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The graduation thesis project seeks to develop a design methodology that could function in a sustainable way within the constraints of the context of overpopulated and heavily decayed building stock of Centro Habana, in the city of Havana, Cuba. The intention of the project is to generate transformation in the stagnated built environment. The possibilities for such transformation are explored through the experimentation of designing small-scale, self-sufficient, sustainable, architectural interventions that can be constructed within and in-between the existing buildings. The methodology proposes these “literal” interventions on the basis of an analysis of the diverse informal collective practices and initiatives that emerged within the physical context of the Spanish Colonial architecture in Centro Habana, during the years following the Socialist revolution of 1959. The thesis suggests that these practices are evident manifestations of how space can influence the transformation of a society beyond the desires, or control, of an effective authority, and aims to explore the potential of them with respect to architectural practice.