This dissertation explores how different Maya people, with varying degrees of social, economic, and political power have responded to the settler colonial project in the southeastern Yucatan Peninsula. In particular, this dissertation examined how Maya communities have attempted to establish land access and economic security as the town of Tihosuco (Quintana Roo, MX) and the surrounding subtropical forests shifted in and out of settler colonial imaginaries from the 16th through 20th centuries. Using archaeological survey, archival, and oral history data my dissertation examined two landed estates within the Tihosuco to document evidence for Maya settlement and investment in a landscape frequently designated as terrenos baldios, or empty lands. Landed estates with capital and labor investments in apsidal houses as well as infrastructure for livestock raising, small-scale sugar cultivation, and regional trade are evidence of a growing number of Maya property owners in the years leading up to the Maya Social War (1847-1901). Although landed estates throughout the region were abandoned following the outbreak of the Maya Social War, archaeological and oral history data indicate that these estates were reoccupied in the early 20th century. Patterns of site reuse and renovation documented with both archaeological survey data and oral histories indicate that the labor and capital invested in these late 18th – early 19th century estates provided critical infrastructure for Maya families looking to establish land security in the early 20th century.