Aspects of territorial behavior of Nearctic-neotropical migratory birds during the nonbreeding period are poorly studied. Information about territoriality, site persistence, between-year site fidelity, and territory sizes are not available for most birds, especially in tropical agroecosystems. Given the rapid expansion of oil palm in the neotropics, determining how oil palm affects the territorial behaviors of overwintering migratory birds is an important line of inquiry with conservation implications. The American Redstart (Setophaga ruticilla) is considered a model species for the study of population dynamics in the neotropics; however, territory size for American Redstart has only been assessed in native habitats. In this study, we outfitted individual redstarts with radio tags, across two winter seasons, to determine variation in territory sizes across oil palm plantations and native forest patches in the State of Tabasco, Mexico. Average redstart territory size was 0.29 ha in oil palm plantations and 0.17 ha in native forest. Albeit presenting larger territories in oil palm plantations, which could indicate poorer habitat quality, the difference between both habitats was not statistically significant. Our results demonstrate, for the first time, that American Redstarts hold territories in oil palm plantations and that territory size may serve as an important indicator of relative habitat quality for redstart populations in tropical working landscapes.