Retail Dining Developments

Winter Park Village slated to get a $50M renovation in 2021

The reimagined Main Street in Winter Park Village will have updated exterior finishes, curbless streets, string lights and outdoor furniture that invites visitors to linger.

It’s been 20 years since Ohio-based mall developer Casto Lifestyle Properties razed the old Winter Park Mall and relaunched it as the outdoor lifestyle center, Winter Park Village.

Now the popular shopping, dining and entertainment complex is due for refresh, and Casto is planning a multimillion dollar renovation in 2021. Casto Southeast Partner Brett Hutchens, who managed the original transformation of the property in 1999, told GrowthSpotter he’s excited to bring the village into the 21st century.


“It’s old. It’s 20 years old, and it’s not as relevant to the consumer as it was 20 years ago from the standpoint of tenancy and just from the standpoint of the general feel and look of the property,” Hutchens said.

The Regal Cinema will get a new light tower reminiscent of the old Winter Park Mall and a new fountain.

The Main Street section between Orlando Avenue and the Regal Cinema would be rebuilt without curbs to provide a seamless transition from the expanded sidewalk plazas. On-street parking will be eliminated in favor of pedestrian spaces. String lights will be draped across the entire area to create a more festive, welcoming atmosphere, and outdoor living room furniture will be placed throughout the property, along with art and light installations.


“Everybody tries to create Instagram moments in whatever public space they have, whether it’s a hotel or a shopping center or a stadium. It’s certainly something that’s in the back of our mind, because it’s so relevant to today’s consumer. But we really want it to be a place of entertainment with restaurants with other activities, the theater — that’s our vision.”

The theater itself will get a new light tower on the roof reminiscent of the old Winter Park Mall and light projections along the west wall. A water feature will go in the plaza where the queue for the ticket windows is now.

Parking spaces along East Avenue will give way to a new grassy park with plenty of outdoor games and places to lounge.

“Regal remodeled the cinema about four years ago, and they went from 3,700 to 1,600 seats and installed a reservation system,” Hutchens said. “And that’s been very successful for them, not only in Winter Park but across the country. So they don’t need those large areas for people to wait in line to buy tickets.”

Pocket parks with outdoor games and kiosks will be added to block in front of the Hangry Bison to North Street. Much of the existing landscaping will be replaced with variegated turf, while special care will be taken to preserve the oak tree canopy. “We want people to stay and linger for a few hours, and we think with what we have planned that can happen,” Hutchens said.

Charlan Brock Architects is leading the design team, in partnership with branding specialist Stephanie Darden Bennett at Prismatic and the landscape architects from Dix. Hite.

All of the building exteriors will be modernized with new rooflines and a cool color palette that mixes in wood tones. Outdoor dining will be emphasized, and tenants will get new signage.

“The design is still a work in progress that we’ve just begun,” Hutchens said. “Probably in the next 30 days it’s really going to take shape.”

David Gabbai and Alexie Fonseca with Colliers International are the leasing brokers. They said the mixed-use lifestyle center was under contract to be sold in March, but the buyer pulled out because of COVID. The sale initially came about because Casto’s longtime investment partner, J.P. Morgan Strategic Property Fund, decided to exit the property.

Hutchens said that rather than putting it back on the market, Casto bought J.P. Morgan’s 50% share of company on Dec. 8. and now plans to move forward with the $50 million renovation plans. Hutchens said that’s just a ballpark number for now because the team hasn’t even put together a preliminary budget.


Mark Fallon with Anderson Real Estate, who leads the leasing efforts for Casto’s Midtown Tampa project, also will help curate the renovated Winter Park Village, Hutchens said.

More than 20% of the roughly 462,000 leasable space is currently vacant, including the former Brio restaurant space. Gabbai said he and Fonseca have lined up national tenants for that space. “We will be shifting a lot of tenants around,” he added.

The largest available slots, 35,485 square feet, is the entire second floor of the D building that stretches the length of Main Street and ends across from the movie theater. The second floor of the C building, also on Main Street, has nearly 17,000 square feet available.

“COVID has probably impacted the office business even more than the retail, but there are opportunities,” Hutchens said. “There are office users in Winter Park that have expressed interest in that space.”

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