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 December 2, 2020
85
Listed
69
Avg. DOM
$197.21
Avg. $ / Sq.Ft.
$379,000
Med. List Price
85 Properties
Page 1 of 8
$489,000
Subdivision: Highlands
4
Beds
2F11/2
Baths
2,634
Sq.Ft.
1928
Year Built
2
Days on Site
1574977
MLS
Nestled park side in one of the most charming areas of town, this Highlands classic is move-in ready! Just blocks from both Bardstown Road and Cherokee Park, you'll enjoy living in this fabulous...
$222,500
Subdivision: Highlands
2
Beds
1
Baths
884
Sq.Ft.
1922
Year Built
5
Days on Site
1574860
MLS
RLM Building and Remodel proudly presents 184 Richmond Dr. This 2 Bedroon 1 full bath ranch on a basement. can be purchased outright OR seller will build to suit. Option 1) 3 Bedroom 2 full bath...
$545,000
Subdivision: Cherokee Triangle
5
Beds
2F11/2
Baths
3,627
Sq.Ft.
1899
Year Built
8
Days on Site
1574743
MLS
ONLY home in 40204 available with a carriage house, this home is loaded with quality, charity and value~ a BEST buy in 40204~. This 1900's Victorian home is an unspoiled and refined combination of...
Open 12/6
1058 Cherokee Rd #1b Louisville, KY 40204
3
Beds
2
Baths
1,777
Sq.Ft.
1981
Year Built
9
Days on Site
1574659
MLS
Located on desirable Cherokee Road, this first floor, three bedroom, two full bath condo is beautiful. The marble entrance hall leads into the large living room with tall ceilings and shuttered...
1
Beds
1
Baths
775
Sq.Ft.
1920
Year Built
11
Days on Site
1574575
MLS
Great Location! Walk to all of your favorite shops and restaurants as well as the parks. Well maintained condo with hardwood floors and spacious living room. Move In condition. All appliances to...
$317,000
Subdivision: Tecomah
3
Beds
1F11/2
Baths
1,955
Sq.Ft.
1925
Year Built
13
Days on Site
1571338
MLS
Stunning Traditional home in the Highlands! Welcome to this charming 3 bedroom, 1.5 bath home, within walking distance to Lakeside Swim Club, any many other conveniences. This home offers a...
$499,000
Subdivision: Cherokee Triangle
3
Beds
2F11/2
Baths
2,665
Sq.Ft.
1915
Year Built
13
Days on Site
1574474
MLS
Welcome to 2111 Grinstead Drive where classic style and tradition collide. Located in the Cherokee Triangle Historic Preservation District where you are steps away from Cherokee Park and Bardstown...
$880,000
Subdivision: 1400 Willow
3
Beds
3
Baths
2,236
Sq.Ft.
1980
Year Built
14
Days on Site
1574318
MLS
Bienvenue a la maison! Located in the heart of Cherokee Triangle, overlooking Cherokee Park this condominium has sweeping views from every vantage point. The architecture, the decor -- everything was...
$163,900
Subdivision: Wilshire
2
Beds
1
Baths
923
Sq.Ft.
1923
Year Built
14
Days on Site
1574370
MLS
ACT NOW on this ARCHITECTURALLY STUNNING condo! The Seller is currently offering up to $3500 in Buyer's closing costs and prepaids with an accepted offer! Charming two bedroom Highlands condo near...
Under Contract
1905 Bonnycastle Ave Louisville, KY 40205
2
Beds
1
Baths
1,157
Sq.Ft.
1905
Year Built
14
Days on Site
1574412
MLS
Charming Highlands Cottage with High Ceilings and Beautiful Hardwood Floors. You'll love social distancing on this 46' covered porch, add a fire pit and outdoor heaters and enjoy. This Elegant and...
$547,500
Subdivision: Dundee Terrace
3
Beds
2
Baths
2,500
Sq.Ft.
1948
Year Built
15
Days on Site
1574229
MLS
This one owner home has never been on the market. Sited on a .6 acre lot, this lovingly maintained Highlands home has been updated for contemporary lifestyles. You'll love the newly refinished...
Under Contract
1841 Sherwood Ave Louisville, KY 40205
$284,900
Subdivision: Dukers Addition
2
Beds
2
Baths
1,644
Sq.Ft.
1910
Year Built
15
Days on Site
1574233
MLS
Stunning example of old and new working beautifully together! All the ambiance and charm of a 110 year old Highlands beauty with so many updated features it feels new inside. You get the high...

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