The Machiavelli’s treatise Il Principe (first circulated in the year 1513) is placed in comparison with the preceding Regimina principum and with the vulgar literary prose of the sixteenth century, towards revealing the originality of the content and writing. In effect, the work, detaching itself from all previous and contemporary prose, presents new formal aspects. A lot of constructions, traditionally considered erroneous, are in reality influenced by the spoken Florentine dialect or correspond to particular pragmatic motivations. With respect to previous research, our analysis more clearly delineates the relationship between syntactic structures and textual structures. In particular, the textuality and the syntactic constructions and structures have been studied in relation to observation and assessment of the argumentative discourse. To date, Machiavelli’s prose has been examined above all from a stylistic perspective. This article instead seeks to provide a more precise description of the syntactic and enunciative structures of the treatise. The analysis is especially focused on completive and adverbial sentences, reported speech and the typology of word order.