The play portrays the visit of an elderly professor and his glamorous, much younger second wife, Helena, to the rural estate that supports their urban lifestyle. Two friends – Vanya, brother of the professor's late first wife, who has long managed the estate, and Astroff, the local doctor – both fall under Helena's spell, while bemoaning the ennui of their provincial existence. Sonia, the professor's daughter by his first wife, who has worked with Vanya to keep the estate going, suffers from her unrequited feelings for Dr. Astroff. Matters are brought to a crisis when the professor announces his intention to sell the estate, Vanya and Sonia's home, with a view to investing the proceeds to achieve a higher income for himself and his wife.
Uncle Vanya is unique among Chekhov's major plays because it is essentially an extensive reworking of his own play published a decade earlier, The Wood Demon. By elucidating the specific changes Chekhov made during the revision process – these include reducing the cast-list from almost two dozen down to nine, changing the climactic suicide of The Wood Demon into the famous failed homicide of Uncle Vanya, and altering the original happy ending into a more problematic, less final resolution – critics such as Donald Rayfield, Richard Gilman, and Eric Bentley have sought to chart the development of Chekhov's dramaturgical method through the 1890s.