Jaime Caballero, a real estate professional in Key West, has built a notable career through her dedication to property management and community involvement. Initially entering the field out of necessity, Caballero explained, “I became a real estate agent only because I [needed my license] when I changed companies.” After managing properties for a prominent local family, she joined Century 21, which required her to obtain an agent's license.
In 2009, when the office she worked at closed, Caballero faced new challenges that led her to become a broker. "In a blink of an eye, I had to become a broker," she recalled. This pivotal moment resulted in the creation of her company, Key West Vacation Properties.
The family-run business includes Caballero's daughter, who has 12 years of experience as a real estate agent, and her husband, who serves as project manager after retiring from the fire department. Together, they manage various properties including vacation rentals and long-term rentals such as Pelican Landing and Bahama House.
Caballero was among the first group of 20 Realtors to receive the Florida Realtors® Board Certified Professionals endorsement in 2023. This endorsement recognizes those who have achieved significant leadership, education, and skill-based milestones throughout their careers.
Despite her extensive experience in real estate, Caballero did not engage with local and state Realtor associations until 2012. She expressed regret over missing earlier opportunities: “I didn’t [get involved with] Florida Realtors until probably 2012. I felt like those [previous] nine years, I was robbed [of so many education opportunities], because once I found out about the Realtor organizations, it became like an obsession.”
Community involvement is important to Caballero. She supports various local causes through organizations such as the Chamber of Commerce and focuses on initiatives like providing school meals for children. In 2021, she restored a historic building in downtown Key West, earning two historic preservation awards for her efforts.
Caballero is also passionate about supporting RPAC (Realtor Political Action Committee), which she views as essential for advocating property rights and consumer interests. “Fighting for property rights and helping our consumers... it is just what I’m passionate about,” she said.
Achieving the Florida Realtors Board Certified Professionals endorsement is a source of pride for Caballero. She describes it as “a public endorsement” that highlights her professionalism in a competitive market.
"Half the time I get thanked [just] for answering my phone,” she noted, underscoring the importance of good service.
Reflecting on her career achievements and recognition from peers and clients alike, Caballero feels honored by their testimonials. “I’m always solving problems; Realtors are undervalued as problem solvers,” she said. “I just do it so often; every day it's second nature.”