In large northern and midwestern metropolitan areas, levels of black-white racial segregation have remained very high. Racial segregation limits the choices available to African American homebuyers while making their investments in homes riskier and less rewarding. Under these circumstances, middle-income African Americans face a unique set of challenges when pursuing homeownership. How do middle-income African Americans make decisions about homeownership and what are the implications of that process for the persistence of racial segregation and inequality? This dissertation seeks to illuminate the subjective experience of middle-income African American homebuyers as they navigate the home-buying process in a racially hypersegregated metropolitan area. I interviewed sixty-eight aspiring homebuyers after they decided to buy a home and then followed them throughout their home-buying process. These middle-income African Americans are on the cusp of solidifying their middle-class status, but the landscape of racial segregation presents particular challenges for achieving this goal. While the dynamics of racial segregation are enduring, the geography is frequently shifting, adding to the challenges facing this group. Middle-income African American homebuyers used folk theories to explain the neighborhood change that they saw frequently. The most prevalent of these theories, the theory of voucher-induced neighborhood decline, obscures the role of racial dynamics in neighborhood change. These homebuyers were motivated to pursue homeownership because it was seen as a marker of success under the terms of the American Dream and a signal of racial progress. Furthermore, becoming a homeowner was associated with adult status, moral worth, and respectability. While the homebuyers were highly motivated in their pursuit, they often experienced long delays in the home-buying process. As a result, the needs of households changed during the period when they were considering purchasing a home, and they were often unable to purchase at critical moments. Hyper-racial segregation makes it difficult for middle-income African Americans to find affordable homes that will appreciate well and meet the needs of their households. At the same time, a race-blind turn in housing policy leads to policies that may exacerbate these problems.