The Cherry Orchard describes the lives of a group of Russians, in the wake of the Liberation of the serfs. The action takes place over the course of five or six months, but the histories of the characters are so complex that in many ways, the play begins years earlier.
The play opens in May, inside the cherry orchard estate; friends, neighbors, and servants are preparing for the long-awaited return of Madame Ranevsky, the mistress of the house, and her daughter Anya. Madame Ranevsky has two daughters. She had fled the cherry orchard five years before, after the deaths of her husband and young son. She is now returning from France, where her abusive lover had robbed and abandoned her. She has accrued great debts during her absence.
Lopakhin begins by telling the story of his own success: born a serf, he has managed to make himself a fortune. Another former serf, Firs, readies the house during Lopakhin's speeches. Firs has maintained the same post he always has, despite the Liberation. Dunyasha confesses a potential romance between she and Ephikhodof, but no one is interested.
Finally, Madame Ranevsky returns. Her friends and family are overjoyed to see her. Act I introduces many subplots: a romance between the tutor Trophimof and Anya, another hopeful romance between her sister Barbara and wealthy Lopakhin, a love triangle between the servants Dunyasha, Yasha, and Ephikhodof, the debt of the neighbor Pishtchik, the class struggles of Lopakhin and Firs, the isolation of Charlotte, etc. The main intrigue of the play, however, hinges on Madame Ranevsky's debt. Neither she nor her brother Gayef have money to pay the mortgage on the cherry orchard estate, and unless they find a solution, the state will be auctioned off in August.
Lopakhin suggests that Madame Ranevsky build villas on the estate. She can lease them and use the money to pay the mortgage. Madame Ranevsky and Gayef object to the idea, and prefer to work something out on their own. However, as spring passes into summer, Madame Ranevsky only finds herself more in debt, with no solution in sight. Strange romances between Anya and Trophimof and Dunyasha and Yasha continue, while nothing develops between Lopakhin and Barbara and Dunyasha and Ephikhodof. Firs' health is declining. Madame Ranevsky is receiving letters from her lover, and Gayef begins to consider a job at a bank. Pishtchik takes out loans from Madame Ranevsky, whose own funds are dwindling away to nothing.
On the night of the auction, no solution has arrived. Madame Ranevsky holds a ball. Charlotte performs, and guests and servants alike dance. Madame Ranevsky and Trophimof have a serious conversation about Madame Ranevsky's extravagance; not only does she continue to run up debts, but she is now considering returning to her abusive lover in France. Madame Ranevsky is nervous about the outcome of the auction; she is still hoping for a miracle.
Finally Gayef and Lopakhin return: Lopakhin has bought the cherry orchard. Barbara is furious, and Madame Ranevsky is devastated. Lopakhin, however, cannot hide his happiness: he has bought the estate where his family lived as serfs. Ironically, he encourages the party to continue, even though the hosts are no longer in the mood to celebrate.
Act IV shows Madame Ranevsky leaving the cherry orchard for the last time. Lopakhin has bought champagne, but no one except the uppity servant Yasha will drink it. Lopakhin and Trophimof share a tender farewell: Trophimof will return to the university. Charlotte complains that she no longer has a position; Ephikhodof has a new position with Lopakhin. Pishtchik is able to pay off some of his debts. Gayef has a job at a bank, Barbara a position as a housekeeper, and Yasha will stay on with Madame Ranevsky, who is returning to France. Many characters try to confirm that Firs has been sent to the hospital. Lopakhin misses his last chance with Barbara, and Dunyasha cries that Yasha is leaving.
Madame Ranevsky and Gayef share a nostalgic moment alone before leaving on a relatively optimistic note. In the last moment, we hear axes cutting down the orchard, and Firs stumbles on to stage, forgotten, locked in the house. He lies down to rest and presumably dies.