Luxury-home ambitions meet everyday code problems in Redington Beach

REDINGTON BEACH — Jason Matthews has big plans for this little beach town: as many as 36 luxury homes, part of a broader effort to amass a 100-unit short-term rental portfolio across the Tampa Bay area.

But as the Tampa real estate investor and developer looks to expand, dozens of properties owned by companies he manages have repeatedly landed before Redington Beach's code enforcement magistrate.

In July alone, 23 properties tied to Matthews appeared on a single code enforcement docket for allegedly failing to maintain required garbage service. Special Magistrate Jorge Martin found violations at 22 and ordered service to begin within 15 days.

Six weeks later, another 14 properties owned by Matthews-affiliated companies were before Martin, this time for overgrown grass.

Martin's Sept. 1 order found that all 14 properties had vegetation exceeding the town's 12-inch limit on July 29 or 30. None had been brought into compliance by the Aug. 21 hearing.

Martin gave the companies 15 days to mow or trim the properties before fines of $40 per day per property could begin accruing. Twelve of those 14 companies had also been among the group found in violation of the garbage ordinance in July.

The cases come as the former Pitt basketball player mounts a full-court press with ambitious redevelopment plans in this barrier island town of just 1,463 residents, still recovering from back-to-back hurricanes in 2024.

Through one of his companies, 16 Redington Development, Matthews is marketing a plan to build 36 luxury beach homes and raise up to $6 million from investors. Its website says the company specializes in "premium luxury properties and investment-ready lots in the heart of Redington Beach" and advertises projected annual returns of 20% to 28%, with a $100,000 minimum investment.

Matthews, who could not be reached for comment, has publicly described the homes as roughly 4,000-square-foot properties designed in part for short-term rentals.

In a May 12 article in Board of Advisors Magazine, Matthews said three homes had been completed, three were under construction and another 30 were planned. He said the company expected to sell about 25 and retain 11 as long-term assets.

The 16 Redington website currently lists three completed homes — Taylor's Landing, Brandon's Cove and Casa De Marina — for sale at $3.55 million each. The three-story homes share similar contemporary designs and floor plans, with variations in their exterior colors and finishes.

Those three homes also are being marketed as short-term rentals through MyLux Vacation Rentals, whose website shows Merin Hospitality Group as the operator. Matthews is identified as CEO of Merin Hospitality Group on the 16 Redington website.

The rental listings show the homes are being pitched to families and groups of up to 10, although town code generally limits vacation rentals to a maximum of eight occupants. The site recently showed nightly rates of $523, marked down from $654.

One of the homes, Casa De Marina at 16113 2nd St. E., was the subject of a separate code case over its failure to register as a short-term rental.

‘I didn't know that’

At the July 7 hearing, Matthews appeared and identified himself as managing member of Monica Street Investments LLC, which owns Casa De Marina.

A town code officer testified that the home had been advertised online as a short-term rental but was not registered with Redington Beach. The town had first sent the company a warning in May 2025 and found it still advertised without a registration a year later.

Matthews did not dispute that the registration was incomplete.

He said a property manager had submitted paperwork the previous year but a registration fee of more than $1,000 had not been paid. Matthews told Martin he had discovered the problem two days before the hearing and planned to pay the fee before leaving Town Hall.

“We're very familiar with the process,” Matthews said, noting that his organization has properties elsewhere in Pinellas County. “I thought we took care of all this.”

Martin found the company in violation and gave it 45 days to complete the registration process. If it failed to do so, the order called for a $40-per-day fine.

The remaining cases dealt with something even more mundane: garbage.

Town code officer CJ Withrow said he obtained a list from the town's waste contractor showing properties that did not have collection service, which the town requires for every dwelling and commercial establishment.

Matthews said many of the properties were vacant and he had not realized they still needed service.

“This one is real easy,” he told the magistrate. “I did not know on a vacant property that you actually still need to have waste collection services because we don't have any trash, so to speak.”

At about $22 a month, he said, the cost wasn't an issue.

“So I didn't know that. Now I do,” Matthews said. “My executive assistant can start today on signing up the properties that CJ emailed me that needed to have the service. It's not a problem.”

Rather than repeat essentially identical testimony for each property, Matthews, the town and Martin agreed to handle the 22 cases together. The resulting omnibus order says Matthews was the manager of each LLC and testified that the companies were in violation “due to inadvertence.”

The order gave the companies 15 days to obtain service, after which a $40 daily fine could accrue for each property that remained out of compliance.

The companies listed on the docket bore an assortment of unusual names, many of them bird-themed: Mountain Plover 5, Woodstork 22 and Goldfinch 55 among them.

Florida corporate records identify Matthews as manager or registered agent of numerous companies that own Redington Beach properties. At the July hearing, the magistrate asked whether Matthews had authority to make decisions for all of the cited LLCs.

Matthews did.

A second sweep

By late July, the town had another issue with many of the same properties.

Withrow testified Aug. 21 that he personally inspected 14 properties and found grass or other vegetation exceeding 12 inches. The LLCs that own the properties share the same Tampa mailing address on Platt Street, and the town grouped their cases together as it had done in July. Town counsel told Martin the different LLCs were under the same management and involved the “same gentleman” as the earlier cases.

One was Yellow Jessamine 11 LLC's property at 16110 1st St. E.

“This property is one that I continually monitor just because of the grass issue,” Withrow told the magistrate. “When I pulled up, I could tell the grass was more than 12 inches.”

“An overgrowth case?” Martin asked.

“Yes.”

“For basically the grass?”

“Yes.”

Matthews did not attend the August hearing. Martin took the cases under advisement and later found all 14 in violation.

Five of the properties appeared to have been recently mowed when The Pinellas Current visited them this past week.

Before the hurricanes

The recent cases weren't Matthews' first run-ins with Redington Beach code enforcement.

In April 2025, WFLA-TV reported that the town had previously prosecuted a code case involving a home Matthews was building and had issued courtesy notices involving two vacation rentals he operated that had not completed the town's registration process.

Matthews' interest in Redington Beach, however, predates those disputes — and Hurricane Helene.

A business promotion published Sept. 24, 2024 — two days before Helene struck Florida's Gulf Coast — described Matthews and partner Joe Ebanks as leading an effort to replace aging Redington Beach homes with new luxury residences.

After the hurricanes struck, Matthews' efforts to acquire storm-damaged properties generated controversy.

In the same WFLA report, several homeowners told the station that agreements to sell their storm-damaged properties to Matthews or 16 Redington Development fell apart shortly before closing.

Toray Leonard said she and her husband had dipped into retirement savings to buy another home after theirs was left uninhabitable, only to have their cash deal with Matthews fall through about a week before a scheduled January closing.

Leonard said Matthews' broker cited market conditions and that some other homeowners were later offered substantially less. She also said Matthews had not released the escrow deposit on her failed transaction. WFLA said Matthews did not respond to its requests for comment.

Leonard could not be reached for comment this week by The Pinellas Current. County property records show she ultimately sold the home to John M. Creamer Jr. in August 2025 for $570,000.

By the following year, Matthews was publicly promoting his plans for Redington Beach.

In his interview with Board of Advisors Magazine — the publication of a private peer group for entrepreneurs, CEOs and investors in which Matthews participates — he said the 36 planned homes could be rented individually or combined to accommodate larger groups such as family reunions, weddings and corporate events.

In an ironic twist given his recent code cases, Matthews also recalled that his first business as a child was taking his neighbors' garbage cans to the curb.

His Instagram profile describes him as a “Luxury Beach Home Developer and Real Estate Investor” who operates properties as short- and mid-term rentals.

A biography for E126 Investments, a company owned by Matthews and his wife, Jules, goes further, saying the company is acquiring a 100-unit short-term rental portfolio in the Tampa-St. Petersburg area.

Matthews also has been raising money through other companies.

A June 30 filing with the U.S. Securities and Exchange Commission for E22 Gore Partners LLC, a Matthews-managed company that owns property in Redington Beach, reported that it had sold $1.8 million in equity to one investor through a private offering. The filing classifies E22's business as residential real estate.

E22 was among the companies found in violation of Redington Beach's garbage-service requirement in July.

For all of Matthews' activity in Redington Beach, much about the scope and status of his plans remains unclear.

Exactly how many properties Matthews or affiliated companies now own in the town, how much of the advertised $6 million for the 36-home development has been raised and how far the larger 100-unit short-term rental plan has progressed are among the unanswered questions.

The Pinellas Current emailed a list of questions to Matthews at an address he provided in state corporate records and to the address shown on 16 Redington Development's website.

He did not respond.