"Gated communities: Gated communities are systematically seen as safe places to live, especially by an affluent urban middle class. All spatial elements of control such as high walls, porters and guarded gates are seen as strong deterrents of crime and enabling safe live. However, recent reports show that communities became hostages of their own space and security, developing most of their socialization within these places. There is widespread belief that common social rules and laws applied to the city are not applied inside gated places; walls and gates separate them from the outside society's laws. As a result, young children are allowed to drive cars, which are parked on public spaces, authority and rules are questioned and the dwellers are lenient to transgressions. This article compares American gated communities with Brazilian condominiums showing the similarities and peculiarities of both urban structures. It also investigates the impact of this widespread new urban configuration on peoples experience of common and public spaces, sense of urbanity, transgression and impunity. Examples of social practices in gated neighborhoods are presented, building up evidence showing the spatial segregation, the lack of social respect, the weak role of administrations and a different concept of community. This paper discusses the effect of experiencing "legal" transgressions of spatial and social rules and norms in gated communities and the emergence of a permissive generation of citizens Gated communities and residential condominiums; similarities and differences: The paper explores concepts such as community and classic authors(Tonnies, Weber). The notion of public versus private realms of life are also discussed (Tönnies, Sennett, Hall, Maffesoli, L. Dumont, B. Anderson, S. Zukin, H. Lefebvre) and finally studies on gated communities (Sennett, M. Davis, Jock Young, Stuart Hall, Teresa Caldeira, Setha Low and E. Blakely).The examples provided were product of ethnographic analysis of life in residential neighbourhoods in Brazil: observations of social practices correlated with questionnaires with dwellers, staff and managers of those communities. Security for transgressions: The results discuss the problems of living in places outside society rules and laws. Are children and youths raised in gated communities prone to replicate their behaviour in outside public spaces?Gated communities are new phenomena in Latin American cities. Cities are witnessing the spread of these places and the emergence of cultures of transgresion. It is necessary to assess the social and cultural outcome of life in these self regulated places."