Charles Darrow started producing Monopoly games in 1933. He started by making sets by hand for friends who came to his house to play with him and had to have a set of their own. These first sets had oilcloth boards, hand cut houses and hotels, hand-typed Chance, COMMUNITY CHEST, and property cards, and play money and dice from a dime store (some money was hand-typed as well). Some of these boards were round (presumably the shape of his kitchen table) and later boards were square.
He found that he couldn't keep up with demand and enlisted the help of a print shop (Patterson and White) to help. The printer produced the black sections of the board which Darrow then hand painted to complete. These games were housed in tie boxes. These pictures show a set with later components added. The tokens as well as the Darrow type one and two money are not original to this game. The hand typed money at the bottom of the picture would be original to this set.
By 1934 this still wasn’t enough to keep up with demand (an order from Philadelphia department store Wannamaker’s didn’t help the problem) so he had Patterson and White completely make 500 sets for him. As these sold out he had another 500 made.
By 1935 demand had grown to the point this time Parker Brother’s noticed the popularity of the game and made a deal with Darrow to purchase it. The remaining stock of 5900 games went with the purchase.