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 March 4, 2021
66
Listed
80
Avg. DOM
$206.58
Avg. $ / Sq.Ft.
$409,200
Med. List Price
66 Properties
Page 1 of 6
$459,900
Subdivision: Highlands
2
Beds
2
Baths
1,970
Sq.Ft.
1926
Year Built
2
Days on Site
1580060
MLS
Fabulous double unit in the restored Tudor Terrace Condos, just steps from Cherokee Park! This 2 story unit has its own covered stone porch and private entrance- perfect for entertaining! Grand...
Open 3/7
2000 Millvale Rd Louisville, KY 40205
5
Beds
5F21/2
Baths
7,195
Sq.Ft.
1912
Year Built
3
Days on Site
1579992
MLS
The historic and iconic ''Pine Hill'' residence is now being offered for sale! The last time this residence was purchased was in 1976. The home sits majestically on 5 acres overlooking the Big Rock...
Open 3/7
2110 Cherokee Pkwy #B Louisville, KY 40204
$345,000
Subdivision: Cherokee Triangle
2
Beds
2
Baths
1,550
Sq.Ft.
1910
Year Built
4
Days on Site
1579922
MLS
Don't miss this totally special first floor condo in awesome The Pennington. Located in the heart of Cherokee Triangle, a short block from Willow Park and Cherokee Park, this nicely updated condo...
$360,000
Subdivision: Original Highlands
2
Beds
2F11/2
Baths
1,779
Sq.Ft.
1895
Year Built
6
Days on Site
1579817
MLS
Welcome to the Hepburn! This historic home is steps away from Bardstown Rd and some of Louisville's top restaurants, boutiques, and entertainment. Walking up to this 1890's Victorian style home you...
Open 3/6
1801 Shady Ln #6 Louisville, KY 40205
$129,900
Subdivision: Norris Place
2
Beds
1
Baths
768
Sq.Ft.
1946
Year Built
7
Days on Site
1579712
MLS
Yes, you can live in the Highlands for under $130,000. Only 2 blocks from the excitement and activity of Bardstown Road, this lovely 2nd floor condo offers two bedrooms, off-street parking and a...
$475,000
Subdivision: Belknap
3
Beds
2F21/2
Baths
2,548
Sq.Ft.
1920
Year Built
7
Days on Site
1579729
MLS
Welcome home to your fabulous new brick bungalow in the Highlands. Located in the desirable Belknap neighborhood, this home boasts a total of 2,548 finished square feet. It has undergone an entire...
1
Beds
1
Baths
1,112
Sq.Ft.
1910
Year Built
8
Days on Site
1579581
MLS
Located in the Heart of Douglas Loop...less than a block to Bardstown Rd. You will love this renovated shotgun. As you step inside, you'll be delighted by the character and charm that offers a...
Under Contract
2117 Cherokee Pkwy Louisville, KY 40204
$995,000
Subdivision: Cherokee Triangle
5
Beds
3F21/2
Baths
4,734
Sq.Ft.
1905
Year Built
8
Days on Site
1579600
MLS
Located in the heart of Cherokee Triangle, a historic preservation district in the Highlands, 2117 Cherokee Parkway is just one block up the hill from the historic entrance to Cherokee Park and only...
$194,500
Subdivision: Edgehill
2
Beds
1
Baths
1,083
Sq.Ft.
1920
Year Built
8
Days on Site
1579605
MLS
Welcome to this spacious third floor condo in the sought-after area of the Highlands in a wonderful Tudor Style building. This third floor Unit features the original hardwood floors throughout, an...
Under Contract
2233 Woodford Pl Louisville, KY 40205
$635,000
Subdivision: Cherokee Hills
4
Beds
2F21/2
Baths
3,346
Sq.Ft.
1925
Year Built
8
Days on Site
1579626
MLS
It is an absolute privilege to present this stunning four-bedroom brick Colonial on one of the most sought-after streets in the Highlands. There is nothing that excites me more than walking in a home...
Under Contract
1628 Deer Ln Louisville, KY 40205
$275,000
Subdivision: Deer Park
3
Beds
2
Baths
2,014
Sq.Ft.
1945
Year Built
8
Days on Site
1579682
MLS
No description available...
Under Contract
1706 Fernwood Ave Louisville, KY 40205
$329,000
Subdivision: Highlands
3
Beds
2
Baths
1,568
Sq.Ft.
1915
Year Built
9
Days on Site
1579531
MLS
This charming bungalow is in a prime Highlands location. Walking distance to some of the best restaurants Louisville has to offer. Fall in love at first sight when you step onto the covered front...

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