Association Welcomes New General Manager

The Ocean Pines Association has rolled out the welcome mat for Mr. John Bailey as the premier residential and resort community’s new General Manager.

Mr. Bailey, who began his employment with the Association on Sept. 11, was greeted by more than 130 people, including the Board of Directors, at a ‘meet and greet’ event that evening. Local dignitary Worcester County Commissioner Chip Bertino was also in attendance.

Mr. Bailey, who dubbed himself as the “preacher’s kid,” addressed the crowded banquet room, offering words of encouragement and optimism.

He now 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.

For more information, contact Denise Sawyer, director of marketing and public relations for the Ocean Pines Association, at (410) 641-7717 ext. 3006 or

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