The Church of St. George the Victorious is one of the oldest architectural monuments in Staraya Russa. It is known that the first church on this site was built in 1410. Next to the single-domed four-pillar church was the chapel of the Annunciation of the Blessed Virgin Mary, each having a separate entrance. The chronicles of 1625 mention that, despite the destruction caused by Lithuanian and Swedish troops, the George Church and its bell tower with two bells remained intact. However, nearly a hundred years later, the church had deteriorated significantly. From 1710 to 1740, its condition worsened to the point that services ceased. Ultimately, the church was dismantled to its foundations, and construction of a new, more spacious church with larger windows and beautiful trim began. The walls were painted cream, while the decor and stucco were in red. In 1782, the church was reconstructed and expanded. At that time, with the blessing of the Most Reverend Gabriel, the chapel in honor of the Annunciation of the Blessed Virgin Mary was restored, and a narthex was built. At that time, the church had no paintings; it was decorated only with numerous icons. The bell tower was built in the Russian style and looked magnificent. By the end of the 19th century, an expansion of the church was again needed. Interestingly, during that time, the Annunciation chapel was considered the main one, not the George chapel, but later their roles changed. By 1910, the church had its floors replaced with mosaics, and for the first time, paintings appeared, created based on sketches of frescoes by V.M. Vasnetsov from the Kiev Cathedral of Prince Vladimir. Artists from Palekh were invited for this work. Unfortunately, almost nothing remains of those frescoes, as they were often repainted.

After the 1917 revolution, the church suffered little damage, only the 35-meter bell tower lost its dome. However, after the Great Patriotic War, it was completely dismantled due to a lack of building materials. The church was closed in 1939 by the decision of the Leningrad Oblast Executive Committee, but services resumed just two years later. When residents were evacuated from occupied Staraya Russa, the church began to fall into disrepair. In the winter of 1945, after the city was liberated, a workers' dormitory was opened in the building. By summer, the Annunciation chapel was repaired and consecrated, and a year later, the main altar was also consecrated. In the mid-1960s, restoration began, as the ancient structures needed repair. Twenty years later, a wooden baptismal church in honor of St. Nicholas of Myra was built on the premises. In another building, which previously housed one of the buildings of the Dostoevsky parish school, a Sunday school was opened. In the early 1990s, work began on the artistic decoration of the church. In the 21st century, the dome was restored, and in 2007, a cross was installed on it. Later, the outer walls were decorated with tiles styled after 17th-century ceramics, and a fragment of ancient masonry was uncovered. A temporary bell tower was set up. For the 600th anniversary of the church, another restoration was carried out, updating the facades, wall paintings in the Annunciation chapel, and planting flowerbeds on the premises.