Realtor® Benjamin Gilbert: Broker Associate and Community Builder
ORLANDO, Fla. – Years before he earned his broker’s license, Benjamin Gilbert found himself standing in a courtroom, face to face with a 17-year-old kid who had stolen his car. But instead of pressing charges, Benjamin asked to speak to him. “I told him, ‘You’ve got a choice right now. You can keep going down this path, or you can take this as a wake-up call.” That conversation left a lasting impression on Benjamin.
“That moment stuck with me,” he says. “It made me realize how much of an impact one person can have just by showing up, listening, and offering a way forward.”
Gilbert brings that same mindset to real estate. As a broker-associate with Keller Williams at the Parks in Orlando, he’s built his solo business around high-emotion transactions — probate and divorce sales that demand legal fluency and emotional intelligence. Whether negotiating on behalf of siblings at odds or helping heirs navigate the loss of a loved one, he takes pride in being the calm in the chaos.
His journey in real estate began in November 2016, and since his first sale in February 2017, Gilbert has maintained a strong pace, closing 10 transactions in his first full year and building on that momentum ever since.
Today, in his eighth year in the industry, Gilbert is known for more than just his numbers. He holds multiple designations, including Seniors Real Estate Specialist and Accredited Buyer’s Representative, and is a proud recipient of the 20 Under 40 Rising Star in Real Estate Award.
Gilbert’s business focuses on complex, high-emotion transactions, specifically probate and divorce. “I started in 2016 working in bankruptcies, and I worked with some attorneys... so I know a lot of people in the legal field,” he explains. That legal network and personal experience helping his grandmother through probate drew him toward this specialty.
He describes each deal as having “its nuance” and emphasizes the importance of custom strategies and close collaboration with attorneys. When facing family disputes or emotionally charged decisions, Gilbert's approach is logical, transparent, and grounded in market realities: “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.”
His commitment to continued education, particularly in the legalities of probate and divorce, keeps him at the forefront of this complex segment. “I try to take as many CE courses within the legal industry... and I’m always talking to my attorney friends,” he says. These conversations help him navigate sensitive dynamics and provide clients with clarity during uncertain times.
However, his passion for people, especially the underserved, truly sets Gilbert apart. In 2021, he officially launched Team Up FSL, a nonprofit he founded to provide structured sports, education, mentoring, and healthy entertainment for underprivileged youth.
Inspired by a deeply personal experience where he intervened to help a young man avoid a felony conviction, Gilbert has built an initiative that teaches basketball and life skills, how to set goals, and STEAM (Science, Technology, Engineering, Arts and Mathematics) education.
“We’re teaching them how to be happy,” he shares. Team Up FSL partners with existing community programs without a physical facility to keep participation affordable and accessible.
Gilbert is equally passionate about broader systemic issues in real estate. “Affordable housing and our nationwide inventory shortage” top his list of concerns, both of which he believes are pivotal to the future of homeownership.
With board certification from Florida Realtors – an honor he calls “tremendously powerful” – Gilbert sees this endorsement as both a validation and a responsibility. “It’s not just sitting in a classroom... You have to live it every day,” he says.
Benjamin Gilbert is redefining what it means to be a full-service real estate professional: legally literate, community-driven, and deeply passionate. In a market that demands more from its agents, he delivers – one transaction, one life, and one youth at a time.
Florida Realtors® serves as the voice for real estate in Florida. It provides programs, services, continuing education, research, and legislative representation to 238,000 members in 50 boards/associations. Florida Realtors® Newsroom website is available at floridarealtors.org/newsroom.