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Transit-oriented development has been a widely accepted tool among transportation planning practitioners; however, there are concerns about the risk of increasing residential property values leading to gentrification or displacements. Therefore, it is critical to provide precise investigations of the relationships between public transit and gentrification. Although numerous studies have explored this topic, few have discussed these relationships based on detailed measurements of gentrification from a regional perspective. This study aims to fill the research gap by measuring the gentrification subcategories through a hierarchical definition based on data in the New York–Northern New Jersey–Long Island areas and applying the transit desert concept as the measurement of transit services. Through multinomial logistic regression and machine-learning approaches, findings indicate that the rate of transit deserts in economically disadvantaged neighborhoods is higher than the others. In addition, the impacts of transit services are significant in gentrification but insignificant in super-gentrification. These findings can advance the knowledge of the role of the transit service in different gentrification progresses. Based on these findings, policymakers need to be careful when allocating public transit budgets and note the effects of these investments on neighborhoods with different socioeconomic statuses.