Over the years, the estate was home to Baroness Duka and the Nelidovs, Karamzin (the son of the writer), and Kleinmechel. In 1874, it was acquired by Alexander Smetzky, whose wooden palace remained in Makarovka until the early 21st century.

Alexander Nikolaevich was a prominent industrialist: he owned calico and woolen factories in Moscow and Kostroma, as well as stocks of red construction timber and businesses in Voronezh. In Makarovka, Smetzky built a large distillery. The main estate house was a monument of early 20th-century architecture. The wooden eclectic building combined elements of Art Nouveau and Neoclassicism, with decorations in Greek and Italian styles. The facades were adorned with columns of the Ionic and Tuscan orders, as well as decor featuring female masks with floral ornamentation.

In the early 19th century, Prince Vladimir Shirkov settled in Makarovka with his family. Since 1780, the village had its own serf theater, choir, and symphony orchestra. The prince was a close friend of Mikhail Glinka and, according to some sources, it was he who suggested the composer the idea for "Kamarinskaya," as well as being the author of the lyrics to the aria of Gorislava "The Luxurious Star of Love" and the libretto for the first part of "Ruslan and Lyudmila." This is indicated by published letters from Glinka to Shirkov, in which the composer detailed the development of the action and discussed the details of the libretto. Their collaboration continued even after the prince moved to the village.

From May 1924, the main estate house housed a regional anti-tuberculosis sanatorium. In 1999, all buildings were closed for repairs, which lasted several years, but there were not enough funds for the restoration of the main house. The estate burned down on September 24, 2016.