Awareness of greenery is an important factor in the lifestyles of those living in detached houses located in urban districts. This awareness changes over time with resident life stage and greenery growth. In this study, we aimed to investigate residents’ awareness of greenery along a common garden path shared by 16 houses, comparing this awareness when their houses were first built with that 5 years later. We found that the Green View Index increased by 18% over the 5-year term. Around 80% of the residents were positive about the growing greenery because they felt close to it. In particular, residents preferred the pathway that was covered by tree canopies. The pruning was initially designed by a gardener to create the image of "houses in a copse" and as a result, the narrow pathways have been successfully covered by tree canopies, bringing the landscape closer to the intended design, leading to more positive evaluations by the residents. It was suggested that the landscape agreement containing the centralized management of tall trees and the continuous relationship between the residents and the gardener, kept the landscape to meet the preferences of the residents and increased the sense of unity throughout the residential area.