Arguably the most tragic element of Chekhov's The Cherry Orchard is the auctioning off of the titular cherry orchard which belongs to Lyubov Andreyevna Ranevskaya and her brother, Leonid Andreieveitch Gayev. The orchard must be sold off in August to the highest bidder in order to pay off the debts of the family; the only alternative option—the destruction of the orchard to make room for summer cottages—does not appeal to this sentimental family.

Other tragic elements within the play include:

- The death by drowning of Ravenskaya's son, Grisha, a tragedy which prompted her to run off to France for five years and leave the ancestral estate unattended, and which is brought back to the surface by the arrival of Peter Trofimov, Grisha's former tutor.

- Ravenskaya's subsequent suicide attempt, which prompted her daughter, Anya, to bring her back from France.

- The heartbreak of Dunyasha, whose feeling are selfishly toyed with by a fellow servant, Yasha. 

- The strange passivity between Varya, the adopted daughter of Ravenskaya, and Lopakhin—a relationship which is doomed by inaction.

- The purchase of the orchard by Lopakhin, who decides to tear down the orchard with an axe—the ultimate betrayal of the family. This comes to fruition as the last thing that the audience hears: the sound of axes tearing into the orchard.

- The death of Firs, the elderly manservant, who is accidentally left behind in the abandoned house and boarded up with no way out.

Those who view the play as satire are considering the critique of the extravagance of Russian aristocrats; that said, these characters—no matter how rich—really do experience tragic events and circumstances. Their wealth does not erase the very real impact of things like death, heartbreak, and loss.