In the 16 century a traveller from Whitehall to Hampton Court Palace who could not afford the easier and safer route,
(often taken by Thomas More by boat on the River Thames) would cross the footpath(mugger) infested Putney Heath where the highwayman Tibbet was hanged.
He descended the hill to cross Beverley Brook near the present Robin Hood Gate. He then climbed Kingston Hill to pass another gallows near the junction of the hill with Crescent Road where the priest William Way was martyred for his Catholic faith in 1588.
Descending the hill to Kingston, he crossed the Thames at a point that the Bishop of Winchester, anxious to keep an eye on the intrigues at Hampton Court and Whitehall, built his town house on the site of the present Young's pub.
In the 19th century development began on either side of the important highway of Kingston Hill with the building of large houses with small estates for the rising professional class from London. Among these was ‘Coombe Leigh’, the boyhood home of the novelist John Galsworthy, author of The Forsyte Saga, (later a famous TV costume drama) which he set in this area.
Development was severely constrained by the presence of common land – Wimbledon Common – on one side and royal land – Richmond Park – on the other.
These two domains came together at Robin Hood Gate to form the apex of a triangle embracing the highway formed by Kingston Hill. It was at the apex of this triangle that further development occurred in the 1930s with the building of the Kingston Vale Estate.
This estate, together with the earlier development on either side of Kingston Hill, formed part of the parish of St Agatha's. The estate was, however, two-and-a-half miles from the parish church, which was something of a challenge in the days when few people had a car and public transport did not start until lunch-time on Sundays.
Archbishop Amigo expressed concern about this so Fr Jenner, Parish Priest of St Agatha's, looked for a site for a church in Kingston Vale. He secured an option on a house 'Robin Wood' but planning permission was refused after a public enquiry. The outbreak of the 1939-45 war halted further efforts to find a site on which to build a church.
After the war, the search for a site for a church in Kingston Vale was resumed without success. Meantime, some relief came to the residents when the neighbouring parish of St Joseph in Roehampton was faced with a similar problem of serving a new, outlying estate in Roehampton Vale. It opened a Mass centre at the KLG sparkplug factory on the site of the present Asda superstore. People from Kingston Vale walked there to Mass in the canteen, returning full of grace, some with liberal helpings of jelly custard adhering to their Sunday best!
This arrangement continued until 1955 when Arnold Brenninkmeyer of C A Modes, grandson of the founder, offered his house at ‘Holmwood’ on Kingston Hill as a Mass centre. The first Mass was said there on the Second Sunday of Advent (4 Dec) 1955.
Thereafter, an average of 50 people(on special occasions as many as 90) crowded into the library of the house for Mass each week for the next two-and-a-half years. In 1958, the house 'Coombe Leigh' (the history of which was chronicled by Ann Roper in The Story of a House - Coombe Leigh was published in 1985) was offered for sale.
It was too far from Kingston Vale to be ideal but, as there was no prospect of securing a suitable site in the Vale, it was purchased by an anonymous donor.
The first Mass was said in the house on 18 May 1958 by Fr. Cremin, parish priest of St Agatha's, who then set about building a church. This was during one of the economic downturns when bank loans were prohibited...undeterred Fr Cremin secured a loan of £26,000 from the Bank of Ireland.
Work began in January 1960 and, as the summer was good, the church was completed in record time. Fr Cremin said the first Mass on the morning of the feast of the Immaculate Conception (8 December 1960) and Archbishop Cowderoy blessed the church of St. Ann and said Mass in the evening.
The Church was served by the priests from St. Agatha's for over five years when Archbishop Cowderoy decided it should become a separate parish.
Fr. Cremin objected strongly on the, not unreasonable, grounds that the parish of St. Agatha as a whole had paid for the Church, paying off the debt in the record time of three years and was now building a primary school. He thought the parish should remain undivided until this had been paid for.
Archbishop Cowderoy insisted, however, and Fr. Joe Sullivan, parish priest of St. Bede’s, Clapham Park was appointed as the parish priest of the new parish of St. Ann’s, Kingston Hill.
A number of priest have served as parish priest and parish administrators and these are Fr. Michael Gwinnell, Fr. Denise Keating OP, Fr. Paul Fennessey, Fr. John Wingfield, Fr. Geoffrey Smiths, Fr. Desmond Doherty and the incumbent parish priest Fr. Michael Sileshi.