I know someone that attempted the same thing. It proved to be a colossal flop. The house and property were worth around $219,000 He figured if he could get 250 people to by chances to buy the house at $1000 a pop, he could sell the house, pay all expenses, and make a make a little profit on the deal. He even paid an advertising agency $5000 to promote his contest. He also had to buy a gaming permit from the state at a cost of $590.
The contest ran for one year. He extended it 6 months. Then another 6 months. Some of the entrants starting asking for their money back because of the delays. He ended up giving all the money back and the whole ordeal cost him over $10,000. The 2 years the contest ran, he receive a total of 31 entries.
The first place you should check out are your state and local gaming authorities. They can probably answer most of your questions.
