack of awareness stunted progress to the west while making progress on the east more rapid and, being a popular vacation spot, the extra influx of money from vacationers only helped to progress the eastern community further. Perception for years, then, were wholly focused on the popular vacation spot, the eastern wealthy community, and Winter Park as a whole became associated with this wealthy living.
In recent years, awareness has allowed Hannibal Square and the rest of the community to be renovated and integrated with the eastern portion of Winter Park, allowing it to become part of the whole picture of Winter Park instead of the un-cared for community. This gradual unity is slowly adjusting, although not wholly changing, the perception of Winter Park as a whole.