The play begins in the pre-dawn hours of a May morning in Russia. We learn that the cherry trees are in bloom even though it is frosty outside. Yermolay Lopakhin, a friend of the family, and Dunyasha a maid on the Ranevsky estate, wait for the estate's owner Ranevsky at the estate's main house, in a room called "the nursery". Lopakhin reveals that Ranevsky has been in Paris for the last five years. Lopakhin is a local businessman in his mid- thirties, dressed in a fine white suit (with gaudy yellow shoes), whose feelings towards Ranevsky are mixed between affectionate gratitude for past kindnesses, and resentment at her condescension toward him because of his humble, peasant origins. Also on the estate is Simon Yephikodov, a hapless youth nicknamed "Simple Simon" because of his frequent and ridiculous accidents.

Soon, Ranevsky arrives from Paris, along with her daughter Anya, who has been with her there since Easter of that year; Yasha, a young manservant who has accompanied her on her travels; and Charlotte, Anya's governess, who brings along her dog. Also accompanying her are Firs, her 87-year old manservant; her elder, yet still infantile, brother Leonid Gayev; and her adopted daughter Varya; these last three have stayed in Russia but went to the station to greet Ranevsky on her return

Ranevksy expresses her joy and amazement to be home again, while Anya reveals to Varya the relative poverty in which she found her mother when she arrived in Paris and the way in which she continues to spend money. Varya reveals that the family's estate is to be sold at auction on the 22nd of August, in order to pay their debts. Anya reveals that Ranevsky's departure for Paris was caused by her grief over two deaths: that of her husband six years before and that of her son, Grisha, who drowned a month thereafter.

Soon, Anya departs for bed, and Lopakhin brings up the issue of the imminent sale. He proposes a solution; Ranevksy should parcel out the land on her estate, build cottages on the parcels, and lease them out to summer cottage-holders, who are becoming increasingly numerous. Gayev and Ranevsky dismiss thr idea, because it would necessitate cutting down the family's beloved (and gigantic) cherry orchard. Before he leaves, Lopakhin offers them a loan of 50,000 rubles to buy their property at auction if they change their minds, and predicts there will be no other way of saving the orchard. Ranevsky then lends some money to a fellow impoverished landowner, Boris Simeonov-Pischik. Peter Trofimov arrives; he was Grisha's tutor before the drowning, and thus he brings back painful memories for Ranevsky. Before the end of the act, after complaining about Ranevksy's inability to curb her spending, Gayev outlines three alternatives to Lopakhin's plan: a financing scheme involving some banker friends of his, Ranevsky borrowing some money from Lopakhin (without the condition that they then cut down the orchard), and a wealthy aunt in Yaroslavl who might provide a loan.

In the Second Act, we are introduced more closely to the young servants on the estate, Dunyasha, Yasha, and Yephikodov, who are involved in a love triangle: Yephikodov loves Dunyasha, Dunyasha loves Yasha, and Yasha is very much in love with himself. Soon, Lopakhin, Ranevsky, Gayev, Anya and Varya appear, and they are again debating over Lopakhin's plan to turn the orchard into cottage country. Lopakhin becomes frustrated with Ranevsky's reluctance; she, in turn, thinks his plan is vulgar, and says that if they plan to sell the cherry orchard, she wants to be sold along with it. Ranevsky reveals that she has a lover in Paris who has been sending her telegrams, asking her to return, and who robbed her, left her, and as a result drove her to a suicide attempt.

Soon, Trofimov appears, and gives several speeches about the importance of work and the laziness and stupidity of Russian intellectuals. In a quiet moment, the sound of a snapping string is heard, and no one can identify its source. A drunkard appears, asking for directions, and then money; Ranevsky ends up giving him several gold pieces. Disturbed, most of the group leave, except for Anya and Trofimov. They discuss Varya's growing suspicion that Anya and Trofimov are having an affair, which they are not; Trofimov declares that they are "above love". The act ends with Yephikodov sadly playing his guitar and Varya calling out, in vain, for Anya.

In the Third Act, Ranevsky throws a party on the day of the auction. The guests consist of several local bureaucratic officials such as the stationmaster and a post-office clerk. Charlotte entertains the guests with a series of magic tricks. Ranevsky worries anxiously about why Gayev and Lopakhin have not yet returned. Ranevsky fears that the orchard has been lost, that the aunt in Yaroslavl has apparently not given them enough money to buy it, and that Gayev's other sources have failed to come through. She and Trofimov get into an argument; Trofimov accuses her of not being able to face the truth, and she accuses him of being unusual for never having fallen in love. Lopakhin and Gayev soon return from the auction. Lopakhin reveals to everyone that he has bought the estate and intends to carry out his plans for the orchard's destruction. Anya tries, in vain, to comfort her mother.

In the last act, it is October, and the trees in the cherry orchard are already being cut down. All the characters are in the process of leaving; Lopakhin will depart to Kharkov for the winter, Varya to the Ragulins', another family that lives fifty miles away. Gayev plans to live in the town, working at a bank, Anya will go off to school, and Ranevksy will leave for Paris with Yasha, to rejoin her lover. Charlotte has no idea what she will do, but Lopakhin assures her he will help her find something. Trofimov and Lopakhin exchange an affectionate if contentious farewell; Yasha leaves Dunyasha, weeping, without a second thought; and Anya tearfully says goodbye to her mother. Anya worries that Firs, who has taken ill, has not been sent to the hospital as he was supposed to be, but Yasha indignantly assures Anya that he has. Ranevsky encourages Lopakhin to propose to Varya; but the proposal is never made—Lopakhin leaves Varya alone, and in tears. Finally, Gayev and Ranevsky bid a tearful farewell to their house. Everyone leaves, locking the doors behind them.

But Firs is, in fact, accidentally left behind, having fallen ill and being forgotten in the rush of the departure. He walks onstage after everyone else has left, quietly muttering about how life has left him by. He lies on the couch, and silently expires as two sounds are heard; again, the sound of a string snapping, and the sound of an axe cutting down a cherry tree in the orchard.