Located in the easternmost section of Newton, the village of Chestnut Hill was originally settled by the Hammond family in 1665. The initial Hammond property encompassed all of what is now the Newton portion of Chestnut Hill. The family remained in the area for generations, giving its name to Hammond Street, Hammond Woods and Hammond Pond.

Originally isolated and relatively inaccessible, the area remained sparsely settled well into the 1800s and long after development had begun in the rest of Newton. With the advent of railway access to Brookline and Boston via the Beacon Street extension in 1850 and the Charles River Railroad in 1852, the character of the area began to change. When Capt. Joseph Lee of Beverly purchased his farm from the Hammond family in 1822, he was one of only a handful of residents in the area.Upon his death in 1845, though, the property passed to his six nieces and nephews, several of whom moved to the old farm, built houses and laid out an ambitious development plan for a community of country estates called Chestnut Hill. As rail service improved, more of the Lee family, along with their associates from Essex County, moved to Chestnut Hill. These included members of such prominent North Shore families as the Lowells, the Cabots, the Lawrences, and the Saltonstalls. Thus the “Essex Colony” was established.

Despite this early influx, the majority of Chestnut Hill was not developed until after 1880 when transportation to the area had improved. Between 1880 and 1910, the remaining land was carved into a combination of large building lots, private estates, and even a “working” farm. The prominent architectural styles of the period– Georgian, Colonial Revival, and Shingle – are all well represented and the area is distinguished by a number of significant architect designed homes. While the neighborhood continued to develop well into the 20th century, it still retains the rural neighborhood character established in the mid and late 19th century. In 1991, the Chestnut Hill Local Historic District was established to preserve and extend the architectural elements and character defining aspects of this neighborhood.