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Increasing wealth inequality in the United States and other societies has renewed interest in homeownership as housing is a primary source of wealth. Despite numbers studies that examine determinants and consequences of homeownership, existing literature is limited in that it typically measures homeownership at a single point in time and has not applied the life course approach to examine how homeownership changes over the long-term span of life course. Following the same individuals over 25 years from age 25 to 50 with data from the Panel Study of Income Dynamics (PSID), we examine homeownership trajectories over 25 years, which are identified as latent classes. Our latent class analysis reveals three distinctive homeownership trajectories for men: “consistent owners,” “late owners,” and “consistent non-owners.” In addition to the same three trajectories, another trajectory is identified among women who are classified as “tumultuous owners.” Next, we conduct multinomial logistic regression analysis to investigate socioeconomic and demographic factors associated with homeownership trajectories uncovered as latent classes. Race, education, and lengthy marriage prove the most consistent and impactful factors for belonging to one homeownership trajectory over another. Finally, to demonstrate utility of homeownership trajectories as relevant family background measures, we assess whether children of original PSID mothers who have different homeownership trajectories differ in their likelihood of college attendance. The result of logistic regression shows that children of mothers with the consistent non-ownership trajectory or the tumultuous ownership are significantly less likely to attend college than children of mothers with the consistent ownership trajectory. We discuss utility and relevance of long-term homeownership trajectories for understanding social stratification processes.