Abstract: This dissertation will provide a detailed quantitative analysis of the effect that rail transit stations have on housing property values in San Diego, CA. Past research has shown that property near rail stations sells at a modest premium in many US cities. The new research presented here will build on previous work by looking at the conditional nature of rail transit capitalization. In other words, the findings from this research go beyond simply answering whether rail transit capitalization occurs but also illustrate that the capitalization benefits vary depending on a property's attributes and location within a region. This research will make use of hedonic price models with interaction terms to statistically determine how the characteristics of a location and property condition rail capitalization. More specifically, the models will test whether various elements or transit-oriented development (TOD) enhance capitalization benefits. The results of these models show that the higher density housing, permissive zoning regulations, a pedestrian-oriented built environment, and higher quality transit service can greatly increase the size of the premiums associated with rail proximity. This suggests a fairly strong market for TOD in San Diego. The findings also provide evidence that the development impacts of rail transit investment depend on station location, system design, and complementary land use policy.