Several studies have shown a positive relationship between local greenspace availability and residents’ health, which may offer opportunities for health improvement. This study focuses on three mechanisms through which greenery might exert its positive effect on health: stress reduction, stimulating physical activity and facilitating social cohesion. Knowledge on mechanisms helps to identify which type of greenspace is most effective in generating health benefits. In eighty neighbourhoods in four Dutch cities data on quantity and quality of streetscape greenery were collected by observations. Data on self-reported health and proposed mediators were obtained for adults by mail questionnaires (N = 1641). Multilevel regression analyses, controlling for socio-demographic characteristics, revealed that both quantity and quality of streetscape greenery were related to perceived general health, acute health-related complaints, and mental health. Relationships were generally stronger for quality than for quantity. Stress and social cohesion were the strongest mediators. Total physical activity was not a mediator. Physical activity that could be undertaken in the public space (green activity) was, but less so than stress and social cohesion. With all three mediators included in the analysis, complete mediation could statistically be proven in five out of six cases. In these analyses the contribution of green activity was often not significant. The possibility that the effect of green activity is mediated by stress and social cohesion, rather than that it has a direct health effect, is discussed.