Demand side management can add flexibility to a district heating (DH) system by balancing the customer’s hourly fluctuating heat demand. The aim of this study is to analyze how different demand side management control strategies, implemented into different customer segments, impact DH production. A city scale heat demand model is constructed from the hourly heat consumption data of different customer segments. This model is used to build several demand side management scenarios to examine the effect of them on both, the heat producer, and the customers. The simulations are run for three different-sized DH systems, representing typical DH systems in Finland, in order to understand how the demand side management implementations affect the production. The findings imply that the demand side management strategy must be built individually for each specific DH system; the changing consumption profiles of different customer segments should be taken into consideration. The results show that the value of demand side management for a DH companies remains low (less than 2% in cost savings), having an effect mostly upon the medium loads without any significant decrease in annual peak heat loads. Also, the findings reflect that the DH pricing models should be developed to make demand side management more attractive to DH customers.