© Copyright 2019, Mary Ann Liebert, Inc., publishers 2019. Relationships that traverse sociodemographic categories may improve community attitudes toward marginalized groups and potentially protect members of those groups from stigma and discrimination. The present study evaluated whether internalized HIV stigma and perceived HIV-related discrimination in health care settings differ based on individual-and neighborhood-level characteristics of women living with HIV (WLHIV). We also sought to extend previous conceptual and empirical work to explore whether perceived HIV-related discrimination mediated the association between neighborhood racial diversity and internalized HIV stigma. A total of 1256 WLHIV in the Women's Interagency HIV Study (WIHS) attending 10 sites in metropolitan areas across the United States completed measures of internalized HIV stigma and perceived HIV-related discrimination in health care settings. Participants also provided residential information that was geocoded into Federal Information Processing Standard (FIPS) codes and linked with census-tract level indicators. In cross-sectional analyses, greater neighborhood racial diversity was associated with less internalized HIV stigma and less perceived HIV-related discrimination regardless of individual race. Neighborhood median income was positively associated with internalized HIV stigma and perceived discrimination, while individual income was negatively associated with perceptions of stigma and discrimination. In an exploratory mediation analysis, neighborhood racial diversity had a significant indirect effect on internalized HIV stigma through perceived HIV-related discrimination. An indirect effect between neighborhood income and internalized stigma was not supported. These findings suggest that greater neighborhood racial diversity may lessen HIV stigma processes at the individual level and that HIV stigma-reduction interventions may be most needed in communities that lack racial diversity.