The 1,500 acre (6 km²) property has been home to sires such as Youth and Exceller and numerous others who are buried on the property. The tradition-bound land echoes the past, present and future of countless Thoroughbred Champions including the first Derby winner Aristides in 1875. Among the current stallion roster is Tapit, sire of 4 Breeders' Cup winners since 2008 and 2013 Leading U.S.-based Yearling Sire.
In 1995, under the name Gainesway Stable, owner Graham Beck partnered with Robert and Beverly Lewis and William T. Young of Overbrook Farm in the ownership and racing of Timber Country who won the 1994 Breeders' Cup Juvenile and 1995 Preakness Stakes.
Gainesway is home to many past and present well-known Stallions, including Afleet Alex who narrowly missed becoming the twelfth Triple Crown champion in the history of horse racing when he came in third after winning both the Preakness Stakes, and the Belmont Stakes.
- Afleet Alex -- 2005 Preakness Stakes and Belmont Stakes winner
- Afleet Express -- 2010 Travers Stakes winner
- Birdstone -- Sire of 2009 Kentucky Derby winner Mine That Bird and 2009 Belmont Stakes winner Summer Bird
- Hat Trick
- Tapit -- Sire of 2008 Breeder's Cup Juvenile Fillies Champion Stardom Bound,2009 Breeders' Cup Juvenile Fillies Turf Winner Tapitsfly, 2011 Breeders' Cup Juvenile Dirt Champion Hansen and 2012 Breeders' Cup Dirt Mile Winner Tapizar
- Tapizar -- 2012 Breeders' Cup Dirt Mile Winner
- To Honor and Serve -- 2011 Cigar Mile Winner
- Vaguely Noble (1965–1989)
- Blushing Groom (1974–1992)
- Cannonade (1971–1993)
- Riverman (1969–1999)
- Irish River (1976–2004)
- Lyphard (1969–2005)
- Cozzene (1980–2008)
- Broad Brush 1983-2009)
- Mt. Livermore
- Mr. Greeley (1992–2010)
The Farm was formed by John R. Gaines, the man behind the creation of the Breeders Cup. Originally located off of Tates Creek Pike in Lexington, this property was sold for development, and the thoroughbred division of Gainesway Farm, under the ownership of John R. Gaines, was moved to the present location on Paris Pike in Lexington.
In 1989, Gainesway Farm was sold to South African horseman Graham J. Beck whose acquisition included what was once the Cornelius Vanderbilt Whitney farm properties established in 1915 by his father Harry Payne Whitney, plus the parcel belonging to Payne Whitney's Greentree Stud.
One of the most notable managers of Gainesway Farm was Joseph Lannon Taylor. He began his successful career in the horse industry as the farm manager at Gainesway Farm, where he raised many world-class standardbreds and thoroughbreds and was influential in developing Gainesway Farm into one of the leading thoroughbred stallion farms in the world. During his time at Gainesway Farm, Taylor saw six Gainesway stallions lead the world's sire list, the American sire list, or the European sire list: Bold Bidder, Vaguely Noble, Lyphard, Blushing Groom, Riverman, and Sharpen Up. After managing at Gainesway for 40 years, he retired in 1990.
Gainesway Farm has also been designated as an arboretum by the American Public Garden Association. The farm has over 1,500 acres (6 km²) of decorative plants, floral displays, and tree collections that are nurtured by a full-time horticulture staff. Of particular note are the more than 45 different kinds of oaks, including a California Valley Oak and an Oglethorpe, that have been planted.
At the Saratoga Yearling sales in August, Gainesway had a sales topper with a chestnut Mr. Greeley colt that sold for $2.2 million to Team Valor and will be syndicated. The colt has been named Kinsella after well-known baseball writer W. P. Kinsella, whose book, Shoeless Joe, was adapted into the movie "Field of Dreams".