In this paper, a time domain reflectometry (TDR)-based solution for detecting water leaks in underground pipes is described and experimentally validated. The proposed method strongly reduces the inspection time that is typically required by traditional leak detection methods. In fact, it can successfully inspect pipes that are hundreds of meters long. In this work, two different configurations of the system are described: one can be used for detecting leaks in ‘already-installed’ metal pipes; whereas the other is suitable to be employed for detecting leaks in ‘newly-installed’ pipes made of any material. The performance of both these system configurations was assessed through an extensive, on-site experimental campaign, carried out with the collaboration of one of the largest European water operators, Acquedotto Pugliese S.p.A. (AQP). Representative results, related to both configurations, of three experimental cases (ECs) are reported and commented on. Finally, some practical considerations on the applicability of the system are provided.