Realtor^® Jaime Caballero: Preserving Key West's History

Caballero, a real estate professional since 2003, got her start in the industry out of necessity.

“I became a real estate agent only because I [needed my license] when I changed companies,” she said. “After managing properties for a prominent Key West family, she transitioned to work for Century 21, which mandated her licensure as an agent.”

And, in a twist of fate in 2009 when the office she was with closed, she had a new challenge to meet, which pushed her to become a broker to manage the properties under her care.

"In a blink of an eye, I had to become a broker," she recalled. That moment of change laid the foundation for her current company – Key West Vacation Properties.

The family-centric company includes Jaime's daughter, a real estate agent with 12 years under her belt, and her husband, who joined the venture as a project manager after retiring from the fire department. Together, they manage vacation rentals, long-term rentals, sales, and even have properties like Pelican Landing and Bahama House under their purview.

Caballero is one of 20 Realtors in the first class of Florida Realtors® Board Certified Professionals in 2023, a new endorsement for Realtors who have reached the pinnacle of their profession and fulfilled leadership, education and skill-based achievements over the life of their real estate careers.

Despite her years in the field, Caballero didn’t learn about the products and services offered by her local and state Realtor associations until 2012. “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,” she explained.

It's important to Caballero to be involved in her community. From the Chamber of Commerce to local organizations, she supports local causes and residents. One initiative close to her heart is assisting local kids with their school meals, recognizing the value of ensuring no child goes hungry.

And in 2021, she purchased and restored a historic building in downtown Key West, a feat that earned her two historic preservation awards.

Beyond her business ventures, Caballero is passionate about her profession. She is a strong supporter of RPAC (Realtor Political Action Committee), a program she views as crucial. “Fighting for property rights and helping our consumers... it is just what I’m passionate about,” she said.

The pursuit of Florida Realtors Board Certified Professionals endorsement is an achievement that Caballero points to with pride. This endorsement, in her eyes, is “a public endorsement, not a peer endorsement,” and distinguishes her services in a crowded market along with her professionalism.

"Half the time I get thanked [just] for answering my phone,” she said, emphasizing the simplicity and reward of good service.

Reflecting on the recognition and testimonials she has received from her peers and clients, Caballero confessed that she feels humbly honored.

“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.”