The automatic monitoring of shortenings of vertical members in high-rise buildings under construction is a challenging issue in the high-rise building construction field. In this study, a practical system for monitoring column shortening in a high-rise building under construction is presented. The proposed monitoring system comprises the following components: (1) a wireless sensing system and (2) the corresponding monitoring software. The wireless sensing system comprises the sensors and energy-efficient wireless sensing units (sensor nodes, master nodes, and repeater nodes), which automate the processes for measuring the strains of vertical members and transmitting the measured data to the remote server. The monitoring software enables construction administrators to monitor real-time data collected by the server via an Internet connection. The proposed monitoring system is applied to actual 66-floor and 72-floor high-rise buildings under construction. The system enables automatic and real-time measurements of the shortening of vertical members, which can result in more precise construction.