Monitoring a building’s structural performance is critical for the identification of incipient damages and the optimization of maintenance programs. The characteristics and spatial deployment of any sensing system plays an essential role in the reliability of the monitored data and, therefore, on the actual capability of the monitoring system to reveal early-stage structural damage. A promising strategy for enhancing the quality of a structural health monitoring system is the use of sensors fabricated using materials exhibiting similar mechanical properties and durability as those of the construction materials. Based on this philosophy, the authors have recently proposed the concept of "smart-bricks" that are nanocomposite clay bricks capable of transducing a change in volumetric strain into a change in a selected electrical property. Such brick-like sensors could be easily placed at critical locations within masonry walls, being an integral part of the structure itself. The sensing is enabled through the dispersion of fillers into the constitutive material. Examples of fillers include titania, carbon-based particles, and metallic microfibers. In this paper, experimental tests are conducted on bricks doped with different types of carbon-based fillers, tested both as standalone sensors and within small wall systems. Results show that mechanical properties as well as the smart brick’s strain sensitivity depend on the type of filler used. The capability of the bricks to work as strain monitoring sensors within small masonry specimens is also demonstrated.