Sugar production, as an agro-industrial sector, promoted a variety of urban types and acted significantly in the construction of the territory in the Americas: Slave and convict quarters, industrial villages, company towns, agricultural colonies, large-span refineries, assortment of low-cost housing projects, temporary shelters, and buildings for collective use. The production of sugar was one if the main reasons for European colonization in the New World during the 17th and 19th centuries. Thus, one of the earliest forms of architectural expression and urbanization emerged in sugar plantations. Sugar production landscapes have been facing profound changes over the last four decades. Sugar towns, which flourished mostly until 1940s, represent a small-scale urban-rural hybrid with agricultural, industrial, and residential features. Sugar plantations based on slavery and convict leasing were often the starting point for the development of company towns. This paper investigates the architecture and urban form promoted by and for sugar production and the preservation of the industrial heritage. It focuses on housing from the perspective of one product (sugar), by surveying over cases and typologies in various regions in Brazil and United States North, examining early practices and spatial changes. A comparative study attempts to reveal common models and typology and, on the other hand, to distinguish specific characteristics of each place, observing the influence of foreign rules, constraints of climate and traditions, variety of styles and typology, and issues related to heritage preservation. Finally, this paper examines the preservation of sugar company towns and industrial heritage in Brazil and in the Unites States with focus on the relationship between history and heritage preservation (or lack of) through adaptive reuse. The study attempts to compare quintessential sugar heritage sites, in particular Sugar Land, Texas, in the United States, and the Piracicaba region in Brazil; (2) examine in a historical perspective the similarities and differences the adaptive reuse projects and conservation issues; and (3) present the activities of the stakeholders in both countries.