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Winter Garden's Dillard Street revamp to prompt millions in redevelopment

Winter Garden City Manager Mike Bollhoefer says the revitalization of Dillard Street will be a boon to developers and the community.

Winter Garden is redoing one of its main arteries and entryways into the city, Dillard Street, a project that will cost the city close to $10 million and lead to hundreds of millions of dollars in estimated private development over the next two decades.

The one-mile stretch of Dillard will be completely torn up to make way for a promenade for cars, pedestrian and bike riders, in what City Manager Mike Bollhoefer calls "probably the last major redevelopment project in Winter Garden."


The city recently contracted for a conceptual design by Toole Design Group, and it shows the roadway going from five lanes to two, with a flex lane in the middle for ease of use and hundreds of trees, shrubs and flowers lining eight-foot-wide sidewalks.

The Dillard Street project is expected to begin in late 2017, and take a year to complete.


"We will go from a gateway that is ugly and industrial to a pathway that encourages new development," said Bollhoefer, who estimates the project at $8 million, which will be paid for by general fund revenue, impact fees and grants if the city can get them.

He projects hundreds of millions of dollars in spending in the coming years by developers, builders, engineers and others in the building trade as they turn the area into a mix of fresh businesses and apartment buildings that will boost the city's tax base.

The project is ripe for Orlando's building community. Not a single request for proposals has been issued, but those are expected to come this fall.

The revamping is receiving a shot in the arm with the recent razing of the run-down Budget Inn & Suites at one of Dillard's entryways, at W. Colonial Drive. Plans by developer Intram Investments are for the lot to be transformed into a multi-tenant center that will include Culver's first restaurant in Orange County.

Bollhoefer said he has already met with "a big developer who wants to build along Dillard," although he would not disclose the company's name.

Bollhoefer also said individuals that know about the project are making overtures about the land along Dillard, in hopes of making a tidy profit when it is sold for construction. He again declined to disclose specific names.

The city is looking for higher-end commercial development, including retailers, restaurants and apartments.

The goal is a cohesive look. Right now, the street contains more of a hodgepodge of industrial buildings, offices, restaurants and some car lots.


The Dillard Street remodeling is the latest in steps the city has taken over the past two decades to improve itself.

Twenty years ago it was full of warehouses and other industrial structures. Winter Garden is now considered a middle- to upper class community whose population base has grown to 40,000 residents, from 9,000 in 1996.

Bollhoefer said the trajectory is for 55,000 residents 10 years from now.

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