Real Estate in The Highlands

The Highlands is one of the most unique and interesting places to live within the City of Louisville, KY. Homes in this Jefferson County community are both varied and sought after. A single street in some areas might house a working-class family at one end and a well-heeled socialite at the other.

Real estate in the Highlands has always been in high demand due to its proximity to downtown Louisville, Cherokee and Seneca Parks. Rarely does this area fall victim to falling prices, even during down-turns in the housing market.

View real estate in The Highlands, or read more about homes and amenities.

Real Estate in The Highlands

With homes rich in character, and the close proximity to the famed Cherokee Park, (part of the park system designed by the famous Olmstead Brothers), real estate in The Highlands is in high demand. The Bonnycastle neighborhood and the Cherokee Triangle are two of the most popular areas. Both are situated between thriving Bardstown Road and Cherokee Park.  It is unusual to find newer homes here, but you might get lucky to find a home for sale under 20 years old at The Springs near Big Springs Country Club, or at Kensington Place off Newburg Road near the Louisville Zoo.

Look for the estate on Spring Drive where the famous Barnstable Brown Party is held at Derby time and onlookers gather to snap photos of the rich and famous who come to be seen at the most celebrated horse racing event in the US.

Parks & Amenities

When it comes to local industry, we think The Highlands is the single best area for homegrown Louisville businesses to thrive. Other than the necessary Starbucks or Panera, you won’t find very many franchise restaurants here. A bevy of “Louisville Originals” make up “Restaurant Row” along Bardstown Road including the original Bristol (who claims to have won more “Best of Louisville” dining awards than any other restaurant), Ramsi’s Café on the World and Seviche.

If the shopping and night life doesn’t suit you, take a stroll through some of Louisville’s most beautiful parks located in the heart of the Highlands. The charm and appeal of an eclectic city and an abundance of green space are a perfect combination in this distinctive neighborhood. 

Any of our agents will be glad to assist with any questions you may have about The Highlands real estate, or the surrounding area. Please call 502-554-9554, or email for more information.

Highlands September 22, 2020
95
Listed
61
Avg. DOM
$194.06
Avg. $ / Sq.Ft.
$399,900
Med. List Price
95 Properties
Page 1 of 8
Open 9/27
1258 Bassett Ave Louisville, KY 40204
$565,000
Subdivision: Cherokee Triangle
3
Beds
1F11/2
Baths
2,221
Sq.Ft.
1915
Year Built
1
Day on Site
1569839
MLS
Located on one of the most desirable and quiet blocks in the Cherokee Triangle, steps from all the restaurants, boutiques, entertainment and options available in the Highland's and Olmsted's Cherokee...
$249,900
Subdivision: Deer Park
2
Beds
1
Baths
1,100
Sq.Ft.
1900
Year Built
2
Days on Site
1569783
MLS
Charming Highlands home located one block away from Bardstown Road shops and restaurants in the highly sought after Deer Park neighborhood. This extremely well-cared for home features beautiful...
$595,000
Subdivision: Aberdeen
4
Beds
3F11/2
Baths
3,461
Sq.Ft.
1925
Year Built
3
Days on Site
1569705
MLS
Fully renovated Highlands home w/ over 3400 finished square feet. Unique, inviting floor plan, perfect flow for family living and entertaining, inside and out. Gorgeous hardwood floors. New quartz...
5
Beds
5
Baths
5,792
Sq.Ft.
1951
Year Built
5
Days on Site
1569575
MLS
A rare offering. Stately. Strong. A premier location. This is a home built for a lifetime!This American Colonial is well-built with a solid foundation of limestone sills, slate roof, copper gutters,...
$800,000
Subdivision: Windsor Place
4
Beds
3F11/2
Baths
2,979
Sq.Ft.
1919
Year Built
5
Days on Site
1569592
MLS
Stunning total renovation by Uncle Karl Dyson LLC in conjunction with Jenna Mattingly Interiors. Preserved original features including baseboards, trim, hardware, FABULOUS Rift & Quartered Tiger...
$395,000
Subdivision: Highlands
4
Beds
2F11/2
Baths
2,707
Sq.Ft.
1915
Year Built
6
Days on Site
1569449
MLS
True Highlands appeal w/wide trim, wood floors, fireplace & bookshelves. 4 BD/2.5 BA home on Blvd. Napoleon, one of Louisville's most popular streets. A bed & full bath on 1st floor! Upper bed has a...
$549,900
Subdivision: Parkside
4
Beds
3F11/2
Baths
2,670
Sq.Ft.
1925
Year Built
6
Days on Site
1569485
MLS
FULL RENOVATION, PARKSIDE IN THE HIGHLANDS. The huge front porch welcomes you to the redesigned floor plan with great flow. This house has been completely reimagined, and it is JUST LIKE NEW. All New...
$125,000
Subdivision: The Oaks
2
Beds
1
Baths
789
Sq.Ft.
1979
Year Built
6
Days on Site
1569503
MLS
Location! Location! Location! Welcome to 1129 Willow Ave close to restaurants, shops, watering holes and expressway. This charming first floor condo offers hardwood floors throughout, updated bath...
$199,000
Subdivision: Highlands
1
Beds
1
Baths
1,060
Sq.Ft.
1905
Year Built
7
Days on Site
1569333
MLS
Be prepared to fall in LOVE with this Highlands Charmer! If you want to live on a quaint street just steps from the heart of the action on Bardstown Road, look no further. This open and spacious 1...
$123,000
Subdivision: The International
1
Beds
1
Baths
484
Sq.Ft.
1985
Year Built
7
Days on Site
1569377
MLS
Welcome to the iconic International Building near Douglas Loop in the Highlands. This beautiful move in ready freshly painted one bedroom one bathroom condominium is located on the first floor of the...
$279,900
Subdivision: Highlands
3
Beds
2
Baths
1,583
Sq.Ft.
1925
Year Built
8
Days on Site
1569245
MLS
Sweet Deer Park bungalow, circa 1925, has immense curb appeal with its inviting screened porch and great character to match on the interior! The owner has done updates to the second-floor owner's...
Under Contract
2023 Lauderdale Rd Louisville, KY 40205
$348,800
Subdivision: The Highlands
3
Beds
2
Baths
1,854
Sq.Ft.
1925
Year Built
8
Days on Site
1569311
MLS
This beautiful 1925 Parkside Cottage boasts both privacy and location! It combines Highlands rarities like walk-in closets (three) and oversized bedrooms with all of the conveniences of Highlands...

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