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Developer Jim Karr and Westgate’s Jim Gissy reignite plans for commercial development in downtown Windermere

The 2.2-acre lot sits across from a new 11,000-square-foot municipal town complex under construction.
The 2.2-acre lot sits across from a new 11,000-square-foot municipal town complex under construction. (Orange County Property Appraiser)

Downtown Windermere may be getting more commercial space.

Veteran developer Jim Karr and business partner Jim Gissy, executive vice president of Westgate Resorts, are pushing forward a development plan that would essentially triple the amount of commercial space they own along Main Street.

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The property, located on at main entrance into Windermere’s town center, currently contains two single-family homes, the office of Keene’s Pointe Realty and Allen’s Creamery & Coffee House, Elysium Interiors and a hair salon.

Town planner Wade Trim received preliminary development plans and an application to rezone the property from the partners last month. The plans go before Windermere’s Development Review Board Feb. 16. From there, plans are scheduled to go before the Town Council in March for a first public hearing.

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Karr and Gissy are seeking to demolish the existing structures and develop up to 21,850 square feet of commercial space. Conceptual plans breaks down the development to 6,600 square feet of office space, 11,500 of retail space and 3,750 square feet of restaurant space.

The massive mixed-use project covers over 700 acres. It's also approved for 800,000 square feet of commercial and office development.

Karr told GrowthSpotter he and Gissy plan to hold onto the properties for the long-term and fill up the space with local businesses that can help serve the Town of Windermere.

At least one property within the assemblage has been in Karr’s family since 1989. Before moving to a home on the west side of Lake Butler, Karr spent most of his life living in Windermere.

The town is where his mom and oldest son live, among other relatives, he said. “It’s changed a lot. There just hasn’t been much development.”

The town hosts weekly farmers’ markets and, prior to the pandemic, monthly food truck events. It’s a growing small town, but it has not added more space for new businesses, Karr said.

To move forward project would have to stay consistent with the requirements of the Town Center Overlay District and provide appropriate access, away from the neighboring residential properties. Town staff members have also discussed preserving Heritage Oak trees and a 20-foot buffer and masonry wall along Oakdale Street to separate the development from neighboring homes.

Most of the properties were acquired by Karr and Gissy in 2009 for $500,000, records show. According to an article by the West Orange Times & Observer, former owner Kevin Azzouz of Kosta Holdings tried and failed to approve a proposed 63,000-square-foot development called Main Street Shoppes.

Across the street from the property, the Town of Windermere is currently building a new 11,000-square-foot municipal town complex that will hold its town administration building offices, police facilities and public works department.

Karr is a local real estate developer and major landowner throughout Central Florida. He’s working with Lennar Homes which plans to build nearly 2,000 homes on property he owns in Clermont for a master-planned community called Wellness Way, near Disney.

Apart from his role in Westgate, Gissy is also an early investor of First Green Bank. He and Karr often work together in real estate deals.

Editor’s note: A previous version of the story misstated a quote by Karr saying his brother lives in the Town of Windermere. His brother lives in North Carolina.

Have a tip about Central Florida development? Contact me at arabines@GrowthSpotter.com or (407) 420-5427, or tweet me at @amanda_rabines. Follow GrowthSpotter on Facebook, Twitter and LinkedIn.

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