Aiming for sustainable buildings and cities is critical to achieving a future that is socially just, ecologically regenerative, culturally rich, and economically viable. However, our current concepts of sustainability often exclude the essential domains of data, information, and the knowledge relating to the relationship between buildings and people that inhabit them. Thus, the research questions at the core of this paper have been as follows: Can technologies and artificial intelligence (AI) be used to create systems that enhance relationships between buildings and inhabitants? Can social networks and natural interactions support further research relating to human-centric design tools for the built environment? The Human Observation Meta-Environment (HOME) project was developed to address this question. The ICT architecture has been tested to observe and collect human behaviour data within a sentient room at the Politecnico di Torino (IT), where the inhabitants were strategically aware of their behaviours. Methods of analysis included technologies related to the domain of AI (such as Natural Language Analysis, Computer Vision, Machine Learning and Deep Learning) that have been used in social network analysis in connection with the word 'comfort', and definitions resonate strongly with the realm of regenerative design. Results were used to further research the role of users that could serve as leverages to design (both spaces and related smart systems) according to actual user needs. People from very different disciplinary backgrounds interacted with the prototype in a workshop and provided stimuli for further considerations regarding the possible technological, psychological, cognitive, cultural, social, political, and aesthetical impacts of the use of these technologies inside sentient buildings. The paper enriches the discourse on how ICT data can be organised and read in a human-centric regenerative design process perspective.