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Location: Old Westbury, N.Y.
The Skinny: Cornelia Guest, the only daughter of the late society legend C.Z. Guest and polo-playing Phipps steel heir Winston Frederick Churchill Guest, was a society darling in her youth and was dubbed "Debutante of the Decade" in 1986, but a few missteps—like moving to Hollywood and engaging in ill-fated relationships with Rob Lowe and Sylvester Stallone—tested her spirit for the public life of her mother. Nowadays, the younger Guest has shrugged off the air of formality, started a catering company, and currently keeps a pet donkey on the Long Island family estate, known as Templeton. She recently sold a Salvador Dalí portrait of her mother and, in the ultimate evidence of her desire to move on, she has the Long Island estate listed for sale. “I want a place to make my own memories now,” Guest recently told the New York Times, adding, “This house is too much, it needs a family." Once asking as much as $11.9M, the 15-acre estate and its 17,000-square-foot brick manor—which "has 28 rooms and an understated charm, full of club chairs, potted plants, Scalamandré fabrics, animal print rugs and family portraits," according to the Times—are currently listed for $6.9M.