While a policy of more decentralized stormwater management is increasingly being pursued in areas containing new housing developments, the question arises as to how stormwater management is handled in existing settlements, where restructuring the drainage system is a much more complex affair and often requires the active involvement of property owners. Recognizing that the multidimensional objectives of stormwater management in settlements call for a range of local strategies, this article examines the interaction and strategic contribution of two key municipal institutions for regulating stormwater management, namely, compulsory connection and usage and stormwater charges, in order to examine how they meet these objectives when property owners are involved. The following questions are addressed: How do these two key institutions link the varied objectives of stormwater management with practical options for decentralization? Which institutional designs are capable of integrating property owners into a municipal stormwater strategy in a coherent manner? What is current local government practice? This article begins by analyzing the interactions between different objectives of stormwater management, the interplay of the two key institutions, and options for stormwater management on private properties. On this basis, we then present an empirical study of current practice in 44 medium to large cities in Germany. This shows that while local governments devise very different—and often inconsistent—institutional designs, decentralization is quite commonly pursued in existing settlements.