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 March 22, 2019
117
Listed
72
Avg. DOM
$180.62
Avg. $ / Sq.Ft.
$387,500
Med. List Price
117 Properties Found. Showing 1-12
Sort By:
1727 Bonnycastle Ave
Louisville, KY 40205
1727 Bonnycastle Ave Louisville, KY 40205
1 of 17
$265,000
Subdivision: N/A
BEDS
2
BATHS
2
SQ.FT.
1,100
BUILT
1910
ON SITE
1Day
MLS
1527316
Completely updated beautiful home located on a nice level lot. New kitchen, new stainless steel appliances, baths, everything is new. Newly installed hardwood floors. Also has a 1 car garage, deck...
2025 Lauderdale Rd
Louisville, KY 40205
2025 Lauderdale Rd Louisville, KY 40205
1 of 49
$450,000
Subdivision: Kenilworth
BEDS
3
BATHS
4
SQ.FT.
2,847
BUILT
1930
ON SITE
1Day
MLS
1527337
Beautifully UPDATED 2 Story in the heart of the Highlands! Enter into the bright, front Sun Room which opens to the spacious Living Room with fireplace & Formal Dining Room, both with hardwood...
2007 Grasmere Dr
Louisville, KY 40205
Open House
2007 Grasmere Dr Louisville, KY 40205
1 of 47
$387,500
Subdivision: Kenilworth
BEDS
3
BATHS
3
SQ.FT.
2,600
BUILT
1922
ON SITE
2Days
MLS
1527196
''Parkside'' of Bardstown Rd., walk to Douglass Loop, Cherokee Park or dinner on Bardstown Road from this Highlands-Douglass charmer boasting character and natural light! It's move-in ready with...
1901 Stevens Ave
Louisville, KY 40205
Open House
1901 Stevens Ave Louisville, KY 40205
1 of 30
$320,000
Subdivision: Dukers Addition
BEDS
3
BATHS
2
SQ.FT.
1,888
BUILT
1926
ON SITE
2Days
MLS
1527260
Your home is perfectly situated off Bardstown Rd in the Highlands. When you're not enjoying the neighborhood, you'll love the mix of modern and classic luxuries of your home. A centrally located...
2306 Rutherford Wynd
Louisville, KY 40205
2306 Rutherford Wynd Louisville, KY 40205
1 of 45
$875,000
Subdivision: Highlands
BEDS
4
BATHS
4
SQ.FT.
3,716
BUILT
1915
ON SITE
3Days
MLS
1527116
Impeccable, charming Tudor in superb condition, ready for the most discriminating buyer. This secluded location is part of a walking neighborhood close to Bardstown Road and Cherokee Park. Gorgeous...
2125 Baringer Ave
Louisville, KY 40204
2125 Baringer Ave Louisville, KY 40204
1 of 19
$400,000
Subdivision: N/A
BEDS
3
BATHS
2
SQ.FT.
1,744
BUILT
1920
ON SITE
3Days
MLS
1527127
The right Street. The right location and Area. Solid Brick home.
2411 Ransdell Ave
Louisville, KY 40204
2411 Ransdell Ave Louisville, KY 40204
1 of 31
$515,000
Subdivision: Cherokee Triangle
BEDS
4
BATHS
3
SQ.FT.
2,900
BUILT
1901
ON SITE
3Days
MLS
1527160
Classic details are found in this light filled Cherokee Triangle home. Flexible use of space, flow for entertaining, an open staircase with leaded glass windows, 10' high ceilings, hardwood floors,...
2326 Dundee Rd
Louisville, KY 40205
2326 Dundee Rd Louisville, KY 40205
1 of 42
$640,000
Subdivision: Courtyard Highland
BEDS
3
BATHS
3
SQ.FT.
2,680
BUILT
2000
ON SITE
4Days
MLS
1527011
Upscale Highlands Townhome has an OPEN FLOOR PLAN with lots of NATURAL LIGHTand tremendous Location, South of the Douglas Loop (the eclectic Bardstown Roadneighborhood shops, restaurants, night life.....
2022 Eastern Pkwy #1
Louisville, KY 40204
2022 Eastern Pkwy #1 Louisville, KY 40204
1 of 31
$599,000
Subdivision: N/A
BEDS
3
BATHS
3
SQ.FT.
2,879
BUILT
1920
ON SITE
4Days
MLS
1527049
FOR SALE/LEASE OPTION/OWNER FINANCING GORGEOUS HIGHLANDS COMPLETE RENOVATED CONDO/HOME WITHIN STEPS TO CHEROKEE PARK. THIS HOME HAS BEEN REMODELED FROM THE STUDS IN AND EVERYTHING IS BRAND NEW WITH...
2022 Eastern Pkwy #2
Louisville, KY 40204
2022 Eastern Pkwy #2 Louisville, KY 40204
1 of 33
$449,000
Subdivision: N/A
BEDS
3
BATHS
3
SQ.FT.
2,354
BUILT
1920
ON SITE
4Days
MLS
1527054
FOR SALE/LEASE OPTION/OWNER FINANCING GORGEOUS RENOVATION TO THE STUDS..WITHIN STEPS OF BARDSTOWN ROAD AND CHEROKEE PARK - THIS BEAUTIFUL HOME HAS 3 BEDROOMS, 3 FULL BATHS. LIVING ROOM W/FIREPLACE,...
1717 Bonnycastle Ave
Louisville, KY 40205
1717 Bonnycastle Ave Louisville, KY 40205
1 of 23
$254,900
Subdivision: Deer Park
BEDS
2
BATHS
1
SQ.FT.
960
BUILT
1965
ON SITE
4Days
MLS
1527060
Sophisticated single story home in highly desirable, walkable Highlands Bonnycastle neighborhood. Fully renovated to feature fabulous upgrades throughout. Tastefully redone, this home will welcome...
2112 Kenilworth Pl
Louisville, KY 40205
2112 Kenilworth Pl Louisville, KY 40205
1 of 38
$389,000
Subdivision: Highlands
BEDS
3
BATHS
2
SQ.FT.
2,693
BUILT
1912
ON SITE
4Days
MLS
1527073
Craftsman style charmer! Located at the end of the street-''Cherokee Park'' side with no through traffic. Some entrancing features are high ceilings on main level, hardwood floors on first and second...

Questions?