Kroutstallenia Monastery, dedicated to the Virgin Mary, was already in existence during the 2nd Byzantine era of Crete (961-1204). Its history is closely linked with the history of the plateau of Lassithi and, according to certain sources, it was a centre for the concentration of revolutionaries against the Venetians.
However, between 1293 and 1543, the Venetians decided to abandon the plateau, so the monastery became deserted as well, before becoming operational again in 1543 when it was renovated by Peloponnesian refugees.
The Monastery suffered great destruction and many raids during the revolutions of 1821 and 1866, with its architectural form changing to the point that the present-day buildings have nothing to do with its old form, as most had to be rebuilt.