Highlands Real Estate

Highlands Real Estate

Welcome to Highlands, a captivating subdivision nestled in the heart of Kentucky, where charm and community spirit come together to create an idyllic living experience. This vibrant neighborhood is renowned for its picturesque tree-lined streets, friendly neighbors, and a strong sense of belonging that makes it a perfect place to call home.

Highlands offers a diverse selection of beautifully designed homes, ranging from quaint cottages to modern family residences, catering to various lifestyles and preferences. Each property is thoughtfully situated to maximize privacy while fostering a strong community atmosphere. Residents enjoy spacious yards, well-maintained parks, and recreational facilities that encourage outdoor activities and family gatherings.

One of the standout features of Highlands is its proximity to a myriad of amenities. Just a short drive away, you'll find an array of shopping centers, gourmet restaurants, and local boutiques that add convenience to daily life. The subdivision is also served by highly-rated schools, making it an ideal choice for families seeking quality education for their children.

Nature enthusiasts will appreciate the nearby parks and scenic trails, perfect for hiking, biking, or simply soaking in the natural beauty of Kentucky. The community hosts regular events and gatherings, fostering connections among neighbors and creating lasting friendships.

Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Highlands is a welcoming enclave that provides not just a house, but a true sense of home. Discover the charm and warmth of Highlands today—your perfect Kentucky retreat awaits!

Newest Listings in Highlands

1040 Hudson Ave, Lexington
$230,000
3 Beds ⋅ 1 Baths ⋅ 26027204 MLS
Enjoy comfortable living in this inviting 3-bedroom, 1-bath brick ranch. The home features a living room, a separate family room, and a kitchen with a convenient bar and newer appliances. Plenty of space to relax and gather. separate utility room/cellar lower level . Step outside to a cozy covered front porch or for more privacy step out back to a covered patio. Parking and projects are a breeze with an attached one-car garage plus a detached 24' x 24' two-car garage with 10-foot ceilings and a separate driveway. Conveniently located near parks, restaurants, and shopping, this home offers a great blend of comfort, storage, and location. Situated on a cute, fenced lot with 8X10 storage shed. Property being sold "AS IS" "WHERE IS" with no warranties expressed or implied. Inspections welcome.

1040 Hudson Ave, Lexington
1919 Deerwood Ave, Louisville
$325,000
3 Beds ⋅ 2 Baths ⋅ 1726735 MLS
Location, size, and potential! This Highlands classic has high ceilings, lovely wood trim, replacement windows, and the perfect covered front porch for enjoying a cup of coffee on the swing! Main floor offers a formal living room with the first of 2 original tile fireplaces, formal dining room, and a "library" (formerly used as a bedroom), as well as a full bathroom and the eat-in kitchen. Upstairs is a full bath with dual sink vanity, guest bedroom with exposed brick, guest bedroom with vaulted ceiling, and a 3rd walkthrough/office. The fenced back yard and covered back patio are waiting for the next owner to string some lights and enjoy the evening! Alley access to newer 1 car garage. Due to layout, there is potential to create a duplex with this property, if zoning permits. Seller welcomes inspections, but prefers to sell as is.

1919 Deerwood Ave, Louisville
1421 Morton Ave, Louisville
$320,000
3 Beds ⋅ 2 Baths ⋅ 1730148 MLS
Opportunity awaits in the Original Highlands! This three bedroom, two bath Queen Anne Victorian features characteristic millwork, large rooms with high ceilings, original pine floors, a tiled staircase with hand carved newel post, four unique, decorative fireplaces, built-in shelving, as well as a spacious kitchen with newer appliances and new tile floors. This home is chock full of charm with loads of potential! While some work and cosmetic upgrades may be wanted, many updates have been completed in recent years. To increase the homes energy efficiency, the HVAC was replaced (2023), spray foam insulation added (2023), water heater replaced (2023), and the chimneys were removed, capped and covered(2022). There are double and triple paned windows installed throughout the home. From the front garden, you are welcomed by a large covered porch and there is a screened porch with covered deck at the back of the home to provide a wonderful place to relax. Additionally, off-street parking can be created on the alley. Priced to sell - schedule your private showing today!

1421 Morton Ave, Louisville
1835 Deer Park Ave, Louisville
$325,000
2 Beds ⋅ 2 Baths ⋅ 1730119 MLS
Charming 2 bedroom, 2 full bathroom camelback-style home, meticulously maintained and full of character. The generously sized living room is bathed in natural light from an abundance of windows, creating a warm, airy atmosphere. The well-appointed kitchen features striking butcher block countertops, adding a touch of rustic elegance. Upstairs, a serene master suite offers a private retreat all its own. Ideally situated in the heart of the Highlands, this home puts you within walking distance of beloved local bars and restaurants. Schedule your private showing today!

1835 Deer Park Ave, Louisville
152 Old Post Rd, Paris
$325,000
3 Beds ⋅ 3 Baths ⋅ 26026467 MLS

152 Old Post Rd, Paris
1009 Hudson Ave, Lexington
$209,900
3 Beds ⋅ 1 Baths ⋅ 26025992 MLS
Updated 3 bedroom 1 bathroom ranch home in the Highlands subdivision. This one level home has been thoroughly remodeled including: new windows, new HVAC/gas furnace, new water heater, new electrical panel, new kitchen/appliances, new flooring, new light fixtures... Nothing left to do but moving in!

1009 Hudson Ave, Lexington
2126 Village Dr Unit 5, Louisville
$240,000
2 Beds ⋅ 1 Baths ⋅ 1729481 MLS
Welcome to this charming 2-bedroom, 1-bath condo located in the desirable Highlands neighborhood at 2126 Village Dr. Hardwood flooring flows through the main living areas, complemented by large windows that fill the space with natural light. The inviting living room features a cozy fireplace, perfect for relaxing or entertaining. The kitchen features stainless appliances and a kitchen peninsula, great for additional counter space or dining. The condo offers the convenience of in-unit laundry and two spacious bedrooms with ample room for comfort and flexibility. The unit comes with a parking space in the lower-level garage. Pets and rentals are allowed with restrictions. Ideally situated near neighborhood amenities, dining, and outdoor recreation with its close proximity to Cherokee Park, this condo blends comfort, style, and location. Schedule a private showing today.

2126 Village Dr Unit 5, Louisville
1818 Woodbourne Ave, Louisville
$469,900
3 Beds ⋅ 2 Baths ⋅ 1729358 MLS
Just around the corner from Douglass Loop, this darling home captures the best of Highlands living. Enjoy morning coffee nearby, spend a Saturday at the Douglass Loop Farmers Market, hear the church bells in the distance, and enjoy the convenience of nearby Lakeside Swim Club. Lovingly cared for by the same owners for over 20 years, the home welcomes you with a fabulous front porch, charming entry, beautiful hardwood floors, and a new roof. A lovely dining area sits beside the elegant staircase, while the updated kitchen is an unexpected Highlands surprise with its expansive layout, vaulted ceiling, gorgeous wood beams, and three windows overlooking the backyard. There is even plenty of space for everyday dining. Two bedrooms and a full bath are located on the first floor. Upstairs, the spacious primary suite features a vaulted ceiling, a full bath, a generous walk-in closet, and plenty of room for an office or sitting area. Separate HVAC systems and air handlers serve each floor, adding comfort and flexibility throughout the home. The partially finished basement adds even more usable living space with another family room and office, while the large unfinished area and crawlspace provide excellent storage. Outside, a large deck spans the back of the home and overlooks a spacious backyard with plenty of room for entertaining and recreation. With classic Highlands charm, a new roof, thoughtful updates, and a fantastic location near Douglass Loop, this is a home that offers both character and everyday convenience.

1818 Woodbourne Ave, Louisville
1409 Hepburn Ave, Louisville
$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
2126 Village Dr Unit Unit 3, Louisville
$239,900
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
1821 Stevens Ave, Louisville
$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
2219 Weber Ave, Louisville
$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
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