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 May 14, 2021
59
Listed
57
Avg. DOM
$215.02
Avg. $ / Sq.Ft.
$417,500
Med. List Price
59 Properties
Page 1 of 5
$290,000
Subdivision: Highlands
2
Beds
2
Baths
1,200
Sq.Ft.
1900
Year Built
2
Days on Site
1585527
MLS
ADORABLE HOME in the HIGHLANDS ! Fully Furnished ! Walk to your favorite Highlands destinations! Covered Front Porch, Hardwoods, High Ceilings, 2 Fireplaces (one in Living Room and one in Kitchen)!...
$619,900
Subdivision: Zachary Taylor
4
Beds
3F11/2
Baths
2,700
Sq.Ft.
1925
Year Built
2
Days on Site
1585545
MLS
Wow! Take a step back into time with this decadent French Country style home in the heart of the highlands. Literally just a short walk from Cherokee park, this beautiful home highlights a charming...
Open 5/16
1207 Cherokee Rd Louisville, KY 40204
$550,000
Subdivision: Cherokee Triangle
4
Beds
3F11/2
Baths
3,850
Sq.Ft.
1905
Year Built
2
Days on Site
1585559
MLS
Elegant and updated to a masterpiece of Architectural design. Here's an opportunity to own this meticulously restored and maintained home with the option to have 2 additional rental incomes from a...
$450,000
Subdivision: Highlands
3
Beds
3
Baths
2,201
Sq.Ft.
1920
Year Built
2
Days on Site
1585566
MLS
Delightful Highlands bungalow, with first floor primary suite and laundry, within walking distance to farmer's markets, the Douglass Loop, and all that Bardstown Rd has to offer, yet tucked away on a...
$415,000
Subdivision: Cherokee Triangle
3
Beds
2
Baths
2,314
Sq.Ft.
1900
Year Built
2
Days on Site
1585603
MLS
Welcome to Cherokee Triangle! This charming home offers many original features and is ready for your personal touch. The front porch beckons you to sit, relax and enjoy the day. Just inside you will...
$775,000
Subdivision: Cherokee Triangle
4
Beds
3F11/2
Baths
2,590
Sq.Ft.
1905
Year Built
2
Days on Site
1585618
MLS
Located in the highly sought-after Cherokee Triangle and just a short distance to Bardstown Road and Cherokee Park, this stunning Victorian home is not to be missed. Originally built in 1905, and...
$575,000
Subdivision: Cherokee Triangle
3
Beds
2
Baths
2,600
Sq.Ft.
1915
Year Built
3
Days on Site
1585401
MLS
LOOK OUT!! Create memories from an amazing front porch on this cozy Cherokee Triangle charmer! An abundance of natural light illuminate the hardwood floors + wood trim as the first level flows from...
Open 5/16
1610 Bonnycastle Ave Louisville, KY 40205
$309,900
Subdivision: Bonnycastle
3
Beds
2
Baths
1,600
Sq.Ft.
1923
Year Built
3
Days on Site
1585441
MLS
Beautiful Highlands bungalow features many gorgeous, unique updates. Charming porch leads to stunning living room with vaulted ceiling, custom built-ins and hardwood floors that carry throughout 1st...
Open 5/16
2020 Kenilworth Pl Louisville, KY 40205
$800,000
Subdivision: Kenilworth
4
Beds
3
Baths
3,822
Sq.Ft.
1910
Year Built
4
Days on Site
1585320
MLS
When you pass through the twin limestone gateposts of Kenilworth Place, you'll see one of the best examples of post-Victorian homes in Louisville. All but one home are over 100 years old. 2020...
$179,999
Subdivision: Parklane
1
Beds
1
Baths
901
Sq.Ft.
1912
Year Built
5
Days on Site
1585268
MLS
This charming first-floor condo is right in the heart of The Highlands. Enter from a spectacular courtyard or from your attached underground garage. Yes, there is a 1-car space with an opener for...
$350,000
Subdivision: Lakeside
3
Beds
2
Baths
1,600
Sq.Ft.
1928
Year Built
5
Days on Site
1585310
MLS
Located in the Lakeside Membership District of the Highlands on the vibrant Trevillian Way, is this Classic Dutch Colonial. Covering over 1600 ft., this 3 bedroom 2 bath home is highlighted by its...
$459,900
Subdivision: Highlands
3
Beds
2
Baths
2,112
Sq.Ft.
1939
Year Built
8
Days on Site
1585068
MLS
Location... Location... This wonderful 2-story home built in 1939 offers all of today's modern conveniences in a stellar location just 2 blocks from Cherokee Park and was totally renovated in 2007....

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