This essay analyzes the bi-directional relationship between Ludwig Wittgenstein's philosophy and his architectural experiment of designing the Wittgenstein House. Putting the Wittgenstein House into the chronological context of Wittgenstein's philosophical writings, this research attempts to explore how his architectural design brought about a change in his philosophical thoughts and how his philosophical thinking influenced the decisions in his architectural design. The Wittgenstein House is a unique case in architectural history, which reveals architectural embodiment of transcendental order through the intertwining of language and building where the "meaning of the work" defies the dominant formalist aesthetics of architectural education.