Chestnut Hill (Orange, Virginia)

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.

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.

Formerly called the Doctor Holladay House, the Holladay House in Orange, Virginia (c.a. 1830) is on the nationally recognized Journey Through Hallowed Ground. Named for Dr. Lewis Holladay, a prominent Virginia physician, the Holladay House has witnessed almost two centuries of American history. The building is historically significant because it is one of only a few antebellum structures still standing in Orange, Virginia. Since approximately 1830, the Holladay House has served as a mercantile store, a residence, a doctor’s office, and a Virginia bed and breakfast inn. In the early 20th century, a private schoolhouse for local children was also on the property. Only a handful of proprietors have owned the home, and the Holladay family was its steward for over 100 years. The Holladay House still boasts much of its original woodwork, including floors, mantels, doors and period antiques from the Holladay family. The Holladay House is one of the two oldest standing structures in historic downtown Orange, and is a contributing property to the Orange Commercial Historic District, listed on the National Register of Historic Places. It has been a landmark on Main Street for generations.

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.

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.

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 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.

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.

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.

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 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.

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