In Central and Eastern European countries (CEE) there has been a long debate about the end of the “post-socialist” transitional period and on how long this geographical area will still labelled as such. The prefix “post” reveals a will to disintegrate a former system, rather than a view on the future. It is indeed the lack of a homogeneous view on development that has kept the post-socialist transition alive, which continues to follow the rules originated as antithesis toward the antecedent totalitarian period. These rules follow a “metaphor of the pendulum”, according to which to an extremity one responds with another extremity: the doctrine of central planning has been substituted by the new-liberal doctrine, which aims at integrating the CEE countries in the global economic network. Urban planning no longer occurs at the government level; it is delegated to local administrations and follows the movements of the market, with individual housing solutions and commercial models. The fact that these countries have undergone a second phase of complete social renovation in less than 50 years allow us to view this area as a single laboratory, where the environment has been modelled following the change in the basic principles that regulate society. The landscapes of the socialist period have been contrasted by one of the major sprawling suburban areas of the beginning of the 21st century. The 2008 crisis has offered a first point where to analyze the situation of a model which is no longer sustainable. The aim of this article is to bring to light these meditations, according to which post-socialism can be overcome first of all by accepting, reusing and integrating the socialist heritage, while reflecting on re-balancing individual spheres and collective responsibilities.