This paper presents a water leakage monitoring system that gathers acoustic data of water pipes using wireless communication technology and identifies the sound of water leakage using machine leaning technology. To collect acoustic data effectively, this system combines three types of data-collection methods: drive-by, walk-by, and static. To design this system, it is important to ascertain the wireless communication distance that can be achieved with sensors installed in a basement. This paper also reports on radio propagation from underground manholes made from reinforced concrete and resin concrete in residential and commercial areas using the 920 MHz band. We reveal that it is possible to design a practical system that uses radio communication from underground sensors.