Robert L. Riddle, CCIM

PRESIDENT & FOUNDER, RIDDLE ASSOCIATES, INC.  

Robert L. “Robb” Riddle is a distinguished leader in commercial and industrial real estate with over 41 years of experience. As the founder of Riddle Associates, Inc., established in 1988, he played a pivotal role in shaping the industry across Southeastern Virginia and Northeastern North Carolina. A Certified Commercial Investment Member (CCIM), Robb earned the highest distinction in the field, demonstrating expertise in investment analysis, market strategy, and negotiations. Under his leadership, Riddle Associates grew into a full-service firm, providing comprehensive brokerage, property management, and condominium association management services.

Throughout his career, Robb was actively involved in civic and professional organizations, holding leadership roles such as Past Chairman of the Economic Development Authority for the City of Chesapeake and Past Member of the Chesapeake Rotary Club. He also served on the boards of The Old Point National Bank, The Old Point Financial Corporation, Virginia Air & Space Center, Chesapeake Care Free Clinic, Chesapeake North YMCA, Norfolk Mental Health Hospitality Center, and the Shore Drive Advisory Board for the City of Virginia Beach. Additionally, Robb now serves on the Mathews County Planning Commission and is the Treasurer on the Mathews Land Conservatory Board of Directors.

Robb attended Catonsville Community College and Johns Hopkins Evening College before earning his CCIM designation. Beyond real estate, he enjoys baseball, boating, and cruising in his collection of interesting classic cars. 

After 37 years of passionately building Riddle Associates, Robb has transitioned into semi-retirement, stepping back from daily operations while continuing to provide guidance in an advisory role. Though no longer involved in the firm’s day-to-day activities, his vision and leadership remain integral to its continued success.

For inquiries, Robb can still be reached at rlr@riddleassociates.com or by phone at 757-523-1900. More information about Riddle Associates can be found at www.riddleassociates.com.