The rapid transition from traditional courtyard houses to contemporary apartments has diminished residents’ connection with light, water, vegetation, the sky, and open space, creating a gap between their perceptual needs and the quality of the residential environment. However, the ways in which this landscape transformation affects resident dwelling compatibility have remained unclear. This study aimed to explain the role of residential landscape as an experience arising from the interaction between the physical–natural characteristics of the environment and residents’ perception, meaning-making, and ways of living, and to examine its relationship with resident–dwelling compatibility in two housing types: courtyard houses from the Second Pahlavi period and contemporary housing in Tehran. The research adopted a qualitative and comparative approach, and data were collected through semi-structured interviews with three groups of residents. The data were analyzed using thematic analysis. The findings showed that the effects of physical natural elements on compatibility are not direct; rather, the ways in which residents perceive, use, and attribute meaning to these elements contribute to the formation of a sense of fit or mismatch with the environment. In the narratives of residents of traditional houses from the Second Pahlavi period, multidirectional natural light, courtyards, water, vegetation, and direct connection with the sky were integrated into the structure of everyday life and enhanced feelings of openness, tranquility, and place attachment. In contemporary apartment cases, limitations in natural light, views, and open space reduced sensory interactions and created conditions for perceptual and behavioral incompatibility, prompting residents to adopt compensatory strategies such as adding plants, rearranging furniture, and using balconies. Comparison of the narratives of the three study groups showed that landscape qualities in traditional houses constituted an integral part of spatial organization, whereas in contemporary apartments they were often experienced in limited, mediated, and compensatory forms. Accordingly, the reintegration of natural light, open and semi-open spaces, vegetation, and appropriate views into housing design is proposed as a strategy for reducing the gap between residents’ psychological needs and the constraints of contemporary apartments.