Derek Jeter finally nears “The Flip” of New York castle

Yankees great’s Orange County home faced multiple price chops, failed auction

Derek Jeter Finally Nearing “The Flip” of New York Castle

A photo illustration of Derek Jeter along with 14 Lake Shore Road in Greenwood Lake (Getty, Compass)

“The Captain” is finally steering his ship out of New York.

New York Yankees legend Derek Jeter is in contract to sell his estate north of New York City, Mansion Global reported. Tiedemann Castle, a lakefront compound in Orange County’s Greenwood Lake, was last listed at $6.3 million.

If closed at that asking price, the deal for the 9,000-square-foot home would break down to an even $700 per square foot.

Built in the early 1900s to overlook the town’s eponymous lake, the castle-like home has six bedrooms, 12 bathrooms, a large turret and a replica of the Statue of Liberty. The house on the four-acre site, also has five kitchens — including an outdoor one — and an infinity pool.

A limited liability company connected to Jeter purchased the property in the 2000s for a reported $1.6 million from a trust tied to his family. When his playing career ended, the long quest to sell the estate began. 

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Jeter and his wife, Hannah, listed the 12,000-square-foot home in 2018 for $14.7 million, only to pull it from the market a year later. In 2021, the listing reappeared last year with a $2 million discount. In early 2022, it was relisted again for $9.5 million; an attempt to auction the property followed, without any takers on the $6.5 million minimum bid.

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New York
Serious fans only: Derek Jeter's upstate NY castle is for sale
Derek Jeter and the lakefront mansion (Getty, Redfin, Wikipedia Commons)
Derek Jeter relists lakefront estate outside NYC with $2M price cut
A photo illustration of Derek Jeter and 14 Lake Shore Road in Greenwood Lake (Getty, Compass)
Derek Jeter puts New York castle up for auction

The final sale price and buyer likely won’t emerge until the deal closes. Wright Bros. Real Estate’s Diane Mitchell had the listing.

Following a Hall of Fame playing career spent exclusively with the Bronx Bombers, Jeter has dipped into numerous business pursuits, launching The Players’ Tribune publication, serving as an MLB studio analyst for Fox and as chief executive officer of the Miami Marlins, a tenure that ended in February 2022 as he sold his 4 percent stake in the franchise.

Holden Walter-Warner