Classical approaches to question calibration are either subjective or require newly created questions to be deployed before being calibrated. Recent works explored the possibility of estimating question difficulty from text, but did not experiment with the most recent NLP models, in particular Transformers. In this paper, we compare the performance of previous literature with Transformer models experimenting on a public and a private dataset. Our experimental results show that Transformers are capable of outperforming previously proposed models. Moreover, if an additional corpus of related documents is available, Transformers can leverage that information to further improve calibration accuracy. We characterize the dependence of the model performance on some properties of the questions, showing that it performs best on questions ending with a question mark and Multiple-Choice Questions (MCQs) with one correct choice.