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 26, 2022
53
Listed
47
Avg. DOM
$230.68
Avg. $ / Sq.Ft.
$635,000
Med. List Price
53 Properties
Page 1 of 5
$695,000
Neighborhood: Kenilworth
5
Beds
2F11/2
Baths
2,414
Sq.Ft.
1925
Year Built
1
Day on Site
1622861
MLS
This Dutch Colonial is probably in the best part of the Highlands located at the intersection of Spring Drive and Grasmere. Huge great room adjoining the updated kitchen. Updated 1st floor primary...
$945,000
Neighborhood: Highlands
4
Beds
3F11/2
Baths
3,716
Sq.Ft.
1915
Year Built
3
Days on Site
1622830
MLS
2306 Rutherford Wynd is a Highlands Tudor within walking distance of Bardstown Road and the coveted Cherokee park. The home consists of large open spaces that flow together through rooms adorned with...
$995,000
Neighborhood: Cherokee Plaza
5
Beds
4
Baths
5,997
Sq.Ft.
1927
Year Built
4
Days on Site
1622549
MLS
This stylish contemporary 5 bedroom, 4 full bath home is one of a kind occupying an enviable position within the desirable Belknap neighborhood. This property was extended in 2007 to include on the...
$255,000
Neighborhood: Commodore
2
Beds
1
Baths
1,291
Sq.Ft.
1929
Year Built
4
Days on Site
1622797
MLS
2E is a wonderful unit, packed with character, as well as updated features in one of Louisville's most iconic buildings, The Commodore. This two-bedroom, one bath condo is spacious, elegant, and full...
$725,000
Neighborhood: Highlands
3
Beds
3
Baths
2,509
Sq.Ft.
1925
Year Built
5
Days on Site
1621633
MLS
RARE FIND INDEED! Here's a chance to live in an EXQUISITE CRAFTSMAN-style home nestled in an absolute gem of a neighborhood mere steps from Cherokee Park! From the minute you step through the...
3
Beds
2F11/2
Baths
3,326
Sq.Ft.
1953
Year Built
5
Days on Site
1622646
MLS
Location! Location! This spacious brick ranch has a gorgeous lot, wonderful patio area across the back of the home and an in-ground pool. You are greeted by a covered front porch which is the...
$700,000
Neighborhood: Inverness
3
Beds
3F11/2
Baths
3,066
Sq.Ft.
1929
Year Built
6
Days on Site
1622546
MLS
Enjoy living the carefree life in the historic Highlands Inverness, a gem of a building in sought after Cherokee Triangle near Cherokee Park. This turn-key is one of the larger units, offering 3...
$238,000
Neighborhood: Highlands
2
Beds
1F11/2
Baths
1,364
Sq.Ft.
1927
Year Built
6
Days on Site
1622581
MLS
Condo life is easy in this Highlands Condominium, close to all the restaurants and shops yet the feel of a retreat amidst the hustle and bustle of the Highlands. Originally built in 1927 but...
$699,000
Neighborhood: 1400 Willow
1
Beds
2
Baths
1,766
Sq.Ft.
1980
Year Built
7
Days on Site
1622479
MLS
Located in the heart of Cherokee Triangle, this 12th floor, west facing condominium offers panoramic views of downtown Louisville and the surrounding Highlands. In 2018, the unit was gutted and...
$549,995
Neighborhood: Highlands
4
Beds
2F11/2
Baths
2,060
Sq.Ft.
1923
Year Built
7
Days on Site
1622495
MLS
This BEAUTIFUL Highlands home sits on one of the most desirable and iconic streets. It offers stunning updates throughout while featuring 4 bedrooms and 2.5 baths, a formal dining room, an open...
$1,350,000
Neighborhood: Cherokee Triangle
4
Beds
3F11/2
Baths
5,098
Sq.Ft.
1875
Year Built
11
Days on Site
1622247
MLS
Nestled on Cherokee Road among the verdant tree lined street sits this impressive Italianate home of stone and Spanish tile. Originally built in 1875 and completely remodeled in 2014 while keeping...
3
Beds
1
Baths
1,637
Sq.Ft.
1915
Year Built
11
Days on Site
1622305
MLS
At last, my love has come along... in the form of a beautiful home! And life is like a song in this cheerful cottage located in the heart of the Highlands! From the swing on the front porch, listen...

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