Urban looped water distribution systems are highly vulnerable to water quality issues. They could be subject to contamination events (accidental or deliberate), compromising the water quality inside them and causing damage to the users’ health. An efficient monitoring system must be developed to prevent this, supported by a suitable model for assessing water quality. Currently, several studies use advective–reactive models to analyse water quality, neglecting diffusive transport, which is claimed to be irrelevant in turbulent flows. Although this may be true in simple systems, such as linear transport pipes, the presence of laminar flows in looped systems may be significant, especially at night and in the peripheral parts of the network. In this paper, a numerical optimisation approach has been compared with the results of an experimental campaign using three different numerical models as inputs (EPANET advective model, the AZRED model in which diffusion–dispersion equations have been implemented, and a new diffusive–dispersive model in dynamic conditions using the random walk method, EPANET-DD). The optimisation problem was formulated using the Monte Carlo method. The results demonstrated a significant difference in sensor placement based on the numerical model.