East Winter Garden’s resurgence

The city has a plan in place to rejuvenate its east-side residential area in a multi-year project designed to offer safe, quality, affordable housing.

  • West Orange Times & Observer
  • News
  • Share

Fourteen homes, mostly on Center and Klondike streets, have been demolished so far in the Winter Garden Community Redevelopment Agency’s final major project.

The city established the CRA in 1992 to improve the commercial and residential viability and livability of the business district and neighborhoods within the established CRA area. East Winter Garden is within the CRA.

“Over the past 15 years we have spent several million dollars in the community improving the infrastructure, parks and invested .5 million dollars to bring the Magic gym to the community,” City Manager Mike Bollhoefer said. “The housing project is the next step in the revitalization of the community. This will help to clean up the community, make the neighborhood safer and improve the quality of life for the residents.”

In tearing down these houses, all considered blighted and unsafe, the city worked with the property owners after the community asked the city to intervene. The city paid for the demolition and then placed a lien on the house for the demo work. When the property is sold, the city will recoup its investment.

“To keep it affordable, the city could waive what we've spent as part of the economic development,” Bollhoefer said.

Winter Garden has also been obtaining properties, mostly on Center and Klondike, with the idea of rebuilding on these lands.

“We would keep it residential; we would design it to look like cottages so it would have personality,” the manager said. “By putting together a group of partners, we can build quality homes that are aesthetically pleasing and are also affordable. This year we budgeted $200,000 for building houses in east Winter Garden on those properties owned by the city.”

Another idea is to partner with West Orange Habitat for Humanity on the redevelopment.

“The critical part for us, though, is not just housing and affordable housing, but it has to be quality housing,” Bollhoefer said. “You're not giving them a square house with block and no personality.”

But in doing so, the city is being careful not to create gentrification, a trend in urban neighborhoods where increased property values end up displacing the lower-income residents or businesses.

Home construction is expected to begin before October, he said. The life of the CRA ends in 2023.

“So by 2023, we would like to see significant impact on the community,” Bollhoefer said.



The Winter Garden Heritage Foundation has several documents on file that detail the history of east Winter Garden, written by folks who once lived and raised their children there.

East Winter Garden was established when Florida's black turpentine still workers moved to the area in search of jobs after the still work ended. Among the first pioneers were W.H. and Annie Powells, Reid and Sarah Toney, F.J. and Pidy Nichols, Tyre and Martha Williams, Joe and Ida Drayton and West and Sally Coleman. In time, the community expanded with the addition of Doc and Rosa Massey, the Rev. Neil and Maggie McMillian and Ed and Lilla Jones.

The first black baby born in Winter Garden was Carolyn T. Anderson, a lifelong resident who raised eight children, many of whom built careers in education.

Blacks were sold land in the present Center Street area, considered the lowlands. There were no streets, and Center Street was a wide bumpy road that led to the present Plant Street.



One of the first orders of business was to build a house of worship, and soon the Baptist Church, Free Will Baptist Church and the Methodist Church were part of the community. Residents alternated churches from week to week.

Schools soon followed, and the Baptist Church was used as the first school, with Alzora Caldwell teaching. Books bought from A.B. Newton were carried in bags made by the students' mothers. Students took their lunches in tin buckets and sat under a tree to eat lunch, and they all drank water from a dipper in a tin bucket.

When the school outgrew its location, students were split between schools at Free Will Baptist and Bethlehem Missionary Baptist churches. Sixth-, seventh- and eighth-graders attended school in Ocoee until the 1920 riot.

The Winter Garden Colored School opened in 1923 on Center Street with two teachers.

William S. and Juanita C. Maxey arrived in Winter Garden in 1937, and he became principal of the school, maintaining that position for 28 years. She taught there for 45 years.

When black students finished the eighth grade, they had to ride the city bus to Jones High School, in Orlando, to complete high school. Ninth and 10th grades were added to the Winter Garden school in the early 1950s, and the school was renamed Charles R. Drew Junior High. Grades 11 and 12 were added in the late 1950s, and the word “junior” was dropped from the name.

The elementary was separated from the junior-senior high in 1965, and the new school was named for William S. Maxey.

Drew High closed in 1969; it is now the home of Westside Tech.



Winter Garden's agricultural economy spawned the development of several laborer quarters in various areas of town. One, known as Big Quarters, developed by M.C. Britt and G.T. Smith in the early 1940s, was just east of town, in the existing black community that developed in the first decade of the 20th century.

Bordered by East Plant Street, Klondike Road, 12th Street and East Ninth Street, the area was established to house black farm and packinghouse laborers. Most of the section was redeveloped with new housing in the 1970s and ’80s. 


Related Articles