[2][3] 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.

In early 1962, Bryant began to outline and lay out a unique (for Jacksonville) and exclusive gated golf community that would become Deerwood.

[2] The development was named Deerwood because of an abundance of wildlife: turkeys, wild hogs, raccoons, bears and many deer.

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.

[6] Bryant Skinner worked for Jacksonville's Stockton, Whatley, Davin & Co. (SWD), the largest mortgage banking, real estate and insurance business in Northeast Florida.

Bryant Skinner quit his job at SWD to concentrate on selling homes around the new golf course and started his own firm.

[10] Don Davis was named general manager of Deerwood Country Club in 1965, a position he held for over 20 years.

[2] The establishment and success of the Deerwood Country Club was the springboard that launched dramatic growth along Baymeadows Road and Southside Boulevard.

Retail businesses, residential developments, apartments and commercial properties included "Deerwood" in their name to associate with the club's prestige.

"[2] Gate Petroleum purchased the real estate assets of SWD in 1983, which included ownership of Deerwood Country Club.

In 1989, Gate built a convenience store and filling station at the intersection of Baymeadows Road and Southside Boulevard.

The Deerwood Country Club has an 18-hole golf course & driving range, fitness center, Olympic-size swimming pool, tennis facility with 12 Har-Tru courts (8 lighted), and clubhouse.

The painfully flat course was given contours to move rainwater to underground drainage and features that were omitted in 1961 due to financial constraints were added.

Deerwood Country Club offers two types of memberships opportunities, our Equity members are club owners, and have benefits such as making policy, voting, serving on the Board, tournament placement priority, annual guest passes to share with friends and family, as well as other perks that include the immediate family living at home up to age 26.

In the summer of 2005, a local developer paid $2.6 million to purchase 140 acres (0.57 km2) on the north end of the country club—the last large undeveloped parcel, which was mostly wetlands once viewed as too expensive to utilize.

Every deed in Deerwood includes a comprehensive set of Covenants, Conditions and Restrictions which establish and permit enforcement of standards.

[21] The DIA manages the 3-acre (12,000 m2) recreation area that includes a community walk, basketball court, multi-purpose ball field, unique playground and pavilion.

At that time, the DIA automatic membership did not include voting rights, which were offered for a one-time fee of $3,000 and were transferable if the member's property was sold.

Non-officers chair one of these committees: Standards, Architectural Review, Access Control and Safety, Grounds, Landscape, and Communication/Newsletter.

[25][26] The DIA engages the services of a professional property manager, whose office handles the day-to-day operations and is the primary contact for residents.

[26] The most expensive support activity was Community Access, which cost over $600,000; Repairs and Maintenance was $400,000; Property Management was $120,000; and finally, Utilities were almost $100,000.