This research analyzes the benefits enjoyed by the homeless persons located on the riverbank of the Tama River in Tokyo when they reside in clusters. To conduct this research, we first detect the housing locations of homeless persons using an unmanned aerial system—or a drone—and find the optimal number of clusters of houses based on single-linkage clustering, a hierarchical cluster analysis method. After detecting clusters, we evaluate the effect of residing in a larger cluster on a homeless person’s standard of living, which is measured by the temperature of each house in the winter. Our results show that the larger the cluster in which a house is located is, the higher its temperature, indicating that living in a larger cluster improves their living standards. This finding suggests possibility that homeless persons in the study area benefit from living in a larger community via interaction with those living in the same cluster.