You may notice West Florida Avenue through the historic district is slightly odd. It is placed at a half-block increment between Jessup Ave and Magnolia Ave. There are few drive ways off of it and most homes and businesses’ backs face it instead. That’s because it was not originally a road but a railway. There is a tiny alley-like companion to this called East Florida Avenue on the east side of the tracks, behind some houses’ backyards. There is a small gap, and then its effective continuation is East Magnolia past the Church of the Nazarene.
This was the rail bed of the short-lived and long-defunct Florida Midland Railroad. It was incorporated in 1883 by Carl Cushing, Edward Henck, and S. W. Brewster. The original plan was to run from the Indian River on the east coast to St. Petersburg on the west coast. However, the plans changed, and it ran from Lake Jessup in Winter Springs, through Longwood, past Lake Brantley, to Apopka, and then swung southward and east again past Windermere and to Kissimmee. The Sanford and Indian River Railroad through Winter Springs and Oviedo did not permit them to cross its right of way, so the line never continued past Winter Springs.
The railroad did not last long. Its prospects dried up with the Great Freeze of 1895. It became part of the Plant system of railroads after its insolvency, and the part of the line through Longwood was abandoned by the turn of the century. Its right of way was converted to neighborhood roads, the southwest slanting section of Warren Avenue, and then Highway 434’s path westward to the Little Wekiva River bridge.
The community of “Altamont” (not Altamonte Springs) was located at I-4 and 434. During the 1880s and 1890s, this was the Florida Midland and Orange Belt Railroads intersection. This is marked today by the Seminole-Wekiva Trail (Orange Belt Railroad) and Highway 434 (Florida Midland Railroad) crossing.