While attending ICSC@FLORIDA in Orlando—and spending some additional time in Winter Park—I spoke with a Park Avenue merchant who mentioned that “some group called the Bendersons” had purchased the historic Park Plaza Hotel.
ORLANDO — While attending ICSC@FLORIDA in Orlando—and making the short trip to Winter Park—I spoke with a Park Avenue merchant who mentioned that “some group called the Bendersons” had purchased the historic Park Plaza property.
That immediately caught my attention because I knew exactly who the Bendersons were.
Benderson Development is the company that purchased Park Plaza; it is not the name of a new development. Park Plaza is the existing, century-old mixed-use property at 307 South Park Avenue, with shops at street level and the Park Plaza Hotel above.
Benderson acquired the property in an off-market transaction that closed September 25, 2024, for $16.25 million. Transaction reports described the building as approximately 25,000 square feet, producing a price of about $650 per square foot. The Orlando Business Journal reported that the hotel has 28 rooms, while CoStar reported the sale and calculated the approximate per-square-foot price.
Benderson also described Park Plaza as a 28-room boutique hotel with ground-floor retail. When announcing the acquisition, the company said it intended to enhance the Park Plaza experience while ensuring that it remained a beloved destination.
The building dates to 1922. According to the Park Plaza Hotel’s history, it was designed by architect Peter C. Samwell and originally operated as the Hamilton Hotel. After the Spang family acquired the property, it underwent a major renovation during the late 1970s and became the Park Plaza Hotel.
That history matters because Park Plaza is more than a conventional hotel or retail building. Its balconies, intimate storefronts and position near Central Park have made it part of the visual and commercial identity of Park Avenue. It is a property whose value cannot be understood through square footage alone.
My interest in the acquisition was also personal.
During the recession of the early 1990s, I had the opportunity to spend time with the late Nathan “Nate” Benderson during one of the company’s earlier rounds of Florida shopping-center acquisitions. Working in association with Marine Midland Bank—which was already owned by HSBC and was later renamed HSBC Bank USA—we presented the Bendersons with five Florida shopping-center opportunities.
Owners were scrambling, values were falling and commercial real estate looked like a disaster to many people. Nate Benderson saw opportunity.
He was a bright, enthusiastic and engaging companion during our daylong trip across Florida to inspect the properties. Benderson ultimately acquired the shopping centers at excellent prices and transformed them into successful real estate investments.
That experience taught me something about how the Benderson organization evaluates real estate. The company does not simply look at what a property is producing today. It considers what the property could become under patient ownership, disciplined leasing and stronger execution.
The organization has grown considerably since those early acquisitions. According to Benderson Development, the privately held company now owns more than 1,000 properties totaling over 55 million square feet across 40 states.
Its University Town Center development in the Sarasota area offers a particularly relevant example. The project began in 1998 with the acquisition of a struggling outlet center and approximately 500 surrounding acres. Today, the UTC district reports more than 4 million square feet of development, including over 250 shops, more than 80 restaurants, hotels and office space.
Park Plaza is a much smaller property, but the underlying investment principle appears similar: acquire something difficult to replicate, improve its performance and hold it with a long-term view.
The acquisition also fits within Benderson’s continuing Florida expansion. In August 2026, the company announced three additional retail acquisitions in Dunedin, Venice and Estero totaling approximately 400,000 square feet. Park Plaza may be one of the smallest assets in that growing portfolio, but its Park Avenue address gives it an importance far beyond its physical size.
At the same time, meaningful investment in a historic retail district inevitably creates tension between economic performance and local identity.
That tension became visible in June 2026 when Tuni, a locally owned fashion boutique that had operated on Park Avenue for approximately 40 years, announced that its lease would not be renewed. The boutique said a national retailer was expected to take over its Park Plaza storefront, although the incoming tenant had not been publicly identified. FOX 35 reported that Winter Park officials hoped Tuni would find another location along the avenue.
The departure does not negate the potential benefits of Benderson’s investment, but it does illustrate the responsibility that comes with owning an irreplaceable property. Park Avenue succeeds because it combines national-quality retail, independent businesses, hospitality, public spaces and architecture that feels distinctly connected to Winter Park. If that balance disappears, part of the avenue’s economic value disappears with it.
Winter Park is confronting the same challenge in its public realm. The city is currently undertaking a multiyear Park Avenue Refresh Project intended to improve infrastructure, pedestrian safety, landscaping and aesthetics while maintaining the corridor’s traditional character.
Private investment in Park Plaza should be considered within that larger context. The goal should not be to freeze the property in 1922 or prevent it from evolving. Older buildings require capital, updated systems, competitive tenants and operational improvements. The challenge is making those improvements without removing the qualities that made the property valuable in the first place.
At approximately $650 per square foot, Park Plaza may appear expensive when evaluated through a conventional real estate calculation. But exceptional Park Avenue locations do not trade like ordinary buildings. The opportunity lies in the combination of history, hotel accommodations, street-level retail, pedestrian activity and a prominent position within one of Florida’s most successful downtown districts.
It is fitting to revisit the acquisition while ICSC brings retail real estate professionals together in Orlando. Benderson’s investment demonstrates one of commercial real estate’s enduring lessons: exceptional locations may appear expensive today, but thoughtful ownership, patient capital and strong execution can create lasting value.
I hope Winter Park gives Benderson reasonable flexibility to reinvest in the property while holding the company accountable for preserving the character that makes Park Plaza special.
My experience tells me that the Benderson organization knows how to recognize opportunity and create value. How it balances renovation, tenant mix, financial performance and preservation at Park Plaza will determine the rest of the story.
Stay tuned.
