Large farms covered much of the South West neighborhood through most of the 19th century.

The eastern boundary of the neighborhood is Fairfield Avenue, which runs along a natural ridge of land that is 159 feet above the Connecticut River and was once promoted as the "highest elevation in Hartford." The road was considered to be the main thoroughfare to Wethersfield and attracted leisure drivers with its sweeping vistas eastward and westward. In 1874 the Hartford Courant reported, "[Fairfield Avenue] commands from almost every rod of its entire distance a view of the Connecticut valley on the east and the fine stretch of country lying on the west—a most sightly and beautiful landscape in either direction. It will make altogether the longest direct drive with unobstructed outlooks, and the most attractive too, that we have in Hartford, and that is saying a good deal...."

The Oliver Easton house was built in 1869, and was the second home on the avenue (the first being the George A. Fairfield "Weed Mansion" on the east side of Fairfield Avenue, thus in a different neighborhood).

The third residential structure built on the avenue was the James H. Smith house, built in 1901. Originally, the double house was set on 40 acres of land with outbuildings, including a carriage house, that ran up to White Street. The vintage real estate ad for a "Gentleman's Home for Sale" illustrates how the home looked at that time. The home still stands today, but with considerably less undeveloped land surrounding it.

For many years, the Weed, Easton and Smith homes were the only structures on the road, giving it a rural feeling.