Kentucky Derby: Equestrian Market Insights & Exceptional Estates

The 149th running of the Kentucky Derby takes place at Churchill Downs, on the time-hallowed first Saturday in May.

Then and there, some 45,000 suited, booted, and flamboyantly hatted spectators on hand (with a TV audience of millions more) will sip a mint julep, grow misty-eyed to the strains of My Old Kentucky Home, and brace for the “Greatest Two Minutes in Sports.”  

The Run for the Roses is so named for the traditional garland of 554 red roses for the winner.  

Luxury Defined has its own Derby tradition, annually showcasing the greatest equestrian estates in luxurious locales around the world. This year, we’ve added the insights and expertise of Rusty Underwood, CEO of Christie’s International Real Estate Bluegrass, in Lexington, the beating heart of Kentucky’s horse country. 

Rusty and his wife, Rachel Underwood (COO of Christie’s International Real Estate Bluegrass and its co-owner), have attended the Derby many times. “Our preference is to watch the race on our own back patio in Lexington, surrounded by the spring flowers, with friends and family, good food and some Kentucky Bourbon.” He added; “Derby hats are optional but encouraged.” 

For this Derby Day, Luxury Defined spotlights a selection of great estates for horses and riders of all stripes. In the lineup are a historic horse farm near Pimlico Race Course, a grand Irish manor house in County Tipperary horse country, and a South Carolina trophy estate dedicated to show jumping and dressage at the highest level.  

Back at Churchill Downs, we’re placing our last-minute bets on Rusty’s picks (read on to the end and, yes, we’re saving them to last). The red-coated groom steps to the rostrum, his bugle rises to his lips and the clarion First Call resounds across the track, and … we’re off! 

First things first. For Rusty Underwood, the purchase of an equestrian estate begins with the state of the land, its history, and the connection between human and horse: “The care that the estate owners give to their land and their horses is always the most important part of the story to me,” he said. “Understanding the utilization of the barns, paddocks, and general facilities is paramount to what equestrian owners require.”  

And, of course, there is the provenance of the place, Rusty said. “Being the horse capital of the world, our farms big and small have unique stories and a history that often provides an additional prominence that we always want to make sure we capture and convey.” 

So, let’s begin with one of the finest private equestrian estates on the market, South Carolina’s most expensive residential listing: 

1. Circle Creek Estate in Simpsonville, South Carolina

Circle Creek Farm is an outstanding 54-acre equestrian estate in the Blue Ridge foothills, and with an asking price of $22 million is the most expensive residential listing in the state of South Carolina. 

Built in 2013, the custom-crafted 16,000-square-foot main residence was inspired by the grand English country manors of the Cotswolds. The six-bedroom, seven full, and four-half bathroom home is magnificently beamed, arched, and vaulted, with soaring, 25-foot-high ceilings in many rooms. 

An elevator serves all levels, including the main-level great room and pool terrace and the lower-level recreation suite (complete with an authentic English pub, wine cellar, and rustic-beamed movie theater).  

The owners’ passion for the equestrian lifestyle shows in the estate’s world-class facilities, which include three large arenas: one for warming up, one for dressage, and one for show jumping.

The covered riding ring has irrigated flooring, a mirrored wall, and an adjacent storage area. The deluxe, 12-horse barn was designed by Lucas Equine Equipment, with tack room, a lounge, full bath, kitchenette, office, and a staff apartment.  

The estate, just a short drive from downtown Greenville, is being sold completely turnkey, with all furniture, artwork, and equipment included in the sale.

As Rusty Underwood sees it, the scale and scope of an equestrian estate are to be found in the buyer’s heart, not their purse. “We have equine clients with properties as small as a few acres,” he said. “We also have a large array of boarding opportunities in central Kentucky which allows the perfect venue for equine enthusiasts to enjoy their horses while having them just a few minutes from their home.” 

“We always work to understand the specific short- and long-term goals of our clients to make sure properties we are targeting for them will accommodate them both today and into the future,” he said.

With high-profile commercial operations, it’s important to understand the totality of the business: “The workflow of the farm’s barns and paddocks, the staff integration and community relationships—or anything else that would affect the investment’s potential.” 

2. Goose Green Farm in Glyndon, Maryland 

The 183-acre Goose Green Farm is a once-in-a-generation opportunity to own one of the finest equestrian properties in one of Baltimore County’s most bucolic and sought-after communities. 

The two-story stone farmhouse offers more than 9,000 square feet of thoughtfully updated interiors with elegant reception areas, comfortable accommodations, and expansive porches, decks, and patios.

The vast estate encompasses miles-long views of protected land and riding trails, swimming holes and storybook picnic/fishing hideaways, lush gardens, old-growth trees, sweeping meadows, and both banks of a long stretch of the Western Run. 

The best-in-class equestrian complex includes an 11-stall bank barn, two stables, an Amish-built workshop/tractor shed, a riding ring with updated EFT footing, six run-in sheds, acres of fenced paddocks, and a sporting clay facility. 

An 18th-century stone guesthouse, garage apartment, and a new pool/pool house complex round out the amenities of this beautifully preserved and impeccably updated retreat.

The property is in the heart of Maryland horse country, just a few miles from the historic Thoroughbred racing stables Sagamore Farm. 

Related: Explore 6 Homes with Glorious Gardens and Greenhouses

2. Moyaliffe House in Ballycahill, Thurles, Co. Tipperary, Ireland 

A historic country estate on the banks of Co. Tipperary’s River Clodagh, Moyaliffe House was built in 1810 on the site of a Viking settlement and Norman fortress.

The manor house has been conscientiously restored to preserve its fine period details, principally Georgian in character with an elegant Victorian façade.  

The grandly proportioned six-bedroom residence offers luxurious accommodations, including a ground-floor apartment, currently used as a boutique B&B. A museum, library, gym, and wine cellar are among the amenities. 

The elevated 12-acre grounds are laid out in formal gardens, woodlands, paddocks, stable yards, and several heritage buildings, including a coach house. Of particular note is the two-acre walled garden and the estate’s centuries-old woodlands, a habitat for wildlife. 

A hard tennis court, beech walk, formal parterre, Victorian three-tier cast iron fountain, and a restored well dating from the Norman period add to the allure. 

4. Hillcrest Farm in Wike, West Yorkshire, England 

Hillcrest Farm resides on 10 acres in the beautiful West Yorkshire countryside. The stone farmhouse has a wealth of period details and high-quality finishes and fixtures throughout.   

An entrance vestibule leads into a stately reception hall. Two separate staircases rise to the private quarters. The heart of the home is a lovely drawing room with a Minsterstone fireplace and log-burning stove. The formal dining room is served by an open-plan eat-in kitchen with a classic, four-oven AGA range. Just outside is a pleasant paved and partly cobbled courtyard.  

The mature formal gardens lie principally to the rear of the property, where the heated swimming pool and classic Amdega summerhouse are perfect for entertaining. 

The substantial, detached stone barn, formerly the village forge, offers garaging and entertaining space with a working fireplace. The stable block provides three loose boxes, a tack room, and a hay barn with adjacent paddock land for equestrian pursuits. 

The property is just half a mile from Wike and Moor Allerton golf courses, and 8 miles from Wetherby Racecourse, with ready access into Leeds city center. 

With thanks to Rusty Underwood for his insights into equestrian estates, we asked the Kentuckian for his picks for the Derby.

He went to the far-and-away favorite, multiple Grade 1-winning champion Forte, “Kentucky bred and on a fantastic winning streak,” Rusty noted. “After watching him win the Florida Derby, we would love to see him take it.”   

But for the Long-Shot Louie in us all, Rusty and Rachel point to another Kentucky-bred (peaking, but at much longer odds): Two Phil’s, trained by North Barrington, Illinois-based Larry Rivelli. “We thought it would be fun to also bet on Two Phil’s to celebrate our Chicago ties to Christie’s International Real Estate.”  

Searching for a place to saddle your next winner? Explore our stable of equestrian estates here.