Spruce Street YMCA

The Roger L. Stevens Center is the primary performance venue in downtown Winston-Salem, North Carolina and is owned and operated by the University of North Carolina School of the Arts. It is named after the theatre producer and real estate magnate Roger L. Stevens and was opened on April 22, 1983. The venue serves the major UNCSA productions, the Winston-Salem Symphony, Piedmont Opera, and many other touring and local productions. All in all the theatre is used for rehearsal or performance all but 70 days of the year.

Shamrock Mills, also known as Hanes Hosiery Mill #1, is a historic textile mill building located at Winston-Salem, Forsyth County, North Carolina. It was built in 1911, and is a one-story brick building with daylight basement. It is six bays deep and extends in seven sections with a rhythmic saw-tooth roof and six-foot skylights. An addition was built in 1925. It was the first building used by the Hanes Hosiery Company. The mill closed in 1926, and the building subsequently housed a Cadillac dealership. The building houses the Sawtooth School for Visual Art. It was listed on the National Register of Historic Places in 1978.

The National Black Theatre Festival (NBTF) was founded in 1989 by Larry Leon Hamlin in Winston-Salem, North Carolina. Serving as its executive director, Hamlin’s goal in creating the Festival was "to unite black theatre companies in America to ensure the survival of the genre into the next millennium." Held biennially since 1989 for six days, the NBTF showcases the best in African-American theater.

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.

The Independent Order of Odd Fellows (IOOF) is a non-political, non-sectarian international fraternal order of Odd Fellowship. It was founded in 1819 by Thomas Wildey in Baltimore, Maryland, United States. Evolving from the Order of Odd Fellows founded in England during the 18th century, the IOOF was originally chartered by the Independent Order of Oddfellows Manchester Unity in England but has operated as an independent organization since 1842, although it maintains an inter-fraternal relationship with the English Order. The order is also known as the Triple Link Fraternity, referring to the order's "Triple Links" symbol, alluding to its motto "Friendship, Love and Truth".While several unofficial Odd Fellows Lodges had existed in New York City circa 1806–1818, because of its charter relationship, the American Odd Fellows is regarded as being founded with Washington Lodge No 1 in Baltimore at the Seven Stars Tavern on April 26, 1819, by Thomas Wildey along with some associates who assembled in response to an advertisement in the New Republic. The following year, the lodge affiliated with the Independent Order of Oddfellows Manchester Unity and was granted the authority to institute new lodges. Previously, Wildey had joined the Grand United Order of Oddfellows (1798-) in 1804 but followed through with the split of Independent Order of Oddfellows Manchester Unity (1810–) before immigrating to the United States in 1817. In 1842, after a dispute on authority, the American Lodges formed a governing system separate from the English Order, and in 1843 assumed the name Independent Order of Odd Fellows.Like other fraternities, the Independent Order of Odd Fellows began by limiting their membership to white men only. On September 20, 1851, the IOOF became the first fraternity in the United States to include white women when it adopted the "Beautiful Rebekah Degree" by initiative of Schuyler Colfax, later Vice-President of the United States.Beyond fraternal and recreational activities, the Independent Order of Odd Fellows promotes the ethic of reciprocity and charity, by implied inspiration of Judeo-Christian ethics. The largest Sovereign Grand Lodge of all fraternal orders of Odd Fellows since the 19th century, it enrolls some 600,000 members divided in approximately 10,000 lodges into 26 countries, inter-fraternally recognized by the second largest, the British-seated Independent Order of Oddfellows Manchester Unity.

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 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.

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.

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.

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.

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.