JWB Real Estate Capital christened its latest resurrection of a historic property in Downtown Jacksonville on Feb. 23 during a ceremonial opening of The Greenleaf, its new headquarters.
“One of the reasons we wanted to bring our offices down here is that we believe that having our offices Downtown is going to help us attract the best talent so that we can continue to grow our company and grow the city,” JWB President Alex Sifakis said during a ribbon-cutting for the building at 208 N. Laura St.. “We’ve already seen that. The team has been fired up to be in this office for the last couple of weeks.”
The company purchased The Greenleaf, then known as the Greenleaf & Crosby Building, in 2022 for $7 million and spent $17 million renovating it, Sifakis said. JWB moved its offices into the building Feb. 2 from its previous Southside headquarters, bringing 120 workers Downtown.

JWB has orchestrated several Downtown restorations, including the Porter House Mansion at 510 N. Julia St.; the Downtown Seminole Building at 400 N. Hogan St., now Sweet Pete’s candy store; the adjacent Federal Reserve Building at 424 N. Hogan St., which is being built-out into The June private club; and the Baptist Convention Building at 218 W. Church St.
JWB also is a partner in the Gateway Jax redevelopment team, which is led by principal Bryan Moll and also includes DLP Capital. That partnership is developing the nine-block Pearl Square mixed-use development in the NorthCore district north and west of City Hall, which is part of larger plans for a $2 billion-plus development across Downtown.
Greenleaf tenants
At The Greenleaf building, A HiReformance Institute pilates studio is open on the ground floor, and plans call for an Oak Steakhouse in space previously occupied by Jacobs Jewelers, which operated in the building from 1927 to 2023.
Sifakis said an early 2027 opening is expected for the restaurant.

He also revealed new plans for a basement speakeasy that will include a subway-style entrance from Adams Street.
He said the speakeasy would be built-out in 3,500 square feet of space that was formerly used as a shopping area for VIP customers of Jacobs Jewelers.
As with JWB’s other historic restorations, Sifakis said the developers ran into unseen challenges in revitalizing The Greenleaf.
“The degree of difficulty for this one was probably like a 7 (on a scale of 1 to 10),” he said, based partly on the scope of the 66,000-square-foot project and the height of the building. We had to put in new elevators and bring them down to the basement. There was a 100-year-old water barrier that caused a bunch of issues. There are things you find in these buildings, and it never stops. They’re always over budget. It’s critical to have the city and the Downtown Investment Authority as a partner … because we run into so many issues on these older buildings.”
The Downtown Investment Authority approved a $4.97 million forgivable loan package in August 2023 for the project.

‘Just the beginning’
DIA CEO Colin Tarbert applauded JWB for doing “amazing work” on the building and said it and other recently completed Downtown projects are “just the beginning” of a transformation of the historic core.
“Urban living is coming to Jacksonville,” Tarbert said. “I’ll just share that this morning, even though it was cold, I walked to work from the Southbank. And despite the wind on the bridge, it was a wonderful walk. So I think you’re going to see people living Downtown, you’re going to see people working Downtown, even more and more.”
The opening came as the city considers providing $10 million to EverBank to remain in its headquarters building at 301 W. Bay Street, where it employs more than 800 people. Citing a cost differential in operating Downtown versus the suburbs, where parking and security costs are lower, EverBank sought the incentives and said it was exploring offices outside of Downtown.

Proponents of offering the incentives say losing EverBank’s workforce would deter the momentum of Downtown redevelopment. Opponents say the city would set a dangerous precedent in which other Downtown employers might come forward for incentives with a threat to move away.
The DIA board voted against recommending the incentives, which are subject to a City Council vote.
EverBank’s possible departure, combined with a move out of the 301 W. Bay St. building by Citizens Property Insurance Corp., would follow planned moves out of Downtown by Citizens Property Insurance Co. and Regency Centers.
“I can just say it’s been incredible for our team to be down here,” Sifakis said, asked what he would say to a Downtown business that was considering relocating or a business outside of town that might be reluctant to move in. “And I think it’s only more to come. When you walk around Downtown now, you can see things changing. I do believe that in two years, three, four years, being in Downtown is going to be a huge driver for attracting talent to companies. That’s why we moved down here. Because to have the best and brightest, they want to work in a vibrant, urban area.
“And that’s where Downtown is.”