The tennis house is the only remaining structure of the original 400-acre Winthrop Estate in Woodbury, and it recently came on the market, along with a four-bedroom Colonial that was built on the property in the 1960s, for $1.299 million.
The tennis house was built in the 1920s by Henry Rogers Winthrop, a millionaire banker and director of the Long Island Rail Road, and his wife, Alice Woodward Babcock. Their original mansion was destroyed by a fire in 1964, but the tennis house remains.
The estate was one of the elite playgrounds of the Gatsby Era. During their summer on Long Island, Edward VIII and Wallis Simpson, the duke and duchess of Windsor, played tennis there, according to “An ‘Upstairs, Downstairs’ Look at Oyster Bay Estate Life,” published by the Oyster Bay Historical Society in 2005. In the 1970s, the local pro John Dunn owned the property and invited the Jackson Five to play there while on tour, says Dunn’s daughter, Shirley.
The tennis house has 40-foot glass ceilings that offer natural light for daytime play and it is illuminated for evening tennis. The red clay court also has a heating system for playing in the winter, and the building includes ladies’ and men’s changing rooms.
“It’s all very proper from the 1920s,” says listing agent Patricia Cadavid of Daniel Gale Sotheby’s International Realty.
In 1964, the current owners built a four-bedroom home for their family, who all went on to play tennis, some with scholarships, in college.