Records of a 'flesher' at the premises go back to at least the 1850s when Alexander McGregor ran the business with wife Isabella Morrison and her brother Robert. By 1881, Alexander's son Andrew McGregor had taken over, working alongside his widowed mother. However, ten years later, it was another son - Alexander - who was running the business with his mother.
Around the turn of the century the business was taken over by William Bousie Simpson (himself the son of a butcher) who ran it for decades until his death in 1932. William's wife was Helen Henderson - hence the adjacent house was name 'Helenslea'. Helen moved to Durham Terrace in Lower Largo after WIlliam died (also calling her house there Helenslea) and her son James took over as butcher in Upper Largo for a spell. In the late 1940s, Mr R.T. Walker was butcher here but in 1948 and again in April of 1949 the family were hit by two tragic events and the butcher business ceased.
So late 1949 saw the beginning of a new identity for the shop, as a drapers. Ellen Batty ran the shop for around four years - offering such specialities as alterations on the premises, options for the "above average" figure, evening dresses and twin sets (see advertisements featured in the Leven Mail above). In 1953 the clothes shop was taken on by Mr B. Wallace who continued to trade through the remainder of the 1950s. The Leven Mail adverts below suggest his focus was more on menswear.
Eventually, the building's time as a commercial property came to an end and work was carried out to convert it into a dwelling in 1960. The shop entrance and display window were replaced with the windowed frontage that we still see today. Below are the planning application drawings for its 1960 change of use, a mid-1970s photograph of the property and one more recent image.