General Manager








Mr. John Bailey
General Manager

Ocean Pines Association
239 Ocean Parkway
Ocean Pines, MD  21811   410-641-7717 Ext: 3001

Office Hours:
Monday – Friday 8:00am – 5:00pm

John Bailey Named General Manager

Mr. Bailey, who began his employment with the Association on Sept. 11, serves as the chief administrative officer of the Association and is responsible for the management of the day-to-day operations of the Association.

With more than ten years of homeowners’ association management experience, Mr. Bailey has worked for Lake of the Woods, a private, planned residential community of single-family homes located in the northeastern tip of Orange County, Virginia, as the General Manager. Mr. Bailey’s responsibilities extended throughout all areas of Lake of the Woods, including strategic planning and execution, budget management, amenity development, technology deployment and resident operations. Mr. Bailey led major financial transformation efforts while heading up operations at Lake of the Woods, resulting in a substantial increase of Lake of the Woods’ assets.

In addition, he has worked for Brandermill Community Association, an award-winning waterfront community near Richmond, Virginia, in a similar management role. During his time with Brandermill, Mr. Bailey successfully redesigned the budget and its development process to provide more accountability and transparency.

Mr. Bailey also has experience in municipal management, having served as a County Administrator for Cumberland County and as a Town Manager for Orange and Urbanna, all in Virginia.

As the General Manager for the Ocean Pines Association, Mr. Bailey is tasked with overseeing all aspects of operations, including the preparation of a proposed annual budget that is submitted to the Board of Directors.

Mr. Bailey received his Master of Public Administration from George Mason University and Bachelor of Arts in history from Averett College in Virginia. He currently participates in the Community Association Institute, an international membership organization dedicated to building better communities.

Mr. Bailey, his wife, Meredith, and two children, Chase, 21, and Augusta, 15, are familiar with Ocean Pines, having spent years as vacationers in the community.


The General Manager is appointed by and serves at the pleasure of the Board of Directors as the chief administrative officer of the Association and is responsible for the executive management and staff of the day-to-day operations of the Association. The Executive Assistant assists the General Manager and serves as the Executive Secretary for the Board of Directors.

General Manager’s Office

Michelle Bennett
Executive Assistant
410-641-7717 Ext: 3002

Human Resources



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