The play opens in the early morning hours of a cool day in May in the nursery of Lyubov Andreyevna Ranevskaya's ancestral estate, somewhere in the provinces of Russia just after the turn of the 20th Century. Ranevskaya has been living with an unnamed lover in France for five years, ever since her young son drowned. After receiving news that she had tried to kill herself, Ranevskaya's 17-year-old daughter Anya and Anya's governess Charlotta Ivanovna have gone to fetch her and bring her home to Russia. They are accompanied by Yasha, Ranevskaya's valet who was with her in France. Upon returning, the group is met by Lopakhin, Dunyasha, Varya (who has overseen the estate in Ranevskaya's absence), Leonid Andreyevich Gayev, Boris Borisovich Simeonov-Pishchik, Semyon Yepikhodov, and Firs.
Lopakhin has come to remind Ranevskaya and Gayev that their estate, including the cherry orchard, is due to go to auction in August 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 their famous 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 the former tutor of Ranevskaya's son, Grisha, whose death prompted Ranevskaya to leave Russia five years ago. Much to the consternation of Varya, 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 renewed hope that the estate will be saved and the cherry orchard preserved. Trofimov stares after the departing Anya and mutters "My sunshine, my spring" in adoration.
Act II takes place outdoors in mid-summer on the family estate, near the cherry orchard. The act opens with Yepikhodov and Yasha trying for the affection of Dunyasha, by singing and playing guitar, while Charlotta soliloquizes about her life as she cleans a rifle. In Act I it was revealed that Yepikhodov proposed to Dunyasha around Easter; however, she has since 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. Shortly 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 drunken and disheveled vagrant passes by and begs for money; Ranevskaya thoughtlessly gives him all of her money, despite the protestations of Varya. Shaken by the disturbance, the family departs for dinner, with Lopakhin futilely insisting that the cherry orchard be sold to pay down the debt. Anya stays behind to talk with Trofimov, who disapproves of Varya's constant hawk-like eyes, reassuring Anya that they are 'above love'. To impress Trofimov and win his affection, Anya vows to leave the past behind her and start a new life. The two depart for the river as Varya calls scoldingly in the background.
It is the end of August, and the evening of Ranevskaya's party has come. Offstage the musicians play as the family and their guests drink, carouse, and entertain themselves. It is also the day of the auction of the estate and the cherry orchard; Gayev has received a paltry amount of money from his and Ranevskaya's stingy aunt in Yaroslavl, and the family members, despite the general merriment around them, are both anxious and distracted while they wait for word of their fates. Varya worries about paying the musicians and scolds their neighbour Pishchik for drinking, Dunyasha for dancing, and Yepikhodov for playing billiards. Charlotta entertains the group by performing several magic tricks. Ranevskaya scolds Trofimov for his constant 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 from him as possible. Left alone with Ranevskaya, Trofimov insists that she finally face the truth that the house and the cherry orchard will be sold at auction. Ranevskaya shows him a telegram she has received from Paris and reveals that her former lover is ill again and has begged for her to return to aid him. She says that she is seriously considering joining him, despite his cruel behaviour to her in the past. Trofimov is stunned at this news and the two argue about the nature of love and their respective experiences. Trofimov leaves in a huff, but falls down the stairs offstage and is carried in by the others. Ranevskaya laughs and forgives him for his folly and the two quickly reconcile. Anya enters, declaring a rumour that the cherry orchard has been sold. Lopakhin arrives with Gayev, both of whom are exhausted from the trip and the day's events. Gayev is distant, virtually catatonic, 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 himself is the purchaser and intends to chop down the orchard with his axe. Ranevskaya, distraught, clings to Anya, who tries to calm her and reassure her that the future will be better now that the cherry orchard has been sold.
Several weeks later, once again in the nursery (as in Act I), the family's belongings are being packed away as the family prepares to leave the estate forever. Trofimov enters in search of his galoshes, and he and Lopakhin exchange opposing world views. Anya enters and reprimands Lopakhin for ordering his workers to begin chopping down the cherry orchard even while the family is still in the house. Lopakhin apologizes and rushes out to stop them for the time being, in the hopes that he will be somehow reconciled with the leaving family. Charlotta enters, lost and in a daze, and insists that the family find her a new position. Ranevskaya tearfully bids her old life goodbye and leaves as the house is shut up forever. In the darkness, 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 on the couch and resigns himself to this fate (possibly dying on the spot). Offstage we hear the axes as they cut down the cherry orchard.