Derek Jeter (Finally) Snags a Buyer for His New York Castle

After years of swings and misses, the Yankees legend Derek Jeter has finally found a buyer for his compound in Orange County, N.Y. — after it was re-listed for less than half of its original asking price.

The four-acre lakefront home in Greenwood Lake, N.Y., known as Tiedemann Castle, went into contract on May 25, two years after it failed to sell at auction, and six years after the Hall of Fame shortstop initially put it on the market for more than $14 million. The asking price was slashed to $6.3 million this year, and the sale is currently pending.

The listing agent, Diane Mitchell of Wright Brothers Real Estate, declined to comment on the specifics of the deal, but said that she is “thrilled” that it’s finally under contract. The estate comprises three different parcels, according to the listing, including a main house, guesthouse, pool house and boat house. At more than 12,500 square feet, it has six bedrooms and 13 bathrooms.

Built more than a century ago, the home’s distinguishing features are vast and lavish. There are five kitchens (four indoor, one outdoor), a lagoon, an infinity pool shaped like a baseball diamond, a game room and turrets. It has been compared to a medieval castle.

Mr. Jeter bought the property in the early 2000s, at the peak of his baseball career. He initially listed it for $14.25 million in June 2018. In 2022, it went to auction, at which point Ms. Mitchell, who was the listing agent then as well, said in a statement that “the owner is serious about selling because the owner spends most of his time at other family-owned homes.” The auction, which had a minimum bid of $6.5 million, was unsuccessful, and the property was listed again last month.

In recent years, Mr. Jeter has been reshaping other aspects of his real estate portfolio as well. In 2020, he listed his custom-built, 30,875-square-foot mansion in Tampa, Fla., for $29 million. It sold the following year for $22.5 million, becoming the region’s most expensive home sale at the time. Last year, The Tampa Bay Times reported that the home was set to be demolished and replaced with new mansion.

In the village of Greenwood Lake, which is around 50 miles north of Manhattan, the median listing price is $475,000, according to Realtor.com.

For Mr. Jeter, who was born in Pequannock Township, N.J., and grew up in Michigan, the estate holds sentimental value. His grandfather, William “Sonny” Connors, was the adopted son of John and Julia Tiedemann, who previously owned the home, and the future Yankee captain spent summers there, according to Ian O’Connor’s 2011 book, “The Captain: The Journey of Derek Jeter.” At the time, Mr. O’Connor wrote, he “was not looking for a chance to swim as much as he was looking for a partner in a game of catch.”