Sleepy Hollow Country Club is a historic country club in Scarborough-on-Hudson in Briarcliff Manor, New York. The club was founded in 1911, and its clubhouse was known as Woodlea, a 140-room Vanderbilt mansion owned by Colonel Elliott Fitch Shepard and his wife Margaret Louisa Vanderbilt Shepard. It was built in 1892–95 at a cost of $2 million and was designed by the architectural firm McKim, Mead & White; the estate became a contributing property to the Scarborough Historic District in 1984.

Margaret Louisa Vanderbilt Shepard was an American heiress and a member of the prominent Vanderbilt family. As a philanthropist, she funded the YMCA, helping create a hotel for guests of the organization. She was married to prominent New York City lawyer, banker, and newspaper editor Elliott Fitch Shepard.