Updated January 22, 2021

Oakland is a small town of about 2,500 people just west of Winter Garden Florida.  

Classic Home on Old State Road 50, OaklandClassic Home on Old State Road 50, Oakland

It is also on the southern shore of Lake Apopka and a stop on the West Orange Trail, a popular "rails to trail" bike and pedestrian path in this part of Central Florida.


Oakland began to boom when the Orange Belt Railroad came through town in the 1880's.  The biggest shareholder in that railroad was Peter Demens, who ended up running the railroad to St. Petersburg.

He named St. Petersburg after his hometown in Russia.

Oakland's economic fortunes began to decline when the railroads pulled out of town more than 100 years ago.  The great freezes of 1894 and 1895 killed most of the citrus groves, and the railroads had nothing more to ship. 

Then along came a fire in the late 1890's that destroyed most of the downtown. 


The route of the original railroad is now the West Orange Trail, a favorite of walkers and hikers from everywhere.

Oakland Town HallOakland Town Hall

Most people who live in this town don't want to go back the booming old days in Oakland.

Home in Oakland, FloridaHome in Oakland, Florida

It is primarily a residential community, and the residents prefer the quiet serenity that now prevails. 

You will enjoy a visit to this quiet little Old Florida town.


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Mike Miller of FloridaBackroadsTravel.com has written 25 books on Florida.  

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