An advertising system associates advertisements with virtualized real-estate on a map image. Virtualized real-estate includes locations on a map image that correspond to real world locations associated with a user, such as a home, business, or other location. The system matches a user' s virtualized real-estate with advertisements based on user preferences, advertiser preferences, and tracking information. The system also allows users to auction off virtualized real-estate to advertisers. Thereafter, advertisements matched with virtualized real-estate are overlaid on the virtualized real-estate in the map image.