It is written that John Tufts "much improved" the house during his occupancy. As best I can guess this means it was John Tufts who converted the saltbox roof to the gambrel seen in early photos. It is possible that the ground-floor footprint of the house was increased at this time. It certainly was a substantial project to remove the saltbox roof, expand the second floor, and build the new gambrel roof. And as I have heard no record of a two-chimney saltbox I can guess that during this renovation an original central chimney was removed and replaced by the two chimneys seen today.
Oliver was a scientific and successful farmer, much like his father. Based on one description, Oliver had a potato field west of the house extending from Pembroke street to Medford street (including the modern-day Tennyson street), and from Sycamore street to Central street. On the other side of Sycamore street, Farmer Tufts had his kitchen and flower garden, his barn and barnyard, and the big cornfield extending down to School street and including all of the land where Richdale Ave, Lee and Essex streets are now located. Before the railroad was built, there was a sizable pond in the natural hollow between the hills, right where the bridge is now located. Near the pond Oliver Tufts kept a "duck house" with numerous ducks.
The Tufts farm was bisected by the construction of the Lowell railroad in 1834 and 1835. The duck pond was drained by the digging of the railroad gorge. The first bridge built over the Lowell railroad tracks was at Sycamore Street, to compensate the Tufts Farm for the damage and inconvenience caused by the railroad.
Oliver's niece Caroline, her brother, and her mother moved into the house with "Uncle Oliver" after her father Asa died in 1836. It is mentioned that they lived with him until 1849 when she then married Mr. Franklin Henderson. Caroline Henderson wrote about the rows of button wood or sycamore trees that lined both sides of the lane connecting the house with Medford street, which led this lane to be named Sycamore Street.
In 1838 Oliver married Dorothy Danforth of Chelsea and in 1839 Dorothy gave birth to their only child, Annie Louisa Tufts. Annie married Dr. William Kelley Fletcher in 1874 In the meantime, Somerville incorporated first as a town in 1842, then as a city in 1872. Somerville was separated from Charlestown in 1842 because it was still largely rural while Charlestown proper was rapidly urbanizing. It is hard to imagine that distinction today.
Writings from the 1870's and 1880's describe Farmer Tufts, white-haired and wearing a long blue smock, as a "genial and neighborly friend to the small boys of the vicinity." Farmer Tufts allowed the neighborhood children to jump in his haymow, climb his black and white mulberry trees, help themselves to the fruit that fell to the ground from two tall pear trees in one of his fields, and gather lilacs from the big rows of bushes opposite the barn.”
In 1883 Oliver Tufts passed on and left the farm to Dr. and Mrs. Fletcher. Dr. Fletcher subdivided the farmland in the 1890's, creating Richdale Ave., Lee and Essex Streets, and allowing these to be populated with the Colonial Revival two family houses and three-deckers that sprung up all over the city at the turn of the twentieth century.