This paper presents the development of a condition monitoring system that monitors the operating conditions of a reduction unit, such as the bearing temperature, gearbox vibration, and gear oil deterioration, and notifies the operator of potential problems or abnormal conditions. A series of field tests on high-speed rail and conventional lines was performed to identify the characteristics of temperature rise and vibration levels on the reduction unit during operation. The monitoring system was designed based on the proper sensor selection, measurement method, and signal analysis to optimize the interface with the operating system of high-speed trains. Application of this monitoring system to high-speed trains will play an important role in their proper maintenance and safe operation.