The history of the Douglaston Hill Historic District can be traced back to its time as a colonial village before the American Revolution. By the middle of the 17th century, much of what is now Northern Queens was settled by English and Dutch settlers. Thomas Hicks was given much of the land that makes up Douglaston to settle in 1656. The land was occupied by Matinecoc Indians, who used it for fishing. After settling in the area, Hicks forced the Matinecocs to move elsewhere. The land was used primarily for farming leading up to the American Revolution, with a few estates emerging as well.
For the most part, land in Queens remained with these farmers and estate owners until after the Civil War when inner-city growth and developments in transportation helped turn Queens into suburban neighborhoods. Following the Civil War, estates and farms were sold away to developers who helped form the Douglaston Hill Historic District, along with much of Queens, into a commuter suburb. These suburbs were popular because they allowed Americans, who now had more money and desired property, to buy homes further away from their jobs and travel into the city by railway. The Douglaston Hill Historic District is a surviving example of these late 19th-century community developments.
The property that makes up the Douglaston Hill Historic District was owned by several different wealthy estate owners prior to the development of the district. However, the district gets its name from George Douglas, who bought property on the waterfront side of the district from Wynant Van Zandt in 1831. Van Zandt owned most of the peninsula that makes up Douglaston and the surrounding properties prior to the sale. The estate remained in the Douglas family until 1906 when it was sold and subdivided to make the district as seen today. Most of the land around the Douglas estate had already been sold and was developed or under development when the Douglas estate was sold. The district was listed on the National Register of Historic Places in 2000, but community supporters are still seeking state and city landmark recognitions.