Used Jeep cars for sale near Stoughton, WI under $20,000

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'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.

Follow up review on 2015 online Suburban purchase. Dealership went above and beyond to make things right and actually took responsibility for the items that needed attention. I went from never going back there to being their number one fan. Great customer service after the sale! Great working with you all!

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 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.

I just love everything about my 2021 80th anniversary edition G/C! I purchased new but now has 81000km. So much enjoy all the style comfort with no issues. So much more reliable and better looking than the new body style that was released later in 2021.

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.

We purchased our 2014 Grand Cherokee Overland new and after 11 years and almost 150,000 miles it easily the BEST vehicle we have ever owned. It is comfortable, delivers reasonable mileage, is quiet, well built, incredibly durable and looks as good today as the day we took delivery.

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.

Bought my 2017 Overland 2WD preowned with 74k miles. It’s now Feb of 2024 my Jeep’s got 135k on the odometer and I’ve never once had an issue. I occasionally get car fever, start looking at cars online, but the second I jump behind the wheel of my Grand Cherokee I smile and decide to keep it for a little longer. I still love the look, it’s super comfortable, has plenty of power, all the bells and whistles I want (and beyond), and I love the fact not every single thing is touch screen as most modern vehicles. I love I can turn up the volume, operate the AC and many features with good ‘ole KNOBS without taking my eyes off the road.

How friendly everyone is and how fast the service is. I have not had a problem here in the 14 years I have come here for service.

Bought my first Jeep Grand Cherokee in January of 2022. I was in a wreck where another vehicle hit me and threw me off the road into a ditch. I went airborne and came down hard. It was a miracle I did not flip. All of my driver-side airbags deployed (front and back) and I walked away with minor injuries. This vehicle kept me safe and I will have another one to replace the totaled Jeep from my wreck.

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

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!!

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!

The 2012 Gran Cherokee Overland has been my car for over 12 years. I’ve enjoyed every minute of driving it. Have made several road trips with it and never a complaint. It’s plush with features and luxury items. Love the looks, love the ride, love the comfort and love the low cost of ownership. Jeep lives up to its name and fame.

I bought a 2004 Audi S4 from A to Z and I am very happy with the transaction. We quickly came to a fair price for the car, the car was exactly as described and the customer service and interaction was excellent. The sales rep, Abe Sarhan, was very helpful and quick to return calls or txt msg. I would highly recommend this dealership.

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.

The Cool Car Guys treated me like family with a no pressure buying experience! Drew the owner was awesome to deal with and helped me get into the vehicle I wanted!

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.

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!!

I’ve had my ‘15 latitude, for a year. T-bones a car, last week, and they crumple like a beer can… In other words: had my wife get a ‘16 75th edition TODAY!! Yes, ramen diet, for a few years, + her “special edition” doesn’t have heated seats, or a heated wheel 😖 My latitude does!! I wouldn’t look at different 💯

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!

Everything with this dealership goes smoothly and, in the customers favor. Cannot recommend this place more! If you are ever looking for a car stop by this place first before anywhere else.

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.

Very professional dealership. Jeremiah was wonderful to work for and not pushy towards the sale. I bough a used vehicle but it was in nearly perfect condition. Will definately be looking to purchase antoher jeep from them.

This is my second renagade, I wanted a 2021 limited and that’s what I have now. I have a long history with many models of jeeps, but I have to say this one is my all time favorite . I love everything about it. It’s a tank in the snow and mud . We have climbed to the top of a mountain with it. I feel safe and secure that I will never get stranded in the snow. It’s comfortable, and just the right size . I love the Easter eggs they hid in the car ! We were able to fit all our camping gear in it and bikes and kayaks too. I love the look of it and it’s fun ! I will never get rid of this car , it’s a keeper.

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

Overall experience was o.k., we bought a $60k nearly new car, and had it shipped, the car arrived on the transport with less than 1/8 tank of fuel which we thought was a little crappy, the interior was dirty and had scrapes on the kick panels even after we specifically asked about that area over the phone.

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.

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

I love my little JEEP compass! It’s runs well and is perfect for me and my needs! Holds all the baseball gear and more in the trunk!

I travelled out of state for my purchase and Brad did a great job at answering my multitude of questions! They had a driver pick us up at the airport(1 hour away), washed and filled up the car. Brad sat down with us helped us find some local eats and got us convict way with ease. Paperwork was quick as well. I can't thank them enough for making this car buying experience very productive and hassle free! Thanks again Brad!

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

I drove from Chicago to Janesville to purchase a Nissan Kicks. I was very impressed with the honest, personable service I received from Alan, Jason, and the whole team of salesmen. I can't say enough good things about the way they treated me. They were thorough and prompt. I was in and out of there in no time flat. I would recommend them to anyone going to buy a new Nissan.

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.