The effects of two major demographic forces are traced between 1950 and 2040: the formation and aging of the baby boom generation and the reduction and subsequent return of large-scale immigration. These forces combine to mark several major turning points essential for understanding the changing urban condition. These include the depopulation of "gray areas" that spurred urban renewal in the 1950s, the gentrification initiated in the 1970s, and the collapse of apartment construction in the 1990s followed by its recovery in the 2000s. Looking forward, the authors address the substantial impact of settled immigrants who are now upwardly mobile. Finally, the authors consider the impacts of the sell-off of housing by the aging of the massive baby boom generation that is anticipated to take place beginning in 2020 and discuss whether the expected housing glut can be absorbed by a relatively smaller and less advantaged younger generation in the 2040s.