Historic District

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  • Longwood ACL Train Depot

    This old train depot was located near the southeast intersection of Church Street and 427, immediately behind the Henck-Tinker block (former bank building, now a bar). According to sources, it was first constructed around 1900. However, it looks very similar to the depot in the 1885 aerial drawing of Longwood, so one has to wonder if it was built closer to 1880 (when the rail line first connected Sanford and Orlando via Longwood). To be clear, the old Longwood train depot still exists, but it’s now located a few hours away. In 1965, the depot was given to a train…

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  • Heroes’ Park

    In front of the Longwood Police Department and overlooking Reiter Park, we find Heroes Park. It was constructed in 2005. This round resting spot at the northeast corner of Church and Milwee remembers our fallen heroes: first responders and military. It was dedicated after the tragedy at the World Trade Centers on September 11, 2001.  A piece of the World Trade Center was given to the City of Longwood and then added to this memorial. You will notice a blank space between the three granite pillars on either side of the thin pillar. Look at it again and focus on…

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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 in the old days did not use to be as straight and smooth as today. They were more meandering and often took angles, especially in towns. This section between Sanford and Winter Park was paved in brick in 1916. Where the modern highway takes a smooth jaunt to the northeast toward Sanford, the old road took a line through what is now this brick neighborhood road. It then took a…

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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 Ave and Magnolia Ave. There are a few driveways off of it, and most homes and businesses’ backs face it instead. That’s because it was not originally a road but the right-of-way of the long-defunct Florida Midland Railroad. 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…

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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 prospective settlers and tourists coming down the Sanford-Orlando road via steamboat landing in Sanford.  The structure was built in 1883 and should not be confused with the Longwood Inn. It was sold to Henry Hand. It occupied roughly the same footprint that the gymnasium complex today occupies; however, it was oriented to face north on Warren Avenue, the main road through town. This hotel had fewer rooms than the more…

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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 Longwood. This route used to connect the no longer existent town of Markham to Longwood. It roughly followed the routes of modern Markham Woods, EE Williamson, Rangeline and West Church Avenue. In fact, albeit misplaced no where near Longwood, there is a stretch in northwest Seminole County still bearing the name “Longwood Markham Road.” So as West Church Avenue oddly diverges from its generally straight east-west route to a northwesterly curve…

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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 what is now the Old Longwood School. The building has served the town well for over fifty years, though it has drawn criticism for not matching the historic motif of the surrounding district and that ordinances require. Its architecture is a typical mid-century block structure. Historic Photos

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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 family, who homesteaded on 30 acres off of Warren Avenue in 1919. Much of the land that is now the park was at one time swamp and muck land, which was gradually filled in or drained through the construction of drainage ponds. Jimmy Reiter donated to the City the one-acre parcel that is now the fire department; the city purchased the adjacent 4 acres for the park from Reiter at…

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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. For generations, the building served host to many events and meetings. It was built in 1935 and lasted until 2002, when the new Victorian-style community center was constructed. Originally, it only had a roof; the open-sided recreation area had shuffleboard courts and other outdoor type activities. However, in the 1960s it was enclosed and for years hosted events of all sorts from parties and weddings, to church functions and musical…

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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 Elizabeth, Olive, and Adrienne. The Waits family moved to Longwood from North Carolina. He was a general store merchant. Their oldest daughter, Lillian (1895-1981), was a teacher at the next-door Longwood Schoolhouse. Originally the house probably consisted of a low-pitched hipped roof covering a square plan, surrounded on at least two sides with an open porch and a separate open garage. Due to extensive modifications, today the original house is…

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