Harry Havemeyer Webb was born on January 7th, 1922 — the youngest child of Electra Havemeyer Webb, a prominent collector of early American folk art, and James Watson Webb II, a polo champion and businessman.
Harry attended St. Paul’s School in Concord, New Hampshire, and then graduated from Middlebury College in Middlebury, Vermont.
Harry was an avid athlete, horseman, and sportsman, often accompanying his parents on big game hunting trips to the Adirondacks and Alaska.
During World War II, Harry served as a transport pilot in the U.S. Air Force, where he flew search and rescue operations throughout Europe, Asia, and the Pacific — ferrying wounded troops back home from the front.
In 1947, he married Kate de Forest Jennings, a daughter of Kate de Forest Prentice and Brewster Jennings, who was the chief executive of the Mobil Oil Corporation from 1944 until his retirement in 1958.
Harry and Kate spent the first few years of their marriage living in a private apartment at the southern end of The Brick House in Shelburne, which was home to Harry’s parents, Electra and “Watson.”
In 1948, Electra and Watson gave Harry and Kate the land that would become High Acres Farm, to establish a home for their nascent family.
They had three daughters together: Kate Brewster (born in 1948), Laura Havemeyer (born in 1950), and Dundeen Cromwell (born in 1952).
In 1952, when the Main House was completed, the family moved from The Brick House to a new brick house at High Acres Farm.
During the 1950s, High Acres Farm continued to evolve, with the construction of the barn, stables, shed, and office, and the relocation of the “Trophy Room” building from the Brick House, for Harry to use as a lodge for entertaining friends.
Harry worked as a “gentleman farmer” — raising Hereford cattle for dairy and beef, and also served as the master of the Shelburne Fox Hounds.
In 1960, Harry’s mother and father died within six months of one another, and the following year, his older sister, Lila, died as well — tragic twists of fate.
By the 1960s, Harry and Kate’s marriage was failing, ultimately leading to their separation and divorce — leaving Harry living alone at High Acres Farm.
Harry continued to live at High Acres Farm until his death on January 27, 1975, when the property passed to his eldest daughter, Kate Webb Harris.