High Hollow's design is derived in-part from Howe's thesis while studying under Victor Laloux at the École des Beaux-Arts in France.

Bordering Fairmount Park and overlooking the Wissahickon Valley, High Hollow is often regarded as Howe's most significant residential work and viewed by many as setting the standard for house design in the region through the early 20th Century.

Famed architect and educator Robert A. M. Stern referred to the house as being "often imitated" and "never surpassed" by those that came to design in a similar style.

Renowned American blacksmith Samuel Yellin, who was frequently commissioned by Mellor, Miegs & Howe, fabricated all of the intricate metalwork at the estate.

When Howe left Mellor, Meigs & Howe in 1928, he sold High Hollow to cigar mogul Samuel Paley (see La Palina) and his artist-philanthropist wife, Goldie Paley.