The knowledge of the electromagnetic field levels generated by radio base stations present in an urban environment is a relevant aspect for propagations and coverage issues, as well as for the compliance to national regulations. Despite the growing interest in the novel fifth generation (5G) technology, several aspects related to the investigation of the urban propagation of the Global System of Mobile Communication (GSM), third generation (3G), and fourth generation (4G) mobile systems in peculiar non-rural environments may be improved. To account for irregular geometries and to deal with the propagation in hilly towns, in this work we present an enhanced version of the COST231-Walfisch–Ikegami model, whose parameters have been modified to evaluate the path loss at distances greater than 20 meters from the radio base station. This work addressed the problem of providing an effective, reliable, and quantitative model for the estimation of electromagnetic field levels in built-up areas. In addition, we also developed and tested a pre-industrial software prototype whose aim is to make the estimated electromagnetic field levels available to the key players in the telecom industry, the local authorities, and the general population. We validated the proposed model with a measurement campaign in the small urban and irregular built-up areas of Dorgali (Nuoro), Cala Gonone (Nuoro), and Lunamatrona (Cagliari) in Sardinia (Italy).