A system and method for matching buy and sell orders is provided. A daily cash index of real estate values for a local region is maintained based on real estate transactions and/or real estate transactional activity, and a trading instrument representative of an interest in real estate in the local region is created. In this regard, a cash settlement of the trading instrument is a function of the daily cash index on the date of said cash settlement. In addition, a plurality of buy orders relating to the instrument are generated; a plurality of sell orders relating to the instrument are generated; and the buy and sell orders are matched to determine a purchase and sale of the instrument.