Modern infrastructure heavily relies on robust concrete structures, underscoring the critical need for effective monitoring to ensure their safety and durability. This paper addresses this imperative issue by introducing an innovative automated and wireless system for continuous structural monitoring. By employing embedded electrical resistivity sensors coupled with a wireless-based data transmission mechanism, real-time data collection becomes feasible. We provide a general description of the system’s architecture and its application in a pilot study covering the effects of the devices on concrete properties and data transmission. The dielectric properties of concrete specimens were investigated under natural and accelerated curing/degradation and the results were used in the final design of the antenna device. Furthermore, a pilot test comprising four reinforced concrete columns was used to investigate the range of data transmission from inside to outside of the concrete, the effects of the hardware device on the compressive strength and concrete distribution in the columns, and the data transmission quality in real time under realistic exposure conditions.