Detailed plans for a landscape, villa, and complex of farm buildings were drawn up by the influential Andrew Jackson Downing with assistance of Calvert Vaux prior to the former's death.

Their descendants were more amenable to selling the land for development in the years afterward, which led in turn to the efforts to protect and restore it.

[5] Vassar, a village trustee and founder of the nearby college that bears his name, bought the property from its last owner George Bloom Evertson [6] for $8,000, intending to sell subscriptions to future plots at the cemetery to local investors, a common practice at the time.

[9] The villa they designed to be the main house of the estate, a semi-Jacobethan work, was abandoned (although artists' renderings survive), since Vassar preferred the cottage as a residence.

[8] As Springside continued to grow and develop, Vassar regularly opened the lands to the public until he retired to it full-time in 1867, the year before his death.

There is combined within these precincts every variety of park-like pictorial landscape that is to be found in any part of our country – meadows, woodlands, water-courses, jets and fountains, elevated summits gently sloping into valleys, forming the natural openings for the roads to girdle the hills and knolls, and thence again reaching upward to the highest peaks, from whence the eye at one glance can survey almost every spot of the entire enclosure.

Judge Homer Nelson, the New York Secretary of State, bought the southern half of the property and renamed it Hudson Knolls.

The northern half was purchased by local shoe manufacturer John Whitehouse, who merged it with his own adjoining property to the west of the site, retaining the Springside name.

[8] The NHL designation could not protect the barn complex from being totally destroyed by arson later that month,[13] and the other buildings suffered from continued decay and neglect.

A lawsuit two years later alleging an insufficient environmental impact statement was settled in 1986 with the development of the farm portion of the property, close to Route 9 and the river, while the remaining landscape donated to a newly established non-profit organization, Springside Landscape Preservation, which continues to maintain the property.

[5] The buildings at Springside, both planned and built, used consciously rustic board-and-batten siding, emphasized by some of the thousand trees[19] he had transplanted from nearby forests.

On the ground, the curving pathways follow the contours of the land beneath them and lead to scenic views, sometimes created by planting evergreens around rock outcrops[19] Statuary embellishments unite the buildings and grounds, and Downing took advantage of the property's natural drainage to create streams and fountains.