The flow of international funds in real estate investment between Asian and North American cities in the Pacific Rim is now a major financial force to be recognized. This paper reviews the differences in the characteristics and performances of the real estate markets in Hong Kong, Singapore, and several west coast cities. The residential and office price movements among selected Pacific Rim cities over the last 20 years are compared. The paper attributes the differences in the performances to the differences in economic and planning policies in these cities, the differing strategies adopted by the market players, the differences in East and West cultural values, and the differing opportunities and risks created by the various “rules of the game” in each city. If Asian countries continue to enjoy robust economic growth, and the differences in regional real estate markets persist, the flow of international funds within the region and across the Pacific will continue to dominate the 199