The built environment, even at its ‘greenest’, inevitably entails changing ecosystem structure and function. Multiple sustainable development tools and approaches are available to reduce environmental harm from built development. However, the reality that society exists within fully integrated socio‐ecological systems, wholly interdependent on supporting ecosystems, is not yet adequately represented in regulation or supporting tools. Regenerative development seeks to address this interdependence in part by improving the health of supporting socio‐ecological systems through the development process. We demonstrate the relevance of a series of approaches – Local Nature‐Related Planning Policy (LNRPP), Biodiversity Net Gain (BNG), the Environmental Benefits from Nature Tool (EBN), Nature Assessment Tool for Urban and Rural Environments (NATURE Tool), and RAWES+ (Rapid Assessment of Wetland Ecosystem Services+) – in terms of their ability to meet their stated aims and objectives, and how these relate to wider regenerative themes. A comparative analysis of the five approaches is carried out through their application to a practical case study site, resulting in policy‐ and practice‐relevant learning and recommendations. The research reveals current gaps in methodology, which can lead to adverse outcomes for sustainability. This is particularly clear in relation to the spatial and temporal scales across which each approach operates. In addition, this research discusses the inherent limitations of taking a reductionist approach to examine complex systems.