Cossack Grigory Ivanov of the Yekaterinoslav Don Cossack Army left for the Old Believer Komarovsky skete at the age of 38, where he took monastic vows under the name Gerasim and lived for 10 years. In 1784, he, along with monk Paisiy, moved to a more secluded place in the forests of the Makaryevsky district of Kostroma province, to two monks living on the high bank of the Utrusa River. This settlement became known as the Vysokovsky skete, named after the nearest village, Vysokovo.

On July 13, 1820, Alexander I transformed the Vysokovsky skete into a communal monastery, naming it the Vysokovskaya Assumption Desert. The monastery became a third-class communal monastery. Chief Prosecutor Prince Golitsyn supported the new monastery, assisting in solving its problems. Thanks to his support, on July 14, 1823, builder Hieromonk Gerasim met with Emperor Alexander I at the Winter Palace. During the conversation, he requested help in constructing a monastic abode for the like-minded. The Emperor allocated five thousand rubles for the construction of a stone church dedicated to St. Nicholas. Soon, on January 6, 1825, for good management of the Vysokovskaya Desert, Hieromonk Gerasim was elevated to the rank of igumen. In the same year, on June 29, for converting dissenters to the Orthodox Church, he was elevated to the rank of archimandrite. In 1827, the first stone Nicholas church was consecrated. A village named Vyselok Uspensky emerged near the monastery. On the monastery's territory, there were four churches, including the Cathedral of the Assumption, consecrated in 1834. In 1910, the monastery had 3 hieromonks, 1 hierodeacon, 4 monks, and 14 novices. The small number of residents was explained by the fact that the abode was of like-minded faith and located far from large settlements.

In 1929, the monastery was closed, an asphalt road was laid through its territory, and shops were built in the square. The monastery buildings were handed over to the collective farm: hay was stored in the Assumption Cathedral, woodworking workshops were placed in the Church of the Three Hierarchs, and the abbot's house housed the collective farm office and residential apartments. Nearby, the village of Vyselki appeared. After the collective farm moved, the buildings were left abandoned. In 1979, the architectural ensemble of the monastery was placed under protection as a monument of architecture, and in 1995 it received the status of a federal significance monument.

The revival of the monastery began in 1996. In 1999, with the blessing of Metropolitan Nikolai Kutepov of Nizhny Novgorod and Arzamas, the remaining buildings were handed over to the Church. On April 20, 2000, the Holy Synod decided to revive monastic life. After the appointment of Igumen Alexander Lukin as the abbot in 2002, active restoration of the monastery began. Under his leadership, all buildings were covered with roofing, domes were restored, and crosses were installed within 2.5 years. The bell tower's stairs were restored, the Church of the Three Hierarchs was equipped for summer services, and the former monastery hospital was renovated into a brotherhood building. In 2005, the brotherhood building was the only residential space, housing a chapel in honor of St. Nicholas, where winter services were held. It also had a refectory, boiler room, and storage rooms. In 2005, two people lived in the monastery: Hieromonk Paisiy and monk Andrei, while a dependency with a wooden chapel was located in Balakhna. Builders were engaged in the reconstruction of the abbot's house and finishing works in the bell tower and Nicholas church.