This study enrolled enterprise business owners/managers in the U.S. as the subjects to investigate the relationship among four factors: personal motivation, the social expectation of stakeholders, business performance, and their CSR toward the local community. The research results showed that: (1) small enterprise’s perceived expectation from stakeholders has a positive effect on their decision to engage in CSR toward community; (2) their perception of business performance has a positive effect on their decision to engage in CSR toward the community. Based on these research results, public policymakers or relevant units are advised to further achieve the goal of nurturing a flourishing community by increasing awareness of stakeholder’s expectations for small enterprise’s CSR commitment. Also, it is clearly pronounced in this study that regardless of their personal motivation to support the local community, unless financially successful, small businesses are less likely to engage in CSR toward the local community. This result makes a good sense that having a successful business operation is a necessary condition for small enterprises to pay attention to a higher-level value such as CSR toward the local community.