While urban trees can be important determinants of human health and wellbeing in world cities, the specific influence of nearby urban trees upon human wellbeing has not been adequately explored. While many studies have associated urban greenery abundance with wellbeing scores, many measures of urban greenery do not specify the type of vegetation or the impact of co-location. Here we fill this gap by associating self-reported measures of the presence of nearby trees (tree in front of one's home) with validated subjective wellbeing (SWB) scores. We also tested for the mediating role of what people thought about trees and nature, with a focus on the values people associate with urban trees and nature relatedness (NR). We used electronic panel survey data based on a demographic and geographical representative sample of more than 3400 residents living in Toronto, Canada, and Melbourne, Australia. We analysed these data using regression-based mediation and path analyses. We found that having a tree in front of one's home was strongly and positively associated with SWB scores in both cities with similar results (Melbourne, β = 0.17, p < 0.05; Toronto, β = 0.18, p < 0.05), while accounting for NR, values associated with urban trees, and demographics (e.g., age, education, home ownership). The mediating role of NR and values was small. The specific pathways of association between tree in front of one's home, SWB, NR, and values, varied by city, when accounting for demographics. We discuss how increasing the abundance of nearby urban trees in cities may also increase human wellbeing.