A Historic Equestrian Estate in Kentucky

Few properties in Kentucky have a pedigree quite like Castleton. For more than two centuries, the storied estate in Lexington has been a place where accomplished horsemen and women have bred, raised, and trained some of the sport’s most distinguished horses.

Now, for the first time in more than 25 years, comes the rare opportunity to become the next steward of the legendary estate, whose sprawling grounds encompass a historic mansion, numerous secondary residences, and extensive equine facilities.

Founded in 1793 by future U.S. senator and attorney general John Breckinridge, the farm was originally known as Cabell’s Dale. It later passed to Breckinridge’s daughter before financier James R. Keene transformed it into one of the country’s great Thoroughbred operations in the late 19th century. Keene brought the 1896 Kentucky Derby winner Ben Brush to Castleton as a stallion, part of a remarkable roster of horses associated with the farm. 

Subsequent owners included harness-racing figure David Look and Dodge heiress Frances Dodge, who, with her husband, advertising executive Frederick Van Lennep, expanded Castleton’s operations and established it as a leading Standardbred and American Saddlebred farm. The Van Lennep family held the property until 2001, when Ryanair cofounder Dr. Tony Ryan acquired it for $14 million and restored its focus to Thoroughbreds. The Ryan family has continued to build on the farm’s rich legacy since Ryan’s 2007 death at his home in Ireland.

RELATED: A 72-Acre English Estate With Its Own Polo Ground and Stables Lists for $26.8 Million

The Greek Revival mansion that stands at the heart of the 951-acre estate was built in 1840 by David Castleman, the husband of Breckinridge’s daughter, Mary Ann. Its oversized stone urns and four Doric columns, along with a Greek key frieze, give the symmetrical residence historic gravitas. Ryan undertook extensive restoration work after acquiring Castleton, modernizing the home without sacrificing its historic character. Today it spans about 13,500 square feet with seven bedrooms, elegant reception rooms with period detailing, cozy family spaces, and a horseshoe-shaped swimming pool.

The surrounding landscape is quintessential Bluegrass, with rolling, white-fenced pastures bordered by dense woodland. Beyond the main house, Castleton functions on an almost village-like scale, with nine additional residences, 16 barns containing 268 stalls, and an extensive network of paddocks, breeding and training facilities. The grounds also contain a timber-framed covered bridge over one of the farm’s lakes, ornate iron gates, an equine cemetery, and an improbable 124-foot stone round tower built by Ryan as a replica of the tower at Ireland’s Rock of Cashel.

RELATED: This $7.5 Million Equestrian Estate in L.A. Was Built for a Yugoslavian Princess

RELATED: Tour a 78-Acre Kansas City Equestrian Estate

Castleton’s equine legacy spans generations, from Kentucky Derby winner Ben Brush to more recent standouts. Under the Ryan family, the farm bred and raced Gio Ponti, a three-time Eclipse Award winner who earned more than $6.1 million and won seven Grade 1 races, along with other Grade 1 winners including Jack Christopher, Gormley, and Chi Town Lady.

Castleton is listed for $57.5 million with Ken Donworth of Bluegrass Sotheby’s International Realty and will also be offered as the final lot of the third annual Keeneland Championship Sale on October 28.

Click here for more photos of the historic equestrian estate.