Highland Real Estate

Highland Real Estate

Welcome to Highland, a charming and vibrant subdivision nestled in the heart of Louisville, Kentucky. Known for its rich history and eclectic character, Highland is a community that beautifully blends the old with the new, offering residents a unique living experience that is both inviting and invigorating.

Highland is renowned for its tree-lined streets, historic homes, and an array of local boutiques, cafes, and restaurants that create a lively atmosphere. As you stroll through the neighborhood, you’ll find an impressive mix of architectural styles, from classic Victorian mansions to modern townhomes, each adding to the area's distinctive charm. The sense of community is palpable, with friendly neighbors who take pride in their homes and surroundings.

One of Highland's standout features is its proximity to some of Louisville's best parks and recreational areas. Residents can enjoy a leisurely afternoon at nearby Cherokee Park, where scenic trails and lush landscapes invite outdoor enthusiasts to explore nature at its finest. Additionally, the area is known for its vibrant arts scene, with galleries and theaters that showcase local talent and creativity.

Families will appreciate the excellent schools and educational opportunities available in the area, making Highland an ideal place for raising children. With its convenient access to major highways and public transportation, commuting to downtown Louisville or other parts of the city is a breeze.

Whether you’re looking for a cozy home, a lively community, or a place to enjoy the best of Louisville living, Highland is a delightful choice that promises a fulfilling lifestyle in a picturesque setting. Come discover the charm of Highland—your new home awaits!

Newest Listings in Highland

$325,000
3 Beds ⋅ 2 Baths ⋅ 1726354 MLS
Freshly painted throughout and priced $10,000 below recent appraisal! Nestled in one of Louisville's most sought-after Highlands neighborhoods, this charming bungalow is being offered for just the second time in its history, blending timeless character with thoughtful updates. A welcoming covered front porch sets the tone, while the screened rear porch and adjoining deck provide the perfect place to relax and overlook the partially fenced backyard. Inside, you'll find original refinished hardwood floors and rich mahogany trim that showcase classic Craftsman-inspired character throughout the spacious living room, dining room, and first-floor bedrooms. The kitchen features tile flooring and convenient access to the upper level. The full bath retains its vintage appeal with original penny tile floors, subway tile surround, and an updated tiled shower. The entire second floor is dedicated to a private primary suite, complete with a door at the foot of the staircase, soaring vaulted ceilings, a generous bedroom, and an en suite bath. The unfinished lower level offers laundry, abundant storage, and outstanding potential for future finished living space. Just minutes from Cherokee Park, Bardstown Road, local dining, coffee shops, and neighborhood favorites, this home offers the perfect blend of historic charm, modern comfort, and an unbeatable Highlands lifestyle.

1844 Roanoke Ave, Louisville
$425,000
4 Beds ⋅ 2 Baths ⋅ 1724975 MLS
Discover an exceptional opportunity in the highly sought-after 40205 zip code! This charming 4-bedroom, 2-bath home in the DeerPark neighborhood offers unmatched value—there's simply no other listing like it at this price. Featuring original windows, beautiful hardwood floors, and classic architectural details that capture the true Highlands spirit, this home also includes a garage and a fully fenced backyard for your convenience and privacy. Enjoy the vibrant local lifestyle with favorites like Kern's Korner Lakeside Swim Club, and Douglass Loop just minutes away. Indulge in Heine Brothers coffee, Graeter's ice cream, and Havana Rumba's flavors, or unwind at Shenanigan's. Immediate possession is available and we are ready to make this your new home.

1753 Shady Ln, Louisville
$300,000
3 Beds ⋅ 2 Baths ⋅ 1724814 MLS
Welcome to 1956 Richmond Drive. A beautifully maintained bungalow in the heart of the Highlands. Close to local restaurants, coffee shops, boutiques, the farmers market, and neighborhood other favorites. Behind the mature landscaping and charming façade is a Highlands bungalow that has been thoughtfully cared for while preserving the details that make homes from this era so special. Original hardwood floors, rich wood trim, stained glass windows, arched openings, and solid wood doors create warmth that simply can't be replicated in new construction. The screened front porch quickly becomes a favorite place to spend time. With its original checkerboard tile floor, skylights, and views of the surrounding trees, it feels less like a porch and more like an extension of the home. A place for morning coffee, rainy afternoons, or evenings spent enjoying the neighborhood. Inside, the main living spaces flow naturally from the welcoming living room to the generous dining room before opening into a spacious kitchen with abundant cabinetry, stainless steel appliances, and room to grow. Whether you love the kitchen just as it is or dream of creating your own custom space over time, the layout offers endless possibilities. The first floor features a spacious primary bedroom with direct access to a full bath, while upstairs offers two additional bedrooms, a second full bath, and flexible space that can easily adapt to your needs. The sellers even incorporated a removable section of the stair railing to make moving large furniture upstairs more accessible. Outside, the large deck overlooks a private backyard that feels tucked away from the city, while off-street parking for multiple vehicles adds everyday convenience. Beyond its charm, this home has received numerous meaningful improvements that provide peace of mind, including new plumbing throughout most of the home, with the drain lines and the majority of the water supply lines replaced approximately two years ago. Additional updates include an HVAC system that is less than 10 years old, new siding installed in 2024, a new water heater in 2025, and a freshly painted exterior with new gutters completed in 2026. Some homes impress with trends. This one stands out because it's warm, inviting, beautifully maintained, and ready for its next chapter. Schedule your showing today!

1956 Richmond Dr, Louisville
$399,900
2 Beds ⋅ 3 Baths ⋅ 1722733 MLS
Welcome to this beautifully remodeled bungalow in the heart of the Highlands, just a short walk to local restaurants, the farmers market, shopping, and neighborhood favorites. At first glance, you'll find charming curb appeal and a welcoming front porch perfect for enjoying your morning coffee or connecting with neighbors. Inside, boasts a sizeable living room with a fireplace and a thoughtfully renovated open-concept kitchen featuring a large peninsula that flows seamlessly into the dining room. The original hardwood floors were beautifully refinished during the 2017 renovation, which also included the kitchen remodel and the addition of a convenient half bath on the main level. Upstairs, the spacious landing leads to two comfortable bedrooms, a stylishly renovated full bathroom, The finished lower level offers incredible flexibility with space that can serve as a family room, home office, studio, or workout area. A full bathroom and separate entrance from the laundry room provide added convenience and versatility. Outdoor living is just as inviting, with a large deck overlooking a private, fenced backyard. This area is ideal for entertaining, gardening, or relaxing. A detached garage offers additional storage and parking. Major updates provide peace of mind, including new windows, a new exterior A/C condenser, an upgraded electrical panel, basement waterproofing, and professional weatherization, all completed in 2019 prior to the current owners. Combining timeless Highlands character with thoughtful modern updates and an unbeatable walkable location, this move-in-ready home is one you won't want to miss.

1905 Richmond Dr, Louisville
Start Your Search