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  • Old Dixie Highway

    201 Freeman Street

    What is now 427 / Ronald Reagan used to be part of the Sanford-Orlando Road, and the original Dixie Highway (17-92 path became the new Dixie Highway in 1927). Roads […]

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  • Florida Midland Railroad

    Modern Remnants of the Florida Midland Railroad You may notice that West Florida Avenue is slightly odd through the historic district. It is placed at a half-block increment between Jessup […]

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  • Original Longwood Hotel

    111 North Longwood Street

    The first hotel in Longwood was located at the southeast corner of East Warren and Longwood Avenue. Town founder Edward Henck built the wooden structure to handle the influx of […]

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  • Old Markham Road

    Seminole County residents will generally recognize the name “Markham” as part of the prominent north-to-south Markham Woods Road running along the west side of I-4 from west of Sanford to […]

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  • City Hall

    175 W Warren Ave

    The current Longwood City Hall and municipal complex opened in 1964 and have been serving continuously since. Prior to that, city hall was two blocks south on Wilma Street at […]

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  • Reiter Park

    Reiter Park was created by the City of Longwood in 1980. It was named for longtime, prominent citizen Jimmy Reiter. The park was on land previously owned by the Reiter […]

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  • Ed Myers Recreation Building

    Today it serves as a convenient parking lot located across the street from the current Longwood Community Building. However, on this well-landscaped lot is where its predecessor used to live. […]

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  • Waits House

    402 Wilma Street

    This home was built in 1910 as a residence for the Waits family. James Mumford Waits (1857-1922) lived here with his wife, Louise (1871-1947), and his four daughters: Evelyn, Lillian […]

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  • Bistline House

    241 West Bay Ave

    This one-story home was built in 1920. It is the typical stucco on wood frame. Gable roofs with wide overhangs, tapered porch columns on brick masonry piers and three-over-one double-hung […]

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  • 140 Pine Ave

    140 West Pine Avenue

    Built in 1930 This home is not part of the walking tour, but maybe it should be. More research is needed into its history.

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