We investigated the distribution of wintering woodland bird species in 47 very small, isolated, woodland fragments (0.54–6.01 ha) within an agricultural landscape in north-central Ohio. Our objectives were to determine correlations between temporal, habitat, and landscape variables and avian presence, density, and species richness within the smallest woodlots occupied by such species. Our results suggest that even common species are sensitive to variation in habitat, landscape, and season. Woodlot area explained the most variation in presence, density, and species richness. Shrub cover was also an important predictor variable for presence of the smallest resident birds. Shrub cover might function as both a refuge from predators and as a windbreak, reducing thermal costs in a flat, open landscape. Landscape factors related to isolation and connectedness were also correlated with species presence and density. The species composition of the community changed through the winter, as did the density of individual species, suggesting that the winter season may play an important role in determining the distributions of bird populations across woodlots. The models presented here for Ohio birds in this specific landscape may have biological inference for other species in similar landscapes.