It was one of the longest narrow gauge railroads in the United States at the time of its completion in 1888, with a mainline 152 miles (245 km) in length between Sanford and St.

[1] It carried citrus, vegetables, and passengers; and it interchanged with two standard gauge lines: the Jacksonville, Tampa and Key West Railway at Lake Monroe, and the Florida Central and Peninsular Railroad at Lacoochee.

[2] The railway changed hands several times in its early years due to debt run up during various phases of construction and a citrus freeze that affected freight cargo.

The Orange Belt Railway line brought settlers to towns along its route and fostered development in the region.

They purchased $9,400 worth of crossties from Russian immigrant Peter Demens' sawmill in Longwood, and had to turn over their railroad when they were unable to pay.

[5] Demens formed the Orange Belt Investment Co., borrowed money from friends, and launched a $50,000 bond issue to complete the rail line to Oakland, east of Clermont.

Demens agreed to move the headquarters and train maintenance shop of his Orange Belt Improvement Co. to Oakland from Longwood.

[5] Soon after the first train reached Oakland in November 1886, Demens decided to extend the line 110 miles to the Gulf of Mexico.

[5] The Armour meat packing family in Chicago helped fund the line's extension from Trilby to San Antonio (Florida).

[9][10] The rail line played a major role in the development of several towns along its route including San Antonio, Sutherland (now Palm Harbor), Ozona, Dunedin, Clearwater, and Largo.

Once in control of the line, the Plant System immediately converted the most profitable section of track, from Trilby to St. Petersburg, to 4 ft 8+1⁄2 in (1,435 mm) standard gauge.

[17] In 1980, the Seaboard Coast Line's parent company merged with the Chessie System, creating the CSX Corporation.

In 1986, the company announced its intention to abandon more of the remaining Orange Belt line between Tarpon Springs and Clearwater, which had not seen any rail traffic since the early part of the decade.