School Street Duplexes

The Frederick Squire House is a historic house at 185 North Street in Bennington, Vermont. Built about 1887, it is one of the town's finest examples of Queen Anne Victorian architecture. It was listed on the National Register of Historic Places in 1992.

Mount Anthony Union High School is the public high school serving Bennington, Vermont, as well as the towns of Shaftsbury, Woodford, and Pownal, Glastenbury, and Bennington County. As of the 2023-2024 academic year, the school has about 1,200 students enrolled in grades 9-12 and has a faculty of nearly 130.It is easily accessible from US Route 7, VT Route 279, and the Green Mountain Express Red Line bus. Mount Anthony is the third-largest school in the state of Vermont. The average graduation rate is eighty-five percent. The school yearbook is officially known as the Patriot Ledger, and the school newsletter is called Mount Anthony Connections. Additionally, the school runs a bi-weekly sports newsletter, The Patriot Press, which reports on the school's athletic teams. The sports teams in their athletic program are collectively known as the Patriots. Led by head coach Brian Coon, the Patriots wrestling team holds the national record for most consecutive state titles won as of 2023 (34). Under the guidance of 1st year head coaches Frank Gaudette and Corey Greene, MT. Anthony won their 34th consecutive title, which is the longest current state championship streak in the country including all high school sports.The Mount Anthony Football team is also very successful being state champion runner-ups in the 1986–1987, 1992–1993 and 2021-2022 season and state champions in the 1974-1975, 1994–1995 and 2022-2023 seasons. The Patriots won the state championship in Division II by defeating Bellows Falls in double overtime. As of 11/6/2021 they play in Division II in the state of Vermont. They host home games at Spinelli Field. The Southwest Tech campus is housed on the school's campus.

The Julius and Sophia Norton House is a historic house at 300 Pleasant Street in Bennington, Vermont. Its main block, completed in 1846, is one of the state's finest examples of Greek Revival architecture. It was listed on the National Register of Historic Places in 2021.

Bennington station is a historic former railroad depot at 150 Depot Street in downtown Bennington, Vermont. Built in 1897-98 by the Bennington and Rutland Railroad, it is the only Richardsonian Romanesque railroad station in the state of Vermont. It was listed on the National Register of Historic Places in 1988 as Bennington Railroad Station, and since then housed a restaurant, which closed in 2018. It now is an office space for MSK Engineering and Design and Goldstone Architecture.

The Former Bennington High School is a historic school building at 650 Main Street in Bennington, Vermont. Built in 1913 and enlarged several times, it is architecturally significant as an excellent example of Beaux-Arts architecture, and is historically important for its role in local education. The building, closed in 2004, was listed on the National Register of Historic Places in 2005. Bennington's high school educational services are now provided by Mount Anthony Union High School.

The Carrigan Lane Historic District encompasses four residential structures on or near Carrigan Lane in Bennington, Vermont. All were built between 1875 and 1900, a period of growth in the town, by Thomas Carrigan, a machinist, and are a good example of the town's development at that time. The district was listed on the National Register of Historic Places in 1998.

The Downtown Bennington Historic District encompasses the historic commercial heart of Bennington, Vermont. Centered on the junction of Main, South, and North Streets, it exhibits a variety of commercial architectural styles from the early 19th to mid-20th century. It was listed on the National Register of Historic Places in 1980, and was enlarged in 2008.

The W.H. Bradford Hook and Ladder Fire House is a historic fire station at 212 Stafford Street in Bennington, Vermont, United States. Built in 1893-94, it served for over a century as a fire house for the city, and survived modernizations with much of its historic fabric intact. It has been converted into artist studios and living space. It was listed on the National Register of Historic Places in 1999.

The Ritchie Block is a historic commercial building at 465-473 Main Street in downtown Bennington, Vermont. Built in 1895-96, it is a high quality example of Classical Revival architecture, with a distinctive pressed metal entablature. The building was listed on the National Register of Historic Places in 1986.

Bennington is a census-designated place (CDP) in Bennington County, Vermont, United States. It is located entirely within the town of Bennington. The population of the CDP was 9,074 at the 2010 census, or 57.6% of the population of the entire town.

The Old Bennington Post Office is a historic government building at 118 South Street in Bennington, Vermont, United States. Also known at one time as the U.S. Federal Building, it is a Greek Revival building built in 1914, and now houses the Bennington Police Department. It was listed on the National Register of Historic Places in 1976 for its architecture.

The Holden–Leonard Workers Housing Historic District encompasses a collection of mill-related tenement houses, plus a former mill store, in Bennington, Vermont. They are located on Benmont and Holden Avenues, near the former Holden–Leonard Mill Complex, Bennington's largest employer in the late 19th century. The district was listed on the National Register of Historic Places in 2011.