In post-Independence India, new colonies of garden suburbs served an educated citizenry to integrate science and nature into their daily life. However, one such colony of bungalows (kothi) and gardens, begun in Jaipur in the 1950s, after two generations of incremental construction, has become in the 1990s similar to an old city ward with towering courtyard houses (haveli) abutting the property lines. This longitudinal study compares the middle class occupants’ initial aspirations with real outcomes as documented in the materiality of built form. The biography of these buildings reflects not only a quest for a life style of class, but the adapting of site and building to make secure one’s livelihood and heritage for one’s descendants, and to manage relations with one’s neighbors. The built environment is not simply an outcome of regulation, design, and willful intent. The levels of agency and the variety of actors are multiple and complex, demanding an analysis of social interaction and an assessment of aggregate outcomes.