The year 2016 marked 500 years since publication of Thomas More’ s Utopia. Although More framed the word “Utopia,” it was not the first “ideal” city of the Renaissance. Utopian writers from the mid-fifteenth century on expressed their political and societal ideas within the plans of cities. Writing 50 years before Thomas More, Filarete was the first author to politicize architectural space in the Renaissance. This essay examines how digitally reconstructing Filarete’s descriptions of his ideal city adds details to our knowledge of Utopian literature which cannot be gained by reading the literature and the illustrations alone. Further, this essay demonstrates that a digital reconstruction of architectural description has a distinct pedagogical value in our understanding of the literature.