This study reports on the housing experiences and pathways of different populations living in a gentrifying neighbourhood in Bangkok—newcomers living in condominiums, original residents who have managed to remain and others who have been evicted. The respondents’ accounts reveal contrasting life stories of hardship and progress. For poorer residents, gentrification intensified existing vulnerabilities, and evictions or the threat of evictions disrupted their ability to maintain stable lifestyles and livelihoods. For the more affluent, gentrification offered new lifestyle opportunities and new ways of enhancing personal and family interests. It also promoted for them a renegotiation of family arrangements. Gentrification is a local and personal process but one that is conditioned by broader economic forces and the inequalities of class. The theoretical challenge of gentrification is therefore to provide an account that considers the interaction between the varied experiences of individuals, their biographical habitus, and the differential vulnerabilities of distinct social classes and their structural habitus.