Fayette County

Million dollar listings: Explore the 3 most expensive homes on the Lexington market

Home prices are soaring: The median listing price in the U.S. hit a new, all-time high in March when it rose to $405,000, a year-over-year increase of more than 13%, according to Realtor.com.

But if you’re holding off on entering the market until the apparent bubble bursts, you may be holding your breath for a while.

That’s because while home prices seem to be soaring ever higher, and the market forces driving them aren’t likely to change any time soon.

According to realtors Justin Landon and Rusty Underwood with the Lexington-Bluegrass Association of Realtors, it comes down to the fundamental mechanics of supply and demand. Put simply, there just aren’t enough homes for everyone who wants to buy one.

“We’re not going to get more supply,” said Landon, CEO of LBAR.

Lexington’s housing market

According to Underwood, LBAR’s president, the supply problem is compounded by millennials, currently the largest generation. Once, the conventional wisdom was millennials wouldn’t be interested in home ownership in the same way their baby boomer parents were.

“Millennials are just a little late to the game,” Underwood said. They’ve been slowed by the student debt they carry and are generally starting families later in life than their parents, Underwood added.

All this makes for a mean market for home buyers.

Data from LBAR shows the overall days on market for all price points in Fayette County was just 13 days from Jan. 1 to April 20.

“For properties in Fayette County under $250,000, we’re looking at 12 [days on the market] on average. For properties in Fayette County over $1,000,000 (there have only been 17 sales year-to-date) we’re looking at 64 [days on the market] on average,” Landon wrote in a follow-up email to the Herald-Leader.

Using LBAR’s database of homes, we’ve rounded up the most expensive properties currently on sale in Lexington and Fayette County. Read on for a look at these million-dollar listings.

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A home at Warrenwood Wynd selling for nearly $3.4 million, as listed on the Lexington-Bluegrass Association of Realtors property listings as of April 2022.
A home at Warrenwood Wynd selling for nearly $3.4 million, as listed on the Lexington-Bluegrass Association of Realtors property listings as of April 2022.


Warrenwood Wynd

For close to $3.4 million, this “in-town estate” at 3105 Warrenwood Wynd, just off Chinoe Road, features contemporary design and rooms flooded with natural light.

According to the listing, “light flows through the grand halls of windows and doors, through the cascade of skylights into the main hall, through the litany of windows in the two-story grand living room and through the second story gallery studded with windows.”

In this 10,533 square-foot home, there are six bedrooms, eight-and-a-half bathrooms and a chef’s kitchen with three ovens and two, 60-inch refrigerator freezers.

The primary bedroom suite opens to a lush courtyard and the exterior features a cobblestoned front drive, gated private entry to the garages, a covered front walk with circular masonry columns and an in-ground saltwater pool. It’s complemented by a pool house with a kitchen and full bathroom, masonry decking, gardens, patios and a large, fenced-in yard.

The house was built in 1985. It was originally listed 251 days ago.

Rushing Wind Lane

Coming in at $8.9 million, this stately home at 3371 Rushing Wind Lane is the most expensive home listed for sale in Fayette County through the LBAR Find a Property tool.

Built in 1989, it is fully furnished and features six bedrooms and six-and-a-half bathrooms, with the entire house totaling 10,698 square feet. It sits on 30 acres and promises to “bring the outside beauty of the Bluegrass region inside” with yawning windows that offer views of countryside surroundings.

“Upon entering this stately home, you will get the feeling of Palm Beach living meets Lexington classic grandeur!” the listing description boasts.

This home promises horse country bonafides. It’s just 2 miles from the Kentucky Horse Park and features landscaping by the same landscaper “who has maintained Keeneland for 30 years.”

Inside, each room has custom textiles, wall coverings and hand-selected antique furnishings, along with reclaimed oak and limestone flooring throughout. According to the listing, “The first floor offers an expansive double height great-room with a beautiful fireplace surround and stylish bourbon bar.”

The property’s history notes it was most recently put up for sale Nov. 8, 2021, though back then it was listed at $10.9 million.

According to Underwood, “A lot of people really value the Bluegrass (region) and want to be able to experience horse country.”

Greenwich Pike

On the market for roughly $4 million, this property at 5245 and 5401 Greenwich Pike also aims to offer a horse-lover’s dream abode. The property includes two large, single-family homes on 32 acres.

The main residence has been renovated and has 5 bedrooms, three-and-a-half bathrooms, a spacious open floor plan and views of the farmland surroundings. It was built in 1983 and totals roughly 7,400 square feet.

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Next to the house, there’s a new “oversized,” three-car garage with a large apartment above. The listing touts the property’s entertainment space: “Enjoy entertaining in the covered outdoor patio area with a limestone surface, tongue and groove ceilings overlooking rolling green pasture.”

However, the standout amenity of this property is its horse facilities. You can ride any time of year in the sprawling, indoor riding area totaling approximately 100 feet by 240 feet. Its main barn has 10 stalls and was updated in 2018 with a new roof, according to the listing. There’s a new Kraft horse walker for five horses, six large paddocks and more.

According to the property’s history, it’s been on the market for 115 days and underwent a price drop of $250,010 as recent as April 21.

Do you have a question about real estate in Fayette County or Kentucky? We’d like to hear from you. Fill out the form below or email ask@herald-leader.com.

This story was originally published April 22, 2022 at 12:16 PM.

Aaron Mudd
Lexington Herald-Leader
Aaron Mudd was a service journalism reporter for the Lexington Herald-Leader, Centre Daily Times and Belleville News-Democrat. He was based at the Herald-Leader in Lexington, and left the paper in February 2026. Support my work with a digital subscription
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