In a seismic context, it is fundamental to deploy distributed sensor networks for Structural Health Monitoring (SHM). Indeed, regularly gathering data from a structure/infrastructure gives insight on the structural health status, and Artificial Intelligence (AI) technologies can help in exploiting this information to generate early warnings useful for decision-making purposes. With a perspective of developing a remote monitoring platform for the built environment in a seismic context, the authors tested self-sensing concrete beams in loading tests, focusing on the measured electrical impedance. The formed cracks were objectively assessed through a vision-based system. Also, a comparative analysis of AI-based and statistical prediction methods, including Prophet, ARIMA, and SARIMAX, was conducted for predicting electrical impedance. Results show that the real part of electrical impedance is highly correlated with the applied load (Pearson’s correlation coefficient > 0.9); hence, the piezoresistive ability of the manufactured specimens has been confirmed. Concerning prediction methods, the superiority of the Prophet model over statistical techniques was demonstrated (Mean Absolute Percentage Error, MAPE < 1.00%). Thus, the exploitation of electrical impedance sensors, vision-based systems, and AI technologies can be significant to enhance SHM and maintenance needs prediction in the built environment.