A small district of Central Edinburgh, Greenside lies immediately to the northwest of Calton Hill at the top of Leith Walk. Completely transformed, this is now the location of the Playhouse Theatre, Omni Centre and several gay nightclubs, together with modern offices and a large multi-storey car park (primarily for the St James' Centre opposite). This was once a densely-populated area, with narrow dark alleys, poor sanitation and high tenements (up to nine storeys, built in the late 18th / early 19th C.) on a steeply sloping site. By the middle of the 20th C. this housing had deteriorated into slums. In the 1950s the population was moved out to new peripheral public housing estates and demolition began in the early 1960s but the difficult topography and planning indecision contributed to the area remaining a 'gap' site well into the 1990s.

The Rood Chapel of Greenside was established c.1456 and passed to the Carmelite Order (White Friars) in 1518 but was in ruins within fifty years owing to the Reformation.

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