The Chesterbrook Woods community lies in the southeast corner of McLean in the area bounded roughly by North Albemarle Street on the south, Little Pimmit Run on the west, Pimmit Run on the north, and River Street and the Arlington County line on the east.. In 1950 most of the area was farmland, forest or pastureland. Residential development began in the early 1950s and continued at a fast pace through the late 60s, with a number of builders subdividing various areas into lots, laying out streets and building homes. Most of the current 530 homes in Chesterbrook Woods were built during that 20-year period. Residents of the community consider it a wonderful place to live, especially for families with children. It is quiet and pastoral, with winding streets and attractive homes and yards. It is ideally located to permit quick and easy access to Washington and other places in the metro area.

The Chesterbrook Woods Citizens' Association (CWCA) was formed in 1954. A person very active in getting the Association started was Navy Commander Don Baer, who in 1953 moved with his wife into a newly-built house on Oakdale Road. He served as the Association president for the first three years, beginning in 1954.

Acts of vandalism and burglaries, notably those of the infamous "silver bandit", became a concern during the seventies, and residents in 1977 established a voluntary neighborhood watch program including daily and nightly car patrols by citizen volunteers to help detect and deter criminal activity. It was the first such program in McLean and the second in Fairfax County. Don Baer, having retired from the Navy as a rear admiral in 1970, was active in setting up and supervising the patrol activity. He served as the neighborhood watch coordinator, working closely with the McLean police department, until he and his wife moved to a retirement home in 1999. The patrol program was encouraged and supported by the McLean Police and continues to be conducted. An important element of the neighborhood watch program is watchfulness by all residents for suspicious persons or activities in their neighborhoods and immediately reporting them to the police by phone if warranted.

In 1965 Nancy and George Falck moved into their new home on Basswood Court. In 1968 Nancy was elected President of CWCA and served in that capacity for nine years. She was instrumental in establishing the neighborhood patrol and an annual snow removal arrangement with a private contractor to provide prompt plowing of neighborhood streets. Nancy was elected as the Dranesville District Supervisor in 1979 and served eight years in that office. George served for many years as the Association Treasurer.

The Association President for eight years beginning in March 1999 was Arnold Braswell, a retired lieutenant general of the U.S. Air Force, who moved with his wife Ione to their home on Dahlia Court in 1984. Ione began serving as the recruiter and scheduler of patrol drivers in 1992 and is still doing it in 2007, working in partnership with Virginia Dillon, a long-time member who helped get residents to support the patrol program when it began and has been active in managing it ever since.

All residents of the Chesterbrook Woods community are encouraged to become members of the association and to support it with annual dues and voluntary participation in the patrols as well as other activities. Association bylaws provide for annual election of a president, vice-president, treasurer and secretary, and providing for annual budgets and membership dues to be approved by vote of the members at the first members' meeting of the year, usually held in March. A total of 29 block captains are appointed to help disseminate periodic newsletters and keep in touch with residents within their assigned portions of the community. An association directory of all residents, originally initiated as an occasional publication, is now published once a year. In 2000 an association web site with much useful information was established by a volunteer member, Elinor LeBaron, who continues to maintain the site even while temporarily living far away. In 2002 periodic and timely e-mail notices to residents were initiated to inform them about significant issues or events.

In the early days residents would get together every year for a Valentine's Day party in someone's home. As the number of residents grew that became impractical. So an outdoor Halloween Party in one of our many cul-de-sacs is now scheduled each year and has become very popular as a means of getting families together for a fun event and building community spirit.

While membership in the Association is voluntary, most of the households in Chesterbrook Woods currently pay annual dues and thus become voting members of the Association. The annual dues usually fall between ten and twenty-five dollars per household, the amount each year depending largely on the amount expected to be needed for snow removal expenses, the largest budget expenditure. Officers elected at the March meeting hold office for one year. They may be re-elected if willing and able to continue serving. Volunteer members are appointed by the president to manage programs such as snow removal and vehicle patrols. Committees may be appointed to deal with specific issues. No members who serve in elected office or appointed positions receive compensation for their service.

As stated in the By-Laws, the objectives of CWCA are to encourage and promote civic welfare and improvements affecting the community of Chesterbrook Woods, including health and sanitation, public safety, fire and police protection, zoning laws and regulations, community planning, building restrictions, public schools, highways, utilities, and county and state legislation concerning such matters. As a voluntary association of residents CWCA has no binding covenants nor the authority to regulate the activities of members.