The sustainable development of urbanised space requires the implementation of long-term measures concerning pre-existing and planned development. Development strategies for large and small cities emphasise space transformation following environmental principles. This can be considered as a tool to facilitate the sustainable development of existing urban layouts. Hence, the principal objective is to identify problems with sustainable infill in city centres. This paper will use Raciborz as a case to show how implementation guidelines can be developed that are sensitive to the city’s spatial development history. Against this background, comments will be made on selected design scenarios of a city block that contained the site of the former Raciborz Synagogue. These scenarios are considered optimal from the standpoint of the city’s urban quality, understood as a conglomerate of functional, technical, aesthetic, and social values. It also points to conflicts and conflicting expectations concerning the site in question and defines a framework for compromise.