The positive energy district (PED) concept is attracting growing research interest; however, the need for practical approaches to facilitate their implementation remains crucial. This study, framed in the COST Action ‘Positive Energy Districts European Network’, offers a comprehensive review of the roadmaps, pathways, and guidelines—namely ‘PED-Transition Approaches’—currently available to support the implementation of district-scale innovative models, thereby advancing energy transitions and enhancing livability at the city level. The review involved a systematic search and web scraping of documents, including scientific and grey literature, as well as EU-funded projects’ reports. The studies were identified according to multiple filters and eligibility criteria, then categorised in a structured repository using a multidimensional matrix, and finally examined following three-levels of detail (i.e., bibliometric study) overview and in-depth analysis. The findings reflect the main characteristics, gaps, and challenges in PED implementation by underlying the growing need for effective step-by-step, user-centric, and context-based transition approaches. In conclusion, the research, building on an extensive literature of multiple inspirational methodologies and their associated use cases, is a strong basis to develop sequential pathways to facilitate PED implementation among key stakeholders in a short–medium-term perspective towards a climate-neutral city vision.