Capture–recapture (CRC) is a method of population estimation pioneered in biology that allows the surveyor to approximate the proportion of individuals who evaded sampling efforts (i.e., captures) based on repeated samples from the same population. The current national standard for estimating homelessness is a single-day enumeration called the point-in-time (PIT) count. By using a local community action agency’s homeless outreach program and a cold weather shelter as two distinct sampling sources to capture data using CRC methodology, the current study sought to estimate the homeless population in Kittitas County, Washington, and compare CRC with PIT count estimates. Four months of data collection for the two sampling sources yielded an estimate of 115 (95% CI [93, 137]) homeless individuals in the county using CRC methodology. The PIT count conducted in the same year sampled 61 individuals, supporting the idea that cross-sectional enumeration (i.e., PIT counts) underestimate the homeless population and could be supplemented by CRC methods, particularly in rural areas where resources to conduct PIT counts may be limited. Greater accuracy in homelessness enumeration may aid in advocacy efforts, provide baseline data for researching interventions designed to reduce homelessness, and yield statistics to better guide legislative and policy initiatives.