The Rolling Woods subdivision was developed by Digges Brothers, Inc., of Williamsburg. There are 195 lots within six sections of the subdivision.  The initial Declaration of Covenants and Restrictions for Section One was recorded in James City County in February of 1987.  Because of the neighborhood's beautiful and highly desirable location in the County and historic Colonial Williamsburg and pricing of the lots, sales were brisk.  The first homeowner moved in the last quarter of 1987. The Rolling Woods community currently includes all age groups,including over 200 children.  There is an active Women's Club that sponsors a variety of activities throughout the year.  Rolling Woods was the recipient of the 1998 "Neighborliness Award" sponsored by the James City County/Williamsburg Neighborhoods Connection.

In March of 1989, a group of homeowners initiated the provision in the covenants for a homeowners' association by incorporating the Rolling Woods Homeowners' Association of Williamsburg Inc. and electing a Board of Directors. Since then, the Board has been active in maintaining the integrity and value of the neighborhood.  Annual operating budgets have been set each year, assessments have been billed and collected; a one acre common lot in section three was traded for a four acre common lot in section six, an easement for a sign was obtained and a new sign was installed and landscaped.  In 1992, lighting was added to the entrance sign. In 1993, the recreation area was levelled and seeded and the playground equipment was funded and installed as a joint RWHOA/RWWC project. The 1994 budget included funds for building the access road, parking, and a picnic shelter. In addition, privacy fencing was installed around existing houses adjacent to the Rolling Green and initial landscaping was done.  1995 saw the installation of additional landscaping around the access road. In 1996, the perimeter fence was added.

In 1997, discussions began with James City County on issues concerning responsibilities associated with the three settlement basins and dams which had never been deeded to the Homeowner's Association but were in need of major maintenance.  As these discussions continued into 1998, the Board was also developing the framework for the establishment of a long term Capital Replacement Plan to ensure that when existing improvements at Rolling Green and the front entrance reached the end of their useful "life", funds would be available to replace them. In Nov 1998, JCC spent approximately $30,000 to bring the dams up to "like new" condition in anticipation of the turnover. The 1999 budget included funds to start maintaining the three dams as well as a special assessment to fully fund the Capital Replacement Plan from 1992 to1999.

To prepare for the ownership of the ponds the  Williamsburg Environmental Group produced "Lake Evaluation and Management Recommendations Rolling Woods Subdivision" in 2000.  The report addressed riparian buffers, algaecides, nutrient management and aeration.  The year 2000 saw the final turnover of the Section 3 common area with the three settlement basins and a signed agreement with JCC delineating routine and non-routine maintenance responsibilities.  In 1998 the By-Laws were revised and the board continued to review all of our legal documents in 2001, developing recommendations for modifications that reflect changes over the years and an attorney has been hired to prepare a draft in 2009. In 2001 and 2002, the county performed significant maintenance for ponds #2 and #3. Also in 2002, additional fencing was added at Rolling Green to delineate property lines and the Capital Replacement Plan was reviewed and updated.  2003/2004 was spent dealing with Hurricane Isabel, pond issues and anticipated capital improvements. In 2005, the board adopted a landscape plan to enhance the front entrance to the community and reduce the continuing maintenance cost associated with mulching beds. The front sign was replaced and planting was done at the entrance and along the perimeter of Rolling Green Park. The plan also included naturalizing the perimeters of the ponds and a grant was obtained from James City County for the initial planting phase and mowing and fertilization was suspended along the water edge. 

In 2006, The Board studied two major initiatives: the first to replace the playground equipment in accordance with the Capital Replacement Plan and the second, to look at other options for maintaining the viability of the ponds. 2007 saw the implementation of these plans with the old playground equipment removed as it no longer met OSHA standards and the installation of new equipment oriented toward smaller children. Major drainage improvements were made at the ponds, reducing the need for chemical treatments. In addition, a JCC grant was received to improve landscaping in and around the ponds.   In 2008, our webpage rollingwoods.net was established and two landscaping grants were obtained. The JCC Pride grant continued the landscaping around the perimeters of the ponds and the JCC Beautification Grant was used to landscape the hill along  Rolling Woods Drive and portions of the entrance to the community.  

The Board of Directors meets at least quarterly, works to keep our assessments down, and really appreciates the efforts of all residents of Rolling Woods in keeping it a great place to live.

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