Political philosopher, John Rawls, conceptualizes property-owning democracy (POD) as a constitutional liberal democracy that practices wide social distribution of productive assets, namely property and human capital, that enables citizens to exercise their political freedoms, with security, equality, justice and fairness. However, with their ossified ideological, economic and social structures, contemporary liberal democratic capitalist nations do not possess the material conditions or the political will to realize such a system. In contrast, a postcolonial nation can potentially realize the POD as its nation-building processes unfold, as demonstrated in this case study of Singapore. With its near universal provision of public housing ownership to its citizens, state provision of all levels of education and subsidized programs of new skill acquisitions, retraining and upgrading for its labor force, Singapore may be said to have fulfill the material condition of wide social distribution of productive assets. But politically, the single-party dominant People’s Action Party government disavows liberalism ideologically. However, the elected parliament system as a procedural democracy empowers the electorate to punish the government when it is unresponsive to ground demands. Singaporeans’ dependency on the state for housing has made public housing demand a highly politicized arena in which the citizen/electorate has successfully used their votes to extract positive outcomes to their demands, in so doing refreshes and revitalizes the democratic process.