Urbanization has increased the demand for housing in major cities across the Caribbean. Jamaica is one of several islands dealing with the overwhelming difficulty of providing and improving the living conditions of individuals living in informal settlements. In the heart of Jamaica's capital, Kingston, the inner-city Trench Town neighbourhood is plagued with crime, historic political corruption and urban decay -- posing challenges for sustainable urban development. Through an in-depth analysis of the historical, political, Culture and architectural context of Trench Town, this thesis proposes a series of interventions to promote a higher standard of living. Increasing the supply and quality of housing, as well as accommodating informal economic activity can be a catalyst for community change. This redevelopment proposal for Trench Town will provide residents with the advantages of homeownership, reduce levels of crime, and stimulate employment opportunities and expand tourism.