The living conditions of the urban poor have dramatically changed in Chile in the past two decades. On one hand, through a massive program of investment in subsidized housing, more than a million Chileans have moved out from slums and shantytowns and become property owners. On the other, youth violence, drug trafficking, and other social maladies are increasing in many neighborhoods. It appears that home ownership has not been enough to overcome marginality and disintegration. Moreover, in some cases, moving to subsidized housing projects contributes to increased social problems, especially those related to violence and disintegration. To acquire knowledge about shantytown living conditions and the changes attendant to the move to home ownership, six focus groups were conducted with former residents of La Toma de Penalolen, the last important slum remaining in Santiago and eliminated in 2006. This article analyzes the ways in which residents who have moved out from a shantytown compare the houses and neighborhood in which they used to live with their current setting. It analyzes the changes and continuities in living conditions and the aspects of shantytown living that former residents remember as valuable. The article ends with a discussion regarding the conditions of home ownership, social control, stigmatization, and the identity and value transformation residents have experienced.