The main sight in Chekhov itself is the Lopasnya-Zachatievskoe Estate. In the 1770s it was granted to Aleksandr Vasilchikov, a favourite of Empress Catherine the Great. This would lead to the estate being associated with not only the Vasilchikov noble family but also the Lanskoy, Goncharov and Pushkin families. After Aleksandr Pushkin's death, his widow Natalia married Pyotr Lanskoy, whose sister in turn was married to Nikolai Vasilchikov. This meant that Pushkin's children were often visitors at the Lopasnya-Zachatievskoe Estate. Nowadays the estate is a museum. Its elegant main house and park serve as a fine example of 18th-19th century architecture.

The elaborate Conception of Anna Church is also located on the territory of the Lopasnya-Zachatievskoe Estate. It was constructed between 1684 and 1689 and later a three-tiered Bell Tower was added in 1828. The church's grounds serve as the final resting place for the owners of the estate and for some of Pushkin's descendents, including his son Aleksandr Aleksandrovich Pushkin and several grandchildren.