New York

Just 50 miles from Yankee Stadium sits a four-acre parcel on Greenwood Lake, complete with two castles, owned by Derek Jeter. While it’s not a surprise that he may not be spending much time there, considering his current role 1,300 miles away as CEO of the Miami Marlins, it is a surprise that he would sell the property that has long been part of his life and on which he lavished so much time and money.

Jeter bought the property in 2002 through a holding company, reportedly for $425,000. It was in rough shape, but it had sentimental value for him: He spent summers there with his maternal grandfather while growing up. The home was originally built in the early 1900s by Dr. Rudolph Gudewill for his wife, according to Toptenrealestatedeals.com. It was later sold to John and Julia Tiedemann, who lived there with their 13 children, one of whom, William “Sonny” Connors, they adopted after his parents died. Connors later married a Tiedemann cousin and was Jeter’s grandfather. The Tiedemann family sold the estate in 1996.

The living room. 

Photo: Wright Bros./ TopTenRealEstateDeals.com

When Jeter took it over, the property needed major work. He reportedly spent $3 million on just stone, fixing up the two castles and the grounds, which include a private lagoon with a rock bridge traversing it. At one time the 12,600 square feet of living space was rumored to have held 33 bedrooms. During Jeter’s massive renovation, that was trimmed back to six bedrooms with seven full baths and five half-bathrooms. He also added some extras, like a game room and bar, an office and a gym. There are four indoor kitchens on-site, with a fifth outdoor kitchen. The dark wood-paneled formal dining room and great room are made for large family gatherings.
Other special, and unusual, details include a turret with a widow’s walk, a dungeon with a spiral staircase, a replica of the Statue of Liberty, a stone waterfall and medieval battlements. Jeter also renovated a boathouse at the edge of the lake and built a pool house beside an oversized infinity pool that’s in the shape of a baseball diamond.

The pool. 

Photo: Wright Bros./ TopTenRealEstateDeals.com

The five-story home has an elevator (even pro athletes don’t always take the stairs) and a total of 24 rooms between both the main castle and the guest castle. It also has 700 feet of dedicated shoreline on the picturesque Greenwood Lake, which has long been a haven for tourists and celebrities, including another famous Yankee, Babe Ruth, as well as Greta Garbo. The castle was often featured on local postcards.

Now at its new asking price of $12.75 million, the estate is listed with Mary Lovera of Wright Brothers Real Estate. Check out more photos of it below:

The kitchen. 

Photo: Wright Bros./ TopTenRealEstateDeals.com

The main dining room. 

Photo: Wright Bros./ TopTenRealEstateDeals.com

Another view of the expansive compound. 

Photo: Wright Bros./ TopTenRealEstateDeals.com More