Rolling hills dressed in green sparkling lakes and sunshine brought Dundee its first settlers. A town needs a name and in 1010 a Mr. Menzie from Dundee, Scotland, decreed the tiny settlement here should be called Dundee, after his former home. At that time he also named one of Dundee's many lakes, Lake Menzie. It did not take too long after that for land speculators and developers to what Dundee. In 1911 with the arrival of the Atlantic Coast line Railroad's new Haines City to Sebring branch and the construction of the Dundee railroad station they had a means to bring prospective settlers to get a firsthand view of this beautiful section of Florida. One of the first to recognize Dundee's potential was William W. Shepard of Minneapolis, who with his associates purchased some 14,000 acres of land along the Scenic Ridge from Lake Hamilton to Mountain Lake, including much of present day Dundee. This company, The Highlands Development Co. had two goals: developing citrus groves & selling house lots. They couldn't of accomplished it without the availability of reliable transportation which the railroad provided. Most of Dundee's early growth can be attributed entirely to the railroad. The Highlands Development Co. ran special trains to Dundee bringing hundreds of potential settlers. Those who purchased land were refunded their rail fares. The station, a building 66x26 feet built primarily of Florida pine and cypress, was started on November 2, 1911 and completed just after the first of the following year. Shortly thereafter, Mr. Shepard's organization started their advertising campaign through the middle west and expectant buyers started to arrive at the new Dundee station.

The first settlers to arrive by rail were the Probst & Clark families from Minneapolis, who arrived with their household goods & livestock including two trained mules, not in one of the many passenger cars to bring later arrivals, but in their private, if you don't count the animals, Side Door Pullman. They chose a beautiful tract of land on the east side of Lake Annie and started building their new home. To accommodate the influx of land seekers a large tent was erected near the station soon to be replaced by the Highlands Hotel, a two story structure with broad porches overlooking Dell Lake and the 900 acre citrus nursery and groves of the Glen Saint Mary Nursery Company. In the years to follow trees were to crown the hills of Dundee, but before citrus became king the Dundee area had many stands of tall Southern pine trees. The earliest enterprises in what was to become Dundee exploited this resource. The sawmills of Mr. Nixon and WH Brown, who were to furnish some of the timber for the new depot, and Rayburn's Turpentine Distillery all flourished briefly, but the pines were soon gone and so were they, and the growing citrus took over. The W.C. Lee  Packing House on the shore of Crystal Lake opened to process the fruit. In 1924 Dundee Citrus Assoc. purchased the packing house and in 1929 a new packing house was constructed next to the railroad station. With the advent of the railroad the town grew rapidly. Streets were laid out. main Street was 100 feet wide. 4th Street and 6th Street were clay, paved by a crew under the leadership of Jim Waters. Another early resident  J.P. Lyle laid out many of the other streets and lots for the Highlands Co. He and his bride lived in a tent in the shade of a big camphor tree, which still stands beside the new community center. It was here that  their first child, Louise, was born, the first recorded birth in Dundee.