Winter Park Agrees to Five Habitat Homes for School Workers on OCPS Property
Orange County Public Schools, which has launched a broader effort to make affordable housing more accessible to its employees, and Winter Park must still give final approval to the deal with Habitat for Humanity of Winter Park-Maitland
April 6, 2026
By Beth Kassab
When leaders at Orange County Public Schools learned that a house through Habitat for Humanity of Winter Park-Maitland could be available to a district employee, they put out a call for interest at Winter Park and Maitland schools.
“We had 75 people apply in less than a week,” said Bridget Williams, deputy superintendent for executive services.
Stephanie Vanos, the School Board member who represents Winter Park, helped forge the partnership with Habitat when she learned the original would-be owner of a house in the works fell through.
“I really don’t think people realize the need,” she said. “It’s no secret that the school district is having conversations about health insurance right now. I get emails from teachers pretty much every day begging the district not to increase premiums… We’re hearing every day from educators about the unaffordability of their salary.”
Housing is a particular strain on incomes in Winter Park, where home prices and rents trend higher than most of the region, with the median sales price in the 32789 ZIP code exceeding $800,000.
A teacher from Glenridge Middle School was selected to own the Habitat-built house near Winter Park Village and thanked those involved in a letter read aloud at a February School Board meeting.
“This home is more than just a structure. It’s life-changing for me and my family,” wrote the teacher, who asked to remain anonymous.
She also thanked Winter Park High School students who worked alongside her to help construct the house and called working with Habitat for Humanity a “profound experience.”
Now, Winter Park and school district officials are laying the groundwork for five more school employees to own Habitat houses in the city.
The plan would allow five homes to be constructed on a small section at the rear of the property known as the former Orange Technical College on Webster Avenue.
The project would not affect the nearly 500 Orlando Gifted Academy students using part of the property while their Fern Creek school is being renovated.
The Winter Park City Commission recently agreed to the concept of changing the property’s zoning to allow for the homes. It also agreed to use up to $200,000 — originally intended to help Habitat acquire land in the city — to fund water, sewer and other infrastructure for the proposed homes, which would be just east of Whole Foods Market.
“You cannot get a lot in Winter Park for $200,000,” said Mayor Sheila DeCiccio. “So this is a great way to help instead of putting the money toward purchasing land.”
Jeff Briggs, the city’s former planning director who serves as treasurer for the local Habitat organization, said he was enthusiastic about the deal.
“This is a fantastic opportunity,” he said. “The biggest challenge for Habitat is finding land.”
Under the terms, which still must go before the City Commission and the School Board for final approval, the district would lease the land for 99 years, while eligible homeowners would own the structures.
If one of the owners needed to sell in the future, the new buyer would also have to be a district employee and meet Habitat’s eligibility requirements.
Williams said the project aligns with a broader effort by the district to expand access to affordable housing for its workers.
The district has entered into partnerships with multiple apartment developers and operators to provide priority access to OCPS employees who meet eligibility requirements.
And Winter Park would not be the first example of repurposing district property. The former Catalina Elementary School site in southwest Orlando, for instance, is being developed into housing as part of a partnership with the city of Orlando for both school and city employees.
Williams said the goal is to allow teachers, bus drivers, cafeteria workers, custodians and other staff to live in the communities where they work.
“You’re building all these subdivisions, and our teachers are having to drive in,” she said. “That shouldn’t be the case.”
She said seeing the impact of the program has become one of the most rewarding parts of her job.
Like the day the Glenridge Middle teacher learned she would become a homeowner — and that her two children would get their own rooms.
“Just seeing her cry, and her two children — it’s almost like she did not think this would ever happen,” Williams said. “Watching that is what makes it worth it. It’s worth every minute.”
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How do you participate? My family would like to help on these homes
Here’s the website and they offer volunteer and donation opportunities: https://www.habitatwpm.org/