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This work introduces an automatic classification system for measuring the complexity level of a given Italian text under a linguistic point-of-view. The task of measuring the complexity of a text is cast to a supervised classification problem by exploiting a dataset of texts purposely produced by linguistic experts for second language teaching and assessment purposes. The commonly adopted Common European Framework of Reference for Languages (CEFR) levels were used as target classification classes, texts were elaborated by considering a large set of numeric linguistic features, and an experimental comparison among ten widely used machine learning models was conducted. The results show that the proposed approach is able to obtain a good prediction accuracy, while a further analysis was conducted in order to identify the categories of features that influenced the predictions.