Sibia's Dasmesh LLC bought the land at the northwest corner of Cypress Gardens Boulevard and Cypress Gardens Road in 2015. The property is zoned Highway Commercial, but Investors Realty Chairman John Marling is seeking to rezone the majority of it to Medium-Density Residential for the 258-unit apartment complex.
Marling said new investment in and around Legoland has created demand for more Class-A apartments. His project budget is about $43 million.
"I just think (Winter Haven) deserves a new project," he told GrowthSpotter. "We did (a project on) Lake Ned and then Carlton Arms came in, and there hasn't been much since then. We think it's a great time to do something like we did with The Avenue in Lakeland."
The rezoning application goes to Winter Haven's Planning Commission on Tuesday.
"Our project will have a gated entrance off Cypress Gardens Boulevard, behind the hotel," Marling said. "It's going to be four-story, elevator-served interior corridor product."
The design will be similar to The Avenue apartments in Lakeland, with a mix of one-, two- and three-bedroom floorplans spread among six buildings.
"It's going to be nice," he said. "One building will have the amenities and open out onto the pool, like we have at ChampionsGate."
Other amenities include a dog park and fitness center with the Wellbeats on-demand programming.
Sibia entered the Greater Orlando market in 2017 with a hotel site at 7962 Narcoossee Road, about four miles east of Orlando International Airport.
He told GrowthSpotter he has a deals with Wyndham for a new 120-room Wyndham Garden Hotel and IHG for a Staybridge Suites extended-stay hotel.
"I'm waiting to see if Marling's rezoning goes through," he said. "If it doesn't, I'll do both hotels on that site. If it does, then I'll do one of them on another site on Cypress Gardens Boulevard. I haven't decided which one would go where."
Sibia said he plans to start construction on both hotels next year and expects to open the pair by July 2020.
The theme park has driven new hotel development both on-site, with the opening last year of Legoland Beach Resort, and nearby. Construction is underway now on a 111-room Courtyard by Marriott across from the resort. That developer is planning a second hotel on the site.
Merlin Entertainments Group has also announced plans to build two more Legoland-branded hotels by 2024.