Built environment features can have varying impacts on user behavior depending on the perceptions of the opportunities and obstacles that the environments create. This study systematically evaluated the relationship between neighborhood perceptions and the specific types of self-reported walking behavior for 121 older adults who resided in urban, suburban, or rural neighborhoods. Perceptions of street connectivity, crime and traffic safety, and overall satisfaction were associated with specific types of walking behaviors, and the strength of the relationships differed by neighborhood type. Sociodemographic variables such as age and sex were associated with certain types and amounts of older adults’ walking behaviors both across and within each neighborhood type. The results of this study support the importance of perceived street connectivity regardless of neighborhood type and perceived crime safety in rural neighborhoods to impact the walking behavior among older adults.