Dynamic simulations can accurately estimate the thermal demands for space heating and cooling in buildings, as well as the energy and economic performance of specific energy refurbishment actions. This study aims to evaluate the energy and economic savings resulting from the adoption of particular energy measures applied to a cluster of residential condominium buildings, also considering some possible Italian funding policies. To this scope, dynamic simulation models of several buildings with different features in terms of geometry, shape, and thermo-physical properties are considered. The selected buildings are representative of the most common buildings in the city of Naples, Southern Italy. Two scenarios regarding the possible penetration of the refurbishment actions are considered: the “25% scenario”, where 25% of buildings in the Naples municipality adopt the selected measures, and the “100% scenario”, where all buildings adopt such energy refurbishment actions. The results of the simulations, reported over different time periods, compare the economic, energy, and environmental benefits of the specific energy measures. This study evaluates the replacement of conventional natural gas-fired boilers with natural gas-fired condensing boilers, as well as the use of thermal insulation on the external walls of the buildings. The primary energy demand for space heating decreased by 28% when the proposed energy measures were implemented in all buildings of the Naples municipality.