[7] The area was originally known as Wallage, which is related to a Native American term roughly meaning "ditch" or "hole.

In 2003, the A. Conger Goodyear House was added to the National Register of Historic Places to protect the structure from being demolished to subdivide the expensive land surrounding it.

[9] The estate of Robert Winthrop, an investment banker and member of the Dudley–Winthrop family, for whom Winthrop-University Hospital was named, has been similarly preserved.

Part of Gertrude Vanderbilt Whitney's estate and her sculpture studio has been preserved and maintained by one of her grandchildren, Pamela Tower LeBoutillier.

[10] Originally built as the water tower for the Cornelius Vanderbilt Whitney Residence, it now serves as the club's focal point.

[10][11] When Robert Moses was planning the Northern State Parkway, the powers of Old Westbury forced him to re-site it five miles (8 km) to the south.

Once the parkway was completed, many residents found it to not be the eyesore they had been anticipating and regretted making their commutes more inconvenient than necessary.

In the 1950s, the state purchased land from Charles E. Wilson, a former president of General Motors who needed to sell off his Old Westbury estate to pull himself out of financial crisis and relocate to the nation's capital to serve in President Dwight D. Eisenhower's cabinet.

According to the United States Census Bureau, the village has a total area of 8.57 square miles (22.2 km2), all land.

[41] The controlled study included only households with incomes greater than $200,000, which excluded only residents that are living in college dormitories and the staff of homeowners.

The village is famous for being the seat of many of New York's (and America's) wealthiest families, including the Phippses, Vanderbilts, Whitneys, Webbs, Du Ponts, Winthrops, Mortimers, Belmonts and Huttons.

When Forbes asked billionaire investor Steven Schonfeld what the "wisest investment" he ever made was, his answer was "Old Westbury land".