In this study, we estimate the association of original residents’ resettlement preferences with demographic and socioeconomic characteristics of households matched with local development initiatives accounting for spatial structure and cluster effects. We develop theoretically driven empirical models of recent residential redevelopment projects within a South Korean metropolitan area. Multilevel analysis, categorical data models, and spatial data analysis are employed using survey data collected from former residents matched with secondary data. Results suggest that due to a higher likelihood of housing value increases after redevelopment projects, original residents are more willing to resettle. Additionally, original residents’ willingness to pay for the resettlement is associated with their economic status. Together with the collaboration among original residents, local or central government agencies, and redevelopment corporations, appropriate housing prices to reduce the original dwellers’ financial burden should be considered.