Charlottesville High School

McIntire High School is a now-closed high school built in the early twentieth century by the Public Works Administration, with funding by Charlottesville philanthropist Paul Goodloe McIntire. It now houses a private Christian school, The Covenant School. The structure is a two-story building, made of brick, with a tetrastyle portico, fluted columns, and grouped windows.

Rock Hill Academy was a private high school in Charlottesville, Virginia, established in 1959 when the city's schools were closed rather than comply with orders to desegregate following the landmark Brown v. Board of Education Supreme Court ruling.In 1958, federal courts ordered the city's public high schools, Lane High School and Jackson P. Burley High School to integrate. The city chose instead to close its schools in a political stratagem called Massive resistance. Rock Hill Academy (a high school) and the Robert E. Lee School (elementary) were founded by the Charlottesville Education Foundation and the Parents' Committee for Emergency Schooling in Charlottesville.Tuition at Rock Hill was covered in part by state tuition grants. Grants to a "nonprofit, nonsectarian private school", even segregation academies, were upheld by the Third Circuit Court of Appeals.The campus was taken over by Heritage Christian Academy (now defunct).

Hard Bargain is a historic home located at Charlottesville, Virginia. It was built in 1878, and is a two-story, three-bay, Late Victorian style frame dwelling. It is sheathed in weatherboard and sits on a brick English basement. It has a large two-story rear addition (1890s), one-story bay window, and projecting end pavilion. Also on the property are the contributing stone foundation of an old barn and the remains of a mill on Schenk's Branch.It was listed on the National Register of Historic Places in 1984.

Enderly is a historic home located at Charlottesville, Virginia. It was built in 1859–1860, and is a two-story, three-bay, Greek Revival style brick dwelling. It has an original one-story rear wing, later expanded to two stories in the 20th century. A single-story Colonial Revival front porch replaced the original portico.It was listed on the National Register of Historic Places in 1982.Located at 605 Watson Avenue, adjacent to the Enderly House, is the Enderly kitchen. The kitchen was built in 1858 and prepared all of the meals for the Enderlys. Originally just a two room kitchen, the front 2 over 2 was added during World War I. In 1986, an additional first floor BR suite was added that enlarged the home even more.

Community Lab School (formerly Murray High School, renamed after merging with Community Public Charter Middle School in 2020) is a district-backed public charter school serving grades 6-12 located in Charlottesville, Virginia. It is a part of Albemarle County Public Schools (ACPS). In August 2018, the Albemarle County School Board renewed the school's charter to provide Albemarle County families the option of a small, liberal arts school experience with elective pathways focusing on the creative arts, media, and design. Admission is open to all Albemarle County residents on a lottery basis. The school began offering the International Baccalaureate (IB) Diploma Programme in 2020.

Judge William J. Robertson House is a historic home located at Charlottesville, Virginia. It was built in 1859, and is a two-story, roughly rectangular, brick dwelling with elements of the Italianate and Gothic Revival styles. It has rendered walls scored to simulate ashlar masonry, a hip-and-gable roof with broadly overhanging gable eaves supported by large decoratively carved brackets, and one-story wings and porches. It was built by Justice William J. Robertson (1817-1898), who was the "acknowledged leader of the Virginia bar" during the second half of the 19th century.It was listed on the National Register of Historic Places in 1999.

Jackson P. Burley High School was a segregated school for African American students in Charlottesville, Virginia. Located on Rose Hill Drive, it opened in 1951 to serve students from both the City of Charlottesville and Albemarle County. It graduated its final class of seniors in 1967, and soon after, the City's interest in the school was purchased by Albemarle County. In 1974 it reopened as Jackson P. Burley Middle School.The school was built on a seventeen-acre tract of land purchased from a prominent African American community member, Jackson P. Burley. In November, 2020, the school was listed on the National Register of Historic Places.

The Monticello Wine Company was a Charlottesville, Virginia cooperative founded in 1873 by local grape growers, led by a German, Oscar Reierson. Its four-story winery had a capacity of 200,000 gallons, and was located at the end of Wine Street, near Hedge Street. It was the largest winery in the South. It shut down with the onset of Prohibition in Virginia, which took effect on November 1, 1916. The success of Monticello Wine Company brought Charlottesville to declare itself "the Capital of the Wine Belt in Virginia." The company was best known for its Virginia Claret Wine, produced with Norton grapes—it "won a major international award in 1873 at the Vienna Exposition." It was located in what is now the Monticello American Viticultural Area.

The Marshall–Rucker–Smith House is a historic home located at Charlottesville, Virginia. It was built for J. William and Carrie Marshall in 1894 by William T. Vandegrift, the grandfather of General Alexander Archer Vandegrift, and is a two-story, nearly square, Queen Anne style brick dwelling. It has a three-story octagonal corner tower, a prominent front gable projection of the slate-shingled hip roof, a two-story rear wing, and multiple one-story porches. A two-story solarium and library wing were added by its second owner, William J. Rucker in about 1930. Also on the property is a contributing swimming pool (c. 1930) which is now used as a members-only neighborhood pool. In the mid-20th century, after the house had been made into a rooming house, future Supreme Court Justice Sandra Day O'Connor numbered among its residents while her husband was attending the Judge Advocate General School at the University of Virginia School of Law.It was listed on the National Register of Historic Places in 1999. It is located in the Charlottesville and Albemarle County Courthouse Historic District.

Four Acres is a historic home located at Charlottesville, Virginia. It was built in 1910, and is a 2+1⁄2-story, three-bay, Colonial Revival-style brick dwelling. It sits in a raised basement and has a slate hipped roof. The front facade features a four-columned, Ionic order portico.It was listed on the National Register of Historic Places in 1982. In 2016, it was listed for sale for over $10 million.

Stonefield is a historic home located at Charlottesville, Virginia. It was built about 1860, as a simple, vernacular two-story, one-over-one-room frame house on a high brick basement. A two-story Queen Anne style "facade", two rooms in width and one room deep, effectively masking the original rambling vernacular structure behind. It was added between 1880 and 1884. This section has a hipped roof with a large gable that overhangs a semi-octagonal bay-projection.It was listed on the National Register of Historic Places in 1984.

Abell–Gleason House is a historic home located at Charlottesville, Virginia. It was built in 1859, and is a two-story, three-bay, Greek Revival style brick dwelling. Each of the bays is defined by brick pilasters with Doric order inspired capitals faced with stucco. Also on the property is a contributing four room servants quarters.It was listed on the National Register of Historic Places in 2001. It is located in the Charlottesville and Albemarle County Courthouse Historic District.