Housing a huge population in a small area is and has always been a difficult issue. Unlike other cities such as Hong Kong, the Singapore government plays a very active role in the provision of public housing. This chapter reviews the development of the housing development board’s (HDB) residential estates, and the legal, economic, sustainability and finance issues of the HDB. Finally, case studies on Toa Payoh, 662 Buffalo Road in Little India and the Pinnacle are included in this chapter.