This collection of photographs documents the ongoing development of Historical Winter Park, Florida. Once considered the home to Central Florida's most affluent and influential figures, Winter Park at the turn of the century has been transformed by urban sprawl, increased housing density, disappearing green spaces, a collapsing tree canopy, rampant commercialization and privatization, and low-quality, high-income housing construction. This case study documents Winter Park's shifting built environment, changing character, and resulting displacements—including the historically Black Hannibal Square District. It centers around the following question: What are the costs of super gentrification?