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Christopher Alexander famously maintained that traditional architecture is inherently more ‘whole’ – and consequently more beautiful and alive – than modern architecture because the former is the product of organic processes, while the latter is the product of mechanistic processes. The central concept in Alexander’s theory – that architecture can be more or less whole – has only rarely been quantitatively examined. Furthermore, his claims about the superior wholeness of organic architecture have similarly remained untested. In response, this paper critically re-examines Alexander’s definition of wholeness in the context of A Pattern Language, along with previous attempts to quantify its properties. From this basis, the paper proposes a new pattern-based quantitative method for examining and measuring wholeness. This method is then tested through the analysis of seven ‘organic’ houses by Frank Lloyd Wright and seven ‘mechanistic’ villas by Le Corbusier. Through this process, the paper demonstrates a method for measuring wholeness, and quantitatively tests Alexander’s assertion that organic environments are more whole than mechanistic ones.