Act 1
The play opens on a day in May in the nursery of Lyubov Andreyevna Ranevskaya's home in the provinces of Russia, at the start of the 20th century. Ranevskaya has been living in France since her young son drowned. After she had tried to kill herself, Ranevskaya's 17-year-old daughter Anya and Anya's governess Charlotta Ivanovna have brought her home to Russia, accompanied by Yasha, Ranevskaya's valet. Upon returning, they are met by Lopakhin, Dunyasha, Varya (who has overseen the estate in Ranevskaya's absence), Ranevskaya's brother Gayev, Boris Simeonov-Pishchik, Semyon Yepikhodov, and Firs.
Lopakhin has come to remind Ranevskaya and Gayev that their estate, including the cherry orchard, will be auctioned soon to pay off the family's debts. He proposes to save the estate by allowing part of it to be developed into summer cottages; however, this would require the destruction of the cherry orchard, which is nationally known for its size.
Ranevskaya is enjoying the view of the orchard as day breaks, when she is surprised by Peter Trofimov, a young student and former tutor of Ranevskaya's dead son, Grisha. Trofimov had insisted on seeing Ranevskaya upon her return, and she is grief-stricken at the reminder of this tragedy. After Ranevskaya retires for the evening, Anya confesses to Varya that their mother is heavily in debt. They all go to bed with the hope that the estate will be saved and the cherry orchard preserved. Trofimov stares after the departing Anya in adoration.
Act 2
Act II takes place outdoors near the orchard. Yepikhodov and Yasha vie for the affection of Dunyasha by singing and playing guitar while Charlotta soliloquizes about her life. In Act I it was revealed that Yepikhodov proposed to Dunyasha at Easter; however, she has become infatuated with the more "cultured" Yasha. Charlotta leaves so that Dunyasha and Yasha might have some time alone, but that is interrupted when they hear their employer coming. Yasha shoos Dunyasha away to avoid being caught, and Ranevskaya, Gayev, and Lopakhin appear, once more discussing the uncertain fate of the cherry orchard. Soon Anya, Varya, and Trofimov arrive as well. Lopakhin teases Trofimov for being a perpetual student, and Trofimov espouses his philosophy of work and useful purpose, to the delight and humour of everyone around. During their conversations, a disheveled beggar passes by; Ranevskaya gives him all her money, despite his protestations of Varya. Shaken by the disturbance, the family departs for dinner. Anya stays behind to talk with Trofimov, who disapproves of Varya, reassuring Anya that they are 'above love'. To impress Trofimov, Anya vows to leave the past behind her and start a new life. The two depart for the river as Varya calls in the background.
Act 3
It is the end of August, and Ranevskaya's party is held. Musicians play as the family and guests drink and entertain themselves. It is also the day of the auction; Gayev has received a paltry amount of money from his and Ranevskaya's aunt, and the family members, despite the general merriment around them, are anxious while they wait for news. Varya worries about paying the musicians and scolds their neighbor Pishchik for drinking, Dunyasha for dancing, and Yepikhodov for playing billiards. Charlotta performs magic tricks. Ranevskaya scolds Trofimov for his teasing of Varya, whom he refers to as "Madame Lopakhin". She then urges Varya to marry Lopakhin, but Varya demurs, reminding her that it is Lopakhin's duty to ask for her hand in marriage, not the other way around. She says that if she had money she would move as far away as possible. Alone with Ranevskaya, Trofimov insists that she finally face the fact that the house and orchard will be sold at auction. Ranevskaya shows him a telegram she has received and reveals that her former lover is ill and has begged her to return to Paris. She is seriously considering this, despite his cruel behaviour to her in the past. Trofimov is stunned at this; they argue about the nature of love and their respective experiences. Trofimov leaves, but falls down the stairs off-stage and is carried in by the others. Ranevskaya laughs and forgives him for his folly and the two reconcile. Anya enters with a rumour that the estate has been sold. Lopakhin arrives with Gayev, both of them exhausted from the trip and the day's events. Gayev is distant and goes to bed without saying a word of the outcome of the auction. When Ranevskaya asks who bought the estate, Lopakhin reveals that he is the purchaser, and intends to chop down the orchard. Ranevskaya, distraught, clings to Anya, who reassures her that the future will be better now.
Act 4
Several weeks later the family's belongings are being packed as the family prepares to leave the estate. Trofimov enters, and he and Lopakhin exchange opposing world views. Lopakhin does not propose to Varya. Anya enters and reprimands Lopakhin for ordering his workers to begin chopping down the cherry orchard while the family is still there; Lopakhin apologises and rushes out to stop them for the time being, in the hopes that he will be somehow reconciled with the family. Charlotta enters, lost and in a daze, and insists that the family find her a new position. Ranevskaya bids her old life goodbye and leaves as the house is shut up forever. In the gloom, Firs wanders into the room and discovers that they have left without him and boarded him inside the abandoned house to die. He lies down and resigns himself to this fate. The sound of axes cutting down trees is heard off-stage.
