He reported back to the Supreme Executive Council and its then-president, Benjamin Franklin, on February 19, 1788, warning that the land, including the Fineview area, "abounds with high Hill and deep Hollows, almost inaccessible to a Surveyor.

"[7] The next significant development came under the ownership of banker Thompson Bell, who acquired the same 60 acres in 1847–1848 and began advertising subdivided lots of land for sale in 1849.

[8][9][10] In 1854, Bell sold a five-acre tract of land to St. Mary's Parish, whose predominantly German Catholic parishioners worshiped in East Allegheny, for a cemetery.

[11] Stonemason and engineer James Andrews bought his first section of "Nunnery Hill" in 1864 and commissioned his Heathside Cottage for the site soon thereafter.

While wealthy residents of Allegheny established country estates on Nunnery Hill in the late 19th century, others put the hilltop area to other uses typical of the rural-urban fringe.

Other developments during the late 19th century included the founding in 1880 of a "Home for Colored Orphans," located for a few short years at the intersection of Fountain Street and Sandusky Street; demolition of the old St. Clare's Seminary in 1881 to make way for James Andrews' second and final Nunnery Hill residence, Ingleside Place; installation of a sewer system; establishment of the McNaugher Memorial United Presbyterian Mission, in 1896; forming of a Nunnery Hill Athletic Association; and opening of at least one grocery store.

[19][20][21][22][23][24][25] By the time the Nunnery Hill Inclined Plane Company closed its titular funicular in 1895, due to safety concerns,[26] the area it had served had transformed over the previous century from an "inferior," "inaccessible" hillside, per surveyor David Redick, into an urban neighborhood of such a size that could support a school, a church, a baseball team, and two grocery stores.

Despite challenges involving public health, housing, and abandonment, the neighborhood's population remained relatively stable during this period.

[27] The Pittsburgh Railways Company began operation of its Nunnery Hill streetcar line months later, on March 31, 1908, ending the neighborhood's 13-year transit drought.

As one report later described such housing, alongside a photograph of Fineview's Henderson and Fountain Streets: "rambling structures grafted to hillsides, no outdoor play-spaces except vertical ones.

Two decades after the church had abandoned the site, the secluded, crumbling chapel became an ideal spot for boxing matches, chicken fights, and card games.

[37] The Fineview Board of Trade built a new grandstand at their baseball field (home of the "Highlanders") in 1923;[38] by the end of the decade, the estate overlooking the ballpark, the Andrews family's Ingleside Place, was vacant.

[39] By the time applications for its 282 apartments opened in July 1942, war had intervened, and the project had been reclassified as being for defense workers first, low-income families second.

Seventeen distinct flights of city steps connect pedestrians to public transportation and provide an easy way to travel through this hilly area.