New Merrywood Owner is Orlando Businessman Who Also Owns Corkcicle
In addition to the drinkware brand with local roots his interests also include a healthcare staffing firm that serves as a large government contractor
Oct. 7, 2026
By Beth Kassab
Editor’s note: This story has been updated to include comments from Steve Lockwood that were included in a press release from his attorney after the original story was published.
The person behind the limited liability company that purchased Merrywood, a lot on Palmer Avenue, is Steve Lockwood, an east Orlando resident who last year bought the Orlando-grown drinkware brand Corkcicle.
State corporate records also list him as a manager for a healthcare staffing firm that has been awarded $1.9 billion in government contracts, according to a federal database.
Lockwood is meeting with city officials and others in the community about splitting the lot in two ahead of a City Commission vote scheduled for next week.
After this report was first published on Wednesday morning, Lockwood issued a press release through his attorney Jason Searl of Maynard Nexsen.
“My intention when I purchased Merrywood was to create a home for my family, while also considering the possibility of splitting the property with a close family friend,” Lockwood said in the statement. “As I’ve learned more about Merrywood and what the property means to Winter Park, I’ve appreciated the opportunity to have constructive conversations with people who care deeply about its history and its future.”
Commission Elizabeth Ingram is one of the officials he has met with so far.
“It was hopeful that he was interested in hearing more about historic preservation and that there could be potential to save the home,” Ingram said. “I don’t feel we should approve the comp plan amendment without the city getting something back in return.”
Betsy Owens, executive director of Friends of Casa Feliz, said she met with Lockwood and would like to help him find “an elegant solution that allows him to build what he wants to build on the property” while also preserving Merrywood.
“I think what that looks like is where the conversation will take place,” she said. “It was a good meeting.”
Lockwood does not live in Winter Park, and it’s not clear how he became interested in the nearly 4-acre property, which has recently been in the spotlight because it includes a nearly 90-year-old estate designed by James Gamble Rogers II. The home is listed on the Florida Master Site File, an inventory of historic and cultural assets kept by the Division of Historical Resources under the Florida Department of State.
He indicated in his statement that he would like to find a solution that preservationists are comfortable with.
“I bought Merrywood because I saw it as a special place where my family could build a home and become part of the community,” Lockwood said. “I also understand that the property means something to many people in Winter Park. I’m listening, keeping an open mind and hopeful that we can find a path forward that everyone can feel good about.”
Last month, city officials granted an extension on the permit to demolish the house while the property was being sold to Lake Osceola Holdings LLC, the entity that closed on the lot in August for $15 million.
Lockwood is seeking to continue the process of gaining approval to split the lot in two. That would require the City Commission to approve a special carve-out in the city’s long-term development plan, known as the comprehensive plan, which generally prohibits the splitting of lakefront lots. A split would increase the property’s value by allowing two lakefront homes instead of one.
“My client desires to continue with the pending Comp Plan Amendment and will accept responsibility for the application going forward,” Searl wrote to the city in September.
The second of two required commission votes to finalize the change to the comprehensive plan is scheduled for Oct. 14. The first vote on June 24 was 3-2 in favor of the lot split with Mayor Sheila DeCiccio and commissioners Kris Cruzada and Craig Russell voting yes and commissioners Warren Lindsey and Ingram voting no.
Lockwood’s LinkedIn profile lists him as the principal owner of Corkcicle and a graduate of the University of Central Florida. In state business records, he is listed as a manager or director for a number of companies, including Corkcicle Capital Group LLC, created in 2025, and Corkcicle Capital Group Holdings LLC, created earlier this year.
Cascadia Capital, an investment bank, announced last year that Corkcicle had been acquired by a private investor group. The company, which started in Orlando’s College Park neighborhood, sells stylish reusable water bottles and coffee thermoses, plus coolers, barware and more. Its website says it has collaborations featuring designs from Winter Park-based Rifle Paper Co., Disney and others.
Lockwood is also listed as a director or manager for Loyal Source Government Services and Loyal Source Worldwide. Orlando-based Loyal Source, founded in 2009, describes itself as a privately held healthcare, workforce, technology and mission-support company. In 2021, for example, the company provided “turnkey medical services to more than 20,000 Afghan evacuees at Camp Atterbury, Indiana and Fort McCoy, Wisconsin,” according to its website. The site also says the company provided care and services at a temporary shelter in Texas, under a government contract, to unaccompanied migrant children arriving at the U.S. border.
USAspending.gov, the federal database of government contracts created as a public access tool by the Federal Funding Accountability and Transparency Act of 2006, lists $1.9 billion in contracts to Loyal Source Government Services LLC since 2009. Most were awarded by the Department of Veterans Affairs, followed by the Department of Homeland Security, for services such as medical evaluations and screenings, nursing services and medical coding.
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