Home numeracy and literacy environments are related to the development of children’s early academic skills. However, the home learning environments of preschool children have been mainly explored with children from North America, Europe, and Asia. In this study we assessed the home numeracy and literacy environments of three-to-five-year-old children from Mexico (n = 54) and Chile (n = 41) and compared the patterns of results to those of children from Canada (n = 42). Parents completed a questionnaire about their expectations for children’s academic performance prior to Grade 1 and the home numeracy and literacy activities they provide for their children. To analyze differences among countries in the home learning environments, we performed mixed and one-way ANOVAs (Analysis of Variance), followed-up by post-hoc comparisons. Mexican parents had higher expectations for children’s early skills than Chileans or Canadians. The frequency with which Mexican, Canadian, and Chilean parents reported home numeracy and literacy activities showed both similarities and differences. Our findings speak to the importance of developing culturally sensitive models of early home learning environments and illustrate the complexities of comparing home learning environments across countries.