Deerwood was the first gated community in Florida, US. After it was established in the mid-1960s, it was the most exclusive residential area on Jacksonville's Southside. 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 looking for tracts of pine trees to harvest 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 (16,000 ha; 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.

Bryant Skinner built the golf course in 1960-61, designed on a limited budget by notable golf course architect George Cobb. He then constructed the first home in the Deerwood development (his own) the following year. Brother Richard Jr. built his home there in 1963. In early 1962, Bryant began to outline and lay out a unique (for Jacksonville) and exclusive gated golf community that would become Deerwood. Within his rural Florida location he envisioned a neighborhood that incorporated curving roadways, panoramas, and distinctive homes on voluminous lots with large open common areas incorporating lakes, built around a country club that would feature golf, swimming and tennis. There was plenty of room for a riding stable and bridle paths. The development was named Deerwood because of an abundance of wildlife: turkeys, wild hogs, raccoons, bears and many deer.

Bryant was confident that people would embrace it, but to get there from the established city required an 8 miles (13 km) drive down U.S. 1 (Philips Highway), then east for three bumpy miles on a rough dirt road named San Clerc, which would eventually become Baymeadows Road. In 1960, the area south of Beach Boulevard, east of US 1, and extending ten miles (16 km) to the Intracoastal Waterway (approximately 50 square miles) was wilderness consisting of sand dunes and pine trees. In order to solve the problem of their isolated location, the Skinners donated land and convinced the Jacksonville Expressway Authority to build a road that would connect Beach Boulevard to Philips Highway. That thoroughfare, now called Southside Boulevard, opened Deerwood to development. In the 1970s, they gave land for State Road 202 (Butler Boulevard), which opened more of their property, as did the extension of Baymeadows Road, east from Southside Blvd to a point where State Road 9A (now I-295) was built. When the University of North Florida was being developed, the Skinner family granted approximately 500 acres (200 ha) for the first campus of the college.

Jacksonville Country Day School was constructed at the southwest corner of Deerwood in 1960. The school sold their 4.3 acres (1.7 ha) of frontage on Southside Boulevard in 1989 for over $1 million to help pay for capital improvements. The buyers used the property to build two strip centers for retail businesses. The school occupies a parcel of nearly 17 acres (69,000 m²) and has two entrances; public access is from Baymeadows Road, and there is a private drop-off entrance from within the Deerwood gated community.

Bryant Skinner worked for Jacksonville's Stockton, Whatley, Davin & Co. (SWD), the largest mortgage banking, real estate and insurance business in Northeast Florida. The Skinners had abundant land, but not the financial resources necessary to develop his Deerwood project. J.J. Daniel became president of SWD in 1960 and made a deal to purchase Deerwood's 900 acres (3.6 km²) from the Skinners. SWD financed the development of Deerwood Country Club. Bryant Skinner quit his job at SWD to concentrate on selling homes around the new golf course and started his own firm. The Bryant Skinner Company eventually became one of Jacksonville's most successful real estate development businesses. In 1980, they combined with Gate Petroleum to develop the 250-acre (1.0 km²) Southpoint office park.

Don Davis was named general manager of Deerwood Country Club in 1965, a position he held for over 20 years. In 1978, Davis was promoted to operations vice president of SWD, responsible for all Deerwood Club operations, including the sale of residences and home sites. In 1979, 86 families lived at Deerwood.