In the early 18th century, the area between the passage at the Earthen City and the Transit Alleys (now known as Karmanitza and Kamennaya Sloboda) was occupied by garden plots. In the middle of the same century, an estate appeared here, owned by Lieutenant Colonel A. A. Psishchev. In the following decades, it was densely built up. The proximity to the Smolensky market influenced the nature of the construction. In 1799, the estate's owner, merchant Grigory Evdokimov, submitted a request to build a stone forge, a carriage shed, and a residential building. Evdokimov, a merchant of the 3rd guild, traded in carriages and assisted in the procurement of materials for the artillery depot. During the 1812 war, he was awarded a medal for donating two thousand rubles for military needs. After the 1812 fire, which damaged the wooden structures of the estate, Evdokimov received compensation of one thousand rubles. In 1800, he built an L-shaped residential building with a rounded corner at the intersection of modern Karmanitza Alley and Smolensk Square, as well as a forge that opened onto the current Kamennaya Sloboda alley.

By the mid-19th century, the lines of passage from Kudrinsky Market to Smolensk (where the Garden Ring now runs) and the former Transit Alleys, known then as Small and Large Tolstovsky, formed a dense row of houses with arches and passages. In 1847, a two-story building with an arch was added to the one-story structure along the red line of Smolensk Square. The facade was executed in a classical style with arched elements typical for commercial establishments. Later, the arched openings were replaced with shop windows. The first floor remained commercial until 1917, while the second floor housed offices and furnished rooms. At the back of the lot, an L-shaped residential building was constructed, which expanded with extensions to Large Tolstovsky (Karmanitza) Alley.

In the late 1860s, between 120 and 180 people of various classes lived in the buildings on the territory owned by Evdokimov's descendants. There were apartments, shops, warehouses, and workshops. In the mid-19th century, old items and household goods were sold at Smolensky Market, but in 1875, the City Duma built a two-story building for selling meat and vegetables. However, the market could not fit in this building, and the houses facing the market had numerous shops and taverns. In 1867, a tenement house in eclectic style was built in the back courtyard according to the design of architect Kherodinov. In the early 20th century, craftsmen lived here, and their workshops were located in the area.

From the mid-1870s until 1917, the property belonged to Staff Captain D. S. Seleznev, and then to his widow and daughter Olga, who was married to Princess Gagarina. In 1925, 415 people lived in the housing cooperative. Until the 1930s, the previous buildings remained, but during these years, a substation was built. In the 1960s, during the construction of an underground passage, part of the buildings along Smolensk Square was demolished. In the late 1980s, a three-story building in the northeast corner of the lot was torn down. In the 1990s, the tenement house was reconstructed, losing its original appearance.

In 2000-2001, the building along Smolensk Square was renovated, and the facades were restored. A modern two-story extension was also built over the underground passage. Today, the building on Smolensk Square, like two centuries ago, houses commercial and food enterprises. Organizations are located in the back courtyard, and in the reconstructed building facing Kamennaya Sloboda alley, there is a hotel.