Meet the Realtors: Jaime Caballero is sold on her home town

Key West Realtor/Broker Jaime Caballero is one of that rare breed: A born-and-raised Conch working in the real estate industry in her home town along side her daughter Alexandria who is a Realtor. She graduated from KWHS in ‘85, and immediately got to work at property management. In ’89 Caballero landed a job at Spottswood Companies, where in addition to property management, served as their bookkeeper. Eventually, Caballero decided to strike out on her own, and obtained her Real Estate License in ‘03. For the next six years she worked for Century 21 in Key West, before becoming a broker, and opening her own company, Key West Vacation Properties & Realty. Caballero also opened Key West Residential Property Management in order to expand her long-term property rental pool. “The thing I like best about my job is the property management aspect,” Caballero said. “In that capacity, I get to meet a lot of different people I wouldn’t ordinarily cross paths with.” A dedicated professional, Caballero is very active in the National Association of Residential Property Managers as Florida State Chapter President, and with Florida Realtors as Property Management Chair. Caballero is a Major Investor in Realtors Political Action Committee(RPAC).
She plans to travel to Tallahassee at the end of March for Great American Realtor Day, with Florida Realtor, and to Washington DC in May with National Association of Realtors. 
Caballero’s resume brimmith over with awards and recognitions for her work over the past three decades.
On the philanthropic side, she has served as a KW Junior Football League cheerleading coach and secretary, Conch Athletic Booster Club secretary, and Old Firehouse Preservation Board treasurer. She donates to the Wounded Warrior Project, and American Cancer Society, fully supports the work of Fair Insurance Rates in Monroe (FIRM.)
When she’s not working, which is seldom, according to Caballero, she enjoys traveling, boating, and spending time with her husband of 32 years, Arnold, their three daughters, son in laws, grandson and granddaughter. “I’m a bit of a workaholic, but I definitely love boating and traveling,” Caballero said. “And I love living in Key West.”
For more information on Jaime Caballero’s businesses, call 305-797-5252, email, or visit