Act I

Act I opens in the early morning hours of a day in May in the nursery of Madame Ranevskaya's ancestral estate somewhere in the provinces of Russia just after the turn of the 20th Century. Lyubov Andreyevna Ranevskaya returns to her country house with her 17-year old daughter Anya and her German governess Charlotta Ivanovna, as well as her valet, Yasha, from Paris where they have been living for the past five years. The trio is met by Varya, Mme. Ranevskaya's adopted daughter who has overseen the estate in her absence; Yermolai Alexeevich Lopakhin, a local merchant and family friend; Leonid Andreevich Gayev, Mme. Ranevskaya's brother; as well as members of the household staff including Dunyasha, the chambermaid who behaves like a refined lady; Semyon Yepikhodov a clumsy clerk in the Ranevskaya household who has proposed to Dunyasha; and the aged footman, Firs, who was once a serf to the Ranevskaya family and who, after the emancipation of the serfs in 1861, remained in their service for lack of a better opportunity for work. Dunyasha becomes smitten with the cultured Yasha, who steals a kiss from her while the two are alone.

Mme. Ranevskaya is reminded that the estate will be auctioned in August to pay the estate's mortgage. Lopakhin offers a plan to save the estate if only she will allow part of it to be developed into summer cottages. However, this will incur the destruction of the famous cherry orchard which Mme. Ranevskaya states is nationally known. It is clear that the orchard has become to her a symbol of her youth and childhood. Other solutions to the debt are also proposed but nothing is resolved and the conversation is diverted to other topics. While Ranevskaya enjoys the view of the orchard as day breaks, she is surprised by Petya Trofimov, a young student who acted as tutor to Ranevskaya's son, Grisha. We learn that Grisha drowned five years prior to the beginning of the play, and that this was a contributing factor to Ranevskaya's fleeing Russia and her home. Ranevskaya is grief-stricken at the reminder of this tragedy, despite Trofimov's insistence on seeing her upon her return (much to the consternation of Varya.)

After Ranevskaya retires for the evening, Anya confesses to Varya that their mother is heavily in debt and their uncle Gayev suggests sending Anya to Yaroslavl where their great aunt lives in the hopes that she will lend them the money to save the estate. Gayev also reminds Varya that Lophakhin is a wealthy man and has always been enamoured of her, and that a marriage with him would ensure the family's survival. They all go to bed with a 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

Act II opens on a road bordering the cherry orchard in mid-summer. The estate is still in jeopardy but the family seems more concerned with courtships. Yasha and Yepikhodov are each attempting to attract the attentions of Dunyasha. The young Anya has fallen in love with Trofimov, infuriating Varya, who herself has become the subject of rumours that she will be engaged to Lopakhin. Lopakhin tries to steer the conversation towards the business of the estate but Mme. Ranevskaya reveals the sad truth about her finances and her relationship with a man in Paris who cruelly took advantage of her money and feelings. The old footman Firs speaks of the past on the estate before the emancipation of the serfs. The sound of a Jewish band is heard in the distance and Ranevskaya decides to hold a party and invite them to play. When Trofimov appears, Lopakhin teases the boy for his 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 dishevelled 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.

Act III

Several months have passed, 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 for 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 about them, are both anxious and distracted while they wait for word of their fates. Varya worries about paying the musicians and scolds their neighbour Pischik 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 his aid. She also reveals 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 offstage falls down the stairs 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 attack the orchard with his axe. Varya, enraged, hurls the keys to the estate on the floor, and Lopakhin, half-drunk and smug, tells how he outbid everyone and gleefully (and angrily) celebrates his victory. 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.

Act IV

It is several weeks later, once again in the nursery (as in Act I), only this time the room is being packed and taken apart as the family prepares to leave the estate forever. Lopakhin arrives with champagne as a going-away present but Ranevskaya snubs him - despite his best intentions for the family he loves, she views him as a destroyer of her youth and happiness. 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 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 them. Anya also inquires about Firs' health and Yasha informs her that he has been taken to a hospital that morning. Dunyasha enters and begs Yasha for some sort of affectionate parting; Yasha for his part wants nothing to do with her or life in Russia, as he hungers to return to Paris and to live in style. Charlotta enters, lost and in a daze, and insists that the family find her a new position. Gayev and Ranevskaya return to say goodbye to the room where they grew up and spent their childhood. Gayev gaily announces that he has a job at the local bank, and Ranevskaya reveals that she is indeed returning to Paris to be with her former lover. She also scolds Lopakhin for not yet asking Varya to marry him. Lopakhin concedes to do so, and the rest withdraw to give the two some privacy. When Varya enters (knowing that he will propose to her), Lopakhin and she converse about the weather and various mundane subjects, both trying to find a way to reveal their feelings. One of the workers calls for Lopakhin and he exits hastily without asking Varya to marry him. Varya is devastated and Ranevskaya comforts her when she returns. The family and their servants all gather to say their respective goodbyes to the estate and the cherry orchard, one by one departing for their new lives. 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 his fate (apparently dying on the spot), as offstage we hear the axes as they cut down the cherry orchard.