ABOUT / COLE WHITAKER REALTY

Cole Whitaker Realty was initially founded in 1987 by Cole Whitaker Sr. and is now a father-and-son team dedicated to helping buyers and sellers navigate the land market across Central Florida. With deep local roots and a hands-on approach, we believe the best strategy to sell land is simple: know the land, price it right, and market it to the right buyers. We combine local expertise with detailed property insights and targeted outreach to connect each piece of land with the right owner, whether it’s for farming, building, hunting, or investing.

At the heart of everything we do is honesty, hard work, and a genuine commitment to doing right for our clients.

Driven by Dedication, Defined by Hard Work

Cole Whitaker Sr. / President & Founder

Cole Whitaker Sr. began his real estate career in 1983, selling apartments for Comvest Investments, Inc. in Winter Park, Florida. Building on this early experience, he founded Cole Whitaker Realty, Inc. in 1987, specializing in land syndications and apartment investment sales. Over the years, Cole Sr. has held senior leadership roles at top industry firms including The Apartment Group, Cushman & Wakefield, and Hendrick & Partners. Today, he serves as Senior Managing Director at Berkadia while continuing to lead Cole Whitaker Realty, Inc. as President. With decades of experience and a reputation for integrity and results, Cole Sr. brings a deep understanding of the real estate market and a strong work ethic to every client relationship. Outside of work, he enjoys relaxing at the beach, spending time on his Florida hunting lease, and visiting the family farm near Princeton, Kentucky. In addition, Cole Sr. is the Chairman of the Board for Wounded Warrior Outdoors, Inc. a nonprofit that takes wounded service men and women on therapeutic outdoors hunting and fishing adventures throughout the US and Canada.

Cole Whitaker Jr. / Realtor

Cole Whitaker Jr. began his real estate career in early 2025, running Cole Whitaker Realty, Inc. alongside his father and mentor, Cole Whitaker Sr. Before entering the real estate industry, he gained valuable experience at Accurate Productions from 2022 to 2024. Cole Jr. now specializes in Central Florida land sales, combining market insight with a deep-rooted passion for the outdoors. His hands-on knowledge of Florida’s landscapes, developed through years of hunting, exploring, and managing land, gives him a unique perspective and genuine enthusiasm for helping clients find the perfect rural or agricultural property. Whether you're buying or selling land, Cole Jr. brings energy, dedication, and a strong work ethic to every transaction.

W O R K W I T H U S

The Whitakers are more than just a real estate team, they are family. As a father-son duo with a shared love for helping clients find their perfect property, the Whitakers bring a unique blend of experience, energy, and personal touch to every transaction.

When you work with The Whitakers, you're not just getting real estate agents. You're gaining a trusted team, a family-focused experience, and a commitment to helping you feel at home every step of the way.

Our Approach

When working with sellers, Cole’s team takes a thoughtful, hands-on approach to every stage of the selling journey:

  • Preparing land to make its best first impression

  • Skillfully negotiating offers

  • Navigating inspections and contingencies with with historical knowledge and expertise

  • Coordinating a smooth and stress-free closing

Throughout the entire process, the team stays grounded in what matters most—thoughtful analysis, active listening, creative problem-solving, and open, honest communication. With dedication, Cole Whitaker’s team is committed to guiding sellers every step of the way.