In the late 1860s, a young nobleman, Lev Sergeyevich Golitsyn, a representative of an ancient princely family, appeared in Chulkovo village. Born in 1845, he graduated from the Sorbonne and returned to Russia in 1864, where he enrolled in the law faculty of Moscow University. There, he studied Roman law and planned to become a professor. However, in 1868, after the death of his father, Sergey Grigoryevich Golitsyn, the owner of 3166 souls, he had to deal with inheritance issues. Although serfdom had already been abolished, land matters required resolution. Since then, several houses of prosperous peasants, built in the late 19th and early 20th centuries, have remained in the village.

The first of these houses is located at the central intersection of the village. The name of its owner is unknown. The carving on the house is done in a peasant style, somewhat rough, but otherwise, the building corresponds to the style: complete asymmetry, windows of different sizes, carved belts and cornices, as well as a small balcony and a turreted veranda. The western part of the house opens into a garden.

The second house is built in the Art Nouveau style and belonged to the peasant trunk maker Tulupov. This two-story building has a corner tower that transitions into a third floor. All facades of the house are asymmetrical and do not resemble each other. Two main facades face the church and the main street leading to the Oka River. The Tulupovs were engaged in trunk making and became wealthy as buyers. They organized the work of home-based craftsmen, providing them with materials and collecting finished products for sale. Tulupov built a stone church in Chulkovo, covering all expenses. The church, in honor of the Elevation of the Life-Giving Cross of the Lord, was consecrated in 1897. Tulupov began constructing the wooden house after the church was completed. The house is oriented towards the church, so the owners could cross themselves simply by looking out the window.

In 1888, the artist Isaac Levitan visited Chulkovo with friends, arriving on a Ryazan steamboat. He was very fond of the surroundings and even captured them in one of his works.