Caleb McFadden joined Hylton & Company in November 2024, bringing over 15 years of diverse professional experience to his role as Property Manager. With a unique background that spans insurance, operations management, digital marketing, and law enforcement, Caleb approaches property management with a strategic mindset and a commitment to excellence.
In his role at Hylton & Company, Caleb oversees daily operations for a mixed portfolio of residential and commercial properties across the Richmond area. From managing leasing activities and maintaining high occupancy rates to coordinating maintenance teams and ensuring lease compliance, Caleb keeps properties running smoothly while delivering responsive service to residents and property owners alike. His expertise in client relationship management and operations oversight ensures that every detail receives the attention it deserves.
Before joining Hylton & Company, Caleb built an impressive career that includes founding McFadden Benefit Group and Family Crest Life, where he became a licensed insurance agent in 13 states. His entrepreneurial spirit and consultative approach to business development have equipped him with invaluable skills in negotiation, problem-solving, and building lasting relationships. Caleb's background also includes nearly a decade in law enforcement with the Austin Community College Police Department and Petersburg Sheriff's Office, where he developed a keen eye for safety, risk management, and community service.
A self-described lover of ideas that make people better, Caleb believes in approaching challenges with what he calls "a handsome mind"—one that's open to the world of possibilities and continuous improvement. When he's not managing properties or creating marketing content in Canva (a personal favorite), you might find Caleb producing vibe music, strategizing over a chess match, or immersed in a good book.
Caleb holds a Class B Commercial Driver's License and is passionate about leveraging technology and innovative solutions to elevate the property management experience for everyone involved.

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