Essays for the farm must be postmarked by October 1. After reviewing them, the couple - Randy Silvers and Carolyn Berry - will select 25 finalists and pass the essays along to a panel of three judges - an educator, a hobby farmer and a horse enthusiast - who will select a winner on November 26.
They are hoping to receive 5,000 essays, for a total of USD 1 million.
If the couple does not receive the anticipated number of essays (or something close to it), the couple will list the property, valued at USD 600,000.
"In that case, we would return all the money," Berry was quoted as saying by Washington Post.
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"It's his dream," Berry said of the property. "It's like he's living his dream. And it's sad, but his dream needs to morph into another dream."
Silvers, 64, was diagnosed with rheumatoid arthritis last year, which has made upkeep of the farm difficult at times.
Silvers and Berry have day jobs - he is a construction foreman; she is a director of a tutoring facility. And they cherish their life of solitude on the farm.
Berry said she was inspired by an essay contest for the Center Lovell Inn in Maine, a bed and breakfast that was won for USD 100 in 1993 by a woman named Janice Sage. Sage wrote a 250-word essay that demonstrated her culinary and hospitality savvy, and her ability to care for the inn.
Meanwhile, a few people have raised questions about the legality of giving away homes through a raffle.
Essex County Commonwealth's Attorney Vince Donoghue said that "the matter is under review." But, he said he is not treating the issue as if the family has malicious intentions.
"This is a nice family just trying to give away a house and pay off the mortgage," Donoghue said.