Gay neighbourhoods have historically served as vital places for gay socialising, and gay social networks are important sources of social support. Yet, few studies have examined the influence of these forms of community on sexual health. Informed by theoretical frameworks on neighbourhoods and networks, we employ multi-level modelling to test hypotheses concerning whether gay neighbourhoods and social network factors are associated with five sexual risk behaviours: receptive and insertive unprotected anal intercourse (UAI), barebacking identity, recent internet use for finding sexual partners, and 'Party and Play' (PnP). Our analyses of a community-based sample of gay men in New York City reveal little evidence for the direct effect of gay enclaves on sexual risk with the exception of PnP, which was more likely among gay enclave residents. Having a network composed predominantly of other gay men was associated with insertive UAI, PnP, and internet use for meeting sexual partners. This network type also mediated the association between gay neighbourhoods and higher odds of insertive UAI as well as PnP. Our findings highlight the sexual health implications of two important facets of gay community and, in doing so, indicate the need to better contextualise the sexual health risks faced by gay men.