The ground on both sides of York Street (now Duke of York Street) formed part of the land granted freehold to the Earl of St. Albans's trustees in 1665. South of the line of Apple Tree Yard (formerly Angier Street) and Ormond Yard (sometimes also called Angier Street, or Blackamoor Street or Blackmoor Head Yard) the street was flanked by the return frontages of the corner sites in St. James's Square. The ground to the north of Apple Tree Yard and Ormond Yard probably formed part of the plots of the corner houses facing Jermyn Street.

York Street was probably so named in honour of James, Duke of York, who succeeded to the throne as James II in 1685. It is first mentioned by name in the ratebooks in 1686, when there were five houses on the west side and three on the east. It is likely that some of these houses had been built a few years earlier. In 1720 John Strype described York Street as 'a broad Street; but the greatest part is taken up by the Garden Walls of the late Duke of Ormond's House, on the one Side, and on the other Side by the House inhabited by the Lord Cornwallis. So that towards the Church there are not above two or three Houses on each Side.'

A public house known as the Red Lion has stood on the southern part of the site of the present building since at least 1788.

In December 1820 Janet Wimberley of Brighton, spinster, granted to Henry Watts, victualler, of the Red Lion, York Street, a thirtysix-year lease of two messuages on the west side of the street. Watts covenanted to demolish the existing houses, one of which he already occupied, and erect one house in their place at a cost of at least £1000. The ratebooks show that rebuilding took place in the following year. The freehold was acquired by Meux's Brewery in 1907.

The upper part of the Red Lion is a typical house-front of the early nineteenth century, faced with stock brick and containing two tiers of three evenly spaced windows with the sashes set in plain openings having flat arches of gauged brickwork, the lower windows being framed by shallow roundarched recesses. The front face of the slated mansard roof contains two round-headed casement dormers.

The interest of this building resides in the late Victorian public house on the ground storey, which has an elaborate front of five bays, each end one a doorway with a Doric arch set against Corinthian pilasters, the middle doorway being framed in an eared classical architrave below a console-flanked fanlight. Above the glass fascia is a cast-iron railing of elaborately scrolled design. The small interior has a ceiling of cigar-brown lincrusta, the walls and partitions being formed in light arcaded frames of polished mahogany, enclosing glass panels enriched in every possible way with frosted, brilliant-cut and partly mirrored arabesque patterns. It has been described and illustrated in The Architectural Review as a 'perfect example, except for bomb damage, of the small Victorian Gin Palace at its best'.