Abstract: This article discusses the implementation of two large-scale urban waterfront projects that are currently under construction in the Central and Eastern European (CEE) capital cities of Belgrade and Bratislava. Against the backdrop of postsocialist urban studies and recent reflections on urban or ‘world-city’ entrepreneurialism (Golubchikov, 2010), we reveal how both elite-serving projects are being shaped according to their very own structure and agency relations. Our comparative analysis unravels the power-geometry of the decision-making processes that reshape urban planning regulations of both transforming waterfronts. The path-dependent character of “multiple transformations” (Sykora & Bouzarovski, 2012) in the CEE region can, even after three decades, still be traced within the institutional environments, which have been adapting to the existing institutional architecture of global capitalism. Yet, at the same time, the dynamic globalization of this part of the world intensifies its further attractiveness for transnational private investors. As a consequence, public urban planning institutions are lagging behind private investors’ interests, which reshape the temporarily-fixed flows of capital on local waterfronts into landscapes of profits, politics and power. We argue that suchlike large urban developments, focused on promoting urban growth, accelerate the dual character of these cities. Thus, while the differences between both investigated case studies are being highlighted, we simultaneously illustrate how national and local state actors respectively paved the way for private investors, and how this corresponds to similar overarching structural conditions as well as outcomes.