This paper aims to tell the story of Leslieville, a small neighbourhood in Toronto's east end, from its early settlement in the 1850s to the present. Looking back at the area's progression from farming village, to working-class industrial centre, to gentrifying creative hub, provides the historical context for a further consideration of the current challenges and conflicts that are impacting the community today. In 2008 a land dispute over a proposed big-box style retail development divided the community and instigated a yearlong battle at the Ontario Municipal Board between Toronto city council and private developers. In tracing the historical growth of Leslieville and analyzing the current development issues, this study examines how urban development and cultural policy have influenced the transformation of this unique Toronto neighbourhood. An application of the theoretical literature on gentrification and photographs are provided in order to supplement the analysis. By identifying Leslieville as a neighbourhood in transition and examining it as a case study in the process and impact of gentrification and neighbourhood change this research contributes to a further understanding of the nature of urban space and how it should be developed to serve the interests of Toronto's diverse population.