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Rich Cribs: Deep Hollow Farm sells for $11.4 million

Deep Hollow Ranch, the so-called oldest cattle ranch

Deep Hollow Ranch, the so-called oldest cattle ranch in America, is up for sale, bringing a multi-generational tradition to a close.�It�s very hard to let go of something that has been our lives,� said Gardner �Rusty� Leaver, who started working at the ranch in 1963 and bought it in 1971. MANDATORY CREDIT Courtesy of Prudential Douglas Elliman Real Estate Credit: handout/Prudential Douglas Elliman Real

Millard Drexler, J. Crew chief executive officer, bought Montauk’s Deep Hollow Ranch for $11.4 million on Monday.

The 17.8-acre property is the oldest working cattle ranch in the country and has been the site of the benefit concerts with performances by Paul Simon, Billy Joel, Lyle Lovett and Jimmy Buffett. “It’s like a historic landmark. Everybody knows Deep Hollow Ranch,” says listing agent Paul Brennan of Prudential Douglas Elliman Real Estate, who confirmed the sale.

The sellers, Gardner “Rusty” and Diane Leaver, held living history tours detailing the property’s past. Theodore Roosevelt was quarantined with his men at Deep Hollow in 1898, following his successful Battle of San Juan Hill. The property, an agricultural preserve, includes two original Carl Fisher barns; Fisher was the turn-of-the-century entrepreneur who founded the Indianapolis 500.

Drexler has been in the news this week for his role in the controversial $3 billion buyout of the clothing retailer by private equity investors.

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