This study applies the results of iconological interpretation of Sosaewon and Villa D’este’s constructed areas to the context interpretation methodology of contemporary aesthetics, which is based on writer’s own artistic context derived from writer’s own artistic works. This approach intends to develop and apply new forms of garden art and imagification into writer’s own artistic works by mixture and juxtaposition of these whole heterogeneous implications of Sosaewon and Villa D’este. In addition, the study attempts to construct new value in garden art by applying the diverse artistic aspects of Sosaewon and Villa D’este derived from their diverse iconological interpretation, seeking transition from current standardized garden planning system to compound and fusion system of garden art in the modern times. The study attempts to draw new flow of contemporary garden art. For this, de-constructivism perspective, which contains post-modern cultural characteristic, is applied to examine the Sosaewon and Villa D’este’s hidden but intended factors and spirits by the builders.