The production of urban space and associated neoliberalisation of urban governance limits opportunities for individual and collective freedoms. Such a socio-spatial approach to uneven urban development has influenced a number of authors in their examination of urban community gardens. The research has shown both positive agency and wellbeing benefits of these spaces and also more critical accounts of how the spaces are limited in their ability to truly enhance political freedoms, overcoming asymmetric power relations. In addition to ongoing issues of insecurity of tenure, such well-intentioned community garden initiatives may be seen as light green, weak approaches to urban sustainability rather than a true oppositional discourse of practice, therefore seen to continue neoliberal forms of both unsustainable and uneven development. Using qualitative, visual methods, the chapter focuses on the potential of community gardens to enhance both human agency and ecological sustainability of passive adult users, and active youth and child users in urban areas. The sites chosen are specifically designed with ecological principles and associated features. In order to examine the freedoms valued within these sites, Amartya Sen’s Capability Approach (CA) is operationalised in five such sites in the UK and Ireland. Various critiques of the CA are addressed, and a particular approach to evaluating human wellbeing, linking the sustainable and just use of urban resources is developed. Such a re-conceptualisation of the CA is significant in realising the potential role of the sites in enhancing a more expressive mode of being for individuals, along with the enhancement of participative and critical capacity in urban areas.