District heating (DH) is an alternative technology to Individual Heating (IH) for satisfying end-user’s needs. This paper assesses the competitiveness of a DH network in the center of Italy from energy, environmental, and economic points of view considering both thermal power plant and end-users’ sides. On the thermal power plant side, the energy analysis considers the Primary Energy Saving (PES) and the specific energy (Esp) of the fuel actually exploited in the thermal power plant compared to its Low Heating Value (LHV), while the environmental analysis considers the avoided CO2 and the economic analysis considers the Energy Efficiency Certificates (EECs). Results showed that the current thermal power plant configuration with two boilers and a Combined Heat and Power (CHP) unit reaches a yearly PES of 21.3% as well as 1099 tCO2 avoided. From the economic analysis of the thermal power plant side, 829 EECs with an economic return of 207,222€ are obtained, while from the end-users’ side the DH network is cheaper than IH in 84.7% of the cases. Further technologies are also studied to enhance the CHP unit flexibility.