Used Jeep cars for sale near Madison, WI under $19,978

Sought out our salesman from a previous purchase, Mike Glowacki. Appreciate is non pressure attitude and is trustworthy. Both visits were great experiences. Would reccomend Russ Darrow to anyone.

I HATE is the warning 'Place Two Hands On Wheel' as it goes off even when I have both hands on the wheel - No matter where I place my hands on the wheel it goes off. Since it is connected to the Lane Departure feature in order to not have to hear a constant warning alarm for Two Hands on Wheel I have to turn off the Lane Departure feature (which I love).

They just got a Jeep in on trade and were able to deliver it the same day we looked at it. Terry is a great salesman and a pleasure to work with. I recommend him and Don Miller Chrysler for a great buying experience.

I purchased it used in 2022, it had 76k and now has 96 in 2025. It's 4wd with the 5.7 Hemi in the Overland trim. It hasn't given me any trouble.

Brian stayed in touch with me, eager to meet with me and help in any way. He showed me the cars I was focused on and didn't try to steer me in another direction. A very nice experience. Haven't completed the sale. Probably going somewhere else.

The 2019 Grand Cherokee Limited was the Jeep I had my eye on for a while. I've owned a 2012 Laredo X, and a 2018 Limited Anniversary/Heritage Edition. I was specifically looking for Limited trim without the 20" rims, although, I love the look of the Altitude versions, I just didn't really care/want to deal with less side-wall, nicer-looking rims. I avoided the Overland and Trailhawk because of the air-suspension. Overall the interior is fine, it's comfortable and familiar for me, since I've owned them before, but that's also the only issue/complaint I would have. The interior is updated from the 2012, however, basically it's a very light update, U-Connect, Gauges, Shifter, and possibly a few other items here and there. But essentially, the dashboard is the same dashboard I've seen since 2012. While owning the previous (2) I never experienced any mechanical issues that left me stranded. One had a weird issue with blowing lights in the tailgate, but it would just randomly decide to burn out, replace one it would blow another. No other major issues. The 2019 leather on the steering wheel feels smooth and buttery like they always have. The suspension feels great, still solid and tight. Brakes are strong and grippy, pedal feel is nice and firm. So far I'm super satisfied with this Jeep, I got the perfect combination of all the features I wanted, Memory Seats, Sunroof, power trunk, heated-seats and wheel. Not sure if I'd be willing to sell this one and get a newer model, but, I'd possibly get another WK2.

Went specifically to look at one car. Loved it. Clean. Well maintained. Ready to go but they still wanted to clean it again so wth! Sure!

The most American vehicular on the planet. I love my Jeep. It’s an acquired taste but I do so love my taste. Lift kit, 35’s, black and sexy as xxxx!!

The difference between Skyline and larger dealerships is like night and day. After getting the run around with Madison Dealers I was lucky to find Skyline and Martin. I arrived and drove 2 cars, picked 1,a 2008 Acura TSX went into the shop and paperwork for taxes, registrations etc. was done at no cost. I gave Martin a check and drove home. Now 4 months later I have had zero issues with the Acura TSX and am extremely happy to have found Skyline. I recommend Skyline to anyone who wants a good, reasonably priced car, while dealing with an honest man.

One of the best vehicles I have ever owned! Dependable, lots of features, stylish, fun to drive on and off road. A vehicle you can enjoy and be proud of!

So far above and beyond what I could have expected or even hoped! Before I was able to drive my new purchase home, Legacy Auto wanted to, as is their practice, go through every inch of the car replacing everything that seemed in need of being replaced, regardless of whether an actual safety issue or not as might come out of a cursory safety inspection. I wasn't surprised yet I was a little disappointed that it would take a while for their shop to get my car in for the inspection and corrections, primarily because my insurance company could not cover my rental car for as long as it would take but, Legacy Auto provided a loaner so I at least had a car to drive away with and use until mine was ready. That though turned out the be the least of the professionalism in the service they provided as the cost out of their pocket that they put in for parts alone for issues they dealt with, far beyond any safety concerns, was 10% of the agreed-to price in the first place! They put in 10% of the price of the car AFTER I had already paid for it. In any other dealership I have experience with the best I could have expected is a legally required safety inspection and a detailing of the body and interior. I had to drive about 45 minutes to reach Legacy Auto but the time and effort was more than worth it!

I already owned this vehicle when I took it in for service. But. I love the vehicle. I haven't had any major problems with my Jeep Summit

They always treat you like an honored guest. They know my vehicles history and any recalls are taken care of while the oil is changed. And a wash is given with every service!

Owning my 2020 Jeep Renegade Limited has been an absolute joy. This SUV strikes the perfect balance between style, comfort, and capability. From the moment I got behind the wheel, I was impressed by its smooth ride, responsive handling, and surprisingly spacious interior. The premium features—like the leather-trimmed seats, intuitive Uconnect infotainment system, and advanced safety technology—make every drive comfortable and convenient. Whether I’m commuting in the city or taking a weekend getaway, the Renegade Limited handles it all with ease. What really stands out is its versatility. The 4x4 capability gives me confidence in any weather condition, and the fuel efficiency is great for an SUV of its size. Plus, the unique design turns heads wherever I go—Jeep really nailed the balance between rugged and modern. If you're looking for a compact SUV that delivers reliability, technology, and a sense of adventure, the 2020 Jeep Renegade Limited is a fantastic choice. I couldn’t be happier with mine!

Antonio was amazing to work with and made the buying process so smooth! Definitely recommend!

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

This is the 4th car I bought from an excellent sales guy Charlie. Its so nice to just get what I want for a great deal. Just pick up the phone and call Charlie and he has everything ready to go no waiting. I know he has what it takes to get things done in a rapid pace. Thanks again Charlie ! You did it again!!

Like the look and has plenty of power we have the v6 option The interior is very comfortable with all the bells and whistles you can appreciate. We traded in a Liberty and the ride is so much smoother.

Jean, was very helpful and pleasant with our purchase yesterday. We had been looking for a Grand highlander and he had it ready for us when we arrived. The vehicle was also discounted after only 11 days on the lot which was also great. Had just the right features and we like it very much so far! The purchase did take 2 hours, but we were not sitting around much the attendant who told us about our car features, was also great although I cannot quite remember his name at the moment. We are a satisfied customer. All the employees we interacted with were great!

  I have the Trailhawk trim, the serious off-road version.  Finally, a car that I can confidently drive in and out of rough construction sites, and not be afraid that I'll break it or get it stuck.   It is possessed by a powerful spirit of wanderlust, and frequently demands that I take it on drives just to see places it hasn't yet been, preferably places that normal cars cannot go.   If Don Quixote de La Mancha lived in our time, he would surely drive a vehicle like this one; a vehicle truly fit for a modern Knight Errant.   I didn't know until a few days after I bought it, and I don't think the dealership knew either, but this one has about a 2" aftermarket lift, and slightly larger tires than stock.

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.

I used to work at s dealership do buying cars is not my favorite thing to do. I hate sales pitches and unnecessary products etc. Trevor and the entire team where accommodating, professional, and everything was exactly as quoted etc. Way better deal than local dealership.

Overall, pretty decent car. As professional reviews will note, the transmission is a little finicky, but nothing over the top. Learn to work with it, it works with you. Bought this car used last year with 68k and I drive a lot, so I've already put 30k on it. Handling wise, this works great, even in the snow (FWD, not 4x4). Good cargo room, and room for the kiddo's carseat. Now, this is a Jeep, and hasn't been without issue. The front struts have been replaced, probably as part of my driving style and the rough roads in my area. Part of the bumper got pulled off a while back, not a big deal. Mechanically, decently sound, the car has thrown a few check engine lights but for non-issues. It had an issue a while back where it would turn off or restart on its own when stopping (not to be confused with the auto-stop, which is annoying but can be turned off, this car would just flat out turn off), but that fixed itself. Developed an engine tick that does appear in Jeeps, but that has also righted itself. As such, no major maintenance has needed to be done besides my struts. So all in all, it works. If you're in a situation like mine, yeah, buy the 2019.

Starting the process for looking for a new to us van and CarMax was one of our stops. They had one we were really interested in, but between trade-in value and non-negotiable pricing (which we knew in advance) we realized it wouldn't fit our price range. Ryan was responsive, but not oppressive.

I bought my 2019 Cherokee new in July 2019. I have had it for 4 and a half years now and I have had no problems at all. I have over 61k miles on it. I do worry about the warranty being up that something might happen but it has not given me any issues so I shouldn't really be letting it bother me. This is the longest I have had a vehicle. I usually keep a car and trade it in around 3 years but I have loved driving this car so much that I have no desire in letting it go. I hate that Jeep is no longer producing more of these.

Great dealership! Answered all questions I had in a timely and professional matter. Ordered my vehicle and it came in took delivery of it which was very informative and efficient. Thanks again!

Vehicle handles well easy to park and maneuver I don’t like the fuel tank capacity very small also I don’t like the fact it has no spare tire unless you purchase it for three hundred plus you offer a air compressor which is great for a slow leak but don’t get a blow out in the boondocks you’ll be screwed. I don’t think a space saver spare will break the bank.

I worked with Aaron A. and he was very pleasant to work with, and him and the team at Goben made things go smoothly!

I've added aftermarket exhaust and a computer chip and the roar pedal also KNN air filter and bigger tires 35 so far it is a lot of fun to drive

Robert delivered great service and I appreciated that they were able to transfer the vehicle to the Stoughton location for easier pick up.

Would recommend this vehicle. Overall very good value and has proven very reliable. Sorry to hear it is being discontinued Jeep had a winner and what I thought was a great tweeter between the Compass and Grand Cherokee.

I was extremely happy that Stuart, my service representative took the time to listen to my concerns. Once the inspection was complete, he explained each line item. I made the decision to only do 2 or the 7 recommendations at this time. I never once felt pressured to get all done immediately. He even highlighted the items that would be wise for me to do next. I will definitely go back for the additional recommendations to this location

We purchased the same night a wrangler sport JLU 3.6 manual trans and this Cherokee Limited with the same engine and the 9-speed automatic. And oh boy, these cars were completely different despite having the same 3.6 Pentastar engine. Launching the Wrangler was never an issue. Launching the Cherokee and even more reaccelerating was truly painful and required a lot of preparation. Sometimes, the transmission would take few seconds before downshifting making the throttle response slow at best. Other than that, the car proved to be reliable and was extremely silent and very well equipped. I would recommend that car as a commuter for someone who is not seeking any driving fun. For families who enjoy long trips, there are better and more responsive options out there.

Stopped in after 5pm and Jason was very kind & helpful. He helped solve courtesy light question.

the car is largest enough to haul baseball equipment around, yet easy parking and handling. i like the interior and the room. the seats are very comfortable

Honestly the best dealership iv ever been to, super friendly and welcoming staff, aaron alderson was quick to greet us at the front door! Took us around the lot explaining details about each car i was interested in when we found the car we liked he was really good at explaining everything about the features! I highly recommend first time buyers to come here! Extremely good place to work with!

Even though they were short handed on the day I stopped to look at a used vehicle, they were polite and professional. I was able to test drive the truck I wanted to and the process of getting the paper work done to buy the it went smoothly.

I drive a lot my car is a 2014 and it has currently 277,400 miles and still ticking. I’ve had very few maintenance issues overall the basic wear and tear as expected! I didn’t expect it would last as long as it has but I am being pleasantly surprised. It is great on gas compared to most SUVs and overall a comfortable car !