Bernard Berenson and his wife Mary bought Villa I Tatti in 1905. In 1909, they commissioned the English architect Cecil Ross Pinsent (1884–1963) to supervise a series of extensions and alterations to Villa I Tatti, as well as to design a garden and supervise its planting and construction with the help of the English writer-scholar Geoffrey Scott (1884–1929). The surviving documentation suggests that, while Pinsent was certainly the maitre d’oeuvre for this job, he had to contend with patrons who had clear ideas about what they wanted their garden to look like. Both Bernard and Mary Berenson did not fail to ask their architect for some substantial modifications to his original project. Their intervention was all the more understandable, as this was Pinsent’s first major commission.
Work on the garden of Villa I Tatti began with the construction of a little house at the bottom of the property to house the head gardener, as well as a large cistern sunk into the ground at the very top of the garden to provide a more adequate water supply for the planned plantings. This cistern, fed by spring water that still ensures the necessary water supply for the garden, was above all destined to keep the Berenson's "English lawns" flourishing in a climate that was hardly favorable to such a luxury.
In the spring and summer of 1912, the intricate and much admired pebble mosaics were completed on the landings of the staircase of the Italian garden and in various other parts of the garden. Work in the garden continued well into 1914, although it came to a halt in late August due to the beginning of the World War I. Fears of a conflict that would involve all of the peninsula, combined with apprehensions with respect to possible difficulties in transferring funds, stopped most of the building activity at that point in time. When work was resumed some years later the garden was finally brought to completion, with only some small modifications that did not significantly alter the construction and plantings that had been accomplished before the war.
After Harvard inherited I Tatti from Mr. Berenson, little work was done on the garden for many years. Thanks to an extraordinarily generous gift from Lila Acheson Wallace, co-founder of Reader’s Digest, extensive restoration work has been carried out over the past thirty years. Recent work in the garden, completed in 2010, created a work area in the most appropriate location; a gardener’s building in a state of disrepair has been completely rebuilt, and a state-of-the-art greenhouse has replaced an old one. A recently constructed staircase leads directly from the new Anne Pellegrino Garden in the Scholars’ Court to the historic garden.