The price of a Harley Davidson depends on a number of factors. Model year, mileage, and model are some of these factors. However, the Harley Davidson Bucherer Blue Edition is the most expensive Harley ever. It is worth $2.4 million. On the other hand, the Harley Davidson Street 500 is one of the cheapest Harleys you can buy. It has a starting price of just $6899.