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 February 17, 2020
71
Listed
68
Avg. DOM
$195.34
Avg. $ / Sq.Ft.
$399,000
Med. List Price
71 Properties
Page 1 of 6
$565,000
Subdivision: Cherokee Triangle
4
Beds
3
Baths
2,938
Sq.Ft.
1900
Year Built
4
Days on Site
1553018
MLS
Simply fabulous Cherokee Triangle home located in the heart of one of Louisville's favorite neighborhoods! Nestled between Cherokee Park and the incredible restaurants and shopping on Bardstown Road,...
$955,000
Subdivision: 1400 Willow
3
Beds
3
Baths
2,236
Sq.Ft.
1980
Year Built
4
Days on Site
1553076
MLS
Bienvenue a la maison! Located in the heart of Cherokee Triangle, overlooking Cherokee Park this condominium has sweeping views from every vantage point. The architecture, the decor -- everything was...
1
Beds
2
Baths
1,057
Sq.Ft.
1983
Year Built
4
Days on Site
1546801
MLS
Fabulous restored condo in the Highlands. A wonderful park side location near restaurants and shopping on Bardstown road. This 3rd floor spacious condo offers high ceilings with an open living,...
$423,000
Subdivision: Highlands
4
Beds
2F11/2
Baths
2,900
Sq.Ft.
1901
Year Built
4
Days on Site
1553083
MLS
OPEN SUNDAY 2 -4! Built in 1897, this beauty offers all original woodwork, & 6 beautiful (non-functional) fireplaces , original tile, gorgeous leaded windows & feather-painted steel are intact. The...
$132,500
Subdivision: Park Arms
2
Beds
1F11/2
Baths
1,026
Sq.Ft.
1979
Year Built
4
Days on Site
1553086
MLS
Welcome to Park Arms! Just a block away from the historic and beautiful Cave Hill Cemetery, this Victorian era national Cemetery and arboretum and the whole of the neighborhood of Park Arms, is,...
$499,900
Subdivision: Highlands
4
Beds
2F11/2
Baths
2,660
Sq.Ft.
1900
Year Built
3
Days on Site
1553137
MLS
Wow! Wow! Wow! McKree Properties hit a home run on this one. This Home was originally built in 1900 and has been restored to better than original. All of the character and beauty is here but so much...
$509,900
Subdivision: Woodbourne Heights
5
Beds
3F11/2
Baths
3,693
Sq.Ft.
1928
Year Built
5
Days on Site
1552930
MLS
Dreaming about New Construction in the Highlands?? This fantastic five-bedroom, three and a half bath has it all, including TWO Master Suites. Not only is this home gorgeous but it also has a New...
$382,000
Subdivision: Kenilworth
4
Beds
2
Baths
2,011
Sq.Ft.
1920
Year Built
6
Days on Site
1552889
MLS
This 1920's Craftsman Bungalow is located in the Highlands (park-side) - just a three block walk to Cherokee Park! This beautifully maintained home offers 4 bedrooms, 2 full bathrooms, living room,...
2
Beds
1
Baths
1,238
Sq.Ft.
1925
Year Built
8
Days on Site
1552703
MLS
An excellent Highlands house! This unique 2 bedroom, 1 bath home is ready for your personalized touch. Throughout the home you will find beautiful hardwood flooring. The 1st floor features a large...
$119,500
Subdivision: Baxter Loop Condominum
2
Beds
1
Baths
713
Sq.Ft.
1945
Year Built
11
Days on Site
1552562
MLS
Located in the heart of the highlands, this 2 bed, 1 full bath condo will delight you with its updates and convenience to fun! Situated on the second floor, this home overlooks the quaint courtyard...
$280,000
Subdivision: Pennington
3
Beds
1F11/2
Baths
1,550
Sq.Ft.
1905
Year Built
11
Days on Site
1529420
MLS
NEWLY RENOVATED! If you looked at this unit before, you need to look at it again. The seller has installed a new kitchen, updated lighting, fresh paint, added an additional closet with a barn door,...
$119,900
Subdivision: Highlands
2
Beds
1
Baths
682
Sq.Ft.
1945
Year Built
11
Days on Site
1552598
MLS
Located in the Heart of the Highlands, this UPDATED, FIRST FLOOR condo is MOVE IN READY. This unit is perfectly situated for urban living; EVERYTHING is within walking distance! This home features...

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