Deerwood is the oldest gated community and country club in Jacksonville, Florida. After it was established in the mid-1960s, it was the most exclusive residential area on the south side of Jacksonville and remains so today, with round-the-clock guard service at two entrances and high standards for membership and residency. The golf course hosted the Greater Jacksonville Open in the late 1960s and early 1970s, forerunner of The Players Championship, and was once the site of talks between President Gerald Ford and Egyptian President Anwar Sadat in November, 1975.
Richard Green Skinner came to Jacksonville in 1899 in search of pine trees for harvesting sap to produce turpentine for his marine supply business. Land to the south and east of the St. Johns River was mostly pine trees, sand dunes or marsh; inhabited by wildlife. After 1900, the Skinner family owned close to 40,000 acres (160 km2). That land was distributed to his six sons upon his death in the 1920s. The oldest brother, Bright, and two other brothers moved to Tampa and received the land owned there. The acreage nearest to the downtown went to Ben Skinner, who built the Skinner Dairy and Farm, which was closed and developed as Southpoint in the late 1970s.
Chester and Richard were given the biggest tracts because the land was quite remote—miles from existing roads. Richard Skinner, in turn, gave his children, Richard, Jr., Bryant, and Dottie his land, including the property on which Deerwood would be built.