Playgrounds are envisaged as spaces designed to provide a safe and enjoyable environment that facilitates physical activity among children and adolescents. However, in various instances within cities formerly under socialist governance, these playgrounds have suffered neglect and lacked maintenance, coherent conceptual frameworks, professional oversight, suitable materials for playground structures, and attention to vegetation or potentially toxic elements. They became residual areas in the city’s built environment. Presently, the evaluation and the regeneration of playgrounds in cities have emerged as a significant task. Amidst the densely populated urban fabric, these spaces hold considerable importance for outdoor activities, social interaction, recreational pursuits, and the healthy development of future generations. Simultaneously, these places can play a crucial role in a city’s green infrastructure, local landscapes, and the challenges of sustainability prompted by climate change. The landscape analysis of 22 playgrounds classified them based on land use characteristics, location, functions, equipment, quality, and accessibility. A case study in Târgu-Mureș, scrutinized in detail within this analysis due to its proximity to the city center, within a densely populated urban area, and its multifaceted functionalities, underscores the need for a comprehensive approach encompassing diverse disciplines to address its manifold usage requirements.