Highlands Real Estate

Highlands Real Estate

Welcome to Highlands, a vibrant and charming subdivision nestled in the heart of Kentucky! This picturesque community is known for its unique blend of historic charm and modern convenience, making it an ideal place for families, young professionals, and retirees alike.

Highlands is characterized by its tree-lined streets, beautifully manicured lawns, and a variety of architectural styles that reflect the area's rich history. The neighborhood boasts an inviting atmosphere, where neighbors become friends and community spirit thrives. Residents enjoy access to a wealth of amenities, including parks, walking trails, and recreational facilities that promote an active and healthy lifestyle.

One of the standout features of Highlands is its proximity to a diverse array of shopping, dining, and entertainment options. Just a short drive away, you'll find local boutiques, trendy cafes, and popular restaurants that cater to all tastes. For those who appreciate the arts, the area is also home to galleries and theaters, providing endless opportunities to immerse yourself in Kentucky's vibrant culture.

Families will appreciate the highly-rated schools in the vicinity, ensuring that children receive a quality education in a nurturing environment. With its strong sense of community, Highlands is a place where lifelong friendships are forged and memories are made.

Whether you’re looking to buy your first home, downsize, or invest in a rental property, Highlands offers a range of real estate options to suit your needs. Discover the charm of Highlands and experience the perfect blend of comfort, convenience, and community in beautiful Kentucky!

Newest Listings in Highlands

$950,000
6 Beds ⋅ 6 Baths ⋅ 1728487 MLS
The amazing renovation is complete on this incredible brick painted lady in the Original Highlands. A brand new 2 bedroom, 2 bathroom 1000+ sf carriage house sits atop a 3-car garage with plenty of room for the owner and tenant to park. Separate meters allow tenants to pay their own electric and the rent will make a huge dent in a monthly mortgage payment. The main house is simply astounding. Enter this picturesque home through the large foyer. On your right is a grand living room or parlor that can be closed off with beautiful doors to make a private guest space or office. You will next notice the incredible woodwork indicative of turn of the century homes. A grand stair case and full bathroom tucked underneath is perfect for guests. The kitchen and great room area are open to each other and totally re-imagined with plenty of space for your family and guests. High-end tall cabinetry, quartz countertops and top of the line appliances are awaiting your cooking adventures. A sun-drenched breakfast room looks out onto your well landscaped rear yard. The second floor has an incredible and large primary suite with two huge closets, a modern fireplace and new bathroom with two vanities, beautiful tile shower and tasteful fixtures. There is also a small martini deck off the primary bedroom. Additionally on this floor are two other large bedrooms sharing a charming Jack-and-Jill bathroom. One of the bedrooms has its own private screened porch overlooking the backyard. There is room for a stack laundry on this floor. The third floor has a wonderful bedroom, office area and full bathroom. The carriage house is well-designed with a very livable open floorplan and a private deck. It can be configured to offer tenants one of the garage spaces while keeping the other two private for the main house. Updates and renovations include 4 HVAC systems, updated water heaters, new kitchen, new bathrooms, refinished antique hardwood and new hardwood flooring, newly constructed carriage house, etc. With 3700 sf of living space in the main house and over 1000 sf in the new carriage house, this property checks all the boxes.

1409 Hepburn Ave, Louisville

Listing courtesy of THINK Real Estate LLC.

$245,000
2 Beds ⋅ 1 Baths ⋅ 1728348 MLS
Welcome to 2126 Village Drive, Unit 3, tucked away in a charming courtyard setting in the heart of the Highlands. This spacious two-bedroom condo offers the character and warmth you expect from one of Louisville's most desirable neighborhoods, along with the convenience of low-maintenance living. Beautiful hardwood floors flow throughout much of the home, while abundant windows provide great natural light. The inviting living room features a classic fireplace and opens to a generous dining area and kitchen with white cabinetry, granite countertops, stainless appliances and breakfast-bar seating. Both bedrooms offer plenty of space, including a primary bedroom with excellent closet storage. Additional highlights include in-unit laundry, a large bath, ample storage and dedicated covered parking. Outside, mature landscaping, winding sidewalks and a peaceful central courtyard create a setting that feels tucked away while still being close to everything that makes the Highlands such a sought-after place to live. A wonderful opportunity to enjoy classic Louisville character, comfortable living and an outstanding Highlands location.

2126 Village Dr Unit Unit 3, Louisville

Listing courtesy of EXP Realty LLC.

$439,900
3 Beds ⋅ 2 Baths ⋅ 1727152 MLS
Beautiful Highlands home full of charm, character, and flexible living space! This 3 bedroom, 2 full and 1 half bath home offers the perfect blend of historic detail and everyday functionality. Gorgeous woodwork, inviting living and entertaining spaces, and abundant storage can be found throughout. The first floor includes a bedroom currently used as an office, offering great flexibility depending on your needs. The spacious kitchen opens to a lovely four season sunroom, creating the perfect space to relax or entertain. Upstairs, you'll find two bedrooms with a half bath. This layout can function as two bedrooms, with one being a walk through bedroom, or as a primary bedroom with an adjoining sitting room or office. The basement adds even more versatility with a nicely sized den currently being used as a guest room/work out space, plus a full bath, workshop area, laundry, and an oversized closet. Additional peace of mind comes with the HVAC system, which was replaced in 2024. Enjoy peaceful mornings on the welcoming front porch or dine outdoors on the backyard deck overlooking the beautifully landscaped yard. A one car garage plus an additional one space carport accessible from the alley complete this fabulous Highlands property.

1821 Stevens Ave, Louisville

Listing courtesy of RE/MAX Premier Properties.

$550,000
3 Beds ⋅ 3 Baths ⋅ 1726748 MLS
This stunning bungalow in the Highlands offers the perfect blend of modern comfort and classic charm. The spacious, open layout features two primary suites-one conveniently located on the first floor, and one upstairs for added privacy. The main level offers a bright living room featuring charming built-ins and a cozy fireplace, flowing seamlessly into the dining area and chef's kitchen. The Kitchen is absolutely wonderful, complete with a large island, granite countertops, and a generous pantry. The first-floor primary suite includes a walk-in closet and private en suite bathroom offering convenience & relaxation. A large laundry room and a half bath is also located on the main level. Upstairs, you'll find a loft area, a second primary bedroom suite with two closets a luxurious en suite bathroom that includes a standing shower and double vanity, along with a third bedroom. The walk-out finished basement offers an open layout with family room, a wine room, and a cozy media room. Enjoy the outdoors with a covered front and back porches overlooking a lovely yard. The two-car detached garage adds extra storage, an EV charging port and alley parking space. This home offers style, charm and functionality in a beautiful and convenient Highland setting.

2219 Weber Ave, Louisville

Listing courtesy of Semonin Realtors.

$200,000
2 Beds ⋅ 2 Baths ⋅ 1726581 MLS
Enjoy the energy of the Highlands with the ease of low-maintenance condo living! Tucked into one of Louisville's most walkable neighborhoods, this charming second-floor unit puts favorite restaurants, coffee shops, boutiques and entertainment just outside your door. Inside, hardwood flooring runs throughout both levels, adding warmth and character to the open main living space. A flexible bonus room on the main level is perfect for a home office, bedroom (no closet), den or guest space, while the private screened porch offers a peaceful spot to relax or enjoy your morning coffee. Upstairs, the spacious primary bedroom features hardwood flooring and a convenient half bath. Full of character and ideally located, this condo is a great opportunity to enjoy everything the Highlands lifestyle ha s to offer.

2008 Murray Ave Unit 4, Louisville

Listing courtesy of Nest Realty.

$320,000
2 Beds ⋅ 3 Baths ⋅ 1726386 MLS
GREAT New Price...Check out this move in modern condo in the Highlands Cherokee Triangle! This condo has a modern feel with the tall ceilings, hardwood floors, granite counter tops, and the GE Profile Stainless Appliance Kitchen. The main level is a family room, kitchen, dining room, and a half bathroom. Upstairs are 2 bedrooms, each with its own private bathroom. Laundry is on the same floor as the bedrooms for convenience. This is the perfect location if you love the Highlands, Nulu, or if you go downtown. Assigned parking spot #6 is for this unit.

927 Cherokee Rd Unit 6, Louisville

Listing courtesy of Semonin Realtors.

$275,000
2 Beds ⋅ 1 Baths ⋅ 1726164 MLS
Openhouse Sunday 9/13 2pm-4pm. Nestled in the heart of Louisville's vibrant Highlands neighborhood, this charming home gives easy access to local dining, shops, and parks. Warm hardwood floors flow through the main living areas, leading to a beautifully remodeled kitchen (2021) featuring sleek GE appliances (stove is gas). Updates include a new roof (July 2026), furnace and air (~6 yrs), and water heater (~4 yrs). For added convenience washer/dryer hookups are on the 2nd floor and in the basement; both sets of washers and dryers stay with the home! The unfinished basement features interior/exterior access and exceptional storage potential. Rear alley access makes adding an off-street parking pad simple. The fenced backyard is perfect for entertaining.

1416 Rufer Ave, Louisville

Listing courtesy of Schuler Bauer Real Estate Services ERA Powered.

$480,000
4 Beds ⋅ 3 Baths ⋅ 1725750 MLS
Luxury, convenience, and thoughtful design ALL in this completely renovated home, featuring a stunning FIRST FLOOR PRIMARY and an exceptional custom kitchen. The spacious primary suite offers an oversized closet with built-ins, spa-inspired bathroom with beautiful extra large shower, and private water closet, creating a true sanctuary on the main level. At the heart of the home, the custom chef's kitchen is designed to impress, featuring a striking quartz waterfall island, custom cabinetry, updated appliances (hardly used), and beautifully integrated and motion activated accent lighting. The open living and dining spaces provide an inviting space for both everyday living and entertaining. Original oak hardwood floors have been meticulously refinished throughout, with new matching hardwoods added on the main level for a seamless, elevated finish. All bathrooms have been completely remodeled with custom vanities, new plumbing, incredible tile work, and updated fixtures. The renovation goes beyond cosmetic updates, with new drywall, electrical, insulation, lighting, outlets, switches, plumbing improvements, custom closet systems, and motorized blinds. The basement offers additional flexible space and features durable epoxy flooring. Every element of this home has been thoughtfully considered to create a sophisticated, move-in-ready residence with high-end finishes and modern functionality in an incredible Highlands location. Large, fully fenced backyard provides opportunities to entertain outdoors - Large carport for covered parking. A rare opportunity to enjoy a truly comprehensive renovation where every detail matters. Schedule your private showing for this move in ready home today!

1608 Dunbarton Wynde, Louisville

Listing courtesy of Rainey Allen Shaw East.

$825,000
4 Beds ⋅ 3 Baths ⋅ 1725708 MLS
This contemporary treehouse in the Louisville Highlands has been lovingly updated and offers 4 bedrooms and 2 full baths on the main level! Designed in 1972 as a local architect's personal family residence and thoughtfully preserved for more than five decades, 1513 Thackeray Drive offers an uncommon combination of midcentury character, natural beauty and enduring craftsmanship. Tucked beneath a mature tree canopy across from Joe Creason Park, the home feels private and secluded while remaining closely connected to the culture, conveniences, and the energy of the area.

1513 Thackeray Dr, Louisville

Listing courtesy of Semonin Realtors.

$459,950
4 Beds ⋅ 2 Baths ⋅ 1724194 MLS
Historic Highlands charm meets modern versatility in this beautifully restored turn-of-the-century home, ideally located moments from some of Louisville's best dining, shopping, parks, and entertainment. Situated on a prominent corner lot, this impressive two-and-a-half-story home features a virtually maintenance-free exterior framed by a beautiful creek-stone retaining wall. Inside, refinished heart pine floors and custom six-panel doors crafted to complement the home's original style preserve its timeless character while offering the comfort and functionality today's buyers are looking for. The updated kitchen is equipped with a six-burner stainless steel gas range, matching refrigerator, and matching dishwasher, making it equally suited for everyday living and entertaining. The spacious primary bedroom includes two separate closets and a comfortable seating area. The home currently offers three bedrooms and two full bathrooms, along with a highly flexible floor plan with easy potential for a four-bedroom, three-bath layout. The first-floor workout room, previously used as a fourth bedroom, could easily transition back into a bedroom, home office, study, or guest space. Even more opportunity awaits on the third floor, where plumbing, electrical, and ductwork are already in place for a future bathroom. This would allow the next owner to create a full bathroom on every level while also incorporating space for a stackable washer and dryer. Outside, the 1.5-car garage features a brand-new door, adding both convenience and functionality. Located in the heart of the Highlands and moments from everything the area has to offer, this home also presents strong investment potential. Its desirable location, flexible layout, and potential for additional finished living space could make it an excellent long-term rental or short-term rental opportunity, subject to applicable local regulations and approvals. Whether you are searching for a character-filled primary residence, a versatile investment property, or a home with room to grow, this one is ready for its next chapter and waiting for YOU!

1332 Winter Ave, Louisville

Listing courtesy of Segrest Flaherty Realtors LLC.

$339,900
3 Beds ⋅ 1 Baths ⋅ 1723040 MLS
Welcome to 1603 Bonnycastle Ave, Louisville, KY 40205 in the Highlands. This 3-Car Garage is Steps from Cherokee Park in Bonnycastle. On a tree-lined stretch of Bonnycastle Ave, in the heart of the historic Bonnycastle Neighborhood, this 1935 brick two-story sits on a 0.12-acre lot with something few Highlands addresses can offer: a detached 3-car garage with real room to grow. Inside, a formal living room opens around the home's original fireplace, a striking architectural focal point that is currently decorative and not in working order. The formal dining room connects to an eat-in kitchen with a butler's pantry, a layout built for the way homes from this era were meant to entertain. Hardwood floors run throughout the main level. Upstairs holds 3 bedrooms and 1 full bath, each bedroom bright with second-floor natural light. Downstairs, an 850 square foot unfinished basement adds storage, workshop space, or a future finished square footage project. Out back, a deck steps down to a large cement patio and fenced yard. Then there is the garage. At 750 square feet and built for 3 cars, it is sized for far more than parking. Home office. Art studio. Guest retreat. It is the kind of flex space Highlands buyers keep asking for and rarely find. The garage door will be getting a fresh coat of paint. Bonnycastle Avenue runs between Bardstown Road and Cherokee Road, putting Cherokee Park's trails and the restaurants, coffee shops, and boutiques of Bardstown Road within easy reach. Photos do not capture how this one lives. Schedule your private showing today.

1603 Bonnycastle Ave, Louisville

Listing courtesy of simpler.realestate.

$316,900
4 Beds ⋅ 2 Baths ⋅ 1722992 MLS
Welcome to 2417 Wallace Avenue—a rare opportunity to own a home in the heart of Louisville's sought-after Historic Highlands. Offered for the first time in over 40 years, this charming home features original hardwood floors, classic character, a large level lot, and a covered front porch. The roof was replaced just two years ago, making this a home that primarily needs updating rather than extensive repairs. Bring your vision and make it your own while enjoying a premier Louisville location just minutes from Bardstown Road, restaurants, shopping, parks, and entertainment. A great opportunity to create value in one of Louisville's most desirable neighborhoods!

2417 Wallace Ave, Louisville

Listing courtesy of Premier Homes Realty.

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