Jordan Pyle

Jordan Pyle is a seasoned real estate expert with over 12 years of experience, proudly licensed in both Florida and Illinois. This dual-market advantage allows him to serve clients across Southwest Florida and the city of Chicago, with a particular focus on those seeking second homes, investment properties or relocation needs in either market.

Jordan began his real estate journey in Chicago in 2014, where he built a successful business as the founder of PYLE Residential, representing buyers, sellers, and investors throughout the city. His mission from day one has been clear: “Build Community & Foster Infinite Possibility through Real Estate.”

Today, Jordan resides in Naples, Florida, and is a key member of The Gulf Coast Collective under team lead Madeline Tracy. His ability to seamlessly bridge two distinct markets makes him an invaluable asset for clients transitioning between city life and coastal living. Being born and raised for 34 years in the midwest allowed Jordan to cultivate a robust network that makes his reach and exposure for clients undeniable and a true value-add to their buying or selling journey here in Naples.

A recipient of the National Association of Realtors’ 30 Under 30 award, Jordan is a consistent top producer recognized for his leadership, innovation, and drive. He’s also the Founder & National Director of Compass Young Professionals, where he helps shape the next generation of real estate leaders.

Jordan is known for his exceptional customer service, strategic marketing, and calm, collaborative approach. He combines deep market knowledge with digital expertise to help sellers achieve top-dollar results and guide buyers through fast-moving, competitive markets.

Whether you're buying, selling, relocating, or investing—Jordan is here to help. Feel free to reach out with any real estate questions. He looks forward to connecting with you!