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 29, 2022
32
Listed
25
Avg. DOM
$227.39
Avg. $ / Sq.Ft.
$494,000
Med. List Price
32 Properties
Page 1 of 3
4
Beds
2
Baths
1,776
Sq.Ft.
1900
Year Built
3
Days on Site
1613355
MLS
Check out this Beautiful property centrally located in the heart of Cherokee Triangle. Walking distance to the popular restaurants and shopping on Bardstown Rd. Could make a great Airbnb! Book your...
Open 5/29
2060 Douglass Blvd Louisville, KY 40205
$895,000
Neighborhood: Highlands
5
Beds
5
Baths
4,626
Sq.Ft.
1925
Year Built
4
Days on Site
1613206
MLS
This handsome brick Highlands home is located on one of the most desirable and prestigious park side streets in the heart of the Highlands, where one can embrace the Highlands lifestyle with easy...
Open 5/29
1823 Gresham Rd Louisville, KY 40205
$335,000
Neighborhood: Tecomah
2
Beds
1F11/2
Baths
1,703
Sq.Ft.
1938
Year Built
4
Days on Site
1613210
MLS
No description available...
Open 5/29
2237 Saratoga Dr Louisville, KY 40205
$405,000
Neighborhood: Aberdeen
4
Beds
1F11/2
Baths
2,240
Sq.Ft.
1926
Year Built
5
Days on Site
1613056
MLS
Stunning Highlands Gem located on quiet Saratoga Drive just blocks from Bardstown Road shopping & dining, Bellarmine University, and Lakeside. This picture-perfect stone Tudor has been well-loved...
$399,000
Neighborhood: Highlands
3
Beds
2
Baths
2,019
Sq.Ft.
1912
Year Built
5
Days on Site
1613058
MLS
Gorgeous Bungalow in desirable Highlands! Close to Tyler Park & Bardstown Road. Inviting front porch welcomes you into the formal living room with fireplace, extensive mill work & gleaming hardwood...
5
Beds
4
Baths
3,370
Sq.Ft.
1908
Year Built
5
Days on Site
1613069
MLS
Home in the heart of the highlands for sale. The property includes 3 updated units. Family and guests love the location because it is a short walk to many local restaurants and shops. This home has...
4
Beds
2
Baths
2,740
Sq.Ft.
1923
Year Built
5
Days on Site
1613089
MLS
If you are looking for a beautiful Highlands house full of character, you have found your dream home!!! This home has all of the beautiful features you love... built-in shelving, french doors, high...
2
Beds
2F11/2
Baths
2,800
Sq.Ft.
1982
Year Built
6
Days on Site
1612992
MLS
Welcome home to this beautiful condo located in the prestigious Cherokee Triangle neighborhood. This home has it all: in-ground pool, in-unit elevator, 2 car attached tandem garage, 2 primary suites,...
$465,000
Neighborhood: Cherokee Triangle
4
Beds
2F11/2
Baths
3,043
Sq.Ft.
1905
Year Built
6
Days on Site
1612476
MLS
Cherokee Triangle home with 4 bedrooms and 2.5 baths. Fireplace in the living room, beautiful bay window in the dining room, eat in kitchen and family room all on the first floor. The large second...
$679,000
Neighborhood: Highlands
3
Beds
2F11/2
Baths
2,800
Sq.Ft.
1903
Year Built
6
Days on Site
1613044
MLS
Welcome to 1628 Rosewood Avenue, a fully restored and renovated 3 bedroom, 2.5 bath home in the Highlands. This 2800 sq ft home features a hard-to-find carriage house with an additional 600 sq ft of...
$575,000
Neighborhood: Cherokee Triangle
4
Beds
2F21/2
Baths
2,678
Sq.Ft.
1894
Year Built
7
Days on Site
1612922
MLS
Updated style and Victorian charm are united at 2210 Longest Avenue. This gorgeous Victorian is nestled in the heart of the Cherokee Triangle, steps away from Cherokee Park and Bardstown Road. This...
$459,000
Neighborhood: Highlands
4
Beds
3
Baths
2,864
Sq.Ft.
1925
Year Built
10
Days on Site
1612800
MLS
COMPLETELY remodeled Highlands home. This beautiful 4BR, 3BA home comes with 3165sf of updated space and has top of the line gorgeous features including a first floor open floor plan, tall ceilings,...

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