Highlands Homes for Sale

The Highlands is one of the oldest neighborhoods in Louisville, Kentucky, set atop a flood-resistant ridge back in the Civil War Era. History lovers can still see a number of remaining structures and historic properties, though much of the modern community arose in the 1960s. In fact, many locals consider Bardstown Road, the commercial epicenter of The Highlands, to be the “Haight-Ashbury” of Louisville, our own version of “Greenwich Village,” or a “Little Portland” -- with its interesting collection of mom-and-pop shops. Louisvillians are in love with this part of town because it has “something for everyone” as an affordable place to live, close to everything, and full of diversity. It’s also a 5-15 minute drive from top employers like Ford, GE Appliances, YUM! Brands, and the Norton healthcare complex.

A Tale of Two Highlands…


Lenihan Sotheby's International Realty agents will tell you there are “two distinct Highlands”:

  • The “Original” Highlands (40204 zip code, Irish Hill, Cherokee Triangle, Tyler Park, Deer Park, Bonnie Castle, the Douglas Loop) – which is characterized by a more urban, modern, walkable feel with shops, restaurants, and amenities at the end of these quieter, tree-lined, residential streets.
  • The “Upper” Highlands (40205 zip code, Bardstown Road, just beyond Taylorsville Road, Strathmore Village, Strathmore Manor, Wellington, Kingsley, Lakeside) – which is characterized by a wonderful, 1950s residential, classic “neighborhood” feel where people walk dogs and children ride bikes down the sidewalk, but the houses are more tucked away in a suburban type setting.

The Highlands: An Eclectic, funky blend of people and places.


As Lenihan Sotheby’s International Realty Agent Josh Laughlin points out: “You have the working class, the artists, and the students, living right next door to the doctors, professionals, and executives.”

Bardstown Road is a fantastic corridor that attracts tourists and visitors from all across the city who come here for world-class restaurants, cozy coffee shops, locally owned boutiques, antique stores, microbreweries, entertainment, and nightlife. You’ll find guitar stores, lighting shops, custom t-shirt printing, and vintage furniture stores. Long before the commercial strips developed, residential homes existed in The Highlands, so you’ll notice that many of the businesses have a lot of original character as former homes.

Though the saying around these parts is “Keep Louisville Weird,” you will also find a Wal-Mart, Rite-Aid, CVS, Costco, Kohl’s, and Kroger in the area, so you can pick up all the staples you need.
The Kentucky Derby is an exciting time of year to live in The Highlands. Many high-profile parties take place here, with Churchill Downs just 3.4 miles away.

Restaurants, Restaurants, Restaurants!


If you’re a “foodie” in Louisville, there is no better spot to set down roots! You’ll be treated to amazing culinary experiences in comfortable environments. It’s hard to pick favorites, but you’ll definitely want to try nearby establishments such as:

  • La Chasse – French and comfort food and craft cocktails
  • Seviche – Latin fare with out-of-this-world chimichurri sauce and mashed potatoes, and superb service
  • El Taco Luchador – Quick Mexican fare
  • Jack Fry’s – Southern fare, a celebrity favorite “see & be seen” establishment, popular for special occasions
  • LouVino – Wine and tapas pairings, incredible cocktails
  • Hammerheads – Gastropub fare like duck fat fries, pulled pork, and brisket, popular among tourists
  • Ward 426 – A renowned Dean Corbett eatery with a fresh, seasonal menu of local and Southern fare
  • Butchertown Grocery – In nearby Butchertown, you’ll find amazing cheese and charcuterie boards in a lounge environment open til 3 a.m.

From Cherokee Triangle, to the 900-block of Baxter Avenue, to Bardstown Road – Highlands residents want for nothing!

Recreation beyond the backyard


City life has its rewards, but sometimes even the hardiest residents need to take a break from the concrete jungle and enjoy the great outdoors. New Yorkers have Central Park, and people living in The Highlands have Cherokee Park – a 409-acre oasis that is ranked among the Top 100 Municipal Parks in the United States and attracts 500,000 visitors a year.

The park features:

  • Walking, biking, and horseback riding trails
  • Lake fishing
  • Sports fields
  • Bird watching
  • Tennis and basketball courts
  • Winter sledding
  • Picnic tables, grills, and shelters
  • Archery ranges
  • Rugby and soccer fields
  • Ultimate Frisbee courses
  • Horseshoe pits
  • Dog parks
  • Playgrounds

Other local sanctuaries for recreation in The Highlands include: Douglas Park, Seneca Park, Tyler Park, and Willow Park.

Quiet residential streets with a diverse house mix and affordable prices.


Despite the exciting commercial strips, you’ll find quiet neighborhood streets with mature trees and relatively low traffic. Generally, homes tend to be less expensive than neighboring St. Matthews and the cost of living is just 1 percent higher than the rest of Louisville, even though there are so many great amenities.  

Most homes in The Highlands were constructed in the late 1800s to 1947. You could settle into a modest post-war shotgun house for as low as $145,000 or you could splurge on a multi-million-dollar executive mansion in Cherokee Triangle. The homes of The Highlands, KY truly run the full gamut in terms of price points and architectural styles, from beautiful Victorian mansions down Cherokee Road and Craftsman Bungalows on Deer Park, to shotgun homes on Breckenridge and multi-million-dollar modern park-side estates in the Douglas Loop. Some of the most expensive estates run in the Millionaire’s Row along Spring Drive.

Hidden architectural gems of these homes may include rectangular floorplans, wainscoting, intricate millwork, tall and narrow windows, master suite fireplaces, butler’s pantries, steep-pitched roofs, and more. Many homes feature German-style architecture brought to Louisville, Kentucky from some of the earliest settlers.  

The housing styles vary just going down many of the blocks as well. Some houses may be in pristine condition, while others are fixer-uppers. There are flipped homes and lovingly maintained, updated homes, too. That’s all part of the excitement and appeal of house hunting here. You never know what you’ll find!

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