F. W. Woolworth Building (Lexington, Kentucky)

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 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.

Lexington is the second-most-populous city in the Commonwealth of Kentucky (after Louisville), and the 60th-most populous city in the United States. It is the county seat of Fayette County. By land area, it is the country's 30th-largest city. Lexington is known as the "Horse Capital of the World". It is within the state's Bluegrass region. Notable locations within the city include the Kentucky Horse Park, The Red Mile and Keeneland race courses, Rupp Arena, Central Bank Center, Transylvania University, the University of Kentucky, Bluegrass Community and Technical College, and the National Thoroughbred Racing Association (NTRA) Headquarters. As of the 2020 census the city's population was 322,570, anchoring a metropolitan area of 516,811 people and a combined statistical area of 747,919 people. Lexington is consolidated entirely within Fayette County, and vice versa. It has a nonpartisan mayor-council form of government, with 12 council districts and three members elected at large, with the highest vote-getter designated vice mayor.

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 Phoenix Hotel was a historical structure located on East Main Street in Lexington, Kentucky, United States. It was established in the 1820s and became a prominent landmark as well as the oldest hostelry by succession in the area. After several reincarnations, the hotel closed in 1977. The building was demolished in 1987 and replaced by Phoenix Park.

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 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.

Park Plaza Apartments is a 202 unit 21 story residential high-rise in Lexington, Kentucky. It is located between Main and Vine Streets at South Limestone, and is adjacent to Phoenix Park. The complex features a 425-space seven story parking structure, with residential units beginning at the eighth floor. It is connected to the Lexington Public Library.The apartment structure at 120 East Main features an exercise room on the eighth floor, although most of the equipment is broken.

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 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 World Coal Center was a proposed skyscraper in Lexington, Kentucky where the Phoenix Hotel had once stood at South Limestone, East Main Street and East Vine Street. The $100.5 million project would have included the 41-level skyscraper and a retail shopping center. It is today home to the main branch of the Lexington Public Library, Park Plaza Apartments and Phoenix Park.

The Lexington Public Library opened in 1905 in Lexington, Kentucky. It incorporated the collection of the former Lexington Library Company (est.1801) and the former Transylvania Library (est.1795). Today the main location of the Lexington Public Library system is Central Library along East Main Street connected to Park Plaza Apartments. The Library's facade includes rose-colored granite, with large windows facing the street and Phoenix Park. A rotunda in the lobby, the focal point of the building, spans all five floors and houses the world's largest ceiling clock and Foucault pendulum, designed by Lexington sculptor Adalin Wichman. The rotunda also includes a frieze depicting the history of the horse in the Bluegrass. Included within the complex is the 138-seat Farish Theater, meeting rooms and an atrium reading lounge. An art gallery is located on the ground floor. One of the areas for researchers is the Central Library's Kentucky Room, which houses Kentucky census records and numerous other genealogy and local history resources. It also contains microfilm of the Lexington Herald-Leader, as well as its forerunners, the Lexington Herald and the Lexington Leader, along with other local newspapers. Central Library is complemented by five branch locations. The Northside Branch, located on Russell Cave Rd., replaced the previous Northside location in 2008. The Tates Creek Branch, located on Walden Drive just off Tates Creek Rd., replaced the Lansdowne Branch in 2001. The Eastside Branch, located on Blake James Dr. at Man o' War Blvd. and Palumbo Dr., replaced the Eagle Creek Branch in 2016. The Beaumont Branch, located on Fieldstone Way just off Harrodsburg Rd., replaced the Southside Branch in 1997. The Village Branch, located on Versailles Rd. at Village Dr., opened in 2004. It boasts the distinction of being an English-Spanish bilingual branch, with bilingual staff.