The declining port/industrial activities near the urban structure of cities generate new challenges for contemporary societies. Among others, these challenges interest the desolation of urban districts and the creation of large urban voids, one of the major problems affecting, nowadays, the Greek cities. This phenomenon is witnessed in a larger extent during the last years of the strong socio-economic recession, particularly in coastal zone areas. Therefore, currently, there is a large amount of areas waiting for regeneration projects in order to be reconnected to the cities’ built environment and society. Despite the large amount of such undeveloped areas, there is a lack of formal knowledge and experience in implementing regeneration strategies in Greece. For that reason, this research is seeking to identify and understand the motives, in terms of drives and barriers, of opting for (re)development schemes by focusing on an exemplary brownfield waterfront area in the seaport city of Piraeus, called “Lipasmata”. The purpose of analysing this case is to illustrate the conflicts between the stakeholders committed to the area, and the plans made until now, in order to examine the opposing views for the area’s future. Additionally, based on the main case study’s findings and the knowledge from the international practice of waterfront development, it is explored the possibility of implementing alternative strategies as a solution for the (re)development of the area. In particular the solution is searched within the boundaries of the community-orientated development approach, which has flourished in challenging socio-economic context, as the one in Greece. The expectations of this research are to contribute to the academic knowledge and a policy debate regarding the management of waterfront developments in the country. This will help policy-makers and other stakeholders search for more effective solutions for managing and implementing waterfront development projects.