George C. Marshall's Dodona Manor

Orion Anderson (1875–1889) was a 14-year-old African American who was hanged and shot, on November 8, 1889, in Leesburg, Virginia, by a white mob. His murder was the second of three recorded lynchings in Loudoun County, Virginia, between 1880 and 1902. On Juneteenth 2019, a historical marker was placed at the site of the old rail station where he was killed.

Leesburg is the county seat of Loudoun County, Virginia. It was built in 1740 and is named for the Lee family, early leaders of the town and ancestors of Robert E. Lee. In the War of 1812, it was a refuge for important federal documents evacuated from Washington, DC, and in the Civil War, it changed hands several times. The town is situated at the base of Catoctin Mountain and adjacent to the Potomac River, 33 miles (53 km) northwest of Washington, D.C., for which it has largely become a commuter suburb. Its population was 42,616 as of the 2010 census and an estimated 53,727 in 2019. It is Virginia's largest incorporated town within a county (rather than being an independent city).

Douglass High School was built in 1941 in what was then a rural area just outside Leesburg, Virginia as the first high school for African-American students in Loudoun County. The school was built on land purchased by the black community and donated to the county. It was the only high school for African-American students until the end of segregation in Loudoun County in 1968.

The Leesburg Historic District in Leesburg, Virginia is a historic district that includes Classical Revival, Greek Revival, and Georgian architecture and dates back to 1757. It was listed on the National Register of Historic Places in 1970 and its boundaries were increased in 2002.In 2004, the Victorian era Second Empire - Italianate influenced Carlheim Mansion and 16-acre (65,000 m2) grounds (aka "Paxton") were added as a non-contiguous part of the Leesburg Historic District. The property is held in private trust and became the home of the Margaret Paxton Memorial Learning and Resource Campus, which includes the Aurora School, in November 2009.

Glenfiddich House, also known as Harrison Hall, is a historic house in Leesburg, Virginia. The house was built in three sections, with the first section completed in 1780. When viewing the house from the street, the left wing of the residence is the original home. Between 1850 and 1860, the main block of the home was built for Henry and Jane Harrison (hence Harrison Hall), by the Norris Brothers of Leesburg, and is a good example of the Italianate style of home. The property still includes historic outbuildings: a log springhouse with V-notched corners, circa 1800, and a brick meat house, circa 1855.During the Civil War Harrison Hall became a hospitality center for Confederate officers passing through the area. After the Battle of Ball's Bluff on October 21, 1861, wounded soldiers were tended to at Harrison Hall. Among those was Colonel E. R. Burt of the 18th Mississippi. He died of his wound four days after the battle. The most famous Civil War visitor was none other than General Robert E. Lee. The general broke one of his hands and sprained the other when his horse, Traveller, shied from a fast approaching courier. On September 4, 1862, General Lee received treatment at Harrison Hall; that evening he held a war council, planning the confederate invasion of Maryland, which ended with the Battle of Antietam. Among the planners in attendance were Generals Lewis Armistead, Thomas “Stonewall” Jackson, James Longstreet, and James Ewell Brown “Jeb” Stuart.From 1966 to 1968 poet and author James Dickey resided at Glenfiddich House, an easy commute to his position as poetry consultant to the Library of Congress in Washington, D.C. It was during his stay that he began his manuscript for his novel Deliverance. The desk that he wrote the first drafts of the novel is still at Glenfiddich House.

The Old Stone Church Site encompasses a location in Leesburg, Virginia that was the site of property of the Methodist church from c. 1770 to 1900. On May 11, 1766, Nicholas Minor, a founder of the new town of Leesburg, deeded a half acre of property to Robert Hamilton, a Methodist convert, for ″four pounds current money of Virginia, for no other use but for a church or meeting house and grave yard.″ The site is the earliest known Methodist-owned church site in America. On September 28, 1768, the deed was delivered to members of the Methodist society. The deed, recorded in Deed Book L at pages 451–453, may be seen today in the Clerk's office of the Loudoun Courthouse. Soon thereafter a soft stone building was erected. It was replaced in the late 1780s by a larger structure, which was further enlarged in the early 1800s. The mixed-race congregation split in the late 1840s over the issue of slavery, and a legal battle began for control over the building. In 1897 a Loudoun County court ordered the property to be sold and the proceeds to be divided between the two congregations. The church was demolished c. 1900 and its building materials used elsewhere in the city. The site was purchased in 1961 by the Virginia Conference of the Methodist Church as a historic landmark.The site was listed on the National Register of Historic Places in 1989.

Carlheim (also called Paxton) is a mansion located in the northeast part of Leesburg, Virginia. It was constructed in about 1872 for Pennsylvania industrialist Charles R. Paxton (1816–1889) and his wife Rachel who continued to live there until her death in December 1921. When constructed, it sat on over 760 acres (3.1 km2) roughly bounded on the north end by the Red Rock Wilderness Overlook Regional Park, the Balls Bluff Battlefield and the Potomac River. In accordance with Mrs. Paxton's will, the buildings and 50 surrounding acres were preserved and organized into a charitable trust to benefit "needy children." Designed by New York architect Henry Dudley, the nearly 20,000-square-foot (1,900 m2) 32-room Second Empire building was listed on the National Register of Historic Places in 1979 for its architectural and local significance. In 2004, the property became a non-contiguous part of the Leesburg Historic District. The estate of Mr. and Mrs. Paxton was originally entered down a long tree lined driveway off of King Street. Today, that entrance is gone and there are two more contemporary entrances; Wildman Street (normally closed) and the new main entrance that was completed in 2009 at 601 Catoctin Circle. Among the buildings that remain from the original estate but are outside the present campus include the Farm Managers Home (now the Exeter Community Club House) and the stabilized creamery ruins at Red Rock Park along Edwards Ferry Road. The mansion and remaining 16-acre (65,000 m2) grounds are currently the home of The Arc of Loudoun, Northern Virginia's premier advocacy, education and therapy organization dedicated to serving people with disabilities and their families. The Arc's constituents encompass all ages and ranges of intellectual/developmental disabilities (I/DD), cognitive impairments, and other neurodevelopmental disorders (to include Autism Spectrum Disorder, Down Syndrome, and Fragile X); and/or neurophysical injuries and dysfunctions (to include spinal cord and brain injuries, stroke, Multiple Sclerosis, Parkinson's Disease, cerebral palsy, and balance disorders). The Arc's onsite programs include Ability Fitness Center, Aurora Behavior Clinic, Aurora School, A Life Like Yours ALLY Advocacy Center, and Open Door Learning Center. The Campus is privately owned property but holds several events open to the general public. The major annual fundraising events on the property include: Music at the Manor free concert series (May) Shocktober Haunted House (One of The Scariest Haunted Houses in the US) (October) My Bloody Valentine Haunted House (February)

Waverly is a mansion in Leesburg, Virginia that was built for Robert Townley Hempstone (1842–1913) about 1890. The turreted frame house combines the Queen Anne style with elements of Colonial Revival architecture. Hempstone, a Baltimore businessman, retired to the property that was then on the southern outskirts of Leesburg. The house was built by John Norris and Sons, who were responsible for many prominent houses, churches and commercial structures in Leesburg. Norris' son, Lemuel Watson Norris, became an architect in Washington, D.C. and designed projects for his father's firm.

Edward Nichols House, also known as Hillcrest, is a historic home located at Leesburg, Loudoun County, Virginia. It was built in 1899, and is a 2+1⁄2-story, irregularly shaped, beige brick dwelling with Queen Anne and Colonial Revival style decorative details. It has a tall hipped roof, two-story rear ell, and features projecting two-story bay windows topped with gables on the front and east elevations. Also on the property are the contributing laundry, carriage house / barn with attached water tower, and storage shed.It was listed on the National Register of Historic Places in 1987.

Exeter was a late 18th-century Georgian house near Leesburg, Virginia, that was listed on the National Register of Historic Places from 1973 to August 1980, when it was destroyed by fire and subsequently de-listed from the National Register. The house and its dependencies were unusually elaborate for northern Virginia.

Rock Spring Farm is a historic home located at Leesburg, Loudoun County, Virginia. The original section of the house was built about 1826, with wing and one-story addition built about 1906, and hyphen in 1980 to connect to the original brick kitchen. It consists of a 2+1⁄2-story, four-bay, brick main block in the Federal style with a two-story rear ell and flanking wings. The house was updated near the turn of the 20th century with Colonial Revival style details. Also on the property are a contributing spring house, smokehouse, barn, dairy, silo, tractor shed, and stable.It was listed on the National Register of Historic Places in 2002.

Tuscarora High School is a public high school located in Leesburg, a town in Loudoun County, Virginia, United States, and is part of Loudoun County Public Schools. The school opened in the 2010–2011 school year and consists of students from Leesburg and Lucketts.