The relationship between urban greenspaces and the benefits to psychological, social, and physical aspects of human wellbeing are important to study, particularly in rapidly urbanizing areas and underrepresented communities. This interaction was theorized, analyzed, and measured in this paper through the transactional paradigm and operationalized through the use of a volunteer geographic information questionnaire, SoftGIS, which activated the urban greenspace–human wellbeing interaction through its map-based data collection. Over 450 unique place-based relationships were statistically analyzed within the Greater Glasgow Urban Region of Paisley, Scotland, a vulnerable community. This study revealed that multiple components of human wellbeing are supported through interactions with urban greenspaces. The Paisley region’s respondents visited greenspaces, generally, and most often to receive psychological benefits such as reduction of stress and mental relaxation through interactions which included sitting and relaxing in quiet spaces, enjoying natural surroundings, and viewing nature and wildlife. The physical and social wellbeing benefits were not as frequent in these urban greenspace interactions but were distinctly present. The results imply pathways towards management and multifunctional greenspace design responses in urbanizing regions and indicate strategies for public policy, human health, and urban planning, which deliver wellbeing benefits to communities.