Benjamin Gilbert, a broker-associate with Keller Williams at the Parks in Orlando, has developed his real estate business around transactions that often involve significant emotional and legal complexity. He specializes in probate and divorce sales, which require both legal knowledge and sensitivity to family dynamics.
Gilbert began his career in real estate in November 2016. His first sale was completed in February 2017, and he closed 10 transactions during his first full year. Over the past eight years, he has continued to build on this foundation. He holds several professional designations, including Seniors Real Estate Specialist and Accredited Buyer’s Representative, and has received the 20 Under 40 Rising Star in Real Estate Award.
His focus on high-emotion transactions stems from early work with bankruptcies and relationships within the legal community. “I started in 2016 working in bankruptcies, and I worked with some attorneys… so I know a lot of people in the legal field,” Gilbert said. Personal experience helping his grandmother through probate also influenced his choice of specialty.
Each transaction presents unique challenges, according to Gilbert. He works closely with attorneys to develop custom strategies for each situation. “I do a pros and cons sheet… and eight times out of 10, siblings end up saying, okay, it looks like we might be better to sell this,” he explained.
To stay current on legal matters related to probate and divorce sales, Gilbert pursues ongoing education. “I try to take as many CE courses within the legal industry… and I’m always talking to my attorney friends,” he said.
Beyond real estate transactions, Gilbert is committed to supporting underserved communities. In 2021, he founded Team Up FSL, a nonprofit organization providing sports programs, education, mentoring, and healthy entertainment for underprivileged youth. The initiative partners with existing community programs rather than operating its own facility to keep participation affordable.
The idea for Team Up FSL came from a personal experience where Gilbert helped a young man avoid a felony conviction by intervening at a critical moment. The organization focuses on teaching basketball skills alongside life skills such as goal-setting and STEAM (Science, Technology, Engineering, Arts and Mathematics) education. “We’re teaching them how to be happy,” Gilbert said.
Gilbert also expresses concern about broader issues affecting homeownership: “Affordable housing and our nationwide inventory shortage” are priorities for him as he considers the future of the industry.
He holds board certification from Florida Realtors — an achievement he describes as meaningful recognition of his commitment to professionalism: “It’s not just sitting in a classroom… You have to live it every day.”
Gilbert continues to emphasize legal literacy and community engagement as central elements of his approach as a real estate professional.
