Currently undergoing a substantial rehabilitation to update mechanical systems and retain historic architectural features that make this building one of the finest in the downtown Historic District, The Greenleaf will provide 44,000 square feet total of leasable space. The building received local landmark status in October 2023.

The Oak Steakhouse intends to open on the first floor in the former Jacobs Jewelers space. Indigo Road Hospitality Group announced that the steakhouse will open in early 2026. Regus coworking currently leases space on the eighth and ninth floors.

JWB Real Estate Capital anticipates using the second, fourth, fifth, 11th, and 12th floors for its headquarters. The project cost for four of the company’s targeted five floors is almost $2.53 million. Interior build-out permits were issued June 2025.

The building was completed in 1927 and is one of the few remaining examples of the mixed-use commercial buildings constructed in Downtown soon after the Great Fire of 1901. It was designed by Marsh & Saxelbye, a prominent local architecture firm during the Florida land boom.

The Downtown Investment Authority approved a $4.97 million forgivable loan package in August 2023 for JWB to finance improvements at the building at an estimated cost of $16.88 million.