East Raleigh Street Historic District

Gregson-Hadley House is a historic home located at Siler City, Chatham County, North Carolina. The house was built in approximately 1903, and is named for leading Siler City industrialist Julius Clarence Gregson, for whom it was built, and his brother-in-law Wade Hadley, to whom it was sold in 1920. It is a 1+1⁄2-story, richly decorated Queen Anne style dwelling. It features an exaggerated hip roof with several projecting gables, a pentagonal corner turret, and Eastlake movement wraparound porch.It was listed on the National Register of Historic Places in 1985.

Siler City High School, also known as the Paul Braxton School, is a historic high school building located at Siler City, Chatham County, North Carolina. It was built in 1922, and is a two-story, T-shaped, five-bay school building with streamlined Art Deco design elements. It has a two-story-high auditorium wing. Also on the property are the contributing mid-1930s one-story brick woodworking shop building which now serves as a community center, a 1+1⁄2-story frame gymnasium begun in 1930, and an early 1930s dirt baseball field which was initially a football field.It was listed on the National Register of Historic Places in 1998.

Siler City is a town in western Chatham County, North Carolina, United States. As of the 2020 census, the town's population was 7,702.

Cadmus N. Bray House is a historic house located at 229 West Second Street in Siler City, Chatham County, North Carolina. James W. Turner, a local builder, constructed the house, and it remains a nearly unaltered representative of early 20th century architectural preferences in a small North Carolina rail town.

North Third Avenue Historic District is a national historic district located at Siler City, Chatham County, North Carolina. The district encompasses seven contributing buildings in a predominantly residential section of Siler City. They were built between about 1890 and 1930, and includes five primary residential dwellings and the First Baptist Church and parsonage. They are representative examples of the Classical Revival and Bungalow / American Craftsman architectural styles.It was listed on the National Register of Historic Places in 2000.

Hotel Hadley is a historic hotel building located at Siler City, Chatham County, North Carolina. It was built in 1907, and is two-story brick building with elaborate eclectic Victorian design elements. It served as the city's most desirable hotel and as Hadley's residence into the 1940s.It was listed on the National Register of Historic Places in 1985. It is located in the Siler City Commercial Historic District.

Siler City Commercial Historic District is a national historic district located at Siler City, Chatham County, North Carolina. The district encompasses 45 contributing buildings in the central business district of Siler City. They are primarily one- and two-story brick buildings dated between 1897 and 1945. Located in the district is the separately listed Hotel Hadley. Other notable buildings include the Farmers Alliance Store (1909), Edwards-Wren Building (1906), Chatham Bank (1913), Wren Building (1912), former Siler City Furniture Building (1928), Colonial Revival style United States Post Office (1940), Phillips Office Supplies Building, Thorpe and Associates Building, and Fred C. Justice Building.It was listed on the National Register of Historic Places in 2000.

Siler City City Hall, also known as the Siler City Town Hall or Municipal Building, is a historic city hall located at Siler City, Chatham County, North Carolina. It is a two-story, T-shaped, seven-bay Colonial Revival style building. It is faced in granite and features a two-story, tetrastyle pedimented pavilion with a portico in antis. It is one of three extant Works Progress Administration buildings in Chatham County.The building was constructed on the site of the former Thompson School, a private school that had operated in the late 1800s and that had been torn down in 1932. In 1939 the town signed an agreement to purchase the property for $6,701.In February 1939, the town board of commissioners selected R. R. Markley, a Durham architect, to design the building and selected Carl Phillips, a Siler City contractor, to oversee construction. Granite for the construction was mined from the R. F. Hedrick quarry in Randolph County, and construction was completed in September 1940. The total cost of construction was $72,289, $51,000 of which was provided by a grant from the Works Progress Administration. Use of the building began in the autumn of 1940, and the formal dedication was held November 11, 1941.It was listed on the National Register of Historic Places in 1998.

Jordan-Matthews High School is found in Siler City, North Carolina. This high school is a 2-A classification with about 840 students and 80 staff members. It is often referred to as J-M. Its county rivals include Chatham Central High School (Bear Creek, NC), and Northwood High School (Pittsboro, NC).

The former High Point Bending and Chair Company, also known as Boling Chair Company and Boling Company, is a historic factory complex located at Siler City, Chatham County, North Carolina. The complex includes the original 1908 factory building, along with brick factory buildings built about 1920 and 1948. The original factory is a three-story, brick building with several additions. Also on the property is a contributing section of Cape Fear and Yadkin Railroad tracks (c. 1884).Any furniture left from the disaster can be worth thousands of dollars given rarity and condition. It was listed on the National Register of Historic Places in 1999.

Snipes–Fox House is a historic home located at Siler City, Chatham County, North Carolina. It was built about 1900, and is a two-story, three bay Late Victorian style frame dwelling. It features an expansive wrap-around porch and unique interior woodwork. Also on the property is a contributing frame front-gabled smokehouse.It was listed on the National Register of Historic Places in 1998.

Chatham Charter High School is a charter school in Siler City, North Carolina serving student from kindergarten through high school. The school sits on 39 acres and a 43,000 square foot facility. The education for grades 9–12 is a middle college model; students take core classes as 9th and 10th graders, then take courses through Central Carolina Community College as 11th and 12th graders. This results in students earning transferable college credits while simultaneously earning their high school diplomas.