Amidst concern about the implications of an aging U.S. population, recent evidence suggests that there is a unique aging trend among the homeless population. Building on this, we use data from New York City and from the last three decennial Census enumerations to assess how the age composition of the homeless population—both single adults and adults in families—has changed over time. Findings show diverging trends in aging patterns for single adults and adults in families over the past 20 years. Among single adults, the bulk of the sheltered population is comprised of persons born during the latter part of the baby boom era whose high risk for homelessness has continued as they have aged. Specifically, the age group in this population facing the highest risk for homelessness was 34–36 (born 1954–1956) in 1990; 37–42 (born 1958–1963) in 2000; and 49–51 (born 1959–1961) in 2010. In contrast, among adults in sheltered families, there is no indication of any progressive aging of the family household heads. The modal age across the study period remains at 21–23 years of age. We consider implications for the health care and social welfare systems, and policy responses to homelessness.