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 July 11, 2020
94
Listed
57
Avg. DOM
$196.65
Avg. $ / Sq.Ft.
$431,450
Med. List Price
94 Properties
Page 1 of 8
$299,900
Subdivision: Highland
3
Beds
2
Baths
1,630
Sq.Ft.
1915
Year Built
2
Days on Site
1563885
MLS
***First Showings Sunday July 12th at Open House from 2-4***Welcome to 1955 Richmond Dr! Don't miss this RARE Highlands opportunity! This 3 bedroom, 2 FULL bath beauty feature rock solid exterior...
$215,000
Subdivision: Highlands
1
Beds
2
Baths
1,025
Sq.Ft.
1983
Year Built
2
Days on Site
1563899
MLS
This FABULOUS first floor unit has nice architectural features such as crown molding, hardwood floors, classic tiles, and working pocket doors. The beautifully proportioned master bedroom has an...
$499,000
Subdivision: Cherokee Triangle
4
Beds
1F11/2
Baths
3,075
Sq.Ft.
1915
Year Built
2
Days on Site
1563907
MLS
Welcome to 2113 Grinstead Drive where charm and tradition collide. Located in the Cherokee Triangle Historic Preservation District where you are steps away from Cherokee Park and Bardstown Road...
$585,000
Subdivision: Cherokee Plaza
5
Beds
3F11/2
Baths
3,128
Sq.Ft.
1920
Year Built
2
Days on Site
1563927
MLS
Welcome to this Highlands charmer.....Three full floors of updates but in keeping with the charm and age of the home. This 5 bedroom home, an unusual find in the Highlands, went through extensive...
$585,000
Subdivision: Cherokee Triangle
4
Beds
4F11/2
Baths
4,740
Sq.Ft.
1905
Year Built
2
Days on Site
1563945
MLS
Wonderful 4 bedroom, 4 1/2 bath home with a fabulous Carriage House in historic Cherokee Triangle! Abundant charm and character blend seamlessly with the home's updates including an incredible...
$398,500
Subdivision: Original Highlands
4
Beds
2
Baths
2,628
Sq.Ft.
1900
Year Built
3
Days on Site
1563748
MLS
Located in the Original Highlands just blocks from all that this fabulous neighborhood has to offer, this historic classic has been impeccably restored and is move-in ready! Freshly painted, this...
$450,000
Subdivision: Highlands
3
Beds
2F11/2
Baths
2,348
Sq.Ft.
1900
Year Built
3
Days on Site
1563756
MLS
Charming Highlands home with tons of updates and stylish finishes! This 3 bedroom, 2 1/2 bath home with over 2,300 square feet of living space is situated close to dining, shops, and all that the...
$475,000
Subdivision: Original Highlands
3
Beds
3
Baths
2,525
Sq.Ft.
2020
Year Built
3
Days on Site
1563816
MLS
MODERN + NEW in the Original Highlands. This low-maintenance home features an open floor plan, flexible spaces, soaring ceilings and tons of natural light. With thoughtful material finishes...
$324,900
Subdivision: University Park
3
Beds
1F11/2
Baths
1,919
Sq.Ft.
1925
Year Built
3
Days on Site
1563819
MLS
Wonderful opportunity to live in the heart of the Highlands within walking distance to Douglas Loop and Bardstown Road! This quaint 3 bedroom, 1 1/2 bath, tudor-style home is well built and has the...
1
Beds
1
Baths
563
Sq.Ft.
1922
Year Built
3
Days on Site
1563837
MLS
No description available...
$290,000
Subdivision: Highlands
3
Beds
1F11/2
Baths
2,056
Sq.Ft.
1937
Year Built
4
Days on Site
1563656
MLS
Welcome to your new Highlands home! This traditional style 3 bedroom and 1.5 bath is move in ready with all the features and updates you would expect. Located in the sought-after Belknap neighborhood...
$290,000
Subdivision: Baxter Walk Condo
1
Beds
1F11/2
Baths
1,599
Sq.Ft.
1924
Year Built
4
Days on Site
1563661
MLS
Hurry to see this unique Highlands condo with the spaciousness of a home PLUS attached garage located in the former Architectural Glass Building, with almost 1600 sq ft, its the size of many 2-3...

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