Ostashkovsky Znamensky nunnery appeared on the wasteland of Old Strugovishche, or Ubogoe, north of the city walls. This place was revered sacred - there were buried wanderers and fools. Immediately settled nuns. In the description of the Znamensky Monastery it is said: "... in 1655 there were 23 of them nuns and the main among them were Paraskeva and Golendukha. Patriarch Nikon, who was passing through Ostashkov this year, granted them alms to every old man by the hryvnia ... "(Uspensky V." Description of the Ostashkovsky Znamensky Monastery. "Tver, 1890, p.8).
The permission to found the monastery was given by Tsar Aleksei Mikhailovich in 1673 at the request of Ostashkov's old men, who lived in the city under the churches. The further history of the Znamensky monastery differs little from the fate of the like. The monastery of the old people began to acquire land, mowing very soon, to receive deposits, donations, and already in 1692 a new wooden church was laid, and fifty years later a solemn stone consecration took place. Unfortunately, this temple, built during the period of the revival of stone construction that began all over Russia, has reached us with great losses. It was rebuilt several times, expanded in the XVIII-XIX centuries, and after a large urban fire in 1868, when the whole monastery was burnt out, the cathedral was altered according to the project of the local technique of Demidov. But what the Demidov intended, was not fully implemented. After his death, the architect who arrived from Tver was afraid to continue the construction and ordered to start decorating the interiors, ordering them to stop these works immediately, if any cracks are seen in the walls and vaults. The abundance of all "ryushechek", widths, kokoshnikov, crosses in the decoration of the cathedral, which Demidov did not spare for its decoration, turned the building into a cheaply decorated tower. Only from the side of the apse one can see small remains of the ancient building, according to which its initial appearance is difficult. Only by descriptions in monastic documents can you try to reconstruct this church. She was "about one chapter. And the church and the aisles are covered with bats ... The belltower with the tent top ... Near the church and the chapels were arranged in four places of the porch, or porch ... on the pillars. At the aisles there is a retail and official tent, a bread and kelar's tent. "(Uspensky V." Description of the Ostashkovsky Znamensky Monastery. "Tver, 1890, p. 11).
The traditional five-domed church appeared at the monastery church during its repair in 1780, for which it was necessary to arrange four semicircular pediments. Besides this cathedral in the monastery there was one more, now not preserved Tikhvin church, which stood above the eastern gate. The fence around the monastery was erected in 1760 on the donations of merchant Savva Yakovlevich Yakovlev (Sobakin), who got rich on trade in St. Petersburg and received the rank of collegiate assessor. With the construction of the fence with four towers, the formation of the monastic territory basically ended. At the same time, the fence, as it were, formalized the front entrance to the city along the main street. In its architecture, along with baroque elements, the forms and decor of the pre-Petrine architecture continued to live. The walls are divided by the shoulder blades and decorated with wide baroque "overhead boards", from the side of the courtyard are decorated with an arcade. Low towers with a metal hipped roof (in the beginning, the walls and towers were covered with grass) is given an imposing appearance. In 1864, the north-western part of the wall was rebuilt, the monastery was enlarged, made the fifth tower and the new holy gate. In the additional territory there are monastery cells. Part of them, built soon after the city's fire, has survived to this day. Low wooden houses, covered with chips, sprouting mossy greenery, surrounded the cathedral, form small monasteries in the monastery and, despite their later origin, give a visual representation of the wooden buildings of the outskirts of the old Ostashkov.
The monastery does not work, the buildings are given for housing and institutions, but the temple is now (as of the end of November 2002) - the only active church in Ostashkov.