This article examines the largely neglected history of African American struggles to obtain housing in Cleveland Heights, a first-ring suburb of Cleveland, Ohio, between 1900 and 1960, prior to the fair housing and managed integration campaigns that emerged thereafter. The article explores the experiences of black live-in servants, resident apartment building janitors, independent renters, and homeowners. It offers a rare look at the ways that domestic and custodial arrangements opened opportunities in housing and education, as well as the methods, calculations, risks, and rewards of working through white intermediaries to secure homeownership. It argues that the continued black presence laid a foundation for later advances beginning in the 1960s that made Cleveland Heights, like better-known Shaker Heights, a national model for suburban racial integration.