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 August 4, 2021
62
Listed
58
Avg. DOM
$199.21
Avg. $ / Sq.Ft.
$392,500
Med. List Price
62 Properties
Page 1 of 6
2
Beds
2
Baths
1,450
Sq.Ft.
1905
Year Built
4
Days on Site
1592627
MLS
This early 1900s home is conveniently located walking distance to all of the entertainment Bardstown Road has to offer. The front entry has a covered porch and a custom front door. As you walk...
3
Beds
2
Baths
2,300
Sq.Ft.
1900
Year Built
5
Days on Site
1592615
MLS
Looking for the perfect home that's walking distance to many restaurants and shops? Look no more! This gorgeous home in the heart of the highlands has 3 bedrooms, tons of storage, and a private...
$235,000
Subdivision: Highlands
1
Beds
1F11/2
Baths
980
Sq.Ft.
1900
Year Built
6
Days on Site
1592428
MLS
Come see this wonderful Camelback home nestled on Deer Park in a sought after neighborhood. It has an open and spacious living room, which has a decorative fireplace. The dining room is currently...
Under Contract
1642 Spring Dr Louisville, KY 40205
$1,595,000
Subdivision: Bonnycastle
6
Beds
4F21/2
Baths
5,848
Sq.Ft.
1910
Year Built
6
Days on Site
1592453
MLS
Over the last 7 years nearly every part of this gorgeous property has been given a new and luxurious life, bringing the essence of a posh Mediterranean villa to 1642 Spring Drive in Louisville,...
$484,500
Subdivision: Hiawatha
3
Beds
2
Baths
2,554
Sq.Ft.
1974
Year Built
6
Days on Site
1592478
MLS
Beautiful 3 bed/2 bath 1st floor condo located in the heart of the Highlands. Beautiful hardwood floors with inlays, historically correct wood clad windows, built-in bookcases, new HVAC, custom...
$599,900
Subdivision: Highlands
3
Beds
3
Baths
2,814
Sq.Ft.
1920
Year Built
7
Days on Site
1592253
MLS
Dream of living in a low-maintenance condo that lives like a single-family home but without the hassle of yardwork? Look no further! Your dreams will come true with this park-side luxurious...
$369,900
Subdivision: Aberdeen
3
Beds
2
Baths
1,564
Sq.Ft.
1936
Year Built
7
Days on Site
1592290
MLS
A lovely Highlands location in an established neighborhood of lovely homes. From the moment you walk into the foyer, you will be welcomed into a spotless brick home with loads of character. It has...
$399,900
Subdivision: Highlands
4
Beds
2
Baths
2,857
Sq.Ft.
1900
Year Built
7
Days on Site
1592336
MLS
1941 Deerwood Avenue is the rare Highlands home that has all newly updated mechanicals. All major home systems such as heating and air, hot water heater, roof, and energy-efficient windows are less...
1
Beds
1F11/2
Baths
907
Sq.Ft.
1983
Year Built
9
Days on Site
1592065
MLS
Fantastic Highlands condo!! This 1st floor condo is conveniently located near both Cherokee and Seneca Park along with a ton of local restaurants, shops, and a short walk up to the Douglass Loop!...
Under Contract
2314 Grinstead Dr #1 Louisville, KY 40204
$99,900
Subdivision: The Oaks
2
Beds
1
Baths
789
Sq.Ft.
1979
Year Built
9
Days on Site
1592099
MLS
PRIME LOCATION in the heart of the HIGHLANDS! A great opportunity to be in the Cherokee Triangle. This two bedroom first floor condo in The Oaks has a great floorplan with a good size living room,...
$899,000
Subdivision: Highlands
2
Beds
2F21/2
Baths
3,423
Sq.Ft.
2010
Year Built
14
Days on Site
1591694
MLS
Once in a lifetime opportunity to live in a masterpiece! This 2010 American Institute of Architects Honor Award winning home was designed by Michael Koch and built by Shedd Designs. The home features...
Under Contract
1506 Cherokee Rd #4 Louisville, KY 40205
$367,500
Subdivision: Park Vista
3
Beds
2
Baths
1,550
Sq.Ft.
1995
Year Built
14
Days on Site
1591706
MLS
Convenient Parkside condominium with tree top views of Enid Bland Yandell's statue of Daniel Boone and Frederick Law Olmsted's Cherokee Park. This lovely unit offers the best of both worlds: period...

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