Market innovative entrepreneurs have the desire of exploring declining economic markets to seek for windfall. They seek to profit heavily from adverse market conditions. The Great Recession may have presented some economic disasters, rage, and hardship to many people in the housing market in the 2000s but to the innovative market entrepreneurs, it presented some economic opportunities for experiencing a market windfall. Mostly, the objective of this exploratory study is to highlight the impact of the opportunistic events created by the housing foreclosure fillings, completed foreclosures, and home repossessions on the indexed price of housing that harbors the related opportunity cost. The increased indexed price of the housing driven by the fluctuation of both the quantity demanded and produced of housing seems to have led to the entrepreneurial windfall profit during the recession.