The Henslow's Sparrow (Centronyx henslowii) is a grassland bird species that overwinters in the southeastern United States and is a species of conservation concern due to population declines primarily caused by habitat loss. Henslow's Sparrows often overwinter in marginal habitats, such as powerline rights-of-way (ROWs), clear cuts, and field edges that provide some of their desired habitat characteristics, such as low-to-no tree cover and a diverse herbaceous understory. Using remote sensing methods, we evaluated the habitat characteristics of Henslow's Sparrow–occupied ROWs in southeastern Georgia. We calculated 22 satellite imagery metrics from Sentinel 2-L2 10 m resolution imagery, including single-pixel variables (e.g., Enhanced Vegetation Index, EVI) as well as “image texture” metrics that represent spatial heterogeneity. Using Random Forest models, we evaluated whether satellite imagery metrics could be used to discriminate between Henslow's Sparrow used areas (delineated from telemetry data) and surrounding available areas. Satellite imagery metrics were successful in predicting habitat characteristics in the ROWs (as evaluated by out-of-bag error and 3 goodness-of-fit tests), with image texture metrics performing better than single-pixel metrics. Image texture metrics were 9 of the top 10 most important predictors of habitat use in the best performing model that had a 500 m available buffer around use areas (out-of-bag error rate 21.21%). The most important image texture metric, cluster shade, was positively correlated with tree cover; Henslow's Sparrows were more likely to use areas with intermediate levels of cluster shade. From our results, we concluded that image texture metrics derived from 10 m satellite imagery could be used to predict sites that have suitable overwintering habitat for Henslow's Sparrows, but only at coarse resolutions and broader extents (hundreds of meters to kilometers). Therefore, this tool could be used to identify other ROWs (and possibly non-ROWs) with habitat that may support this and other declining grassland species.