The history of house number 27 begins in the mid-18th century. In the 1750s, the plot belonged to state councilor and colonel Vasily Borisovich Tolstoy, who came from the elder non-noble line of the Tolstoys, also known as the Undor line. The estate was designed in the style of early Moscow classicism: in the center of the courtyard stood a wooden main house, with outbuildings on either side. In front of the house was a large courtyard, and behind it, a garden with a forge and greenhouses.

In 1773, a fire destroyed the estate's buildings and damaged neighboring properties. On September 4 of the same year, Tolstoy applied to the Moscow police chief's office for permission to build anew. Architect P.F. Bortnikov, who worked in the police chief's office, likely built a new house for Tolstoy.

After the fire, a new two-story stone mansion was erected in the center of the courtyard. Symmetrically located along the street line were a servant's hut and a cellar. Behind the house were the kitchen and bathhouse, and beyond stretched a garden with surviving wooden structures. The main house was adorned with an Ionic pilaster portico and pilasters framing the windows. The garden facade was more elaborate: under the cornice were small decorative elements, the windows had intricate frames, and the center of the facade was decorated with semicircular windows and an ornate balcony. According to legend, from this balcony, Napoleon watched the burning Moscow in 1812.

The original interior preserved the layout and a fragment of painting in one of the halls. Vasily Borisovich was married to Darya Nikitichna Zmeeva. Their daughter Anna married Count F.A. Osterman, and their son Nikolai was killed by Pugachev's men. Alexander became the governor of Simbirsk and the grandfather of Decembrist V.P. Ivashov, while Lev was the grandfather of poet F. Tyutchev.

In 1791, the house passed to the elder daughter Marfa Vasilyevna Tolstaya. After her death in 1808, the estate was purchased by the Borisov merchants, who owned it until 1906. They were engaged in the trade of sugar and tea, and also owned a linen factory in Pereslavl-Zalessky.

In 1871, Maria Ivanovna Borisovskaya and her husband remodeled the mansion, adding a grand staircase and a skylight. In the early 1880s, the Borisovs' affairs worsened, and in 1906 they sold the house to the Moscow-Kursk Railway.

After the revolution, the house was divided into apartments, and part of the garden was lost due to railway construction. In 1970, the building was restored and transferred to the Research Institute of Thermal Concrete, and in 2010, to the Gaidarovets House of Culture.