The origins of Largo Toll House, pictured in the centre of the photograph above, date back to 1839. The 9 May Fifeshire Journal of that year included the notice below, stating the intention of the Turnpike Trustees of St Andrews District to erect additional toll bars and houses at three new locations. Location number 2 was described as "upon the road leading to Lower Largo, immediately to the south of the four cross roads, one of which is the road from Largo, by Loans-Bar to St Andrews".
The new toll bar eventually became operational in 1846, which was more than two decades after the toll bar at Lundin Mill had been established. It is mentioned in the footnote of the notice below (12 March 1846 Fife Herald) regarding the public roup of the district's toll bars. A note is provided of the two previous years' rent amount to help guide those bidding for the forthcoming year. The toll bars with the heaviest traffic presumably attracted greater rents.
The first census after the toll house was built, 1851, records George McKenzie living there as toll keeper, with his wife Margaret. A decade later, at the time of the 1861 census, the Moyes family lived in the toll house, with 32-year-old Joseph Moyes being the "Toll Bar Keeper and Collector". Wife Margaret and three young daughters all aged under 5 completed the household. A few years later William Grubb became toll keeper and on 15 April 1870 his wife, May Drummond, died at the toll house (see 22 April 1870 East of Fife Record below). While the toll bar was operational the house was owned by the 'Turnpike Trustees of St Andrews District' and rented to the toll keeper.
By the late 1870s, the unpopular toll system was being dismantled. Although the role of toll keeper ceased, the former toll house continued to be inhabited for many more decades. Ownership of the building fell to the Largo Estate, which at the time was owned by George Johnston. In many places, former toll keepers and their families were able to continue to lease the toll houses. In 1891, William Grubb, gardener, son of the former toll keeper of the same name, was tenant of the house, living there with his wife and five of their children. He was still there at the time of the 1901 census, along with his wife and two of their adult children.
In 1903 a marriage took place at the Toll House, when William's daughter Margaret Lyall Grubb married James Ballingall Melville on 11 September. William died there in 1913 - 43 years after his mother had passed away in the same house. His widow Betsy continued to live in the Old Tollhouse until her death in 1919. Sometimes the family let out a room to summer visitors - see the advert below from the 13 July 1913 Leven Advertiser.
By the 1921 census, the Toll Cottage was occupied by Mrs Jane Grieve and her daughter Florence. The 23 March 1929 Leven Advertiser piece above tells us that that house suffered a broken pane of glass during a breach of the peace incident. The 1930 valuation roll states that a G Simpson was the tenant. By 1935 the tenancy had passed to Alexander Simpson, and in 1938 Alexander and Mary Simpson were listed on the electoral register as living in Old Tollhouse. By 1940 the house was described as 'uninhabitable' on the valuation roll. It can be seen in that condition in the 1940s image below, with the war memorial cross roads in the background.
Despite being in a state of decline, the old toll house building outlasted many other toll houses. For example the toll house at Muiredge, Buckhaven was demolished in 1933 as it obscured the road and led to accidents. Higham Toll on the St Andrews to Largoward Road was knocked down in 1937, following the death of its long term tenant. The Lower Largo Toll House still appeared on the 1964 map above but within a few years it would be gone.
In 1989 the site and its surroundings were developed when Bett Home built modern detached houses and bungalows. The street was named Toll Court in recognition of the former use of the site. The photograph below shows the development under construction. The Roundel completed this pocket of development in the mid 1990s - the name being a reference to the roundel of trees seen on the map above, south of the toll house.