Climate change and the energy crisis forced industrialized countries to contain CO2 emissions and use indigenous renewable energy sources. Geothermal energy undoubtedly has great potential, particularly thermal energy, given that 48% of the final energy consumption in the EU20 countries in 2021 was related to heating and cooling systems. The present study verifies and compares the feasibility of realizing district heating systems in two different contexts: (i) depleted hydrocarbon fields with the repurposing of existing hydrocarbon wells into geothermal wells and (ii) areas with documented geothermal resources. The two selected case studies are located, respectively, near Romentino (Northern Italy, province of Novara) and Tuscania (Central Italy, province of Viterbo). Following an assessment of the geothermal resources in the two selected case studies, specific methodological tools have been developed to evaluate the energy demand in the municipalities and determine the projects’ economics. Both case studies show positive economic indices assuming heat tariffs aligned with the values recorded in the 2020–2021 period. However, our results show how reusing hydrocarbon wells in geothermal wells constitutes an excellent opportunity to access geothermal resources, significantly reducing the necessary investment and the mining risk and strongly improving the economics of the projects.