While daily contact with nature is essential in large cities, such opportunities are often limited, thus reducing chances for psychological restoration. Even if available, however, such places will not be used if they fail to meet residents’ needs and preferences. This study focuses on the preferred qualities of nearby nature in terms of both environmental affordances and design characteristics in urban neighborhoods. The study was conducted in the Logan Square Neighborhood in Chicago, IL, and involved 53 individuals. The research instrument was a set of 93 photos arranged in columns, depicting a variety of commonly used landscape design elements and urban outdoor scenes. Participants selected their preferred scenes and grouped them based on what they considered meaningful. The findings offer evidence of participants’ preference for small green spaces that provide opportunities for both socializing and growing plants. This study illuminates interconnections between environmental affordances and green space design attributes that address participants’ concerns and expectations. It uncovers the importance of environmental affordances in green space preference studies, a topic that is largely missing from existing work on landscape preference. Further, it showcases a novel method—the use of participant-generated photo grouping to better understand the basis of preferences. The method emerged from pragmatic application of the Environmental Affordances Theory from Environmental Psychology to the landscape planning and design process. Finally, the results were used to create a set of useful recommendations to help urban planners and designers create more livable spaces in dense urban areas.