The trajectory of urban development in Hong Kong has produced a culture where property development has become a powerful force in society that has shaped its key institutions and built up the ethos of property accumulation as the measure of ultimate success. Driven by three key institutions: the government, property developers, and the MTR, Hong Kong’s urban railway company, urban development has massively transformed the territory’s neighbourhoods and communities. This dissertation contributes to the under-researched juncture between urban transformation and community relations in the context of a development-dominant culture by considering the case study of Sai Ying Pun, a Hong Kong neighbourhood that has undergone such urban change. Through a mixed method approach the perspectives of residents and businesses from two key communities, as well as experts, are studied. The findings reveal that the impacts of urban change are not experienced evenly by each community, and even if displacement does not occur, the benefits do not fall symmetrically. The research also demonstrates the continued faith placed in the power of the institutionalised property development apparatus to enhance the urban landscape and to improve the lives of residents, as well as the enduring belief amongst Hong Kong people of its potential as a vehicle for upwards social mobility.