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Greenwich Estate Once Owned by Leona Helmsley Seeks $49.895 Million

On roughly 40 acres overlooking Long Island Sound, the property includes an Elizabethan-style brick house measuring about 17,000 square feet

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Once owned by Leona Helmsley, the Greenwich, Conn., property includes a nine-bedroom house measuring about 17,000 square feet.

STEVE ROSSI
Once owned by Leona Helmsley, the Greenwich, Conn., property includes a nine-bedroom house measuring about 17,000 square feet.
STEVE ROSSI

Leona Helmsley’s onetime estate in Greenwich, Conn., is relisting for $49.895 million, a 23% reduction from its asking price two years ago.

The Elizabethan-style brick house was listed for $65 million with David Ogilvy & Associates in 2014, though the price had been reduced to $58 million by the time it was taken off the market last winter, said co-listing agent Bill Andruss of Sotheby’s International Realty.

In Greenwich, “we’re seeing a bit of a sluggish market” due to it being an election year and a lot of inventory on the market, said Mr. Andruss, who will be listing the property with colleagues Leslie McElwreath and Joseph Barbieri. He added that sales over $20 million in Greenwich are somewhat rare. He said his aim in repricing the property was “to reach a level that I think will create interest.”

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Spanning roughly 40 acres overlooking Long Island Sound, the estate includes a nine-bedroom house measuring about 17,000 square feet with 11 wood-burning fireplaces, Mr. Andruss said. The first floor contains several grand entertaining rooms, including a 42-foot-long living room with a plaster tracery ceiling, a dining room with travertine floors and an oak-paneled library.

Cyd L. Smith, attorney for the sellers, said they bought the gated property from the Helmsley estate in 2010 for $35 million and drew up plans for an extensive renovation. They then “had a change of heart in terms of living at the property,” she said, and put it back on the market less than a year later for nearly $43 million. It has been on and off the market ever since.

Once among New York City’s biggest landlords, Ms. Helmsley and her husband, Harry, bought the property for $11 million in 1983. Ms. Helmsley was convicted of tax evasion and sentenced to 16 years in prison, though she served less than two. She died in 2007 at age 87.

Write to Candace Taylor at Candace.Taylor@wsj.com