The Dame

The Higgins Block, also known as the Fayette Cigar Store, in Lexington, Kentucky, is a 3-story brick building designed by John McMurtry and constructed in 1872. The cast iron, Italianate facade originally contained five storefronts on West Main Street, each with three window bays. The surviving 2-storefront building is a remnant of the original commercial block, shortened in 1912 when construction of the Fayette National Bank Building required demolition of part of the Higgins Block. The remains of the Higgins Block were added to the National Register of Historic Places in 1977.A public auction of the east 18-foot exposure of the Higgins Block was held in 1900 to divide the estate of the Higgins family, and the sale may have helped to preserve what is left of the building.John Allen Higgins (1831-1880) was a planter who owned a farm near Lexington and a plantation in Arkansas. He was a son of Joel Higgins (1802-1859) and lived at Lexington's Higgins Mansion (1837-2017) until his death.

The Fayette National Bank Building, also known as the First National Bank Building or 21C Museum Hotel Lexington, is a historic 15-story high-rise in Lexington, Kentucky. The building was designed by the prominent architecture firm McKim, Mead & White and built by the George A. Fuller Company from 1913 to 1914. It was added to the National Register of Historic Places on February 27, 1980.In 2016 the building was converted into a 21c Museum Hotel. The building was reconfigured into 88 hotel rooms, a restaurant and museum space. Renovations were expected to cost in excess of $43 million. The hotel opened in December 2016. It was then inducted into Historic Hotels of America, the official program of the National Trust for Historic Preservation, in 2019.

The Odd Fellows Temple in Lexington, Kentucky, also known as Skullers Jewelry, Inc., was built in Second Empire and Italianate style between 1869 and 1870. It was listed on the National Register of Historic Places in 1980.It is a 41 feet (12 m) by 97 feet (30 m) building that is primarily Italianate in style, but has a Second Empire-styled top floor.The listing includes "Skuller's Clock", a two-faced clock on an iron column about 10 feet (3.0 m) in front of the store.

The McAdams and Morford Building in Lexington, Kentucky, also known as the Melodeon Hall, is a 3-story commercial building constructed in 1849. An Italianate cast iron facade was added after 1857. Druggists McAdams & Morford occupied a corner space in the building 1898–1994.The building was home to Lexington's Melodeon Hall, a theater and meeting space with seating for 300 patrons. Robert Jefferson Breckinridge addressed a gathering at the Melodeon in 1861, and his remarks helped to preserve Kentucky as a Union state during the American Civil War, although Kentucky maintained separate Union and Confederate state governments during the war.The University of Kentucky (Transylvania University) Commercial College occupied the building for 35 years under the direction of Wilbur R. Smith. In 1908 the college was incorporated separately from the university as the Wilbur R. Smith Business College.In 2017 a vehicle damaged the building, and repair workers uncovered arches from the cast iron facade that had been hidden by previous remodeling.The McAdams and McFord logo appears on the cover of the 2000 album The Sickness from the nu-metal group, Disturbed.

City Center, formerly known as CentrePointe, is a residential, commercial, and retail building in downtown Lexington, Kentucky that opened in 2020. The plan consists of a 12-story office tower incorporating premium luxury condominiums in its top three floors, two hotels, retail spaces and an underground parking garage. The parking garage was completed in 2017.

The Woolworth, F.W., Building was a historic department store building located in Lexington, Kentucky, that served as a retail location for the F. W. Woolworth Company from 1946 to 1990. It was designed by Frederick W. Garber. The store was the site of protests during the Civil Rights Movement against segregation during the 1960s. After 1990, the city government favored creating a business incubator on the site. However, the building was demolished in 2004 and turned into a parking lot. As of 2022, the location is the City Center development which includes a Marriot hotel, restaurants and retail.

The Fayette Safety Vault and Trust Company Building in Lexington, Kentucky, is a commercial building designed by Herman L. Rowe and constructed in 1890. The stone facade was described as "a strange but compelling mixture of Italianate, Neo-Greek, Gothic, and Romanesque motifs," and "not excelled in appearance by any building in Kentucky." It was added to the National Register of Historic Places in 1980.The building was constructed for the Fayette Safety Vault and Trust Company, organized in 1890 and absorbed by the larger Security Trust and Safety Vault Company in 1892. An early tenant of the building was Lexington's Moving Picture Theatorium.Architect Herman L. Rowe also designed Lexington's Carnegie library in the Gratz Park Historic District and Argyle Hall at the former Campbell–Hagerman College. He was the supervising architect for the Lexington Opera House, designed by Oscar Cobb and constructed in 1887. The Opera House and Yates Bookshop Building were listed on the National Register of Historic Places in 1975.

The Dr. Walter Warfield Building in Lexington, Kentucky, is a Second Empire or Georgian building constructed in 1806 on a corner of Jordan's Row, a string of buildings constructed or owned by John Jordan. Originally two stories, the brick building was expanded in 1870 with a third story that includes a Mansard roof and dormers. A later expansion added a 2-story annex to the building.The building was constructed for Dr. Walter Warfield (June 17, 1760 – March 12, 1826), a physician who served in the Continental Army during the American Revolution and who was admitted as an original member of The Society of the Cincinnati in the state of Maryland. Warfield was a distant cousin of Elisha Warfield, both descendants of John Warfield (1672-1718) of Anne Arundel County, Maryland. Walter Warfield was a professor of midwifery in the medical department of Transylvania University in 1801, but his tenure may have been brief. Prior to construction of the Warfield Building, he practiced "physic and surgery" at the former offices of Samuel Brown and Elisha Warfield. In 1807 Walter Warfield purchased 27,500 acres of land in Montgomery County, although he may not have lived there. The previous owner had been John Jordan, namesake of Jordan's Row.

The Old Fayette County Courthouse (Kentucky) is a mixed-use commercial and civic office building located at 215 West Main Street in downtown Lexington, Kentucky, USA. It was originally built in 1898–1900 and designed by Cleveland-based architects Lehman & Schmitt, the fifth structure to be used as the Fayette County Courthouse. The building now contains civic offices, event spaces, and commercial retail space. It has been called the "most iconic building in Lexington."

The Galleria was a proposed skyscraper and mall during the early 1980s in Lexington, Kentucky bounded by Upper, Main, South Mill and Vine Streets. The primary developer of the 24 level complex was the Webb Cos.; retail was to occupy the lower three levels with offices occupying the remainder. It was never constructed after failing to attract a major department store; the original plans called for two major anchor stores with numerous smaller shops and a fast food court covering two downtown blocks. The state of Kentucky had approved $15 million in economic revenue bonds for both the Galleria and the World Coal Center. With the cancellation of the Galleria, the Webb Cos. rebranded the effort towards the World Trade Center and the Radisson Plaza completed later during the same decade.

The Lexington Financial Center, locally known as "Fifth Third", “The World’s Tallest Building”, or the "Big Blue Building", is a 357,361-square-foot (33,199.9 m2), 410-foot (120 m), 31-floor high-rise in Lexington, Kentucky. It is located between Vine Street and Main Street at South Mill Street. Its exterior features blue tinted glass that has become an identifying symbol for the downtown.It was originally proposed as a 26-story skyscraper in 1984 across from the Vine Center and replaced the failed project, the Galleria.$7.5 million in state aid was announced by then-Governor Martha Layne Collins towards the construction of a six-level parking structure that would serve Triangle Center and the Lexington Financial Center.Construction was completed in 1987. Upon completion, it housed the Webb Company, the Bank of Lexington, Sherman, Carter, Barnhart Architects and a law firm. Today, it houses the Fifth Third Bank among other financial institutions, including Kentucky Employers' Mutual Insurance

Cheapside Park was a block in downtown Lexington, Kentucky between Upper Street and Mill Street. Cheapside, originally Public Square, was the town's main marketplace in the nineteenth century and included a large slave market before the Civil War. Cheapside Park played a prominent role in the slave trade, many enslaved people sold here were moved to the lower South, or forced to work in the local areas. The local market served as a conglomerate of local slave traders, slaveholders, and other related individuals. Cheapside Park was renamed Henry A. Tandy Centennial Park, primarily due to local displeasure with the historical context and connotation of the former name. Since renamed, for previously enslaved Henry A. Tandy, it is currently home to the Lexington Farmers Market and popular events like Thursday Night Live.