Today, the impact of climate change is affecting our urban social life in a rapid and increasing way. Urban green regeneration—as one Nature Based Solution (NBS)—offers opportunities to tackle Urban Heat Islands (UHI). The cooling potential of green parks, among many other ecosystem services (ES), is considered a regulatory service. Due to the increasing impact of climate change, there is a need to densify and enlarge existing parks and to create new parks. To enable the development of new green regeneration projects, new cooling plans are being developed in Belgium at the national, regional and local level. However, while there is ample evidence for the effectiveness and benefits of urban green restoration, there are human, social, financial and political barriers that often stand in the way of action. This paper uses several complimentary methodologies, narrating three case studies of open spaces in the city of Ghent (Belgium) to demonstrate the need for a pragmatic and multi-disciplinary approach. A study of an existing park reveals the potential for intensified vegetation to positively impact human wellbeing, but it also points to the potential for the “green gentrification” of a vulnerable neighborhood. A financial study offers a potential model for financing green transformation through value capturing, but this suggests the need for more research as the number of realized examples is rather limited. And a third study explores a potential solution to overcome political inertia in creating new green spaces through a bottom-up initiative, but it suggests the need for municipal support. This research, complimenting the Flemish urban renewal project impaC3t, points to the need for co-creative involvement of the public sector, academia, business, finance and civil society.