Highlands Falls Country Club was born when Highlands was still very young.  In the 1950’s Highlands was an area largely un-discovered. It was during this time that Lloyd K. Gibson and Gordon Gibson, two Florida real estate developers came to the area in search of the ideal location to develop a golfing resort in a higher elevation. After months of searching for just the right property they discovered 300 acres of land owned by Mr. W. Edwards. On October 23, 1958 Lloyd and Gordon Gibson purchased the land now known as Highlands Falls, for $45,000. 

Upon acquiring the property, the Gibsons partnered with Dr. Frank G. Hodnette of Pensacola, FL and established Gib-Net Realty Corp. doing business then as Sky Lake Golf Estates. Gib-Net constructed the golf course using a bulldozer, a jeep with a trailer, a farm tractor and countless hours of manual labor. 

In early 1959 Gib-Net hired golf course architect William Amick of Ft. Walton Beach, FL. Over the next few months Amick completed the design work for the golf course and the work of laying and cutting the center lines of the fairways began along with the tedious job of cutting and clearing trees and shaping the tees and greens. Over the next several years, many challenges were posed by the natural terrain such as; huge boulders and large areas of solid rock hills requiring extensive drilling and blasting, limited equipment to perform these seemingly monstrous tasks, and as always, plenty of help from Mother Nature in the form of frequent downpours of rainfall and brutally cold winters. As a result of their perseverance, vision and their tireless efforts, the corporation proudly opened the nine-hole golf course known as Sky Lake Golf Estates to the public on June 20, 1963. 

The course was later expanded to twelve holes and in April of 1967 the golf course was sold to golf pro William A. Meyers of Daytona Beach, FL, for $20,000, which included an option for Meyers to purchase additional property to complete an 18-hole golf course. In 1969, Edward Callaham of Naples FL organized a group of investors to include Wesley G. Dowling, Earl L. Frye and William L. Tuck. The Naples group then formed a trust to develop Sky Lake Estates and it was around this time that the name was changed from Sky Lake Golf Estates to Highlands Falls Country Club after the course's signature hole, a 100ft. waterfall which serves as a spectacular backdrop for the 15th hole. 

Trout Jenks was employed by the Naples group to redesign the golf course to include 18 holes.  While rebuilding the front nine they abandoned some holes and began work to build the back nine. They also built a new clubhouse, located where the current clubhouse is today, but it was only about 6,000sq. ft. in size. When the decision was made to build a larger clubhouse, the original structure was purchased by Amelia and Tom Ennis and moved to the lot adjacent to the seventh fairway in the early 1970s. 

In 1979 the Joe Lee design for the golf course was approved for construction. His plan would utilize the most significant natural feature of the property on the golf course – the waterfall. His plan included the abandonment of several holes that the Naples investors had built where the swimming pool and tennis courts are today. These were replaced with present day holes 12, 13, 14, 15 and 16. This construction began in 1983. The Clubhouse was remodeled and enlarged in 1991. The Grille Room was enlarged to it present size in 1999.

In the summer of 2004, the HFCC membership approved a proposal to construct a 5000 sq. ft. two-story Fitness Center. Plans were developed that would include two massage therapy rooms, an aerobics room, ladies' and men's locker rooms on the lower level and a strength training/cardiovascular room on the upper level.  Construction was completed in early 2006 and a grand opening party was held for the membership on June 1, 2006. Highlands Falls was the first in this area to install state-of-the-art Technogym® USA fitness equipment in its facility. 

In October of 2010, a major renovation began on the Clubhouse. The entire interior of the Clubhouse was renovated with the outer shell of the building remaining intact. The kitchen underwent changes to improve its overall efficiency. The existing outdoor deck was expanded and an octagonal-shaped gazebo with a magnificent rock fireplace was added as an extension to the deck. The clubhouse at Highlands Falls currently consists of a spacious dining room, three private dining areas, dance floor, grille room, contemporary kitchen, ladies' and men's locker rooms, golf pro shop, an outdoor deck and gazebo with a fireplace.  

In the spring of 2011, consideration was given to the addition of croquet at Highlands Falls. A location was chosen, utilizing a portion of the area formerly a part of the practice hole on #19, and by September 2011, a rendering of the proposed pavilion was presented to the membership for approval.  It was at this point that discussion ensued on if and how to proceed. No such project was in the budget, and so it was determined that the only way to make this happen would be through voluntary donations. If enough money could be raised to cover the monies required to build the croquet facility, the Club would move forward. So successful was this endeavor that on October 1, 2011 the Club broke ground on what was to become a pavilion complete with fireplace, bar, two lavatories, one small croquet court and one full size court, which could be split in to two smaller courts. The project moved from drawing board to completion in just 10 months.  A grand opening ceremony was held on Saturday, June 2, 2012.