A bid estimating system and method is provided according to an exemplary embodiment of the invention includes a processor that accesses a database of existing customer information specific to that customer. The processor identifies information specific to the customer stored in the database and determines an estimate, in real time, for the services provided based on the customer specific information. The estimate is then conveyed to the customer for their approval. According to one preferred embodiment the service provider is a landscaper. According to this embodiment the potential customer provides the customer's address. A processor then access a real estate database for the address and determines a bid based on the database information corresponding to the address. Alternatively, a landscaper can create accurate bids for mailers simply by identifying an address and selecting the types of services to be performed in order to determine the cost of the services.