The Highlands was planned to be an elegant farm and incorporate the sense of space in the country and rich views of the land. Adjacent to the stone octagonal springhouse, Morris placed his fishpond and formal gardens. 

Innovative agricultural methods of crop rotation and of raising livestock made use of the vast landscape which was further expanded by George Sheaff.

As a wine merchant, Mr. Sheaff was involved in growing a variety of grapes and installed the large garden, or “Pleasure Ground,” to the east of the house. To enhance the garden, he constructed the crenelated stone walls, a grapery and a gardener’s cottage. By 1844, the landscape architect Andrew Jackson Downing described The Highlands as “a striking example of science, skill and taste, applied to a country seat, and there are few in the Union, taken as a whole, superior to it.” Downing also wrote of the magnificent white oak tree, the handsome evergreens and deciduous trees. By the early twentieth century the size of the estate and its agricultural use had diminished. However, under the direction of Miss Sinkler and landscape architect Wilson Eyre, the garden plan of the Sheaff era was redefined.

Statuary, reflecting pools and specimen trees were added to the landscape. The Pennsylvania Horticultural Society recognized the beauty of the gardens and awarded Miss Sinkler its Gold Medal in 1933