Old Town Kissimmee is marking its 40th anniversary this year under new ownership, and the merchants who have watched the retro-themed entertainment district through its ups and downs say they're ready for a change. Todd and Radha Rambilas, who own RS Equity Services of Orlando, bought the 20-acre open-air shopping and entertainment hub for $24.5 million in September 2026, and they say they want to preserve its nostalgic character while adding new experiences and refreshing its tired spaces.
According to the Orlando Sentinel, Radha Rambilas said by email that the owners want Old Town to remain welcoming to visitors while improving and strengthening its connection to the community. She's also considering building an annual calendar of events celebrating Central Florida's diverse cultures and traditions, potentially including celebrations inspired by Diwali, Holi and Caribbean holiday traditions, featuring authentic cuisine, music, local vendors and family-friendly activities. Rambilas said local businesses, artisans and cultural organizations should have opportunities to showcase their traditions and introduce visitors to new experiences.
Coverage of the sale elsewhere has varied on the exact purchase price. GrowthSpotter reported the Rambilas family paid $24.45 million, while the Orlando Business Journal put the figure at $24 million in a deal that closed Sept. 16 and encompassed a majority of the district at 5770 W. Irlo Bronson Memorial Highway. Fox 35 Orlando, citing Osceola County records, reported the price at almost $24.5 million.
A District Built on Nostalgia, Now Changing Hands Again
Old Town has deep roots in Kissimmee's tourist corridor. The district has dozens of shops, restaurants and bars, plus an arcade, a virtual reality arena and a walk-through haunted house, per the Sentinel. It includes an 86-foot-tall, Italian-crafted Ferris wheel and totals about 132,000 square feet of retail, dining and entertainment space. The property added new shops and restaurants in 2020, and the site hosts weekly gearhead gatherings that have become local institutions: a muscle car show and cruise on Friday nights, a classic car show and cruise on Saturdays, and a motorcycle bike show on Wednesdays.
Before the Rambilas family took over, Old Town was owned by The Travel Corp., which invested $20 million in improvements after buying the site in 2014. GrowthSpotter reported the property was approximately 95% occupied at the time of the September sale, and that the Rambilas company will keep the current Old Town staff, including Vice President and General Manager Thearon Scurlock, while taking over leasing and property management.
No Immediate Changes, But Expansion on the Horizon
Fox 35 Orlando reported there are no immediate changes planned for current businesses or for regular events like the weekly classic car shows. But the new owners have signaled bigger ambitions down the road. GrowthSpotter reported that the owners plan to invest in improved common areas, new experiences and refreshed spaces, with an eye toward bringing in mom-and-pop businesses with loyal followings, food vendors, and experience-type tenants such as mini-golf, ax-throwing and paint-and-sip venues.
Todd Rambilas told the outlet the car shows and cruises that already draw crowds to Old Town are a priority for expansion. “Part of our plan is to basically double down on that and expand more into it,” he said, per GrowthSpotter. Separately, WESH reported that longtime merchant Cheryl Hill said Old Town's business has recently been on the rise after slow and difficult years, adding, “now it seems to be on the rise.”
Merchants Who've Seen It All Weigh In
Few in Old Town have a longer view than Cheryl Hill, who opened Wound ’n Around with her husband, Ernest, in December 1986 and has operated the shop for 40 years, according to the Sentinel. The store, whose name is a play on words tied to vinyl records, sells reproductions of memorabilia from the 1940s, 1950s and 1960s. Hill said she and Ernest were there from Old Town's first day, and she said the district could use a facelift — a sentiment that lines up with the new owners' stated plans for refreshed common areas. Wound ’n Around has expanded twice over the years, growing from about 775 square feet to about 2,500 square feet.
Newer tenants are also watching closely. Julie Ferreira has managed Faux Paws Dog Shop, which specializes in unique gifts, dog accessories, American-made treats and custom pup apparel, since it opened in 2024.
A Bigger Entertainment Picture Taking Shape Nearby
The investment in Old Town comes as the broader Kissimmee-Orlando tourism corridor keeps expanding. GrowthSpotter reported that Ovation Orlando, a $1 billion mixed-use entertainment development planned at the I-4 interchange, is slated to open in late 2028 with 670,000 square feet of experiential retail, more than a dozen restaurants, entertainment venues and three hotels.
For now, Old Town's new owners say their focus is on balancing growth with the retro charm that's defined the district since 1986. Whether that means new cultural festivals, expanded car cruises, or simply fresh paint on aging storefronts, merchants like Hill and Ferreira say they're hopeful the next chapter brings the facelift the 40-year-old attraction has been waiting for.
