This paper analyses the impact of public spaces regeneration after evaluating users that have recently experienced transformations in their urban environment. The Chilean Government launched the “Bicentenary Projects Competition Found”, financing significant regeneration schemes in selected public areas, assuming that the enhancement of urban environments is a key component for a better quality of life in the short time for Chilean cities. This recently designed and new generation of public spaces have been evaluated in the light of a major research that reviews the kind of emphasis that has been made in the transformation of these schemes. To demonstrate if this development is sustainable or not, depends on the balance of environmental, social and economic goals. To analyse the case studies highlighted in this paper, a matrix was used to compare data before and after urban transformation. This system allowed diagnosing how the residents, professionals and officials in the local government experienced and evaluated the solutions provided. The final conclusions draw attention to potential actions to be considered in the near future, proposing sustainable development as a continuum target and not only sporadically or cosmetic urban changes that will need further transformations and more public expenditure.