This study exploits the recent financial crises as a unique natural experiment to examine relationships in residential real estate brokerage and real estate investment through three essays. The first essay examines the impact of agency disclosure on residential restate transactions in the post-financial crises period and extends the literature with three key findings. First, the overall proportion of buyers that report receipt of agency disclosure has not improved since previous studies were completed. Second, there is no evidence that buyers who do not report receipt of agency disclosure pay different prices for homes than buyers who do report receiving agency disclosure. Finally, there is evidence that the timing of agency disclosure matters. Among buyers that do receive agency disclosure, those receiving disclosure at a time other than the first contact with a broker are associated with 3.2% higher home prices. The results demonstrate the need for continued improvement in mandatory disclosure statutes. The second essay investigates the real estate brokerage market's impact on home prices in both a seller's market (2006) and a buyer's market (2009). In both years, homes sold with brokerage assistance realized higher prices when compared to homes sold without the aid of a broker, even after controlling for selection bias in the seller's choice to use a broker. This is the first study using a national dataset that finds evidence of price segmentation in the residential real estate market. The findings may be the result of the extreme market conditions housing market participants faced in 2006 and 2009. The third essay examines the impact of REITs on the Value-at-Risk (VaR) of a mixed asset portfolio surrounding the financial crises using a new, more accurate method of estimating VaR, conditional autoregressive value at risk (CAViaR). The more accurate VaR estimates show that adding REITs to the portfolio has no significant impact on VaR until after the financial crises begins in 2006. After 2006, adding REITs to a portfolio of stocks and bonds dramatically increases VaR. The results have significant implications for portfolio selection.