Their sons Daniel and John went on to own the Silver Pool property and it was used for raising livestock and for manufacturing products from hemp.

The conforming structures include the original farmhouse from the settlement period, circa 1784–1790, when Virginia families first moved into the region.

Along a portion of the Pisgah Pike that adjoins the property, a natural hedge of Osage orange has grown so tall that it has become a canopy arching over the road, and is also noted on the NRHP as a historically significant feature.

[6] Over time, most of Silver Pool became part of the 400-acre Prestonwood Farm, owned by Houston, Texas oilmen Jack, Art, and J. R. Preston, whose better known horses included Da Hoss and Victory Gallop.

[7] In 2000, Kenny Troutt and Bill Casner, both with long-standing interests in horses, came together to purchase Prestonwood, renaming it WinStar Farm.

[8] Included in the purchase were the stallions Distorted Humor, still standing at WinStar and the sire of 2003 Kentucky Derby winner Funny Cide,[8] and Kris S.[7] Over the years, WinStar has steadily grown, incorporating land from the nearby Olsen, Johnson and Kinkead farms, and as of 2016, consists of over 2,400 acres (970 ha) housing over 20 stallions, as well as a large broodmare band and facilities for weanlings and yearlings.

[2] In 2002, WinStar made its first major stallion acquisition —Tiznow, the only two-time winner of the Breeders' Cup Classic, having won that event in 2000 and 2001.

In 2005, W. Elliott Walden, who had trained Distorted Humor and several WinStar horses, became vice president and racing manager.