It requires exact data to establish an effective homeless support system. This study aims to explore a way to establish a monitoring system that can provide these data to help identify the number of the homeless and its trends as precisely as possible. According to data from the Ministry of Health and Welfare, there are approximately 5,000 or less homeless people in Korea, but the count resulted from their unsystematic monitoring is not correct. It is pointed out that there are methodological weaknesses in homeless counting and enumeration in Korea. The Point In Time Count and the Homeless Management Information Systems in the US, Point In Time rough sleeper counts and the sample survey method in Japan are reviewed as foreign advanced cases. With these cases as a reference point, the study examines theoretical and practical issues of introducing a homeless monitoring system in Korea. It is suggested that the PIT counting method, annual homeless service data analysis, and the sample survey method should be combined and a formal report on the homeless monitoring should be published in Korea.