While the age of physical environments is the central tenet of historic preservation, there is a lack of empirical evidence about how everyday people actually value, perceive, and experience age as an intrinsic part of an urban environment. In order to ameliorate this knowledge deficit, this study employs phenomenology to understand the lived experience of being in a “new” versus an “old” or “historic” urban residential environment. The new environment is the I’On new urbanist development in Mt. Pleasant, South Carolina, and the old environment is the location of the United States’ first historic district in Charleston, South Carolina. These locations are approximately within five miles of each other. In both places, the physical characteristics of the built environment are remarkably similar in density, form, layout, and design, but the age is dramatically different. Through photo elicitation techniques and interviews, the results of this study reveal that residents of historic Charleston and I’On value their built environments in remarkably similar ways. Surprisingly, elements that evoke a strong sense of attachment tend to be landscape features, such as gates, fountains, trees, and gardens rather than buildings. The informants valued the “mystery” that they felt was part of the landscape and which consisted of layered elements such as fences, gates, and paths, such that these features (including buildings) had to be “discovered.” Lastly, the informants strongly valued landscapes that showed “people care” through regular maintenance. The essential difference in people’s experience and valuation of the new environment (I’On) and the old environment (historic Charleston) is in the older environment’s ability to instill creative fantasies in the minds of the informants based on a hypothetical past of their own creation. The informants in I’On did not share these kinds of meanings.