Last month the Clark County-Winchester Heritage Commission gave a historic preservation award to Chad and Emily Grant for their home at 3815 Old Boonesboro Road. I was intrigued to learn that the oldest part of the house still has the remains of a log structure inside. The Kentucky Heritage Council’s inventory sheet (Ck-45) refers to the home as the Pinnell-Osborne House and includes the following description:
“House frame and brick. Original portion is vertical-boarded single pen [cabin]. This was subjugated to a rear ell with the addition a brick three-bay I house. Entire house was painted white, re-detailed and re-oriented in the 1920s.”
The house stands on land that was first granted to William Ledgerwood, a native of Ireland. In 1779 William and his wife Rebecca (née Moody) sold their farm in Virginia and moved to Kentucky. His 500 acre preemption on Lower Howard’s Creek was surveyed in 1783.
William died in Clark County in late 1793 or early 1794. His will lists two sons—James and Samuel—and four daughters—Isabel, Margret, Mary, and Rebeccah. Reports list another son, William Jr. This may be the William Ledgerwood who served in Gen. Charles Scott’s 1791 campaign against Miami and Shawnee villages in Indiana. On their return trip home, young William perished while the company was crossing a rain-swollen river.
William left the homeplace to his wife Rebecca. While it’s nearly impossible to prove who built the original cabin lodged inside the Pinnell-Snowden House, it seems likely that it was William Ledgerwood. The cabin stood at the south end of the present house. The basement under the cabin is laid up with dry-laid stone and the floor joists are made of peeled logs.

Rebecca sold the house and 310 acres of land to Zachariah Field in 1806. Field sold to John Wilkerson in 1808 for $5,000. Wilkerson was still living on the place in 1819 when the property sold for $10,068. The difference in sale price could indicate that Wilkerson made substantial improvements to the house.
Never miss a thing with our FREE weekly newsletter.
Between 1819 and 1885, the house and attached land went through eleven different owners. William E. Pinnell purchased the property in 1885 for $7,000. By that time, the surrounding farmland had decreased to 93 acres. A prominent farmer, Pinnell raised horses, mules, cattle, and hogs. His wife Alice bred Bourbon Red turkeys and kept dairy cows and chickens from which she sold butter and eggs.
Beginning around the turn of the century, W. E. and his wife held frequent parties at “Breeze Hill,” described as their “beautiful country home.” The guest list sometimes included more than 40 people and had the Winchester Orchestra for entertainment. Elaborate descriptions of the home lead one to suppose that it was the Pinnells who enlarged the single-pen south end by the addition of the three-pen I house. W. E. Pinnell died in 1912, and in 1923 Alice sold the place to Nathaniel F. Cheairs.
N. F. Cheairs was engaged in farming, banking, real estate, oil, and bluegrass seed. His wife Ethel was the daughter of Winchester Mayor John Garner. The Cheairs may have been the ones credited with adding a kitchen complex to the rear and reorienting the entrance to face east toward Old Boonesboro Road. The popular couple kept the house and farm for 38 years before selling to Thomas M. Swope in 1948. Beverly White purchased the place from Swope in 1949 and sold it to Fred Osborne in 1953.
Fred Osborne, a farmer and distributor for the White Truck and Auto Company, died in 1965. His wife Ruth continued at the Boonesboro Road home until her passing in 1987. In 1991 Woody and Robin Snowden purchased the home and 23 acres. The Snowdens sold the home to Chad and Emily Grant, the current owners, in 2016.
The Grants have made numerous improvements to the property and the interior and exterior of the home. It looks ready to go for another century or two.


