Opera House and Yates Bookshop Building

The Lexington Opera House is a theatre located at 401 West Short Street in downtown Lexington, Kentucky. Built in 1886, the Opera House replaced the former theatre, located on the corner of Main and Broadway, after fire destroyed it in January 1886. The new Opera House was designed by the renowned architect Oscar Cobb and is listed on the National Register of Historic Places for its historical and architectural significance. It is currently owned and operated by the Lexington Center Corporation, and it hosts ballets, opera, children's productions, family shows, comedy, music and professional national Broadway tours. The Lexington Opera House is one of 14 theatres in the country built before 1900 with less than 1,000 seats that is still in operation as a live performance venue.

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 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.

Triangle Park is a private park built for public use, located at 400 W Main Street in Lexington, Kentucky. The park is currently used as a source of entertainment for local citizens.

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.

Henry Clay's Law Office was the law office of American statesman Henry Clay in Lexington, Kentucky from 1803 to 1810; it is one of the few professional buildings still standing from that time.

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 First Presbyterian Church in Lexington, Kentucky is a historic church at 171 Market Street. The church was designed by the important Lexington architect Cincinnatus Shryock who was also an elder at First Church. The original congregational name was the Mount Zion Church, founded in 1784, making it one of the oldest churches in Lexington, KY. The name was changed when they moved to the present day building in 1874.It was added to the National Register of Historic Places in 1974.

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 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 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 Hunt–Morgan House, historically known as Hopemont, is a Federal style residence in Lexington, Kentucky built in 1814 by John Wesley Hunt, the first millionaire west of the Alleghenies. The house is included in the Gratz Park Historic District. The Alexander T. Hunt Civil War Museum is located on the second floor of the Hunt–Morgan House.Other notable people who resided at Hopemont include John Wesley Hunt's great-grandson, Thomas Hunt Morgan. Born in the house in 1866, he became the first Kentuckian to win the Nobel Prize in Physiology or Medicine. The house has many beautiful architectural features, including the Palladian window with fan and sidelights that grace its front façade. In 1955 the Blue Grass Trust for Historic Preservation was formed to save this home from impending demolition. The organization restored the home to its Federal appearance.The Hunt–Morgan House is located on the corner of Mill and Second Streets, at 201 N. Mill Street, in Gratz Park in Lexington, Kentucky. The Bluegrass Trust for Historic Preservation still maintains the Hunt–Morgan House.