Known locally as The Castle, the resort-like home was bought by the retired New York Yankees star back in 2002. See: World’s best homes – see inside the most jaw-dropping houses across the globe Derek Jeter’s house was originally built in 1903 by New York Doctor Rudolph Gudewill for his wife. The estate is actually two castles - the master castle with a connected tower and a guest castle. After Gudewill died, John and Julia Tiedemann bought the castle, where they lived with their 13 children including an adopted son, William Connors.  Connors later became Jeter’s maternal grandfather. Jeter spent many of his childhood summers at the castle swimming, and playing sports. The Tiedemanns sold the estate in 1996, but when it came back on the market in 2002, Jeter bought it and began a long and expensive restoration.

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The retreat boasts 12,590 square feet of living space between the main and guest castle, and includes four kitchens, an infinity pool, and six bedrooms. There are seven full and five half baths, and a multitude of entertaining spaces, including a great room, plenty of snugs and dens, a sun room, office, gym, and  even a couple of bars.

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There’s also a pretty swanky-looking pool room that oozes gentlemen’s club vibes. The property also enjoys beautiful lake and wood views, and the turret opens out onto a widow’s walk, which is replicated at the guest castle. The home exudes a cabin-meets-lodge style inside, with wooden wall panelling featuring heavily throughout. Greenwood Lake is situated where the borders of New Jersey and New York join, just 50 miles from Manhattan. It’s long been a honeypot for wealthy weekenders and celebrities looking to escape the city for some rest and relaxation.  Greta Garbo loved the area, while baseball icon Babe Ruth owned a home in Greenwood, and spent many hours out on the lake, stopping at the renowned Maplewood Inn for drinks. The seven-mile lake also attracts its fair share of New York Yankee players and fans. Pictures courtesy of Top Ten Real Estate Deals (opens in new tab).

Where does Derek Jeter live now?

Derek is the pair owner and CEO of the Miami Marlins, which surprised many baseball experts by making the MLB playoffs in 2020 and then knocked out the Chicago Cubs in the first round. He lives with his wife Hannah Davis and two children on the 19th floor at the Grove at Grand Bay skyscraper in Miami.  He also owns a number of other properties, including a 31,000 sq ft waterside mansion on Tampa Bay’s Davis Island, which he famously rented to Tom Brady and Gisele Bundchen. He also owns a family home in Marlboro, New Jersey.