This article develops the concept of shoestring democracy as a way to characterize the resulting social relations of private governance structures embedded in two types of collective housing schemes found in New York City and the adjoining suburbs: gated condominium communities (gated condominiums) and market-rate cooperative apartment complexes (co-ops). Drawing from ethnographies of gated condominiums and co-ops in New York City and neighboring Nassau County, New York, we compare these two forms of collective home ownership regarding the impact of private governance structures on residents and their sense of representation and participation in ongoing community life. “Shoestring democracy” encompasses a broad range of behaviors utilized to insulate residents from local conflicts and disagreements, and limits rather than promotes political participation. The greatest differences between the co-ops and gated condominiums were found in discussions of safety and security, in that condominium residents have developed an elaborate discourse of the fear of crime and others, especially racialized others, to explain why they moved to their secured communities. Co-op interviewees, on the other hand, generally felt a sense of safety in their buildings, often due to the gatekeeper effect of the co-op board and doormen. In gated communities, covenants, contracts, and deed restrictions (CC&Rs) guarantee that most problems are resolved before they start. While the same can be said for co-ops, interviewees find that these rules and regulations seem to mystify everyday governing practices for the average co-op resident. Moral minimalism and a lack of structural and procedural knowledge may insulate residents from local conflicts and disagreement, but also may discourage civic participation. Exploring the apathy residents expressed about participation and a lack of representation suggests that although the Rochdale principles of cooperation that are the legal and social basis for co-ops may have been important at one time, current practices of private governing boards do more to restrict participatory democratic practices than encourage them. The policy implications are outlined with suggestions of how to make homeowners associations and co-op boards more accountable and encourage greater adherence to the original co-op mandate.