City of Historic Homes

Windy Hills takes pride in being a City of Historic Homes. Born of rich tradition and historic lineage, the property around the area of Muddy Fork of Beargrass Creek can be traced to deeds originally issued by the Commonwealth of Virginia. Early pioneer families from Virginia and Pennsylvania built the historic homes in Windy Hills. The craftsmanship of these families is evident in the lovingly maintained private homes.

The city of Windy Hills was incorporated in 1952 before the Watterson Expressway connected Brownsboro and Shelbyville Roads. The community is the result of carefully thought-out planning which respects the character and tradition of our historic homes and neighborhoods.

Today Windy Hills is a community of single-family homes, townhouses and condominiums bounded by I-264, Westport Road, North Hubbards Lane and Brownsboro Road.

As a result of our rich history and successful design, Windy Hills is a community of neighbors who know neighbors. Local stores and restaurants are within a short walk or drive. Award winning schools and churche serving many different denominations are also nearby.

Take a walk through Windy Hills and experience the unique qualities that make ours a City of Historic Homes.

Rudy the Bear 1
Rudy I

Rudy The Bear I and II

According to the September 2017 Windy Hills Newsletter, Rudy I had deteriorated and replaced with Rudy II.  Here’s the entire article from the Newsletter.

“There have been numerous phone calls at the city office in regard to Rudy the Bear’s disappearance. Rudy deteriorated beyond repair and was laid to rest. The good news is that the City has purchased Rudy II from Harland Dougherty, a Mount Sterling woodcutter.  Mr. Dougherty won second place for his bear at a woodcarving contest. He drove his specimen over for the Council to view. The Council decided he was a good bear.  With the help of Brownsboro Road Hardware Store owner Jim Leher and his fork lift, Rudy II was transported to Mike and Wendy Skelton’s home for a temporary residence. After consulting an engineer to design a concrete platform for his new home on the Green and hiring a contractor to install him, Rudy should be moving in soon. Hopefully this will be done before the Ice Cream Social September 17.”