Problem Statement: In modern linguistics a certain experience has been accumulated in studying expressions with conditional relations. However, there is no consensus nowadays concerning identification of speech fragment where the condition is explicated. Therefore, the necessity exists to extend an understanding of the conditional sentence, consider its structure in the aspect of translation as well as conduct semantic division of conditional sentences of the novels “Pride and Prejudice” by Jane Austen and “Me Before You” by Jojo Moyes.Purpose: To study semantic peculiarities of conditional sentences functioning in the English classical and modern novels, find out their common and different features as well as reveal the difficulties and specific features of English conditional sentences’ translation into Ukrainian.Methods: Analysis, synthesis, induction method, quantitative method, continuous sampling method, descriptive method, contextual analysis and pragmatic analysis method, comparative method.Discussion: In the mentioned novels in terms of grammar five types of conditional sentences were distinguished: conditional sentences of zero, first, second and third type, and mixed type conditional sentences. In total 271 units were considered in the classical novel and 145 units in the modern novel were taken into consideration. Having analysed semantic peculiarities of different types of conditional sentences in the novels, we have distinguished certain categories of conditional sentences with respect to connotation, in particular: conditional sentences with positive, neutral and negative connotation.Results: The division of conditional sentences with reference to connotation enabled us to conclude that the grammatical type of conditional sentences determines, to some extent, its semantic colouring, though it does not define the connotation of the sentence as a whole. Sentences with the structure I wish comprise a separate semantic group.The article proposes several tendencies in modern translation of English conditional sentences.The studying of conditional sentence communicative function rendering during translation conditional sentences from English into Ukrainian is supposed to be challenging in as much as the communicative function of something being informed is one of the most essential functions for the achievement of pragmatic impact on the reader.Key words: conditional sentence, connotation, classic novel, translation.