The monastery was founded in the 15th century by Prince Dmitry Fyodorovich Vorotynsky, the owner of these lands, in honor of a significant event in the region, the Great Stand on the Ugra River in 1480.

In the area of the village of Spas, where the monastery is located, according to legend, there was a Tatar encampment where the wives of khans lived. It is possible that the founder of the monastery was a disciple of St. Tikhon of Kaluga, the locally venerated saint Nikifor of Medyn.

The first documentary mention of the monastery dates back to 1511 in a charter from Moscow Prince Vasily III, who owned these lands at that time. The monastery was supported by the Vorotynskys, Khitetovys, Streshnevs, Turgenevs, and other local noble families.

The monastery existed peacefully until the reforms of the 18th century, when it was abolished in 1764. By the early 20th century, two churches that remained on its territory became parish churches. In the 1930s, they were closed, property was looted, and the ancient cemetery was destroyed.

Despite its status as a historical heritage site during the Soviet era, the buildings of the monastery fell into disrepair. In the early 21st century, the dilapidated structures were transferred to the Church, and reconstruction began. In 2007, the monastery was revived as a women's monastery and now functions as a skete of the Kaluga Kazan Monastery.

The condition of the buildings was deplorable. There was a hole in the dome of the Transfiguration Church, and the vaults were covered with cracks. The roof was missing from the Introduction Church, leading to the destruction of the dining hall's vaults and cracks in the walls. During the Soviet era, an opening was made in the wall of the first floor for vehicles. Both churches had sunk almost a meter into the ground, distorting their elegant proportions. Restoration took several years.

On January 29, 2007, by decree No. 89-r, the Government of the Russian Federation transferred the monastery to the ownership of the Kaluga Diocese of the Russian Orthodox Church.

The monastery is now active, and daily services are held in its churches.