Leipalingis was first mentioned in written sources in a privilege granted in 1503 by Alexander I Jagiellon, Grand Duke of Lithuania and King of Poland. In the privilege, it is stated that Lepunikai manor (such was the name of Leipalingis at that time) of the Przewałka powiat is granted as a gift to the Smolensk horseman Ivan Feodorovich Pliuskov. Another document is a privilege granted in 1508 by Sigismund I the Old, according to which the Lepunikai manor is granted as a gift to Ivan Bogdanovich Sapieha, a diplomat of the Grand Duchy of Lithuania. The Sapieha dynasty owned Leipalingis until 1742. From 1742 to 1792, it was owned by Bishop Ignacy Jakub Massalski. Archaeological finds suggest that the Sapieha manor stood to the northwest, on the steep bank of the Seira River.
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