Used Jeep cars for sale near Winchester, KY under $899,990

Joshua Fite made my 1st NEW car buying experience... the best I've ever had. He checked all the boxes! I highly recommend Josh for your buying experience.

Two weeks ownership impressions, this Jeep is quite impressive. I've never been a Jeep person. Long time Dodge Charger owner in the sports car world. Cross shopping the Mustang Mach-e, the Grand Cherokee 4xe really got my attention. It's got that "in town" all electric distance, but you have the turbo gas engine for range and flexibility. The interior is not quite oppulent luxury, but it is VERY nice inside. Levels above what typical Jeep interiors and technology have been. It's very well put together with nice materials, and even some nice plastics. The one huge strike is the choice of so much center piano black. This material has to die. UConnect 5 is my absolute favorite. It works extremely well. The TomTom Nav is kinda weak. It only works best when you input the exact address. Combined electric and gas performance is impressive! This big SUV launches off the line when asked to. Electric use is pretty good for a big vehicle, at about 26mi. Which has been perfect for local driving when I'm off the highway. My combined MPG with gas/electric has been 25mpg, on Regular fuel. Which is a huge step up from the old Charger, yet I have all this cargo room. In the recent snow storms, this GC has been a snow BEAST. Very stable, and the stock Bridgestone tires have been acceptable in their snow performance. A few negatives; the dealer helped fixed a squeaky front panel right away. And they updated my UConnect system, where the screen was flashing black. After those fixes, the GC 4xe has been flawless. The engine is a bit noisy at higher rpms, but I don't mind it too much getting to use its performance. I've been Level 1 charging overnight at home, which has been adequate, taking about 14-15hrs for a full charge. That usually gets 2-3 local errand/to highway trips before it runs out. Then I charge again for the next day. When the battery is "dead" there's enough reserve to operate like a Prius hybrid, to help keep fuel efficiency up while in gas mode. Overall very happy! It's a lease to hedge my bets on this new tech, hopefully it keeps going well! I might be a Jeep convert!

BUY YOUR NEXT CAR HERE! I can't say enough great things about the whole experience! Angie was caring, helpful, and extremely knowledgeable! Terence the manager made my deal happen! And I got to meet the legend Zach Toomey, who even introduced me to the owner! My family was treated like royalty!

My wife and I bought a 23' Jeep Compass Limited with 15K miles. We were looking for something small but also a vehicle that could offer 4x4. My initial impression of it at the dealership was that it has an awesome exterior paint color (granite crystal) and black wheels to compliment it. The car drives great on the highway and city. It's a very comfortable ride and the car can turn on a dime! I am currently averaging 30 mpg while commuting to work each day. I have noticed the car will sometimes have difficulty up shifting. As long as I apply more gas it eventually gets over it. Not a big deal for me as my last vehicle would do the same thing. The rear view camera is nice on the Compass, however it is completely useless at night. Overall we are very happy with our purchase.

They were very friendly. Corey did everything to get me a vehicle. And affordable monthly payments!

The Sahara high altitude with the sky one touch roof is awesome. The one touch opens or closed in 15 seconds. This is a game changer as we do not hesitate to open the roof in all different weather conditions. Reason is if bad weather or hot weather gets us we can have the roof closed in little time. The ride is very smooth. Noise is low at highway speeds. Overall, we really all the accessories and sound system. Definitely, recommend.

We have purchased two new cars from Glenn Freedom and are in the process of ordering and buying a 2021 Dodge Challenger RT Scat. The customer service had been prompt and the people I have spoke. With have provided all the information I have requested. Carl is my main salesperson and I’ve also worked with Tim. They are both very knowledgeable, patient and have made my experience a good one.

This has been an amazing vehicle! Super comfortable and will buy again. Loved all of the tech and comfort features to make each trip the best. I have owned a lot of cars and this one has the most intuitive features by far.

Taylor Hagan was very helpful in my purchase of my 2020 Santa Fe. I was on my way in less than an hour. I would highly reccommend Georgetown Auto Sales and when you are there ask for Taylor she was awesome!

Had a rear end collision with it a few days ago. Handled it well. Car that hit me, as I was standing still a traffic light must have been going 40-50 mph. My car took the brunt of the crash, sparing me I am sure. If totaled, will look at same manufacturer.

Just a note to say our salesman Jace and finance officer Brad led us through our buying experience with flying colors… authentic, knowledgeable, polite and helpful. They each were patient, insightful and greatly assisted in their respective roles. Many thanks!

I have had my 22 High Altitude for about 4 months now and the only issue(s) I find are the following: MPG is not as advertised, it's not that great. It's around 24 average, I am about 50/50 city/highway driving - It's fine. It DOES ride like a Jeep - so it's not as "luxurious" as your higher end cars, but YOU BOUGHT A JEEP - The last snow storm we had in Cleveland was about 10" in 2 hours - No problem, even with 235/45/19 tires - Would be way better with not so wide tires. It's slow. Who cares? Are you driving in the F1? Nah - It's plenty. Interior is baller. Infotainment is great, comfortable. Heated steering wheel is a plus. IDK - I read these reviews and everyone is so picky - It's a nice ride. If you find you like it, give it a shot.

I have always had a great service experience. All the people are friendly and knowledgeable and have a desire to assist you. I highly recommend this dealership.

Bought my 2024 used with 13k miles on it. Maybe I'm old school due to prior life with a 97 TJ and and 01 XJ but this car is fantastic to drive and very luxurious. Perhaps not as tech heavy as other SUVs, but it does everything I could hope for, and has been fun for road driving and light off roading.

I had a great experience! Jesse, was very helpful and knowledgeable about what I needed, and helped in every way she possibly could. I definitely recommend them to everyone in the market for a vehicle.

i recently had a 2023 for explorer it was a good truck never a problem but not a comfortable as the jeep grand Cherokee l front seating is amazing no issues at all i did my research and made sure i bought one with the German transmission its a good idea to check that only thing i can say on the down side seam to be a little under powered but i can live with it decent milage 20 around town.

Matt and Hunter at Carmax really made this the best experience for me. Matt worked with me through phone and email up until the day I went in. He was very informative and assisted me through the entire process. Hunter was the salesman I worked with when I went in. He was accommodating and polite. I didn't feel the "pressure" of a sales man at all. And he was very professional. I will recommend this dealer to anyone I know looking to buy a vehicle.

My only complaint are the front seats do not have enough cushion and the seatbelt latch pushes into your hip on the drivers side. and standard lumbar support on all models added

Timothy, Tanner, and Lawrence who helped us where exceptional. The dealership offers transparent pricing, the absolute BEST deals and the guys are courteous, efficient and made the entire process painless and easy. This was the best car buying experience of our lives and we have bought nearly a dozen cars over the years. There was no pressure and it was like working with a friend to get you the car you want at a great price.

The JL exceeded my expectations. In the past Wranglers were clunky and didn't really feel like they were put together too well. My son had a JK and it was a huge advance forward. So I decided to buy the JL and I think it was another huge leap forward. I have fully loaded Ram 2500 but I find myself taking the Jeep most of the time. Okay part of that is trying to park a long bed crew cab, But I do enjoy driving the Jeep and have taken it across country a couple of times. After a 122,000 miles I still love it.

Buying a vehicle online can be a bit nerve-wracking, but Dan Cummins made the entire process smooth, transparent, and surprisingly personal. I purchased my Jeep entirely over the internet, and from start to finish, the team was fantastic. They were honest, responsive, and incredibly kind throughout the entire experience. Every question I had was answered quickly and clearly, and they never made me feel like just another transaction. What really impressed me was how much care and attention they put into every detail—photos, descriptions, paperwork, and delivery were all handled with professionalism and integrity. Even from hundreds of miles away, I felt completely confident that I was in good hands. It's rare to find a dealership that combines online convenience with genuine human connection, but Dan Cummins nailed it. They went above and beyond to make sure I was comfortable and happy with my purchase—and I absolutely am. If you're considering buying a car online, you won't find a more honest and caring team than the folks at Dan Cummins. Highly recommended. Wayne.

It’s currently summer 2025, I’ve owned my 2020 Wrangler Sahara since spring 2021. I LOVE my jeep and have had ZERO issues with it. This is my 2 nd Wrangler, first one was 2915 New. No issues with it at either. Mine is a 4 cl turbo. I didn’t want that I wanted a 6 cl. My husband convinced me to buy it and I’m glad I did. I have 59,000. Miles currently and I haven’t had to replace anything besides general maintenance.

Brandon and his guys are top notch! Wouldn?t take my car anywhere else! Always fast and do a great job on my vehicle! Best service in this area!

ISSUE WITH SUNROOF CLOSING, NEW ONE PUT IN SAME PROBLEM. IN COLD WEATHER SEVERAL DOORS WOULD NOT LOCK AT ALL. AT FIRST I THOUGHT THEY WERE FROZEN THE DEALERSHIP IS STILL NOT SURE WHY THIS HAPPENED. I WAS UNABLE TO DRIVE IT WHEN THIS OCCURRED. JUST HAD THE IGNITION REPLACED - CAR WOULD NOT SHUT OFF. I REALLY LOVED THIS CAR THE SUNROOF IS HUGE, MY FIRST NEW CAR, IT IS A LITTLE SMALL IN THE BACK SEAT FOR PASSENGERS BUT NICE, I LOVE HAVING A HATCH AND NO TRUNK TO MOVE THINGS IF I WANT. I HAVE ALWAYS WANTED A JEEP AND I ABSOLUTELY LOVE THE 4 WHEEL DRIVE AND OPEN FEEL OF THIS CAR. IT DOES VERY WELL ON THE HIGHWAY. THE REAL ISSUE I AM HAVING IS WITH CASTLE JEEP/ RAM IN NAPERVILLE,ILLINOIS COVRING THESE ISSUES WITH MY 100,000 MI WARRANTY.

My husband and I went in last week for a recall and they got us in and out with out an appointment . Michelle and phill I believe we’re definitely great at getting us taken care of so we could go on vacation! Will be returning !!

I have had my 2022 Jeep Compass for 8 months now and no complaints. I can accelerate onto the fwy with no problems. I get the mileage they say. I do wish the storage was a tad bit larger and maybe more leg room in the back, but honestly I only travel with two dogs and rear air is good for them. Love the larger display screen and never a glare so I can’t see it as in some other cars I tried. My backup camera works fine at night. I have the 4X4, so I need to get more info on that. I know the 2023 has a turbo, but I don’t care about that.

Very nice and professional. Pierce did a great job! Quick and efficient. Would 100% recommend.

This is the best Jeep Wrangler model ever made. The past YJ, TJ, JK models are great, but this Jeep JL 2018 Wrangler Sahara Automatic V6 is the best one yet. The comfort and modern amenities are top of the line. The 8” infotainment head unit and Alpine sound system is out of this world. The interior fits my family of four and has enough cargo space for a stroller, scooter, Onewheel XR and beach chairs. The exterior needs no introduction with its iconic round headlights and seven slot grill. Followed by a three piece removable top, which I managed to take off and put back on by myself. FYI, don’t try doing this by yourself. My final favorite thing about my Jeep JL is the ability to customize the Jeep with all of the amazing aftermarket parts and pieces. This allows you to take the best looking car on the road and make it your own.

Dre is awesome, I am still in process of buying but so far so good. Just waiting on some stuff to finish my deal. Love the 2023 Nissan Rogue.

After 100,000 trouble free miles we bought a second Renegade this February. Good car, reasonable mileage, no complaints. Moved up to the Trailhawk trim package

Worked with me, and made me a deal that was worth it! Will definitely shop again

Just bought a gently used `22 Jeep Grand Cherokee WK in diamond black. I love it! It was a prior lease with just 18k miles on it. I have had it for a few weeks and I am thrilled! Stereo is amazing and it even has a nice factory sunroof and tow package!

no concerns with experience that day. the restroom was clean - the waiting area was clean, large, allowing me to get work done while waiting. friendly - professional staff will use service there again

We purchased a 2024 Jeep Compass Limited Elite. This vehicle has far surpassed our expectations for comfort, handling, road noise and quality. There is very little road noise we hear inside the vehicle, and this allows us to keep the radio turned down to a comfortable level. Handling is exceptional and very responsive. The driver safety features of lane guidance, adaptive cruise control (my favorite) and 360-degree backup camera are now features we will not go without after experiencing first hand performance. Thank you Jeep and Jeff Belzer CDJR of New Prague, MN

I purchased recently a used 2020 Cherokee Limited and it has turned out excellent, I have no problems or issues. The only minor issue that I have is the location of the cup holderss.

Talked to Stephanie on the phone and through text. She was able to give me all the info I needed and was very friendly. Called a few days later to pay the shipping fee up front to order my new truck.

The Jeep Renegade proves that you don’t need a massive SUV to enjoy real capability. It is great for everyday practicality, making it a great choice for drivers who want something different—something with personality, performance, and purpose. Whether you're commuting during the week or hitting the trails on the weekend, the Renegade is more than ready to go wherever life takes you.