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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

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.

WCDA (106.3 FM, "Hits 106.3") is a radio station licensed to Versailles, Kentucky, United States, broadcasting to the greater Lexington metropolitan area. It plays adult top 40 music, as it is a Mediabase Hot AC reporter. It is owned by L.M. Communications. The station's studios are located at Triangle Center in downtown Lexington, and its transmitter is located atop Lexington Financial Center, also in downtown.

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.

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 Triangle Center is primarily an office complex with several restaurants and a coffee shop in downtown Lexington, Kentucky. Originally envisioned as a shopping and dining complex bound by Broadway, East Main and South Mill Streets, it was constructed by the Webb Cos, to complement adjacent Victorian Square which had opened only one year prior.It was first announced on October 1, 1984, by the Webb Cos. as a "festival marketplace" with boutiques, shops, and food kiosks. The Festival Marketplace, as it was first named, was a combined effort by the developer with the Lexington Financial Center to replace the failed Galleria project. It was to be modeled after Harbor Place in Baltimore, Maryland, Waterside in Norfolk, Virginia, Faneuil Hall in Boston, Massachusetts and Toledo, Ohio's Portside. The open-air yet enclosed 114,000 sq ft (10,600 m2). structure would contain numerous small shops, a food court with a common dining area and a restaurant or a nightclub. A farmers market was also considered as a tenant. In addition to the marketplace, $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 Festival Marketplace and the Lexington Financial Center.

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.

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.

The Kincaid Towers is a 22-floor high-rise in Lexington, Kentucky. It is located along Vine Street between Broadway and Mill Street. Its exterior is polished buff concrete with blue tinted glass, with terraces on the 5th, 10th, 14th, and 21st floor. It has a three-story atrium, and a skywalk that connects to the adjacent Hyatt Regency Hotel and Central Bank Center. It is named after Garvice Delmar Kincaid.

Monsieur Giron's Confectionery in Lexington, Kentucky, is a 2-story Greek Revival building constructed of brick in 1829. The building replaced an earlier wood frame building at the site, also occupied by Monsieur Giron's Confectionery. A 50-ft ballroom on the second floor was partitioned by folding doors into two spaces. Originally seven bays wide, only three bays in the north half of the building remain. The building's remnant was added to the National Register of Historic Places (NRHP) in 1974.

The Dame was a music hall in downtown Lexington, Kentucky, United States. The venue hosted live music seven nights a week from local, regional, and national headlining acts. Nick Sprouse and Cole Skinner served as talent buyers.The Dame traditionally booked indie rock, punk, alternative country, underground hip-hop, rockabilly, jazz, bluegrass, jam bands, folk, experimental, and reggae. The Dame also hosted film screenings, open mic nights, charity events, and participated in city events such as the annual Mardi Gras celebration. The Dame opened in April 2003. It had a capacity of 390. The room was a traditional music hall with general admission standing room. The Dame was forced to close after the property owners demolished the entire city block to build a multi-use office building and hotel. A second location opened in October 2008 a few blocks down the street but closed in September 2009. Both buildings have since been demolished.

The Hilton Lexington/Downtown is a 240 feet (73 m), 22-story multi-use skyscraper in Downtown Lexington, Kentucky. Floors 1 through 17 comprise the 366-room hotel, while floors 18 through 22 are privately owned condominiums.