Fortune Street is a virtual board game similar to Monopoly, using characters and settings from the Mario and Dragon Quest series. Players roll a die and move the number of spaces represented by the side the die lands on.

When a player lands on a property, they may buy said property, develop it and accept rent when other players land on it. The player collects their money from the bank, where they can also purchase stocks, which generate revenue from the rent collected on other player's properties, provided they have collected a heart, a diamond, a club and a spade, doing so will also increase the player's personal worth. Some spaces on the board will force the player to draw a card which cause a random event, other spaces will cause a specific event, such as all the player's properties closing and not collecting rent.

Victory conditions depend on which map the game is being played on. Some maps will grant the player victory when all the other players are bankrupt, while others may demand that the player gain a certain amount of wealth.