Upgrading existing social housing (SH) requires user-centred participatory processes to promote values. Comparative case studies in Brazil, Germany, the Netherlands, and the UK are presented. Living Labs (LLs) were conducted for the delivery of user values and to promote an informed decision-making process. Tools and LL activities were tested to engage stakeholders in the upgrading process, support the co-creation of solutions and address social and societal challenges. The main research aims were to facilitate SH upgrading processes focusing on the delivery of value for users, achieving end-user empowerment, as well as assessing participatory decision-making through LLs. Research goals were achieved in each case study setting. The evaluation of specific cases informed a conceptual framework and guidelines to facilitate upgrading through LLs in varied SH landscapes.