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The regeneration of decaying housing is becoming paramount in meeting the current international demand for new dwellings within the sustainable agenda. Medium-rise housing is proposed as ideal as it meets the planning guidance's desirable densities and for its social and ecological sustainability possibilities through the landscape. Yet, having few medium-rise housing areas regenerated with a sustainable-oriented landscape approach, the amount of research undertaken in this area is limited. Therefore, the present study addresses this gap in knowledge by studying the short- and long-term contribution that may be made to inform future regeneration of housing. The research investigates a regenerated case study in Sweden and another one in Germany which were assessed for social and ecological sustainability through a set of indicators, a survey, observational records, and semi-structured interviews. Afterwards, the applicability of the results was tested through a survey in an additional case study in Mexico where no regeneration has taken place. It was found that the arrangement of landscape was essential for encouraging socializing and the respondents' design preferences were similar despite cultural differences. It was observed that robustness and interpersonal distancing were most important for socializing whilst visual richness and mystery were clearly favoured by respondents. Interestingly, it was also revealed that involving in ecological improvements facilitated residents in knowing each other. However, it was found that perceptions and unclear ideas of sustainability as well as poor collaboration among stakeholders resulted in poor management of initiatives and a reduced participation of residents. Based on these findings, the study makes design recommendations for landscape designers as well as proposing regeneration and operational guidelines for planning, managing, and maintenance. Further research is required to document more regenerated housing areas to enable sustainability issues to be more generally applied.