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 October 27, 2021
79
Listed
47
Avg. DOM
$195.98
Avg. $ / Sq.Ft.
$399,000
Med. List Price
79 Properties
Page 1 of 7
Open 10/31
2913 Seneca Park Rd Louisville, KY 40205
4
Beds
2F21/2
Baths
2,731
Sq.Ft.
1973
Year Built
2
Days on Site
1599430
MLS
Located between Seneca Park and Cherokee Park, this traditional American Four-Square is complete with 4 bedrooms and 4 baths. It is approximately 2719 square feet, including the finished basement....
$599,000
Subdivision: Highlands
3
Beds
2F11/2
Baths
2,952
Sq.Ft.
1912
Year Built
2
Days on Site
1599434
MLS
Featured in Louisville Magazine, March, 2010 edition, your Arts and Crafts bungalow on one of the Highlands' most-revered streets is finally available! Located on a broad, tree-lined street with easy...
Open 10/31
1918 Rutherford Ave Louisville, KY 40205
$575,000
Subdivision: University Park
4
Beds
2
Baths
3,135
Sq.Ft.
1900
Year Built
2
Days on Site
1599443
MLS
Don't miss this beautifully remodeled, ''Johanna Gaines'' style remodeled home nestled on a quiet street in the Highland! This spacious 3-story, 4-bedroom, 2 bathroom gem has been fully renovated...
$329,900
Subdivision: Cherokee Triangle
3
Beds
3
Baths
2,115
Sq.Ft.
1910
Year Built
5
Days on Site
1599322
MLS
New price as of 10/26/21!!! ATTENTION BARGAIN HUNTERS! What a rare opportunity for your own design-build renovation in the sought after Cherokee Triangle subdivision. One of only 5 homes that have...
$129,900
Subdivision: Chapel View
2
Beds
1
Baths
895
Sq.Ft.
1981
Year Built
6
Days on Site
1599215
MLS
(Not FHA or Va loan approved) What a great place to call home! This Highlands 2nd floor condo is just a short distance from the Bardstown Road dining scene, Bellarmine, and on the bus line. Located...
Under Contract
2502 Longest Ave Louisville, KY 40204
$1,050,000
Subdivision: Cherokee Triangle
6
Beds
3F11/2
Baths
4,622
Sq.Ft.
1926
Year Built
7
Days on Site
1599046
MLS
This prestigious Cherokee Triangle home sits atop Longest Avenue, overlooking Cherokee Park and Amelia Place, offering stunning treetop views from front and back. This stately, 3-story home has 6...
Under Contract
2429 Wallace Ave Louisville, KY 40205
$290,000
Subdivision: Highlands
3
Beds
2
Baths
2,066
Sq.Ft.
1925
Year Built
7
Days on Site
1599124
MLS
Highlands Parkside-Craftsman Style Bungalow! Some special features: Recently redone floors-Oak & Pine on main level. New flooring also in Kit. & Baths. ''Clean as a Whistle'' The inviting front porch...
$240,000
Subdivision: The Commodore
1
Beds
1
Baths
1,072
Sq.Ft.
1929
Year Built
7
Days on Site
1599152
MLS
Truly a one-of-a-kind building in the Highlands! This renovated, light filled, spacious unit in the majestic Commodore overlooks Cherokee Park and is just blocks from Bardstown Rd! Hardwood floors...
$469,000
Subdivision: Cherokee Triangle
2
Beds
2
Baths
1,253
Sq.Ft.
1980
Year Built
7
Days on Site
1599154
MLS
The venerable 1400 Willow is the closest thing to NYC in the Bluegrass. If you've been waiting for that hard to find unit that FINALLY hits the market under $500k, today is your lucky day! This 2...
$309,900
Subdivision: Highlands
3
Beds
2F11/2
Baths
1,544
Sq.Ft.
1890
Year Built
8
Days on Site
1598952
MLS
Highlands Victorian home that is fully renovated for carefree living. Custom art glass transoms, restored tall ceilings, two period fireplaces with heat producing electric inserts, three updated...
Under Contract
2225 Boulevard Napoleon Blvd Louisville, KY 40205
3
Beds
2F11/2
Baths
2,449
Sq.Ft.
1928
Year Built
8
Days on Site
1598980
MLS
FIRST SHOWINGS FRIDAY 11AM--Great bungalow sitting proudly on corner of Blvd Napoleon w all the character you'd expect in the Highlands with some very nice upgrades. The living room spans the full...
Under Contract
2141 Woodbourne Ave Louisville, KY 40205
$329,900
Subdivision: Woodbourne Heights
3
Beds
2
Baths
1,500
Sq.Ft.
1920
Year Built
8
Days on Site
1599007
MLS
This charming bungalow has been lovingly maintained and updated, including the addition of a second floor luxurious primary suite. The kitchen has been updated with stainless appliances including a...

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