100 North Main Street

Winston-Salem City Hall is a historic city hall located at Winston-Salem, Forsyth County, North Carolina. It was designed by the architectural firm Northup and O'Brien and built in 1926. It is a three-story, U-shaped Renaissance Revival building. It is a brick building with a first floor of rusticated stone. It has a flat roof with a limestone cornice and balustrade with shaped balusters. The Salem town offices were housed in the Salem Town Hall until consolidation in 1913. The building was renovated in 2000.It was listed on the National Register of Historic Places in 2001.

8 West Third Street is a 126 ft nine-story skyscraper in Winston-Salem, North Carolina, also known as the Wachovia Bank and Trust Company Building. It was built in 1911 as the headquarters of Wachovia Bank and Trust, with the ninth floor added in 1917. It was Winston-Salem's first steel frame skyscraper, built in the Renaissance Revival style, and it was the city's tallest building from 1911 until the O'Hanlon Building was built in 1915, and again from 1917 until the completion of Hotel Robert E. Lee in 1921. The Wachovia Bank and Trust Company Building served as the bank's headquarters until a new headquarters was built in 1966. It was named to the National Register of Historic Places on May 31, 1984, as "Wachovia Bank and Trust Company Building".It was designed by Frank Pierce Milburn of Milburn, Heister & Company.Wachovia House Inc., an affiliate of JDL Castle Corp., sold the building for $3 million to PMC Property Group in a deal completed December 7, 2021. Plans so far only include the name 8 W 3.

Forsyth County Courthouse is a historic county courthouse located at Winston-Salem, Forsyth County, North Carolina. It was built in 1926, and is a three-story, limestone clad, Beaux-Arts style building that incorporates interior elements of the earlier 1896, Romanesque Revival style courthouse. Between 1959 and 1960, additions were built onto the front and rear. It has been converted into private apartments and in 2018, was owned by Winston Courthouse LLC. In front of it for decades was the Confederate Soldiers Monument, which was removed in 2019. It was listed on the National Register of Historic Places in 2013.

The Winston Tower (formerly Wachovia Building) is a 410 ft (125 m) tall skyscraper in Winston-Salem, Forsyth County, North Carolina, completed in 1966 with 29 floors. It was the tallest building in North Carolina, succeeding the Reynolds Building in Winston-Salem, until it was passed by Charlotte's Jefferson First Union Tower in 1971.It was listed on the National Register of Historic Places in 2001.After a 2003 renovation in which all 6,033 windows were replaced with tinted glass to save energy, the building received its current name. It has 436,000 square feet (40,500 square meters) of office space. As of 2009, Winston Tower is the second tallest office building in the city, behind 100 North Main Street; both have previously served as the corporate headquarters for Wachovia Bank. On December 10, 2021, Truliant Federal Credit Union confirmed it had acquired naming rights to the tower. The name "Truliant" was scheduled to appear on the east and west sides at the top of the building in April 2022, to mark the credit union's 70th anniversary. The company plans "a small presence in the building."An August 17, 2022 Forsyth County Register of Deeds filing shows that Charlotte-based Winston Tower LLC purchased the building for $14 million. The company's manager Jason Tuttle said 100,000 square feet of space was available and it would be marketed to companies formed in business incubators. Tuttle also said Truliant still planned to put its signs on the building. The letters were delayed and are now scheduled to be put in place in July 2023.

The Pepper Building is a historic commercial building located at Winston-Salem, Forsyth County, North Carolina. It was designed by the architectural firm Northup and O'Brien and built in 1928. It is a six-story, brick building with Art Deco style detailing. It has a flat, parapeted roof and terra cotta decorative elements, including lions' heads and pilasters. The building originally housed a department store.It was listed on the National Register of Historic Places in 2014.

BB&T Financial Center is a 340-foot (100 m) postmodern green glass and steel skyscraper at 200 West 2nd Street and is the 2nd tallest building in Winston-Salem, Forsyth County, North Carolina, United States with 271,445 square feet (25,218.1 m2) of space. It was completed in 1987 and has 21 floors. It served as the headquarters of BB&T from the merger of BB&T and Southern National Bank in 1995. The 19th floor has The Piedmont Club, with 13,232 square feet (1,229.3 m2) feet.

O'Hanlon Building is a historic commercial building located at Winston-Salem, Forsyth County, North Carolina. It was designed by architect Willard C. Northup and built in 1915. It is an eight-story, steel frame building clad in brick and terra cotta, and is the city's second-oldest skyscraper. It was Winston-Salem's tallest building until 1917 and according to Ted Kairys of Kairys Real Estate Group, it was the tallest building in North Carolina during that time. Kairys also said E.W. O'Hanlon, who tore down his drugstore at the site, moved the drugstore into the first floor of his building. The building has 26,088 square feet.It was listed on the National Register of Historic Places in 1984.O'Hanlon LLC bought the O'Hanlon Building in 2016 for $2.15 million from seven sellers. SC Deacons OZ LLC of Greenville, South Carolina bought the building for $2.1 million in a deal completed December 15, 2022. Lou Baldwin of Baldwin Properties, which represented both parties, said renovations included a new roof and a new elevator, along with open floor plans on three floors. More renovations were planned.

James Mitchell Rogers House is a historic home located at Winston-Salem, Forsyth County, North Carolina. It was built between 1883 and 1885, and is a large two-story, eclectic Late Victorian frame dwelling. The house design reflects Late Gothic Revival, Italianate, and Queen Anne style design influences. It features steeply pitched gables sheathed in board and batten siding, bay windows, and irregular massing. It was the home of James Mitchell Rogers, a prominent Winston-Salem businessman, and his son, Francis Mitchell Rogers, chief chemist of Standard Oil Company of Indiana.It was listed on the National Register of Historic Places in 1982.

The Reynolds Building is a 314-foot (96 m) Art Deco skyscraper at 51 E. 4th Street in Winston-Salem, Forsyth County, North Carolina with 313,996 square feet (29,171.2 m2) of space. It was completed in 1929 and has 21 floors. For much of its history the building served as headquarters for R. J. Reynolds Tobacco Company. After a sale to PMC Property Group in 2014, the building went through an estimated $60 million in renovations. In March 2016, The Residences @ the R.J. Reynolds Building, apartments located on the top 11 floors, opened. The first six floors opened as the Kimpton Cardinal Hotel in April. Katharine Brasserie & Bar, a restaurant named for Katharine Smith Reynolds, followed in May.

Salem Town Hall is a historic town hall located at Winston-Salem, Forsyth County, North Carolina, United States. It was designed by architect Willard C. Northup and built in 1912. It is a two-story brick building with stone, cement and wood trim. It features a three-story corner bell tower and has Italianate and local Moravian design elements. The building housed the Salem Town offices until it consolidated with the town of Winston in 1913, then moved to the newly built Winston-Salem City Hall in 1926. The building continued to be used as a fire station until the mid 1970s. It was subsequently renovated into offices.It was listed on the National Register of Historic Places in 1983.

Winston-Salem Southbound Railway Freight Warehouse and Office is a historic railway freight warehouse and office building located at Winston-Salem, Forsyth County, North Carolina. It was built in 1913, and is a two-story, brick railroad building with a shallow gable roof and Italianate-style design elements. It measures 40 feet by 224 feet. The building served until 1985 as headquarters for the Winston-Salem Southbound Railway. In 1990, the building was sympathetically renovated for office use.It was listed on the National Register of Historic Places in 1991.

Conrad-Starbuck House is a historic home located at Winston-Salem, Forsyth County, North Carolina. It was built in 1884, and is a 2+1⁄2-story, three-bay, double pile Italianate style brick dwelling. It has a number of rear additions. The central projecting bay once had a three-story tower, but the top level was removed between 1912 and 1917.It was listed on the National Register of Historic Places in 1990. The property was purchased in 2019 by Spear Properties Group, with plans to renovate the house and surrounding land to fit historic roots. The house now serves as office suites for downtown Winston-Salem.