Holladay House

St. Thomas Church is a historic Episcopal church located at Orange, Virginia, United States. It is a rectangular brick structure measuring 40 feet wide and 105 feet deep. The front facade features a recessed portico with two Doric columns flanked by two Doric pilasters. Atop the gable roof is a three-stage tower topped by an octagonal cupola. The original church building was built in 1833–1834, and measured approximately 40 feet wide and 65 feet deep. It was built by William B. Philips, a master mason employed by Thomas Jefferson during the construction of the University of Virginia. It was enlarged and improved in 1853, and enlarged again in 1912. In 1928, the rear addition was raised to a full two stories and a parish hall constructed. The original church is believed to have been based on the plans by Thomas Jefferson for Christ Church in Charlottesville, Virginia. That church was demolished in 1895.It was added to the National Register of Historic Places in 1976. It is located in the Orange Commercial Historic District.

The James Madison Museum located in Orange, Virginia is a museum dedicated to 4th president of the United States James Madison and his wife, Dolley Madison. Exhibits include original furniture used by James Madison, his personal items, portraits of the Madisons, and a statue.Due to Madison's reputation as a farmer, the museum also features a collection of antique farm tools. There is also a partially reconstructed 1733 house to demonstrate building practices.

Orange County Courthouse is a historic courthouse complex located at Orange, Orange County, Virginia. It was built in 1858–1859, and is a 1 1/2-story, Italian Villa style brick structure. The front facade features a three-part arcade consisting of a semi-elliptical arch flanked by small semicircular arches. Above the arcade is a three-stage tower consisting of the main entrance as the first stage; a clock, installed within existing round windows in 1949, as the second stage; and arched openings with louvres covered by a shallow hip roof and topped by a finial complete the tower. Associated with the courthouse are the contributing clerk's office (1894) and jail (1891).It was listed on the National Register of Historic Places in 1979. It is located in the Orange Commercial Historic District.

Orange Commercial Historic District is a national historic district located at Orange, Orange County, Virginia. One of Virginia's Main Street communities, it encompasses 61 contributing buildings in the central business district of Orange's county seat.

Rebel Hall is a historic plantation house located at Orange, Orange County, Virginia. It was built in 1848–1849, and is a two-story, three-bay, Greek Revival style brick dwelling. It sits on a raised brick basement and has a shallow-pitched, standing-seam metal roof. A rear wing was added about 1900.It was listed on the National Register of Historic Places in 2002.

Chestnut Hill is a historic home located at Orange, Orange County, Virginia. It was built about 1860, and is a two-story, frame dwelling in a combination of the Italianate and Greek Revival styles. A Second Empire style mansard roof was added in 1891. The front facade features a central, one-story, one-bay porch with a balustraded deck above and balustraded decks with the same scroll-sawn balusters across the front. The historic floor plan is a double-pile center-passage plan with two interior chimneys serving four fireplaces on each floor. The house was moved to a new location, 150 feet away from its original site, when threatened with demolition in 2003. Also on the property is a small, one-story, single-bay, 19th-century contributing shed.It was listed on the National Register of Historic Places in 2009.

Orange is a town and the county seat of Orange County, Virginia, United States. The population was 5,062 at the 2020 census, representing a 7.2% increase since the 2010 census. Orange is 28 miles (45 km) northeast of Charlottesville, 88 miles (142 km) southwest of Washington, D.C., and 4 miles (6 km) east of Founding Father and fourth U.S. president James Madison's plantation of Montpelier.

Ballard–Marshall House, also known as Marshall House, is a historic home located at Orange, Orange County, Virginia. It was built in 1832, and is a two-story, three-bay, brick late Federal Virginia townhouse dwelling. It is an example of an urban house form influenced by the Jeffersonian Classical style. A two-story rear addition was added about 1900, and the original front and side porches were replaced with ones in the Colonial Revival style in 1910. The house was converted to apartments in 1934–1935, and renovated in 1986–1988.It was listed on the National Register of Historic Places in 1988.

Orange High School is a historic school located in Orange, Virginia. The first school building at the site was built in 1911 based on a design by noted Virginia architect Charles M. Robinson. The original structure is a 2+1⁄2-story building with a monumental Doric portico modeled on the Temple of Albano. In 1925, a one-story annex was added to the school. The school opened in 1911 as an elementary, middle, and high school. It continued in operation until 1970. When plans to demolish the original 1911 building were announced in the late 1990s, local residents protested. The property was converted for use as apartments for senior citizens.The building was listed on the National Register of Historic Places in 2001.

Mayhurst is an 1859 Italianate mansion in Orange, Virginia. It was built by the Willis family relatives of President James Madison as the plantation house for an estate comprising 2,500 acres (10 km2) of fields, pastures and forest. It was a scene of action in the Civil War. It is currently operated as an Inn.

Berry Hill is a historic home located near Orange, Orange County, Virginia. It was built in 1827, and is a 2+1⁄2-story, brick dwelling with a standing-seam metal gable roof. It consists of an arcaded pavilion in the main section with a west wing. It was built by William B. Philips a master mason employed by Thomas Jefferson during the construction of the University of Virginia.It was listed on the National Register of Historic Places in 1980.

Orange County High School is a public high school for students grades 9-12 located in Orange, Virginia.