Housing is central to health, wellbeing and social inclusion, but inappropriate homes currently risk damaging millions of older people. One of the main challenges faced by many researchers is determining the reasons why individuals choose or refuse housing transition. In this pilot study, a housing demonstration unit is used as a test bed for a sample of fifteen older adults approaching the crucial problem of relocation. The demonstration unit consists of a prototypal eco-friendly sustainable housing unit of 55 square meters, equipped with smart home technologies. Overall, data collected through a questionnaire draw a positive picture of the older adults' perceptions on this alternative housing solution. Respondents seem to consider home security, customizable options, and smart technology features as the most important factors influencing their decision to relocate. Results demonstrate the potential of this housing demonstration unit for (1) documenting how joint efforts among cross sectoral partnerships can work together to support sustainable new option in the emerging sector of housing; (2) offering a real example of alternative housing solutions for older adults facing the decision to remain at home or relocate; (3) offering a study to replicate in order to search those evidences that are urgently needed in literature. These findings might be a good starting point to encourage discussion for policy-making and employ practicable changes for the housing sector.