The built environment can affect a resident’s health and wellbeing. Land use planning has the potential promote the health and wellbeing of residents. The provision of greener urban environments is one mechanism through which land use planners might achieve this end. The purpose of this study is to examine how greenspace and physical activity may provide synergistic wellbeing benefits and how any such hypothesised synergy might depend on a resident’s perceptions of neighbourhood affability and incivility. Using data from the Household, Income and Labour Dynamics in Australia (HILDA) survey and Geographic Information Systems (GIS), the results suggest that a friendlier and more supportive neighbourhood amplifies (by more than 10 times) the greenspace and physical activity synergy. In contrast, the results suggest that residents who engage in physical activity and have higher levels of greenspace in their local area suffer a wellbeing burden where the resident perceives higher levels of incivility in the neighbourhood. While certainly not without their own limitations, these results extend on existing research efforts directed at disentangling the complexity underpinning the links between greenspace, physical activity and wellbeing. Moreover, the findings reported in this study may prove useful to land use planners and policy makers seeking to reconcile the challenges of maintaining or improving residents’ wellbeing in the face of pervasive neighbourhood perceptions, continuing population growth and declining per capita greenspace.