Although the integration of sustainability, ecology, and design has been recognized as necessary by scientists and practitioners, most transdisciplinary frameworks are not inclusive of the worldviews, paradigms, aims, processes, and components necessary for sustainability. Landscape sustainability science helps to focus scientist, scholar, practitioner, and stakeholder efforts toward sustainability at a pivotal level; however, collaboration and progress have been slow. Significant potential exists for design to be an integrative and transformational methodology toward landscape sustainability, yet it has not fulfilled this ambitious role. In this paper, we first build a case for regenerative development, a development and design methodology based on an ecological worldview, as an integrative platform for a new paradigm. This new paradigm, which we call regenerative landscape development, has the potential to thoroughly catalyze a shift toward regenerative sustainability. We then detail this new paradigm as a process that could continually enhance the capacities of living systems to increase health, well-being, and happiness. Next, to illustrate regenerative development in practice, we provide brief case studies of projects in Viña del Mar, Chile and Juluchuca, Guerrero, Mexico. Finally, we propose future recommendations and precautions in the construction of regenerative landscape development as a new paradigm. If fully understood, embraced, and realized, regenerative development holds incredible potential for a sustainable future.