The relationship between urban green spaces (UGS) and residential development is complex: UGS have positive and negative immediate impacts on residents’ well-being, residential location choice, housing, and land markets. Property owners and real estate agents might consider how prospective clients perceive UGS and act accordingly, while urban planners influence UGS location and management as well as aim at steering the built environment. Typically, studies focus on one of these perspectives at a time. Here, we provide a synopsis of results from studies, taking different perspectives for a single case study: Leipzig, Germany. We summarise and discuss the findings of eight studies on UGS and residential development. In detail, these studies focus on spatial pattern analysis, hedonic pricing analysis, mixed-methods studies on experts’ perspectives, surveys, and choice experiments exploring residents’ perceptions of UGS. We reflect on the feasibility of deriving a synthesis out of these independent studies and to what extent context matters. We conclude that both triangulating of data and methods, as well as long-term and context-sensitive studies are needed to explain the interlinkages between UGS and residential development and their context dependency.