Mr Trump's doodle was originally donated to a charity in 2005.
"Over the years, Mr Trump has occasionally drawn views of the New York City skyline for donation to worthy charity auctions. The example offered here dates from 2005, and was given to the St Francis Food Pantries and Shelters organization in New York," US-based Heritage Auctions house writes on its official website.
"It is boldly signed with a clearly legible "Donald Trump" signature (it is interesting to note how Mr Trump's signature has changed over the years, as more recent iterations are far less legible)," the auction house adds.
Mr Kennedy's brightly coloured oil painting depicts the skyline of a town by the water. It is believed to be a scene from the South of France and is thought to have been painted when he was still a young senator.
"Unlike other recent presidents... JFK was not endowed with great artistic talent," Heritage Auctions writes. "Perhaps for this reason he rarely painted or drew. According to information supplied by the consignor, this is one of just two known paintings by Kennedy."
Interestingly, a black-and-white photo of Mr Kennedy working at an easel, with his wife Jacqueline Kennedy looking over his shoulder, will also be sold along with the painting.
Heritage Auctions will close the auction featuring the signed artwork of both politicians on December 2. So, in case you were planning to place a bid, you still have some time to do so.
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