This chapter traces how the rise of brothel prostitution embedded commercial sex into the world of urban real estate and urban commercial networks. As a portion of the sex trade moved out of the streets and taverns and into houses, the sex trade became a source of profit for urban real estate investors and speculators. Meanwhile, the conspicuous consumption required to sustain a high-end brothel and the costs associated with maintaining one ensured that money generated by sex work circulated throughout the city and extended its reach far beyond those directly involved in prostitution. Taking up calls by historians to examine the ways that women’s labor contributed to the capitalist economy, this chapter explores the networks of real estate investors, entrepreneurs, laborers, medicine dealers, and proprietors of entertainment establishments who profited from women’s entrepreneurship and sexual labor. Although women were increasingly defined in nineteenth-century America as nonproducing dependents, their labor as sex workers and the commercialized fantasies they created around prostitution contributed in important ways to the urban economy.