The 338 acres of “Washington Irving” hills and woodlands that make up the Sleepy Hollow Country Club were once known as Woodlea, the country estate of Mr. Butler Wright. The former Golf House, which was situated adjacent to the north end of the pool complex, was the family residence. Later this estate was purchased by Colonel Eliot F. Shepard, husband of Cornelius Vanderbilt's granddaughter, Margaret Vanderbilt, and in 1893 the palatial home – now the main Club House – was constructed along with the magnificent stables. The plans were by Stanford White of McKim, Meade & White, and constituted one of the last works of the famous architect.

The entire estate was purchased in 1910 by Mr. William Rockefeller and Mr. Frank A. Vanderlip, who in May 1911 sold and turned it over to the organizers of The Sleepy Hollow Country Club. The following list of the first 27 directors of the corporation includes the names of leaders in the social and business life of the day.

John Jacob Astor
Stephen H. Brown
James C. Colgate
Edward Harden
G.G. Haven, Jr.
William M.V. Hoffman
George W. Perkins
Percy A. Rockefeller
George R. Sheldon
Lispenard Stewart
Moses Taylor
Cornelius Vanderbilt
Frederick W. Whitridge
E.J. Berwind
A.O. Choate
Elisha Dyer
Oliver Harriman
Paul N. Hayes
V. Everit Macy
Franklin A. Plummer
William Rockefeller
Samuel Sloan
James A. Stillman
Oakleigh Thorne
Frank A. Vanderlip
Harrison Williams
F.S. Witherbee

In addition to being voted one of the top 100 most prestigious country clubs in the United States, Sleepy Hollow Country Club is also one of the most picturesque. The Club offers 2 C.B. Macdonald designed courses, an outstanding 18 hole course as well as a 9 hole course. The riding facility includes an indoor ring and 2 outdoor rings plus the use of the 900 acres of beautiful Rockefeller trails. There are 10 clay tennis courts and a swimming pool serviced by a cafe and locker rooms. The main Club House boasts a ballroom, library, grill room, formal dining room, 18 guest rooms, golf shop and locker rooms. For winter sports there is a 4 court squash building with a fitness center, 4 paddle tennis courts, a skeet/trap/log cabin lodge facility and a golf teaching/practice center.