Knowledge of breeding dispersal, defined as shifts in territory location between two successive breeding seasons, remains limited for migratory passerines. We investigated the relationship between two ecological factors, habitat structure and reproductive success, and 499 breeding dispersal events in a Nearctic—Neotropic migratory songbird, the Black-throated Blue Warbler (Setophaga caerulescens) breeding at the Hubbard Brook Experimental Forest, New Hampshire, from 1998 to 2008. Male dispersal distance was correlated with both individual age and habitat structure, with older males moving shorter distances than younger males, and males on the high-shrub-density plot (i.e., higher quality) moving shorter distances than males on the plot with lower shrub density. Female dispersal distance was also correlated with habitat structure; individuals on the higher-quality plot moved shorter distances than those on the lower-quality plot. In contrast to that of males, female dispersal distance was independent of age, but correlated with reproductive success: females that fledged relatively few offspring in a year subsequently dispersed farther than those that experienced high reproductive success. Mean (± SE) breeding dispersal distance for females (245 ± 20 m) was greater than that of males (163 ± 11 m). We also examined reproductive consequences of breeding dispersal and found that males that moved shorter distances fledged more offspring after dispersal than those that moved longer distances; no trend was found for females. These differences in dispersal patterns and outcomes suggest sexspecific selective pressures and life-history strategies.