Climate change is intensifying uncertainty across the built environment— affecting buildings, urban systems, infrastructure, and territorial planning—and undermining design approaches grounded in assumptions of environmental stability. Although regenerative design promotes ecological restoration and positive socioecological relationships, its capacity to address uncertain future climates remains underexplored. This paper argues that regenerative design must incorporate resilience principles to remain effective under changing climatic conditions, with transition design as an integrative framework for operationalizing this combination across architectural, urban, and territorial scales. A distinction is drawn between regenerative design—focused on specific built environment interventions—and regenerative development, which supports the long-term evolution of a place's socioecological potential. The study introduces regenerative resilience, defined as the capacity of socioecological systems to sustain and expand regenerative processes while adapting and transforming in response to change, examined through the Filobobos–El Jobo initiative in Veracruz, Mexico—a territorial case study spanning three decades. The study provides a conceptual foundation for advancing regenerative resilience as a framework for designing, planning, and managing built environments under future climate uncertainty.