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Fort Beauregard was a Civil War-era rectangular earthen fort located on a 430 feet (130 m) promontory above Tuscarora Creek just southeast of Leesburg, Virginia. Built in the winter of 1861–1862 following the Battle of Ball's Bluff, it was one of three forts built by Confederates to defend Leesburg against possible invasion. Fort Beauregard commanded the southern eastern approaches to the town, including the Old Carolina Road and the Alexandria and Winchester Turnpike (present day Virginia State Route 7). The fort may have been only partially constructed, and was never occupied by Confederates in force before Leesburg was evacuated in the spring of 1862. The fort was occupied by Union forces for a brief period in the summer of 1862. The fort was subsequently destroyed, and the exact location remains unknown. The likely site currently sits in the privately owned "Beauregard Estates" neighborhood.

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.

Fort Evans is a Civil War-era rectangular earthen fort located in Leesburg, Virginia. It was the first of three forts constructed in 1861 to protect Leesburg from possible invasion after Virginia seceded from the Union.

Dodona Manor, the former home of General George Catlett Marshall (1880–1959), is a National Historic Landmark and historic house museum at 312 East Market Street in Leesburg, Virginia. It is owned by the George C. Marshall International Center, which has restored the property to its Marshall-era appearance of the 1950s. It is nationally significant as the home of George C. Marshall, Chief of Staff of the United States Army during World War II, Secretary of State, President of the American Red Cross, and Secretary of Defense.

The Village At Leesburg is a regional outdoor center located in Leesburg, Virginia in the United States. The open-air center features a total of 1.2 million square feet of development encompassing 57 acres.

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.

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.

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).

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.

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)

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.