In 1892 Elliott Fitch Shepard began construction of a 140 room mansion near what was then North Tarrytown (today’s Sleepy Hollow) New York. Shepard was the husband of Margaret Louisa Vanderbilt Shepard, sister of Cornelius Vanderbilt II and granddaughter of the Commodore. The house was constructed on a tract of over 500 acres of land, acquired by Shepard, a banker, publisher, attorney, and judge. Their New York home was part of the Vanderbilt row of mansions on Fifth Avenue.
The house was designed to include 70,000 square feet of living space, with an exterior in the Italian Renaissance style. Shepard envisioned the house as a means of expressing influence and political power, supporting his political ambitions, and though he was a man of considerable affluence, Margaret’s money too was poured into the construction. In March 1893, while Woodlea was still under construction, Shepard died suddenly.
Shepard’s estate was about $1.3 million, well below the costs of completing Woodlea, which fell to Margaret. While Woodlea was being built Margaret lived in another house on the property which had been completed several years earlier. The main house was completed in 1895-96. During the remaining construction period, Margaret lived at the property mostly during the spring and early summer months. Her visits to the property became less and less frequent.
In 1906 Margaret sold Woodlea to a New York businessman for the sum of $1.4 million, despite the property being valued at nearly $6 million. Margaret took up residence in her New York home, in the 900 block of Fifth Avenue, where she died in 1924, having never remarried. Her estate was just over $5 million, less than half of the fortune she had inherited from the Vanderbilt wealth from her father, William Vanderbilt.
Woodlea and the surrounding grounds were eventually taken over by a consortium who created the Sleepy Hollow Country Club. Among its founders was Cornelius Vanderbilt III. Another founder was John Jacob Astor IV, who did board the RMS Titanic in 1912 and died in the ship’s sinking. The country club retained much of the gardens and the house served as its clubhouse and event center. Much of its décor remains faithful to that selected by Margaret and her husband in the late 1890s.