Used Jeep cars for sale near Madison, WI under $24,953

I have bought 4 vehicles from Russ Darrow, three from this dealership. You can’t beat them anywhere else! They are fair and truly listen to your needs.

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.

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.

This is the 3rd Jeep product we have owned over the years, first was a Grand Cherokee Laredo, then most recently a 2012 Jeep Liberty Sport. We just purchased the 2019 Jeep Grand Cherokee Ltd in Febrary 2023. This Jeep is the most luxuary we've ever had in a vehicle, it has everything but the cooling seats which would be nice as we live in FL. This will be a dinghy towed vehicle behind our Class A motorhome. We also towed the Liberty Sport.

Aaron Anderson is a great and phenomenal salesman. We came in a lot nervousness but he made our experience so easy.

My dream car since a teenager was a grand Cherokee and when I finally got one in 2021, I’ve loved it the same ever since. They are bold in appearance and look like a strong vehicle. It has always run beautifully and I have had no issues thus far since 2021 and now it’s 2024. Very comfortable interior and attractive to the eye. Love love love my car.

My wife and I were looking to upgrade to a comfortable reliable sedan, we narrowed our focus to a MAZDA6. Did a search on car gurus and found a listing for Mazda6 with this dealer. Jay and John were both very nice and helpful. Visits are by appointment only, so we gave Jay a call, set up an appointment to look at the car and hopefully purchase it same day, my wife and I live 2 hrs away from the dealer so I asked some detailed questions about the car over the phone, Jay provided an accurate verbal description of the car so there would be no surprises once we got there. Jay informed me of some minor cosmetic interior/exterior blemishes and that the tires were getting to be well worn. Once we arrived, we met John who had the car ready for us to test drive. John was very friendly and relaxed and also provided helpful information about the car when asked. In person the car matched the description Jay gave over the phone which was reassuring. My wife and I took it for a test drive by ourselves and everything was as we had hoped so we decided to purchase it. 10/10 experience (excluding the 2 hour drive)

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.

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!

Symdon in Evansville was amazing through the whole car buying process! It was completely stress free! Jason Drees was very knowledgeable and was amazing to work with! I will buy all my future cars from Jason at Symdon in Evansville, WI!

My Grand Cherokee Laredo E just turned 50,000 miles a few days ago. Other than routine maintenance, the only money that I have invested in it was for 4 tires last month. Extremely comfortable, capable and reliable. While not delivering Prius-like gas mileage, given the performance it provides in all types of weather.............NO COMPLAINTS !

So appreciated this car dealership. They were open honest, answered my phone calls and texts in more than a timely fashion. Accommodated my time schedule to pick up the car. Provided more than a fair deal. Competitive in their pricing

Love my jeep. They have come a long way baby!! I am now a Jeep girl for life and recommend them highly. No matter the weather my Grand Cherokee gets me there in comfort and safety.

I've been driving for 43 years now and have owned an array of different vehicles, however I've never been financially fortunate to purchase a luxury model - until now! I was looking for a mid size vehicle that would check many boxes for my snowy Michigan commutes, along with distant travel comfort to and from my cabin and some towing capacity. I have only had this for roughly 1500 miles and wow.. My first impression was luxury. So many base options included in a mid sized and mid priced SUV that pleasantly surprised me. Secondly was the ride quality. Both smooth and quiet and handling. I've read other reviews discussing power inadequacy, but not at all. Plenty of passing and get tup to speed power. Next was the snow. I have Michelin defender tires and wow - what have I been missing? The snow 4x4 duaratac features combined with these tires make this a beast in the snow, slush and rain. It definitely gives me a much more safety reassurance while driving in these conditions. I have not tried the towing yet and have not had any "reliable" issues to report, but we are very fortunate with our pick and one very capable snow commuter.

If outstanding was available that is how I would rate this dealership. Staff is truly amazing with sales and service second to none. Tony LaBerge always takes the time to answer my questions and ensures that he keeps me informed on topics of interest. Facilities are always clean with a excellent selection of cars available. If you are looking for a Mercedes Benz, Audi, Porsche, Smart or Sprinter I highly recommend Zimbrick European.

The turning radius is the best for the size of this suv. The brakes are quick to respond. The 4x4 is a must. The only downside is that they aren't all standard with a trailer hitch. Love the sunroof, the all leather interior.

Great service, everyone was very accommodating and patient with me. They took the time to make sure I understood everything from the car and all its features to my maintenance options and finance options. Made the process very relaxed and enjoyable.

We are very happy with our '21 GC Limited. It is well appointed, with many options, drives nice, comfortable and still sits higher, unlike a lot of other "car" SUV's. We use this as our only vehicle, and flat tow behind our motorhome. Jeeps are the best vehicles made to flat tow!! We have climbed dirt trails in the West and cruised coastal waterways. Love it.

They were able to get me an appointment very quickly. Their Service Department staff are very friendly and knowledgeable. Everything was explained to me very clearly and the billing was exactly what they said it would be.

Love my GC 80th Anniversary Edition. A little over 15K miles and she’s been in the shop 2 times now with a squeaking coming from the engine. Tensioner rod and idle sensor were replaced first, they had it for almost a month. alternator was just replaced, they had it for a week. Picked her up last night, drove her this morning and it’s still squeaking! Very frustrated but hoping to get her fixed!

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.

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!

Awesome buying experience working with Robyn and TJ my finance guy. Great staff and dealership! I keep coming back car after car and will recommend East Madison Toyota to anyone!

  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.

VERY HAPPY with the service I received, especially my sales person, Anotonio Lopez. Antonio answered all question and anticipated things I did not think to ask. When he was unsure of something he did not make up an answer he got someone who could answer my question. The sales manager Alex and GM Devin were helpful too. This is the second consecutive car I purchased from them. My only issue (my fault) I chose to take Kia's follow up survey. I felt the survey was too long so I just started clicking.

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

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!

I bought a 2023 Jeep compass Latitude Lux. Wish they come with all the other specs in driver assists like wireless charging, power tailgate, dual zone AC control, adaptive cruise control etc.

Very easy to work with and I had a good test drive. Salesman Bob was very helpful.

I have been looking at new Jeeps for awhile was needing a new vehicle was driving a 2005 dodge grand caravan sxt drove it everywhere kid's learned how to drive in it. But I'm a jeep guy have a 1979Jeepcj7 since brand new drive it daily. Seen the jeep cherokee trailhawk at my local dealership talked to them about it took it for a test drive and fell in love with it. Had to take it home. Very comfortable all the buttons are in the right places. Display screen is very simple to navigate easy-to-use app's phone linked right up no need to look at it. Mics are in right places above head everyone I call or calls me has no problem hearing me. Has alot of safety features to get use to but not hard. I have had other cherokee in the past but love this one. If you are interested in a Jeep check out the Cherokee line like I said I'am a Jeep guy test drive and you will see what I mean.

Excellent service from Jimmy worked very hard to find the car that was right for me. I can say this. If I happen to be on the market for another vehicle. Definitely I will work with Jimmy 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.

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.

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.

I searched for several months for a specific used car that had all of the options I wanted. I found it at Zimbrick Nissan. I worked with Travis over the phone since I live in Kentucky. He answered every question and sent me all the additional information and pictures I asked for. 4 days later I flew up there and in less than two hours I was driving my car home. I highly recommend this dealership and Travis to anybody looking for a great deal on a used car and an overall positive experience.

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.

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 a red 2017 Jeep Cherokee that I bought used, and I love it. I live in the blue ridge mountains of Virginia and this car has been able to deal with everything i've thrown at it. Deep snow, muddy trails, icy roads... You name it. I have the V6 and I can hook up a heavy uHaul trailer and go up and down all the mountains with it. My wife even hit a deer in this car... It obviously had to go to the repair shop, but my wife was safe. The only thing that bothers me a little is that you can't slam on the brakes and throw it in reverse... You need to stop completely, take two seconds and then put it in reverse.