Jackie O’s estate could be the most expensive home ever sold in Martha’s Vineyard

The 345-acre property is listed for $65M — twice the price of the island's most expensive home sale

If it sells for its asking price of $65 million, Jacqueline Kennedy Onassis’s Martha’s Vineyard home would double what is currently the most expensive real estate record on the island.

As first reported by The Wall Street Journal, the oceanfront estate in Aquinnah, Massachusetts, comes with a 6,456-square-foot, five-bedroom home and four-bedroom guest house, both designed by architect Hugh Newell Jacobson. The former first lady bought the property, known as Red Gate Farm, on the affluent vacation island in the late 1970s for $1 million.

The compound includes a tennis court, a pool, freshwater ponds and more than a mile of private beach. The homes were renovated and expanded in 2000 by acclaimed interior designer Deborah Berke.

Onassis’s daughter, Caroline Kennedy, had been using the estate since the death of her mother in 1994. Kennedy told The Wall Street Journal that she’s choosing to sell the house because her three children are now grown.

LandVest’s Tom LeClair and Gerret Conover are the listing agents in charge of selling the property, which is currently assessed at $37 million, according to the Vineyard Gazette. They did not immediately return Inman’s request for comment.

Onassis would regularly use the property for getaways with her later husband shipping mogul Aristotle Onassis, whom she married five years after former President John F. Kennedy’s assassination. Over the years, the estate has hosted many high-profile guests, including former President Bill Clinton and former Secretary of State Hillary Clinton.

“She loved exploring the Cape, sailing Nantucket Sound with my father, and being part of all the family activities in Hyannis Port,” Kennedy told the WSJ. “But when my brother and I were grown, she wanted a place of her own.”

At the moment, the most expensive recorded sale of a residential property on Martha’s Vineyard sits at $32.5 million. While agents often mark up the asking prices of celebrity properties in the hopes of drawing attention to the listing, the sale of this iconic estate has the potential to make history.

Email Veronika Bondarenko

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