Numerous elements, such as the composition and characteristics of carbon nanomaterials, the composition and characteristics of the matrix material, moisture levels, temperature, and loading circumstances, influence the piezoresistive behavior of self-sensing cementitious composites. While some past research has explored the impact of some of these factors on the performance of self-sensing cementitious composites, additional investigations need to be conducted to delve into how loading conditions affect the sensitivity of self-sensing cement-stabilized composites. Therefore, this study explores the influences of various loading conditions (i.e., location of loading regarding the location of recording electrodes, and loading level) on the electromechanical performance of self-sensing cement-stabilized sand. To this end, firstly, the evaluation of the percolation threshold based on 10% cement-stabilized sand specimens containing various multiwall carbon nanotubes (MWCNTs) and graphene nanoplatelets (GNPs) was performed. Then, 10% cement-stabilized sand containing 4% MWCNTs/GNPs was tested under various cyclic compressive stresses. The results suggested that the distance between the loading area and the electrode location used for recording the electrical resistance significantly impacted the sensitivity of cement-stabilized sand. Optimal sensitivity was achieved when the electrodes were positioned directly beneath the loading area. Moreover, the study showed that the stress sensitivity of self-sensing cement-stabilized sand increased proportionally with the stress level. An examination through scanning electron microscopy (SEM) demonstrated that the loading condition influences the bridging characteristics of carbon nanomaterials in cement-stabilized sand, leading to diverse electromechanical behaviors emerging based on the loading condition. This study underscores the importance of considering specific parameters when designing self-sensing cement-stabilized sand for application in practical field use.