The Most Expensive Homes for Sale in Kentucky

685 Handy Rd. Harrodbsurg,KY © Crystal Gail Smith

As is the case in most of the country, Kentucky’s real estate market is confronted with the lowest inventory levels in years, pushing prices up. In fact, prices in the Bowling Green metro area have gone up 4.7% in the first quarter of the year, according to the National Association of Realtors. Louisville and Lexington saw even more significant surges, with home prices appreciating by more than 8% in both metros, per the same source. When it comes to Kentucky luxury real estate, most of the state’s priciest homes for sale right now are located in these three rapidly appreciating markets.

Priced between $3,856,950 and $7,990,000, Kentucky’s most expensive homes for sale right now offer all the trappings of high-end living with a typical Kentucky twist – it’s all about horses. From historic horse farms to state-of-the-art stables and training facilities, these pricey homes celebrate the quintessential Kentucky love of horses.

Rolling pastures, equestrian facilities and caretaker’s homes are some of the amenities that these luxurious properties can offer, not to mention formal gardens, gourmet kitchens, and wine cellars as well. Pools, in-home elevators, and private theaters are also almost obligatory for pricey Kentucky properties, whether they are historic farms or recently-developed estates with fancy architecture.

As for the #1 most expensive home for sale in Kentucky right now, that luxurious residence sits on a golf course set to host its first PGA tournament in less than two months and boasts a two-story wine cellar, designer landscaping and a massage room among other things in its nearly 22,000 square feet of living space.


222 E Witherspoon Street #2001, Louisville

Asking price: $3,856,950

222 E Witherspoon Street #2001 © Julie D. Klein

Reigning as Kentucky’s #1 most expensive condo, this 6-bed residence in Louisville’s central business district is now on the market with a whopping $943,000 price cut. Built in 2014, the 8,500-square-foot condo takes up the entire 20th floor and boasts panoramic city views throughout the home. Bedecked in Italian marble and high-end finishes, the pricey residence features private elevator access that opens into a grand foyer. Made for entertaining, the Waterfront Park Place condo boasts a chef’s kitchen complete with a catering kitchenette and butler’s pantry, an in-home theater, a gaming lounge and an oversized rec room.

Dual walk-in closets, a spa bathroom and a private terrace add extra lifestyle amenities to the master suite, and this is joined by the guest quarters, as well as a staff suite with its own separate elevator entrance. The high-rise residence has ample storage, an oversized laundry room, and comes with 4 parking spaces.  Owners have access to building amenities, including the private fitness center and pool.


1151 Delong Road, Lexington

Asking price: $3,900,000

For amenities straight out of MTV’s Cribs, look no further than this 6-bed home in Lexington. Its more than 15,000 square feet of indoor living space house a full-sized indoor basketball court, a golf simulator, a games room, a fitness center and an 11-seat theater. Cathedral ceilings are present throughout the home, while the main living area is two-stories high, including the formal living room and the formal dining room complete with stone fireplace.

The gourmet kitchen—outfitted with chef-grade appliances—is expanded by a basement level entertaining kitchen, while the main level master suite is joined by a first story VIP suite and a basement guest apartment. Another signature feature is the executive home office that includes a two-story library. 1151 Delong Road sits on 10 manicured acres bordered by a brook and nearly a mile of Delong Road frontage.


1120 Kidds Mill Road E, Versailles

Asking price: $3,995,000

1120 Kidds Mill Road E © The Prather Team

An equestrian enthusiast’s dream, this 38-acre estate comes with a 7-stall stable complete with an upstairs caretaker’s apartment. There’s also a dressage area overlooked by a gazebo, a storage barn and fenced-in pastures. The 6-bed estate also features a guest home that includes a full kitchen, a living room, a full bath, a laundry room and sleeping quarters, as well as a 3-car detached garage and a 2-car attached garage.

The main residence was built in two stages. The initial 2011 construction was executed by Padgett Construction & Kevin Locke, AIA in a Shaker style, followed by a contemporary addition. Overall, the main residence showcases a chef’s kitchen signed by Mick De Giulio, a library with paneling signed by BG Woodworking, a home office flooded by natural light, 4 fireplaces, and eco-friendly geo-thermal heating. The 8,611-square-foot home also boasts a wet bar, an outdoor kitchen, a sunroom and a two-story living room.


1150 Delong Lane, Lexington

Asking price: $4,250,000

Yet another spectacular estate on Lexington’s Delong byway, this 20-acre property comes with a bevy of fireplaces, detailed millwork, cut stone sills and copper gutters. The 6-bed home enjoys heated tile floors, smart home systems and exposed beams. At nearly 19,000 square feet, the Fayette County residence is made for hosting in style with its chef’s kitchen, butler’s pantry, two bars, entertaining kitchen, in-home theater, and stone porches. Cozy gathering areas alternate with stylish bedrooms and lavishly-appointed bathrooms. There’s also a paneled study, a billiards lounge and a private fitness center.


137 Windmere Court, Bowling Green

Asking price: $4,300,000

Equestrian enthusiasts will love this 19-acre property known as Spirit Filled Farm. Mature trees, landscaped gardens and pastures alternate after you’ve passed the gated entrance which leads to the 9-bedroom main residence. Built in 2003, the Colonial-style house opens into a foyer with a grand staircase and dual balconies and continues through multiple formal entertaining areas, including a two-story great room flooded with natural light. There are 8 bedrooms with a bonus ninth bedroom with 8 bunkbeds.

Pricey amenities here include a private theater complete with concession area and performance stage, gourmet and entertaining kitchens, a full-service fitness center and a study. There’s an oversized games lounge with pool table and built-in trophy cases, a media corner and a bar with booth seating. Warm weather is best enjoyed on the show-stopping pool terrace with its outdoor spa, lounge and a covered outdoor kitchen with barbeque and al fresco dining area. The estate also features spacious stables for prized horses with caretaker’s apartments on top, as well as ponds overlooked by a gracious deck.


5802 River Road, Prospect

Asking price: $4,500,000

Built in 1905, this historic property has been lovingly restored to offer all the comforts of modern living. With more than 10 acres of grounds, 8 paddocks and a 30,000-square-foot outdoor arena, this 6-bed estate is ideal for true Kentucky Derby enthusiasts. Just eight miles from Churchill Downs and Downtown Louisville, the estate nestles against the Little Goose Creek and enjoys views of the Ohio River. Mature trees, forested areas, fenced-in pastures and landscaped gardens offer ample opportunities to enjoy the natural landscape.

The 11,418-square-foot main home sits at the end of a mile-long driveway designed by the famed Olmstead brothers—the same Olmsteads who worked on New York’s Central Park. Oversized windows provide ample natural light, while fireplaces, French doors, crown moldings and wood paneling show off the home’s historic elegance. Amenities include a media room, a gourmet kitchen, a study, and a gentleman’s game lounge. The estate also showcases a detached glass atrium with an inground pool and bar.


1357 Piney Woods Road, Cadiz

Asking price: $6,900,000

For luxurious lakeside living in Kentucky, this 6-bed home in Trigg County is the perfect opportunity. Sprawling on 124.5 wooded acres with generous Lake Barkey frontage, the 2011-built home has ample privacy. Featuring 12,845 square feet of space, this waterfront home serves up plenty of high-end amenities, including walk-in closets, a wet bar, a whirlpool and a game lounge, as well as formal entertaining areas.

The great outdoors can be taken in from the covered porch, multiple patios and balconies or while lounging by the outdoor pool. The generous estate also includes a pool house, a 3-car attached garage and a 4-car detached garage. The generous woods have ample hunting opportunities, while Lake Barkey beckons with watersports.


635 Iron Works Pike, Lexington

Asking price: $7,150,000

Merely 7 miles from downtown Lexington, St. George Farm is a horse lover’s paradise just 12 miles from the world-famous Keeneland racecourse and auction house. Once part of the historic Elmendorf Farm, the 94-acre estate features all the necessities for world-class equestrian activities, including two professional-grade stables totaling dozens of stalls, fenced-in pastures, a state-of-the-art horse walker, and ample staff quarters.

A private lake, water features, landscaped formal gardens and mature trees surround the main residence. Although built in the 1830s, the 6-bed antebellum has all the trappings of luxurious modern living, including a gourmet kitchen, a fitness center and a 3-car garage. There’s also a billiards room, an outdoor pool, an outdoor kitchen and a pool house.


4001 Iron Works Pike, Lexington

Asking price: $7,499,000

For Kentucky horse enthusiasts, it doesn’t get much better than living inside the famed Kentucky Horse Park. Known as After Hours Farm, this 54-acre private estate comes with all the bells and whistles of a professional equestrian property, including a 6-stall barn, 16 paddocks, and a self-irrigating 0.6-acre ebb and flow arena.

Built in 1988, the 8-bed estate comprises two cottages with a bevy of fireplaces and oversized windows for ample natural light and equestrian vistas. Each home boasts its own fully-equipped kitchen, master suites and generous living areas. After Hours Farm also features a spring-fed pond, an outdoor pool, a caretaker’s house and a 2-car garage.


56 Avenue of Champions, Nicholasville

Asking price: $7,990,000

56 Avenue of Champions © Steve Klein

Currently Kentucky’s #1 most expensive home for sale, this Georgian English–inspired property was built in 2010 on the Keene Trace Golf Club, which will see its first ever PGA Tournament in July. The 7-bed main residence is nestled on 5 acres of grounds designed by Jon Carloftis with fountains, lawns, gardens and decorative walls. With nearly 22,000 square feet of indoor living space, the mansion showcases a two-story wine cellar, an in-home theater, a billiards lounge complete with bar, a library, walk-in closets, and a 6-car garage.

Other exclusive amenities include an in-home elevator, a private fitness center, a massage room, formal entertaining areas and a bevy of fireplaces. Golf views and the impeccable landscaping can be enjoyed from wrap-around terraces, patios and an outdoor living room, with ample space for al fresco dining and lounging. The lavish estate also features an outdoor pool and spa.

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In order to determine which were the most expensive homes for sale in Kentucky, we looked at all residential properties listed for sale, taking into account condo, co-op, and single- and two-family homes. All package deals were excluded.

Eliza Theiss

Eliza Theiss

Eliza Theiss is a senior writer reporting real estate trends in the US. Her work has been cited by CBS News, Curbed, The Los Angeles Times, and Forbes among others. With an academic background in journalism, Eliza has been covering real estate since 2012. Before joining PropertyShark, Eliza was an associate editor at Multi-Housing News and Commercial Property Executive. Eliza writes for both PropertyShark and CommercialEdge. Reach her at [email protected]

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