This dissertation focuses on the intertwined worlds of Hebrew and German-Jewish modernism and their impact on the Jewish sense of belonging before the Shoah. Set against the growing impact of the so-called “Jewish question” and the background of World War I, the Holocaust, and the rise of the State of Israel, I argue that Hebrew writers—including David Vogel, Leah Goldberg, and S.Y. Agnon—used the genre of the novel to claim and imagine a home in German-speaking Europe, transforming the possibilities of Jewish writing and the image of Zion in the process. Unlike previous historiographies concentrating on the desire to return to Zion, this study analyzes the Jewish and Hebraic attachment to—and rejection from—the German speaking world, specifically, Vienna and Berlin, as well as the role of the novel in mediating between cultural Zionism and the German-Jewish cultural sphere. My study is organized into three chapters, demonstrating how this poetics operates through several test cases. Chapter one examines the trope of the city as a liminal space in two Viennese novels, David Vogel’s Haye nisuim (Married Life, 1929-1931) and Arthur Schnitzler’s Der Weg ins Freie (The Road into the Open). Drawing on theories derived from urban and cultural studies, I show that while Schnitzler's novel demonstrates a multitude of perspectives on the Jewish condition, he is blind to the Eastern European Jew who lives in poverty in Leopoldstadt and walks the city. Vogel’s deployment of Hebrew speech and Viennese topography, I argue, destabilizes both Schnitzler’s Jewish Vienna and the Zionist narrative of homecoming. Instead, the novel constructs spatial appropriations to implement a new category of belonging: a Hebrew Vienna. Chapter two interrogates the notion of intertextuality as an expression of the threshold in Leah Goldberg's novel Mikhtavim minesi’ah medumah (Letters from an Imagined Journey, 1936/7) and its intermedial exchanges with German poetry, cultural history, and the urban space of Berlin. Taking into account the novel’s reception history, I argue that intertextual exchange in this case serves as a literary technique of non-translation to explore the kinds of cultural, linguistic, and political belongings that were or were not available to the Hebraic Jew in both Palestine and Europe in the mid-1930s. Chapter three explores the notion of the library in S.Y Agnon's novella Ad henah (To This Day, 1952) and his relationship with the German-Jewish intelligentsia in his construction of the “Jewish town,” arguing that for Agnon the imagination of Zion is dependent upon the diaspora, even after the State of Israel is established. Mediating between cultural Zionism and the German-Jewish cultural sphere, these novels establish a space where interspatial and interlinguistic thresholds serves to negotiate the Jewish migrant’s experience of exile in relation to perceptions of homeland, oscillating between the Germanic Heimat and the Hebraic moledet. In the process of these ongoing exchanges, the novel becomes a vehicle, not only for literary experimentation with modernist forms, but also for cultural instruction and political debate.