The ancient settlement on the Chertovitskaya glade appeared in the late 16th and early 17th centuries after the founding of the city of Voronezh. At that time, Ryazan peasants actively settled the banks of the Voronezh River.

In the early 19th century, an estate was built in Chertovitsy, belonging to the Tolstoy counts, representatives of an old noble family. In the book "Russia," published in 1902, it is stated: "15 versts from Ramoni, downstream on the Voronezh, lies the village of Chertovitskoye, where 1400 residents live, there is a school and shops. During the era of peasant liberation, there was the estate of Ivan Matveyevich Tolstoy's wife, which included about 2000 desyatins. Now the estate belongs to his son, Count Ivan Ivanovich Tolstoy."

Ivan Ivanovich was born in 1858 and received a legal education at St. Petersburg University. Many estate owners left their mark on the history and culture of Russia. Ivan Ivanovich Tolstoy was a renowned numismatist and archaeologist. In 1886, he became a member of the Imperial Archaeological Academy, and in 1889, the conference secretary of the Imperial Academy of Arts, later its president. He actively participated in drafting a new charter for the academy and its transformation. Ivan Ivanovich also took part in the creation of the Russian Museum of Emperor Alexander III (now the State Russian Museum). In 1900, he became the chairman of the Russian public printing affairs and became famous for his books, such as "The Earliest Russian Coins of the Kyiv Principality," "Russian Antiquities in Art Monuments," and "On Russian Amulets."

In Chertovitsy, Ivan Ivanovich owned not only lands and forests but also hayfields. He was enchanted by the nature of the Voronezh region. In his estate, the count improved the manor, where a two-story noble house already stood. Next to the house was an artificial pond, the bottom of which was lined with layers of clay and straw to retain water. Once, a German manager decided to deepen it, but the bottom became "a sieve," and all the water drained away. The manager's house was located closer to the river, and behind it was a spring, surrounded by red granite. The servants carefully monitored cleanliness and order, especially before the count's arrival. He came every year and often stayed from spring to autumn.

The count loved to walk and ski around the estate, ride horses, saw and chop wood, work in the library, hunt, and fish.

Before the October Revolution, Ivan Ivanovich Tolstoy served in Witte's office and was the Minister of Public Education. Six months later, he retired, and after the revolution, he emigrated.

In 1928, a rest house for workers of the wagon repair plant opened in the former estate of Count I. I. Tolstoy, later named after F. E. Dzerzhinsky. Now it is a republican health resort. In 1932, a children's sanatorium began operating.

During the Great Patriotic War, Chertovitsy were in the hands of Soviet troops and were a frontline village.

The legacy of the Tolstoy landlords has survived to this day. All buildings have survived, although only the lower floor remains of the noble house, while the upper wooden floor was destroyed during the Civil War. The servants' house now houses a hotel, and the former stable serves as a dining room. The manager's house contains a treatment facility. The Church of Archangel Michael has been restored.