Excerpted from the Highland Park-Overlee Knolls Neighborhood Conservation Plan - "Terrain and History") and Leeway Neighborhood Conservation Plan "Chapter Two (Leeway History)". Corrections or additions are welcome.

The initial European settlement of the Northern Virginia area was accomplished through land grants issued to English colonists. A large portion of the Leeway Overlee area was included in a 1730 land grant to Simon Pearson and James Going. The remainder was included in a 1699 grant to John Colville.

In 1789, Simon Pearson's son, Thomas, sold a 500-acre tract "on the branches of Four Mile Run" to George Minor for 710 English pounds (Virginia specie). The broad land holdings of the Minor family prior to the Civil War are still memorialized by Minor's Hill, the high ground adjacent to the intersection of Williamsburg Boulevard and North Sycamore Street. George Minor's land passed in divided shares to his sons. In the 1820s, one son, Hugh Minor, encountered financial difficulties. In 1829, two tracts he held were sold at public auction by the Alexandria sheriff to cover judgement debts. Daniel Minor of Fairfax purchased the roughly 176 acres for between $2.75 and $4.75 an acre. Daniel sold this farmland in 1849 to Nicholas Febrey. Ten years later it passed to his son, Henry W. Febrey.

Henry Febrey settled on acreage extending from Lee Highway southwards towards Four Mile Run. His home, "Maple Shade," still stands on Powhatan Street, north of 22nd Street. Mr. Febrey was a prominent farmer in the area in the latter half of the 19ths century. About ten years following his death in the early 1880s, his farmland was partitioned among his descendents. The plan attached to the 1893 court partition order divided the 177.75 acres into twelve tracts.

Maps from 1891 and following specifically show descendents of Henry Febrey owning six of the tracts south of 22nd Street ranging in size from 13.5 to 21 acres. Between the Febrey tracts and Four Mile Run, bounded by what is now 18th Street North, the same maps show the first subdivision in the area, "Fostoria", designed to take advantage of the steam, and later the electric railways, built along Four Mile Run.

Much of the Leeway Overlee area east of North Lexington Street passed from John Colville to George Minor and then to his son, Smith Minor. A 56-acre tract of this land was purchased in 1889 by Joseph Fought.

Frame houses and cottages built from 1900 to the early 1920s still stand on 14th and 15th Streets North , North McKinley Road, and North Nicholas Street, recalling the days of trolleys, horse and buggy, kerosene lamps, well-water, and dirt roads. Road access to and from Fostoria was by way of Lubber Lane (now Lexington Street-16th Street.)

In 1907, when the County Board of Supervisors published a map and pamphlet describing the county, the Fostoria subdivision bore a new name, "Highland Park". Following World War I, and with wider use of the automobile, a hard surfaced road, Memorial Drive (now Washington Boulevard) was constructed through the former Febrey properties, linking the community directly to East Falls Church to the west and North Glebe Road to the east. With easier access by car, in the mid-1920s a new subdivision, "Overlee Knolls", was constructed, out of farmlands, north of Washington Boulevard. A 1932 map of the County by W.F. Sunderman shows Overlee Knolls and Tuckahoe Village (east of North Lexington and south of Lee Highway) as the two major subdivisions, along with the Robert E. Lee Elementary School.

Street names in the area changed completely in 1935 when Arlington County unified its system of hamlets and new subdivisions. Mount Olivet Road and Elmhurst Avenue (formerly Greenough's Road) became North Lexington and North Quantico Streets, respectively. Earlier north-south numbered streets, such as 7th Street in Tuckahoe Village, were converted to named streets in alphabetical order (North Kentucky Street). All then-existing east-west roads, were renamed as numbered streets. The following list of renamed streets was obtained from a 1932 map of Arlington by W.F. Sunderman.

Other name changes revealed from the Sunderman map include:

"Parkhurst" was a subdivision built in 1939 to help accommodate the influx of young families prior to World War II. The builder constructed reasonably priced houses around a central park area which he had donated to the community. In rapid succession the schools, Reed and Swanson, and the Westover shopping area were under construction. Subdivision of smaller tracts, mainly in the area west of Powhatan Street, between 18th Road North and Washington Boulevard, continued into the 1950s. By the fall of 1981 only a few vacant lots remained.

Lee Highway, also known as U.S. Highway 29, bisects the Leeway Overlee neighborhood. It began as a dirt road connecting the colonial towns of Falls Church and Georgetown. Its importance grew at the time of the Civil War when it helped to connect military forts defending Washington D.C. It also served as a major farm-to-market route into the city. For many decades, it was known as the Georgetown and Fairfax Road. As highway usage grew, its importance increased. In 1923, President Harding changed its name to Lee Highway and dedicated it as the initial segment of the nation's first transcontinental highway (U.S. Route 50) from the Capital to California. Though this U.S. highway routing was shifted to Arlington Boulevard in 1935, Lee Highway remained a well-traveled route. It was widened to a four-lane roadway through Leeway in the early 1960s.