Increasing gentrification and homelessness have coincided with neighborhoods, communities, cities, and states undergoing transformation and reconstruction. A negative outcome of gentrification is cultural displacement experienced when a group is forced out of the neighborhood due to changes in property taxes and rents. The purpose of this project is to discern the relationship between homelessness and gentrification. Using data from the U.S. Bureau of the Census and Hudex Change (2007, 2009, 2011, 2013, and 2015), this study compares the impact of gentrification on housing stock and homelessness. This thesis applies Guerrieri et al.’s (2010) economic model to measure the relationship between endogenous gentrification and housing price dynamics. This thesis hypothesizes that if gentrification increases the rate of homelessness increases. This research employs Ordinary Least Squares (OLS), as its empirical method of estimating the unknown parameters in the linear regression model.