Highlands Homes for Sale

  • Highlands Introduction
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Highlands Introduction

The Highlands is one of the oldest neighborhoods in Louisville, Kentucky, set atop a flood-resistant ridge back in the Civil War Era. History lovers can still see a number of remaining structures and historic properties, though much of the modern community arose in the 1960s. In fact, many locals consider Bardstown Road, the commercial epicenter of The Highlands, to be the “Haight-Ashbury” of Louisville, our own version of “Greenwich Village,” or a “Little Portland” -- with its interesting collection of mom-and-pop shops. Louisvillians are in love with this part of town because it has “something for everyone” as an affordable place to live, close to everything, and full of diversity. It’s also a 5-15 minute drive from top employers like Ford, GE Appliances, YUM! Brands, and the Norton healthcare complex.

A Tale of Two Highlands…

Lenihan Sotheby's International Realty agents will tell you there are “two distinct Highlands”:

  • The “Original” Highlands (40204 zip code, Irish Hill, Cherokee Triangle, Tyler Park, Deer Park, Bonnie Castle, the Douglas Loop) – which is characterized by a more urban, modern, walkable feel with shops, restaurants, and amenities at the end of these quieter, tree-lined, residential streets.
  • The “Upper” Highlands (40205 zip code, Bardstown Road, just beyond Taylorsville Road, Strathmore Village, Strathmore Manor, Wellington, Kingsley, Lakeside) – which is characterized by a wonderful, 1950s residential, classic “neighborhood” feel where people walk dogs and children ride bikes down the sidewalk, but the houses are more tucked away in a suburban type setting.

The Highlands: An Eclectic, funky blend of people and places.

As Lenihan Sotheby’s International Realty Agent Josh Laughlin points out: “You have the working class, the artists, and the students, living right next door to the doctors, professionals, and executives.”

Bardstown Road is a fantastic corridor that attracts tourists and visitors from all across the city who come here for world-class restaurants, cozy coffee shops, locally owned boutiques, antique stores, microbreweries, entertainment, and nightlife. You’ll find guitar stores, lighting shops, custom t-shirt printing, and vintage furniture stores. Long before the commercial strips developed, residential homes existed in The Highlands, so you’ll notice that many of the businesses have a lot of original character as former homes.

Though the saying around these parts is “Keep Louisville Weird,” you will also find a Wal-Mart, Rite-Aid, CVS, Costco, Kohl’s, and Kroger in the area, so you can pick up all the staples you need.
The Kentucky Derby is an exciting time of year to live in The Highlands. Many high-profile parties take place here, with Churchill Downs just 3.4 miles away.

Restaurants, Restaurants, Restaurants!

If you’re a “foodie” in Louisville, there is no better spot to set down roots! You’ll be treated to amazing culinary experiences in comfortable environments. It’s hard to pick favorites, but you’ll definitely want to try nearby establishments such as:

  • La Chasse – French and comfort food and craft cocktails
  • Seviche – Latin fare with out-of-this-world chimichurri sauce and mashed potatoes, and superb service
  • El Taco Luchador – Quick Mexican fare
  • Jack Fry’s – Southern fare, a celebrity favorite “see & be seen” establishment, popular for special occasions
  • LouVino – Wine and tapas pairings, incredible cocktails
  • Hammerheads – Gastropub fare like duck fat fries, pulled pork, and brisket, popular among tourists
  • Ward 426 – A renowned Dean Corbett eatery with a fresh, seasonal menu of local and Southern fare
  • Butchertown Grocery – In nearby Butchertown, you’ll find amazing cheese and charcuterie boards in a lounge environment open til 3 a.m.

From Cherokee Triangle, to the 900-block of Baxter Avenue, to Bardstown Road – Highlands residents want for nothing!

Recreation beyond the backyard

City life has its rewards, but sometimes even the hardiest residents need to take a break from the concrete jungle and enjoy the great outdoors. New Yorkers have Central Park, and people living in The Highlands have Cherokee Park – a 409-acre oasis that is ranked among the Top 100 Municipal Parks in the United States and attracts 500,000 visitors a year.

The park features:

  • Walking, biking, and horseback riding trails
  • Lake fishing
  • Sports fields
  • Bird watching
  • Tennis and basketball courts
  • Winter sledding
  • Picnic tables, grills, and shelters
  • Archery ranges
  • Rugby and soccer fields
  • Ultimate Frisbee courses
  • Horseshoe pits
  • Dog parks
  • Playgrounds

Other local sanctuaries for recreation in The Highlands include: Douglas Park, Seneca Park, Tyler Park, and Willow Park.

Quiet residential streets with a diverse house mix and affordable prices.

Despite the exciting commercial strips, you’ll find quiet neighborhood streets with mature trees and relatively low traffic. Generally, homes tend to be less expensive than neighboring St. Matthews and the cost of living is just 1 percent higher than the rest of Louisville, even though there are so many great amenities.  

Most homes in The Highlands were constructed in the late 1800s to 1947. You could settle into a modest post-war shotgun house for as low as $145,000 or you could splurge on a multi-million-dollar executive mansion in Cherokee Triangle. The homes of The Highlands, KY truly run the full gamut in terms of price points and architectural styles, from beautiful Victorian mansions down Cherokee Road and Craftsman Bungalows on Deer Park, to shotgun homes on Breckenridge and multi-million-dollar modern park-side estates in the Douglas Loop. Some of the most expensive estates run in the Millionaire’s Row along Spring Drive.

Hidden architectural gems of these homes may include rectangular floorplans, wainscoting, intricate millwork, tall and narrow windows, master suite fireplaces, butler’s pantries, steep-pitched roofs, and more. Many homes feature German-style architecture brought to Louisville, Kentucky from some of the earliest settlers.  

The housing styles vary just going down many of the blocks as well. Some houses may be in pristine condition, while others are fixer-uppers. There are flipped homes and lovingly maintained, updated homes, too. That’s all part of the excitement and appeal of house hunting here. You never know what you’ll find!

More Information

The Highlands Louisville Podcast Transcript:

In this week's episode of our Perspective's podcast series, brought to you by Louisville's Luxury Real Estate Brokerage, Lenihan's Sotheby's International Realty, I speak with Josh Laughlin, one of our agents in the office, who just so happens to live and do a lot of work in the Highlands. Josh, good to see you.

Josh: Good to see you too Greg. Thanks for having me.

Greg: Well, my pleasure. I'm hoping you can help me out. You seem to be the man around town in the highlands and I'm hoping to learn more about that part of town. Is that all right?

Josh: Great, absolutely.

Greg: When I say to you "The Highlands," or someone says to you, "The Highlands," is that one distinct area? Is that a lot of different areas? What do you think of when someone says, "The Highlands."

Josh: Well, I think that's something that always need clarification because it is a lot of different neighborhoods within the Highlands, so for me, the highlands really is kind of from Irish Hill, Cherokee Triangle, Tyler Park, Deer Park, Bonnycastle, up to the Highlands around the Douglas Loop. You can kind of, part of that is the Original Highlands but to a lot of people, you've got the Original Highlands and then there's the Upper Highlands.

When you get into the Upper Highlands, you're getting out to Strathmore Village and Strathmore Manor, Wellington, Kingsley, the Lakeside area so they're kind of 2 distinct Highlands in my mind, being the Original Highlands and then the Upper Highlands.

Greg: That could also be separate or distinct from the MLS. When someone searches on our website or somewhere else and they're looking for area 2, sometimes some people call that the Highlands. Sometimes people think that's outside the Highlands, so it's always good, it seems, to really clarify. It's like, "All right, when you say the Highlands, what are we actually talking about?"

Josh: Right. Absolutely.

Greg: The neighborhoods you were talking about there, the Upper Highlands, is that what you're saying? That's further out Bardstown Road?

Josh: Yeah, that's further out Bardstown Road. That's where you're going to go just beyond Taylorsville Road.

Greg: Then there's a little bit different feel for that part of the Highlands as opposed to the Original Highlands, right?

Josh: Absolutely. All throughout the Highlands you do have a really wonderful neighborhood feel, that is in the part that we're talking about in the Upper Highlands. It's very much more centered around the residential neighborhood. You don't have quite as many businesses or restaurants as you'll find heading back west towards Bardstown Road into the Original Highlands.

Greg: Okay. Bardstown Road as it heads into downtown, that's what we're calling the Original Highlands. You're talking about some of the, I guess, the walkability and some of the amenities that make that part of town so appealing. Can you walk me through-

Josh: Absolutely.

Greg: Literally, I guess, walk me through, what is it that makes that so appealing?

Josh: Well, one the walkability. Two, the diversity of the restaurants, shops and people. You have a very urban-type lifestyle and feeling but yet you are in a, it's a neighborhood feeling as well.

Greg: Okay, so the urban corridor I guess is going to be Bardstown Road and I guess maybe there's some smaller ones, but a lot of restaurants there right?

Josh: Yeah.

Greg: A lot of businesses and then as you branch off and head off either towards the park or away from the park, is that what you mean? That's going to be more residential so if you get off Bardstown Road, it's still lots of houses and people go walking, sit on their front porches?

Josh: Absolutely. Both on the park side and then south of Bardstown Road, yes. Once you leave Bardstown Road, you are in a residential area. Just as you said, people sitting on their front porches, walking their dogs. The beauty of that too is on either side of Bardstown Road you have two parks and notable, the Olmstead brother's, their most notable project I guess I would say would be Central Park in New York City and Prospect Park. They also designed our Cherokee Park and Tyler Park, so on either side you've got a beautiful park for exercise, tennis, hiking, walking your dog, all sorts of things.

Greg: Those parks get used, so it's not as if they just sit there and there's no one there to appreciate it. It's wonderful to go by on a beautiful spring day or whenever, a fall day, and there are people out there using those parks. They get their use, no doubt.

Josh: Oh, absolutely. Absolutely.

Greg: You mentioned restaurants, I'm always hearing about the Highlands and restaurants. I think I've talked to a couple different people on the podcast and they refer to it as Restaurant Row. You're a resident in the Highlands, right?

Josh: I am. Yes.

Greg: Is it okay to ask you for some of your favorites? No offense to anyone else who's up there, there are too many restaurants to list, but why don't you do both? What are some of the best well-known restaurants and maybe some businesses and what are some of your favorites? How much of your life revolves around the Highlands?

Josh: Oh gosh...

Greg: Too many questions right?

Josh: Right. Well, we'll take one at a time. We'll do that. Really the majority of my life does revolve around the highlands. I've got a dog so I utilize the park. I like to exercise, I'm utilizing the parks there. Everything is so walkable.

As far as restaurants, you hit the nail on the head. There are so many wonderful places to mention, but really some of my favorties right now, one being La Chasse and that's Isaac Fox's restaurant with Chef Alex Delaney and they have done a really great job of combining a southern, French and Spanish fusion menu in such a cozy, comfortable environment. Their wine list is phenomenal and then the service is great. You can't beat it that Isaac's the owner and he's behind the bar making drinks and entertaining everyone.

Greg: Oh really?

Josh: Yeah, it's a really great spot.

Greg: I want some other restaurants as well, but it does seem that up and down the Highlands at these restaurants, which are so well-known especially at Derby time, they're all just mobbed, they're not huge so it's by and large a really comfortable number and you don't get the feel of being in a munch ... I don't want to name a, like a national chain that's just in and out the door, but most of them are really ... I don't know what the right word is, but very comfortable and accommodating. It's a nice size, almost all of them.

Josh: Yeah, you're absolutely right and you go in and just what you said, you're not rushed in and rushed out. One, when you're in there, you don't want to be and I find that really you don't have the maitre d' or the servers, nobody's rushing you. They want to keep you there and enjoying some banter back and forth and great food and great wine.

Greg: Okay, how about another restaurant or two, or maybe a business, whatever-

Josh: Well, I would say, we'll continue on the restaurant theme...

Greg: Sure.

Josh: You've got Ward 426. Now that's going to be down at what I would say part of the western most point of the Highlands in the Phoenix Hill neighborhood and it's a collaboration between Dean Corbit, Nirm and Shawn Ward being the chef there. They've done an excellent job with the old brewery space. They kept the original bar which has such great history, one, and two, it's beautiful and then their food there is fantastic also.

It's anything from a great filet to a gourmet burger or pizza. Just that it's a friendly neighborhood restaurant, very comfortable. You can sit in the lounge chairs up in the front window and if there's volleyball going on across the street at Baxter Jack's, it's fun to watch that going on, or you can have a formal dinner with clients. It's a very, very versatile restaurant.

Greg: Do you find that you take clients frequently to some of these restaurants?

Josh: Oh, yes. Absolutely. I want my clients, especially those clients that are interested in the Highlands, I want them to experience my Highlands and what I love about my neighborhood.

Greg: That's really interesting. Is this something you do once they've closed a transaction? Is this like a closing gift or is this, "Hey, let's go out and as we're looking, you'll get to know the neighborhood a little bit more and I promise you, you're going to fall in love with the Highlands because after ..."? You can do shopping right? You can do dinner. You can ... I don't know what else you can do. Get your doctor.

Josh: Oh, yeah. Absolutely and it's always really the latter. It's while we're looking for homes, especially if they're transferring in from somewhere. It's before we found a home, letting them have their experience in the neighborhood getting to know it.

Greg: Okay. You have another restaurant?

Josh: Yeah. Seviche. Anthony Lamas is always serving up fantastic Latin fare. His churassco with the chimichuri sause are amazing and there you've got great bartenders. Chris is phenomenal and then the managers, Hap and Josh, it's just another really great neighborhood spot. You'll find again people there having business dinners or a birthday party and then some regulars having dinner at the bar.

Greg: I've actually found, and if anyone listens to this podcast on a regular basis, I think you and I did one probably close to a year ago and we happened to mention Seviche again.

Josh: Probably yes.

Greg: I've run into more family, of my family ... We don't have time to get together on a regular basis with the family but we'll go to Seviche, and I've seen them at the bar and we end up at a table or something along those lines, so Louisville is a big, small city. Sometimes you just end up at the same place.

Josh: Yes, definitely.

Greg: Okay, so if we're looking, maybe not food, which I really enjoy food but again, if you're living in the Highlands and you're looking for amenities, what else might there be?

Josh: Well, you've got all sorts of shops up and down Bardstown Road. You've got everything from custom T-shirt shops to lighting to the Guitar Emporium. I find myself some of my favorite little spots and that's just because I really do love design and part of my passion for real estate and architecture kind of all comes together, but Andrew Gentile Antiques, some of the pieces that he has in that store are just amazing. Credenza's, anything you could possibly imagine to antique china plates and then some of the art work that he has in there.

Greg: Where's this? I'm not as familiar with this store.

Josh: He is across from Mid-City Mall.

Greg: Okay.

Josh: That's right next to the Joy Luck Club and Asahi, the former Indian restaurant I think is what that was.

Greg: Got you.

Josh: Then also Francis Lee Jasper, their oriental rugs, they've got a huge inventory that includes the one-of-a-kind antique rugs that you just don't find anywhere else. Then really sort of so I think they can appeal to a broad client base, you've got new traditional and contemporary rugs and some really unique gift and accessories there.

Greg: It's in a cool building, right?

Josh: Oh, it's in a great building. It's in an old fire house.

Greg: Which again is part of what so many people like about the Highlands is these homes were there forever and ever and ever and then the commercial, it became commercial over the years. Then a lot of these businesses are now in old homes.

Josh: Right, absolutely.

Greg: Cool. Do you have something else you want to talk about or can you give me a little, maybe a little history lesson? I just talk about how-

Josh: Oh, sure. Well, I don't know if a lot of people know how the Highlands got its name but it's because it's sits on top, the ridge that runs between the middle and the south forks of Beargrass Creek, so it was one of the last areas near downtown Louisville to be urbanized. Really the challenge was, it's got a steep 60 foot incline above the flood plain so it may travel somewhat difficult.

Greg: That's funny to think about now because it's no problem, you just zip down Baxter Avenue or something but-

Josh: What we've got to think about is the early 1800s.

Greg: Right, so I don't even know that trains were ... It was probably pre-train, right?

Josh: Yes, this was definitely pre-train, actually I think it was the late 1700s, not early 1800s, because it wasn't until the late 1800s, specifically I think it's the 1890's where large scale residential development really started and it didn't begin until then, until they had a street car line that extended to the present-day intersection of Bardstown Road and Baxter Avenue.

Greg: That's funny that that close to downtown is something that would've been worthy of a street car, way back when. I think I had heard, I don't know, you check me on this, that one of the biggest groups of people to set up shop in the Highlands were the craftsmen, the working class, or the brick layers and the masons and the ... I don't know if that's true but I always liked that story and especially on the, which side of ... away from Cherokee Park side of Bardstown Road so that side of Bardstown Road was really the working class and then the park side was sort of the upper crust I guess. They had the bigger mansions that have since been chopped up and sold off for smaller houses, but that's what I heard. I don't know if it's true but I kind of like the sound of that.

Josh: I've heard the same thing and have found it to be true from the research that I've done.

Greg: Oh, okay. Then since we're talking about houses and then I'll let you out of the studio, if you want to go. I'll stay here forever and talk.

Josh: You know I can be a little long-winded myself...

Greg: When someone's looking at houses, and again, someone says to you, "I want to buy a house in the Highlands," the first question is, "Okay, what do you consider the Highlands," and then, "What kind of house do you want?" Because some people say they want a house and then they realize it's 100 years old and there's some character to the floors so it's not super level sometimes or, "Oh, I have to replace something."

Josh: That's something that you really have to, I like to educate my buyers on that, seeing, being in the different areas and neighborhoods, I should say, in the Highlands because it's not only what do they think of the Highlands but what do you want to get out of it? What is ideal for you? You could be on Eastern Parkway, in the Highlands, if you're on Eastern Parkway and I'm talking about the working class part, non-park side which you were talking about, you could be in a house for as low as $235,000.

That's going to be your typical shotgun or maybe little craftsman bungalow that's not been updated. It would be a great candidate as a fixer upper or maybe a flip. Then you can go all the way down from there and then get to the Douglas Loop, the Douglas Highlands which is actually next to Cherokee Triangle, my favorite, and then your park side and the home for 1.45 million and up from there.

Greg: I actually think it's a boon that there are so many different kinds of houses and so many different price tags so close together, so instead of everything being so similar, the Highlands is one of those areas of town where you buy a house and you're pretty sure that the house across the street or 5 down or whatever, is not going to look just like your house.

Josh: Exactly. A lot of diversity and I think having that diversity in the types of homes in the price point, it makes for a more diverse population which is again a big draw of the Highlands. You can have your working class, your artists, doctors, professionals of any sort, students even.

Greg: That's really funny that you said artist because I've talked to a few on the podcast and there are more and more artists coming back to town to live in the Highlands because they can afford it. They can be close to everything they want to be close to but they can do, they can work one job or they can afford to support themselves on their artistry where if they lived in New York or San Francisco or something, they'd be working 3 jobs and then do their art on the side. It's a great ... Well, obviously I'm preaching to the choir.

Josh: Yes.

Greg: You love the highlands. Well, Josh, thanks for coming in today and giving us a little education. Appreciate it as always.

Josh: Great Greg. Thanks for having me. It's great to see you and talk with you.

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