Hurricane Sandy struck the east coast of the United States on October 29, 2012, devastating communities in its path. In the aftermath, New York implemented a home buyout program designed to facilitate the permanent relocation of residents out of areas considered to be at risk for future hazards. While home buyout programs are becoming popular as policy tools for disaster mitigation, little is known about what factors influence homeowners to participate in or reject these programs. This study used mixed methods to assess the relationship between community resilience and the relocation decision in two heavily damaged communities in which the majority of residents made different decisions regarding whether or not to pursue a buyout. The sample was composed of residents from Oakwood Beach and Rockaway Park, both working-class communities in New York City, who participated via a community survey (N = 133) and/or in-depth interviews (N = 28). Results suggested that community resilience moderated the relationship between community of residence and the buyout decision, leading to opposite responses on the buyout decision. Contextual community factors, including the history of natural disasters, local cultural norms, and sense of place, were instrumental in explaining these different responses. Implications for disaster policy are discussed.