In recent decades, the sustainability approach has provided valuable improvements to the built environment. Nonetheless, experts agree that the current sustainability paradigm, rooted in a mechanistic worldview, is not enough to address the rapid pace, expansive scale, and urgency of global climate emergencies, suggesting that its efficacy has reached a limit. In response to this urgent need, the concept of regenerative design and development has recently emerged as a promising alternative in the built environment, seeking to reconnect human efforts with nature in a cooperative and co-evolutionary relationship to enhance the adaptive capacity of the built environment and add value to the entire living system. This relatively new concept in the built environment remains largely theoretical, with limited implementation studies primarily focusing on individual buildings and indoor environments, predominantly in educational and commercial settings. This paper aims to bridge the gap in the literature by exploring the real-world implementation of regenerative design and development in the built environment through a comprehensive review of existing international precedent case studies to critically analyse and identify the challenges in implementing regenerative sustainability worldwide. This research employs a qualitative approach, including comparing international precedent case studies. The results can contribute to a better understanding of the current state of regenerative sustainability practices, shedding light on factors contributing to their limited uptake and identifying potential pathways towards a more regenerative built environment.