Urbanization fragments natural landscapes from pristine forest and grassland into concrete urban centers. For birds, increased urbanization decreases area of suitable breeding habitat, with potentially negative consequences for reproductive success. We hypothesized that land use surrounding natural areas affects occupancy and breeding success of a common migratory songbird at 10 sites across southwest Michigan. We focused on cavity nesting house wrens (Troglodytes aedon) and used GIS technology and field observations to ask at what spatial scale do land use and land cover variables best predict the number of males singing at a given site, as well as the number of females attracted to these males across sites. Finally, we compared reproductive success of wrens breeding at five sites within Kalamazoo County to explore whether patterns of reproductive success matched occupancy patterns. Such information helps us understand how animals use natural areas within and near cities and the value of urban nature preserves for reproductive success.