The upcoming decades will be marked by the transformative dual green and digital transition fundamentally reshaping societies. Ensuring these transitions are equitable requires acknowledging disparities and anticipating socio-economic implications. This chapter underscores the importance of implementing strategies that embrace anti-fragility and de-risking (Taleb in Antifragile: things that gain from disorder. Global Penguin Random House, 2014 [134]). It advocates for a shift towards relational, pluriversal (Kothari et al. in Pluriverso. Dizionario del post-sviluppo. Orthotes, Napoli, 2021 [71]) modes of inhabiting urban spaces, preparing the context contents for employing digital tools to safeguard natural heritage, preserve local identity, and enhance community well-being (JRC in Understanding and acting on future risks and opportunities, Portfolio 26, 2023 [166]). This chapter explores the necessity of alternative dwelling modes that integrate communal existence, regenerative knowledge, and digital tools into metropolitan landscapes by challenging traditional design principles and promoting interconnectedness: a new emerging, nurturing diverse, and resilient ways of living. Our research underscores also the importance of metropolitan cultural heritage (Heritopolis Initiative) as a foundation for digital communities sustainable habitats. We translate these resources into actionable data and methodologies that drive policies that uphold heritage while advancing Twin Transition. A decentralised yet coordinated metropolitan framework is a system in which decision-making and authority are distributed across various entities or levels within a metropolitan area. However, a mechanism is still in place to ensure cooperation and alignment of goals among these entities. It implies a balance between local autonomy and collective coordination to efficiently manage urban development and services in a large city or metropolitan region.