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Housing has become a central mechanism of inequality in high-price global cities, yet the processes linking intergenerational advantage to housing stratification remain insufficiently specified in these cities. Hong Kong provides a critical case for examining these dynamics due to its extreme housing prices, high barriers to ownership, and institutionalized housing regime. This study proposes a two-stage framework distinguishing between entry into homeownership and accumulation within the housing market. In contexts where ownership functions simultaneously as shelter and wealth, the determinants of crossing the ownership threshold may differ from those governing subsequent asset differentiation. Using data from the Hong Kong General Social Survey 2025, this study examines how individual socioeconomic resources and family background jointly shape housing outcomes. Logistic regression models show that homeownership is strongly associated with household income and respondent education. However, parental education remains a robust predictor even after controlling for these achieved characteristics, indicating that family background structures access to property through channels beyond individual attainment. KHB decomposition further demonstrates that while part of the parental advantage is mediated by respondents’ education and income, a substantial direct effect persists. Among homeowners, inequality dynamics shift markedly. Housing value and multiple-property ownership are primarily stratified by income, while the independent effects of education and parental background weaken. Sequential logit models reveal that family background is consequential for transitions into ownership but plays a limited role in transitions to multiple-property ownership. These findings highlight the staged structure of housing inequality. Intergenerational advantage primarily operates at market entry, whereas financial capacity governs accumulation among owners. By differentiating access from accumulation, this study clarifies how housing systems reproduce durable inequality in advanced urban contexts.