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To date, most studies on building environments and walking behavior have utilized top-down approaches (e.g., big data or social media data) yet lack bottom-up approaches to verify their findings. Therefore, this study divided urban streets into three main settings (community streets, waterfront paths, and urban greenways) and collected data from a sample of 411 urban residents in Chengdu via an online questionnaire to examine the impact of street environmental factors on their choice of walking path. It was found that: (1) people with higher levels of education preferred streets with water bodies as walking paths; (2) the environmental quality of the physical and aesthetic aspects both had an impact on residents’ choices, and the aesthetic environmental quality had a stronger impact; (3) the impact of most infrastructures on community streets was stronger than on other streets; (4) residents were more concerned about the environmental quality of waterfront paths and urban greenways. Based on these findings, three design patterns for residents’ preferred street environments are proposed.

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