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 January 22, 2019
95
Listed
79
Avg. DOM
$183.46
Avg. $ / Sq.Ft.
$345,000
Med. List Price
95 Properties Found. Showing 1-12
Sort By:
2140 Bonnycastle Ave
Louisville, KY 40205
2140 Bonnycastle Ave Louisville, KY 40205
1 of 13
$155,000
Subdivision: The Commodore
BEDS
1
BATHS
1
SQ.FT.
811
BUILT
1928
ON SITE
2Days
MLS
1523179
Located on the 10th floor in the historic Commodore with beautiful views of the park and the city. Charming unit with newer period chandeliers in every room, newer windows, hardwood floors and brick...
1924 Stevens Ave
Louisville, KY 40205
1924 Stevens Ave Louisville, KY 40205
1 of 25
$249,000
Subdivision: Highlands
BEDS
3
BATHS
1
SQ.FT.
1,071
BUILT
1905
ON SITE
4Days
MLS
1523114
Steps away from restaurants, shops and all the attractions of Bardstown Road, this updated Highlands home can be yours today. The spacious living room that greets you features high ceilings, crown...
1834 Deer Park Ave
Louisville, KY 40205
1834 Deer Park Ave Louisville, KY 40205
1 of 17
$259,000
Subdivision: Highlands
BEDS
3
BATHS
2
SQ.FT.
1,744
BUILT
1910
ON SITE
5Days
MLS
1523071
Don't miss out on this opportunity! Whether you are a first time home buyer, investor looking for an additional rental property or just want to be in an updated home with an open floor plan in the...
2008 Grasmere Dr
Louisville, KY 40205
2008 Grasmere Dr Louisville, KY 40205
1 of 47
$414,000
Subdivision: Kenilworth
BEDS
4
BATHS
3
SQ.FT.
2,496
BUILT
1920
ON SITE
6Days
MLS
1522897
Seller says to Bring an Offer!! Here's your chance to own a timeless Craftsman home in a very sought after location in the Highlands! Over $60,000 in upgrades over the past 18 months with...
1724 Bonnycastle Ave
Louisville, KY 40205
1724 Bonnycastle Ave Louisville, KY 40205
1 of 37
$309,900 ( $15,000 )
Subdivision: Highlands
BEDS
2
BATHS
4
SQ.FT.
1,848
BUILT
1915
ON SITE
6Days
MLS
1522902
Welcome to this beautifully updated bungalow in the perfect Highlands location! This 2-4 bedroom home features refinished original hardwood floors, tall ceilings, and modern, fresh paint throughout....
2507 Cherokee Pkwy
Louisville, KY 40204
2507 Cherokee Pkwy Louisville, KY 40204
1 of 43
$750,000
Subdivision: Cherokee Triangle
BEDS
4
BATHS
4
SQ.FT.
3,936
BUILT
1906
ON SITE
6Days
MLS
1522912
First showings Saturday January 19 by appointment. Wonderful four bedroom brick home with sweeping, tree-top views of Cherokee Park. Tall ceilings, gorgeous hardwood floors and beautiful millwork...
2304 Woodbourne Ave
Louisville, KY 40205
2304 Woodbourne Ave Louisville, KY 40205
1 of 24
$165,000
Subdivision: Woodbourne
BEDS
1
BATHS
1
SQ.FT.
811
BUILT
1901
ON SITE
9Days
MLS
1522629
If you are looking for the PERFECT most METICULOUS condo in the Highlands, this one may be it! FHA approved, proximity CHEROKEE PARK, GARAGE, and all the ORIGINAL LOVELY CHARM with warm and cozy...
1715 Trevilian Way
Louisville, KY 40205
1715 Trevilian Way Louisville, KY 40205
1 of 53
$296,900
Subdivision: Highlands
BEDS
3
BATHS
2
SQ.FT.
1,400
BUILT
1940
ON SITE
9Days
MLS
1522696
Charming cape cod! This cozy house features living room with fireplace, big dining room, first floor guest room and bath, updated kitchen with granite countertops, stainless appliances and tile...
2217 Dearing Ct
Louisville, KY 40204
Open House
2217 Dearing Ct Louisville, KY 40204
1 of 41
$449,900
Subdivision: Cherokee Triangle
BEDS
3
BATHS
3
SQ.FT.
2,573
BUILT
1892
ON SITE
10Days
MLS
1522583
Open Sun Jan 27th--Cherokee Triangle beauty, meticulously maintained, well loved and ready for the next caretaker! Amazing character abounds from the minute you approach with the intricate brick...
1812 Shady Ln
Louisville, KY 40205
Under Contract
1812 Shady Ln Louisville, KY 40205
1 of 38
$249,900
Subdivision: Highlands
BEDS
3
BATHS
2
SQ.FT.
1,303
BUILT
1905
ON SITE
12Days
MLS
1522459
Charming Highlands home with spacious rooms, tall ceilings, and plenty of windows that allow natural light to flow throughout the home! This home features all of the character you would expect in...
1638 Cowling Ave
Louisville, KY 40205
1638 Cowling Ave Louisville, KY 40205
1 of 22
$298,000
Subdivision: Greystone
BEDS
1
BATHS
1
SQ.FT.
660
BUILT
1915
ON SITE
12Days
MLS
1522524
Every once in a while a very unique property comes along, if you are looking for one of a kind Parkside Property in the Highlands look no further. Convenience of condo living in this stand alone...
927 Cherokee Rd
Louisville, KY 40204
927 Cherokee Rd Louisville, KY 40204
1 of 35
$250,000
Subdivision: Highlands
BEDS
2
BATHS
2
SQ.FT.
1,176
BUILT
2010
ON SITE
12Days
MLS
1522539
Highlands FIRST FLOOR CONDO ~~ Two Bedrooms, Two Full Baths ** Walk to Restaurants, Entertainment and Festivals ** Open Concept Floor Plan ** 14' Ceilings ** Beautiful Kitchen with Granite and...

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