The main purpose of this paper is to demonstrate how the old modernist engineering technologies, such as single purpose stormwater infiltration basins, can be transformed into quality environments that integrate ecological and social functions and promote multiple sets of outcomes, including biodiversity restoration, water management, and cultural and recreational purposes, among other urban roles. Using the principles and theories of biophilic urbanism, regenerative design, and qualitative inquiry, this article analyzes and discusses the actors, drivers, strategies, constraints, and values motivating the stakeholders to reinvent Perth’s stormwater infrastructure through two local case studies. The “WGV sump park” was developed through a public-private partnership, including professional consultants with community input, and the “Green Swing sump garden” was an owner-builder community-driven project involving volunteers, who maintain it. The results of this research suggest that both projects are successful at managing stormwater in a way that creates multiple community and biodiversity benefits. Communities could gain improved access to nature, social interaction, health, and well-being if local governments support these alternative approaches to regenerate underutilized stormwater infrastructure by promoting biophilic interventions. Mainstreaming this design approach identified some issues that may arise during the implementation of this biophilic urban approach, and the paper suggests ways to enhance the wider delivery of regenerative and biophilic design into urban planning, involving volunteer delivery and maintenance for small scale projects and fully professional assessments for large scale projects.