Other than casino jackpots I've never won anything like that.
My lady won a mountain bike from a local sporting goods store.
Worst story, her son had some kind of raffle for his work and he was bidding on a Christmas tree with scratch off lottery tickets on it. He quit bidding at $90 and the guy who outbid him got it for $100. One of the tickets was $40k/year for 25 years.