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 November 17, 2018
126
Listed
57
Avg. DOM
$181.56
Avg. $ / Sq.Ft.
$398,250
Med. List Price
126 Properties Found. Showing 1-12
Sort By:
2238 Village Dr
Louisville, KY 40205
2238 Village Dr Louisville, KY 40205
 
$650,000
Subdivision: Cherokee Hills
BEDS
5
BATHS
4
SQ.FT.
7,452
BUILT
1922
ON SITE
2Days
MLS
1519515
No description available...
2411 Ransdell Ave
Louisville, KY 40204
2411 Ransdell Ave Louisville, KY 40204
1 of 31
$525,000
Subdivision: Cherokee Triangle
BEDS
4
BATHS
3
SQ.FT.
2,900
BUILT
1900
ON SITE
2Days
MLS
1519562
New Price on this Cherokee Triangle classic with the iconic front porch and swing! First floor features welcoming entry, living room with fireplace and bookcases, pocket doors to dining room with...
1302 Cherokee Rd
Louisville, KY 40204
Open House
1302 Cherokee Rd Louisville, KY 40204
1 of 54
$824,900
Subdivision: Cherokee Triangle
BEDS
4
BATHS
4
SQ.FT.
4,282
BUILT
1900
ON SITE
1Day
MLS
1519579
You will not want to miss the unique opportunity to own this beautiful home in the Historic Cherokee Triangle that has been fully updated but retains much of the character and charm of 1900. You...
1229 Bassett Ave
Louisville, KY 40204
Open House
1229 Bassett Ave Louisville, KY 40204
1 of 46
$315,000
Subdivision: Eastern Parkland
BEDS
2
BATHS
3
SQ.FT.
1,913
BUILT
1920
ON SITE
3Days
MLS
1519430
Buyer's financing fell through after inspections and appraisal. Welcome to this adorable, cottage style home in the Cherokee Triangle! Located just a half mile from Cherokee Park and Baxter Avenue,...
1525 Christy Ave
Louisville, KY 40204
Open House
1525 Christy Ave Louisville, KY 40204
1 of 35
$198,500 ( $3,500 )
Subdivision: Highlands
BEDS
2
BATHS
1
SQ.FT.
924
BUILT
1900
ON SITE
3Days
MLS
1519459
Looking a spectacular home located in a popular end of town? Then look no further. This tremendous 2 bedroom 1 bathroom Highland home has got you covered. From pristine hardwood flooring to beautiful...
1818 Deerwood Ave
Louisville, KY 40205
Open House
1818 Deerwood Ave Louisville, KY 40205
1 of 44
$329,900
Subdivision: Highlands
BEDS
3
BATHS
2
SQ.FT.
2,350
BUILT
1921
ON SITE
3Days
MLS
1519461
Move right in! This beauty has lots of room, including 2 main floor bedrooms 2 full baths and a partially finished walk up basement. Amazing Kitchen- features top of the line Jenn Air appliances...
1916 Duker Ave
Louisville, KY 40205
1916 Duker Ave Louisville, KY 40205
1 of 43
$360,000
Subdivision: Deer Park
BEDS
5
BATHS
3
SQ.FT.
2,400
BUILT
1910
ON SITE
3Days
MLS
1519485
Welcome to your RENOVATED, MOVE-IN READY 5 Bedroom, 3 Full Bathroom, with a 2 car garage in the heart of the Highlands neighborhood, just a half block from all that Bardstown Road has to offer! Get...
2034 Speed Ave
Louisville, KY 40205
2034 Speed Ave Louisville, KY 40205
 
$252,400
Subdivision: Kenilworth
BEDS
3
BATHS
2
SQ.FT.
2,105
BUILT
1920
ON SITE
4Days
MLS
1519358
Incredible investor opportunity. Located in the Highlands, this property has tremendous upside and is ready to be made over. This cute bungalow is not a short sale or bank owned REO. This property...
1400 Willow Ave
Louisville, KY 40204
1400 Willow Ave Louisville, KY 40204
1 of 37
$650,000
Subdivision: 1400 Willow
BEDS
2
BATHS
2
SQ.FT.
1,631
BUILT
1980
ON SITE
4Days
MLS
1519365
Enjoy the many amenities at 1400 Willow, the Best of the Best. Unit on the 20th floor offers sweeping park and Cherokee Triangle views. Unit is ready for the new owner to personalize the home. New...
2023 Alta Ave
Louisville, KY 40205
Open House
2023 Alta Ave Louisville, KY 40205
1 of 33
$313,900
Subdivision: N/A
BEDS
3
BATHS
1
SQ.FT.
1,527
BUILT
1905
ON SITE
4Days
MLS
1519394
FIRST Open house Sunday, 11/18/18. This Highland's home is a hard-to-find, parkside home with ALL first floor living and a NEW 2 1/2 car garage built in 2015. The hardwood oak floors have gorgeous...
1720 Bonnycastle Ave
Louisville, KY 40205
1720 Bonnycastle Ave Louisville, KY 40205
1 of 28
$210,000
Subdivision: Mrs Maria Gernerts
BEDS
3
BATHS
2
SQ.FT.
1,341
BUILT
1925
ON SITE
6Days
MLS
1516224
Don't miss this darling bungalow in the Highlands! Three bedrooms, one-and-a half baths, with a formal dining room and living room. Kitchen leads out to small back porch and surprisingly HUGE garage...
2632 Mccoy Way
Louisville, KY 40205
2632 Mccoy Way Louisville, KY 40205
1 of 21
$319,900
Subdivision: N/A
BEDS
3
BATHS
2
SQ.FT.
1,643
BUILT
1953
ON SITE
6Days
MLS
1519204
Traditional mid-century brick ranch in very desirable neighborhood close to Seneca Gardens. This spacious renovated home has all the modern updates with the charm of yesterday including new windows,...

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