In the context of urban land-use growth and the consequent impacts on the environment, green spaces provide ecosystem services for human health. The ecosystem services concept synthesises human–environmental interactions through a series of combined components of biodiversity and abiotic elements, linking ecological processes and functions. The concept of green infrastructure (GI) in the urban context emphasises the quality and quantity of urban and peri-urban green spaces and natural areas. In dense urban contexts, the applications of GI are limited and not applied to the potential urban spaces such as roofs and gardens. Often, roofs are characterised by impermeable paved surfaces with negative effects on human well-being, whereas garden designs do not consider social needs and environmental interactions. The role of urban stressors or the urban context as a driving force or pressure of urban green space is not always well understood and employed in the planning of green spaces. This is partly due to a knowledge gap between different science disciplines that operate on different scales, from single processes of the plants (which focus on plant responses to environmental stresses affecting human well-being) to urban ecosystems (which focus on the biodiversity and urban space planning–human well-being relationship). This can create a paradox, as green spaces that are not adequately designed might not produce the expected effects. In this paper, an overview of benefits and limitations of applying the ecosystem services approach when designing green spaces is presented. The focus is on the main urban ecosystem services provided by green roofs and community gardens such as GI that can represent strategies to provide ecological and social multifunctionality to waterproofed surfaces connected to the buildings and low-exploited gardens being the main areas that affect dense urban settlements, and thus, increasing the ecosystem services in the urban environment, such as reducing the Urban Heat Island, as well as flooding events. Specifically, the paper highlights (i) feedback between ecological processes and functions that support ecosystem services, (ii) urban environmental stresses in relation to disservices that these can create for human well-being and (iii) key issues that should be considered in the planning and design of urban ecosystem services. Such a new vision of urban ecosystem services highlights the need to look at GI as an active part of the urban space design in the built environment.