History
View a “Timeline of Historic East Winter Garden Neighborhood” of improvements made since the creation of the Winter Garden Community Redevelopment Agency (CRA) in 1992.
View a Map of Historic East Winter Garden Neighborhood indicating the officially designated named area per resolution passed by the City of Winter Garden Commission on February 8, 2024.
East Winter Garden developed as the African American community of Winter Garden in the first decades of the 20th century. Land was sold to African Americans in the present Center Street area, which was considered the lowlands. At the time, Center Street was nothing more than a bumpy dirt road connecting to Plant Street but would eventually evolve into the heart of the community. Many of the first residents moved to the area to take advantage of the pine forests, harvesting pine tree gum, and turpentine. The citrus industry was also prominent in attracting residents, with several packing houses providing employment.
Grove workers, c. 1925
Two larger developments also helped to shape East Winter Garden in the early years. In 1910, the area bordered by Ninth, 11th, and Plant streets was platted by J.S. Loveless, as the Loveless Addition to Winter Garden. In the early 1940s, Big Quarters (near the intersection of Ninth Street and East Plant Street) was developed as an area to house African American farm and packinghouse laborers.
Bethlehem Missionary Baptist Church, c. 2018
Places of worship have played an important role in community life since the early days of East Winter Garden. Several churches were built early on, including the Bethlehem Missionary Baptist Church, the Free Will Baptist Church, and the St. Paul African Methodist Episcopal Methodist Church. Schools were founded soon after the area was settled, utilizing space at the churches until the Winter Garden Colored School opened in 1923 on Center Street.
Staff at Winter Garden Colored School, c. 1935 (front row, l-r: William S. Maxey,
Azalee W. Holt, unknown, T.H. Charlton, unknown; back row, l-r:
Juanita Maxey, Clara Ware, Alberta Combs, Caleste Boyd)
With the onset of integration and changing social mores, many early East Winter Garden residents opted to move to other neighborhoods throughout Central Florida, and most of the businesses along Center Street eventually closed.
The history of East Winter Garden is rich with trailblazers, laying the foundation for those that have come after. Longtime East Winter Garden resident Charles Alexander King became the City’s first African American officer in 1967. He served the East Winter Garden area throughout his stay with the Police Department which ended in 1970. King continued to live in East Winter Garden until his death at 84 in 2020. The entire King family had a positive influence on East Winter Garden since the 1920s. His grandfather, Jimmy King, moved to Center Street in 1924, and encouraged blacks to vote and fought for higher wages, nearly sacrificing his life in his attempt to do so. Charles and his brother, James King (also an East Winter Garden resident), developed a club to teach black males about society and how to be successful. Jimmy King’s cousin, Egirtha Marion, owned a restaurant and boarding house on 10th Street where black baseball players stayed when the Washington Senators team was in Winter Garden for practice and games. She donated her land to the City to create a children’s park.
Charles King, first black officer for the Winter Garden Police Department (1967-70),
and his wife attend the East Winter Garden Photo Exhibit at City Hall, in which he was honored, c. 2020
Many community institutions and streets now bear the names of early East Winter Garden figures, such as the Maxeys and Mildred Dixon and Carolyn Anderson.
Juanita Coney Maxey was a prominent resident and educator in the community, and in the 1930s became the first African American woman to vote in Winter Garden. Her husband, William Maxey, was a long-time principal of the Winter Garden Colored School where she taught. During the many years of the Maxeys’ leadership, educational institutions in East Winter Garden expanded to gradually establish the large Charles R. Drew High School campus. Their legacy is honored at the Maxey Community Center, located at 830 Klondike Avenue, which serves as a valuable resource to the community. Additionally, Maxey Elementary School bears their name.
A more recent prominent resident was Mildred Dixon (1923-2006), the first elected woman and first elected African American to the Winter Garden City Commission, and the first African American to serve in any political position in West Orange County. She served on and off the Commission for a total of nine years, from 1985 to 1992 and again from 2001 until her death in 2006. Her namesake lives on via Mildred Dixon Way in East Winter Garden and the Mildred Dixon Community Center at 303 S. West Crown Point Road.
Winter Garden Commissioner Mildred Dixon
alongside city officials soon after being elected, c. 1985
Dixon’s vacated seat was filled by another prominent East Winter Garden resident, Charlie Mae Wilder, who served as District 3 Commissioner from 2006 to 2007 to complete Dixon’s term. History continues to be made with current East Winter Garden resident Chloe Johnson starting a four-year term as the City’s District 3 Commissioner in April 2024.
Charlie Mae Wilder, c. 2016. Longtime resident advocate for
East Winter Garden and former Winter Garden Commissioner (2006-2007)
George and Annie Bell Dyson at Dyson’s Taxi Stand, once located on Center Street
Ownership of the Dyson Plaza has remained in the Dyson family since 1939, when George Dyson and his wife Annie Bell Dyson first purchased it. Originally, it was a Beer Garden/Juke Joint, providing a neighborhood option in the 1930s for the predominately African-American laborers to unwind and dance after a hard day’s work. Dyson Plaza has remained in the family for four generations, housing the Dyson Taxi Service, Dyson Ice House, and Dyson Short Stop Convenience Store through the years. Most recently, Taste of Tasha restaurant, Mr. D’s retail store, and A & E Grocery Store were on the site. For 80+ years, Dyson Plaza has continuously served as the core of commerce for the East Winter Garden community, as well as a place for hopeful entrepreneurs, mainly African Americans, to launch their business. A revitalization of the 2,300-square-foot Dyson's Plaza building will be completed in spring 2025 providing an opportunity for new business growth within the community.
The history and legacy of East Winter Garden residents continue to live on in this historic neighborhood.