Used Jeep Grand Cherokee for sale near Waterloo, WI under $99,995

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!

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.

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.

This is my first Jeep I have ever owned. I always liked the looks of the Grand Cherokee. I’m happy with the vehicle. No complaints except it does like to drink gasoline. My previous 4 vehicles were all 8 cylinder full size pickup trucks. The Jeep being a 6 cylinder eats more gas. The Other than that, I’m very happy with my purchase of my 2022 Jeep Grand Cherokee. Good looks, drives well, comfortable and safe.

It was a great car buying experience. We enjoyed it so much we recommended ot to our son. He leased a truck the next day.

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.

Bought a Elantra today, Dale Thorsen was my salesman and he was incredible! Thank you for everything Ewald!

2017 GC Limited 4WD. Bought it 3 years ago with 53k miles and now approaching 108k miles. When we bought it, we went to fill the tank for the first time and the gas pump kept shutting off. Turns out there was a known issue with the fuel filler neck assembly. The selling dealer replaced it under warranty and we literally didn't have another issue until 100k miles. At 100k miles took it in for new spark plugs, which is normal maintenance, and found the radiator leaking. The new radiator was not cheap. Have not had any other issues, just replaced the factory original brakes, they made it almost to 108k! We live in Minnesota and this vehicle is an absolute beast in the snow. Put it in snow mode and it is very stable and feels unstoppable. It is a comfortable long distance cruiser and gets decent mileage on the highway, between 24-27mpg. The UConnect system is very easy to use, and the nav is pretty good, but the whole system operates quite slowly. That's a minor complaint I think. Overall we are pretty happy with our WK2.

FRIENDLY COURTEOUS EXTREMELY HELPFUL HE ARRANGED FINANCING FOR ME HE ARRANGED DELIVERY TO ME I'M VERY HAPPY WITH HOW SMOOTH IT ALL WENT

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).

I had an amazing experience searching for my new car! This Carmax has great customer service and salesmen!

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.

Amazing customer service from this dealer. Highly recommend. The dealer showed a high expertise and helped a lot with all the paper work and bureaucracy

My husband and I love our Grand Jeep Cherokee we purchased from Chrysler, Dodge, Jeep of Winter Haven. We love everything about this vehicle. Matt is our Salesman, and he did everything he could to get us in a Jeep we would like. I highly recommend this company.

I recently purchased a car at Kayser and had the good fortune to have Scott Bornick as my salesman. Scott was great throughout the whole experience. Professional and knowledgeable, he made the whole process seamless. This was my first purchase at this dealership and I highly recommend them!

Second lease on a Grand Cherokee. Different than my 2021 in many ways. The all wheel drive makes the steering more sensitive. Tricky parking brake and much smaller layout of gauges in dash. No Sirius satilitte radio. Seats are harder. Overall better than the 2021.

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!

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.

This car has everything we need and more. 4x4, looks, performance, can be towed behind an RV. Includes sun roof, rear camera, safety braking, more. Rides great.

This was my second time purchasing a vehicle through Carmax. My first time, three years ago, was for myself purchasing and exact vehicle I wanted. I called ahead, was able to work through what I wanted, and re-directed to another location that had the exact vehicle I was looking for. No hassling about buying something from their specific location. Great customer service, the car was in excellent condition (as confirmed by the Volvo dealership I had it serviced at subsequently). I still have and love that car. My most recent experience was at Carmax in Madison, WI. I have been searching for a well-maintained used vehicle for my newly-licensed teen. With the used car market spiking, I've been monitoring my searches for months. The perfect vehicle (with everything both my teen wanted and I required from a safety perspective) popped up in New York. For a reasonable fee they were able to put the vehicle on hold and transfer it to my local dealership in WI. I was able to do the financing over the phone in advance of the vehicle's arrival. Once it arrived, I was notified and an appointment set to test drive. The car was exactly as described, in good condition and no hassling or negotiations needed. The prices are reasonable based on current market conditions with a set margin built in. The financing is a little on the high side, but they provide a 3 day window to bring in a check from your own lender so it makes it easy to balance the rate vs convenience (and GAP coverage). I had one issue with the vehicle after getting it home. I contacted the dealership and it was addressed within a half hour. I am absolutely happy with both my experiences at Carmax and would (and have) recommend them for your next vehicle.

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.

Been going to Zimbrick in Sun Prairie for years. Great people and trusted! Both in purchase of vehicles and service department. Would absolutely refer to a friend/ relative.

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.

I have been buying cars with Jamil and Kunes for the past five years now. They always treat me with respect and better than any other dealership I have been to. Will keep coming here

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.

I've owned 3 Jeep products (2 Cherokees, and 1 Wrangler) and bought Cherokees 3 for my kids. Now they bought their own. Reliable, durable, and affordable. I love my 2017 Altitude. Looks great. The only thing I had to replace was a water pump at 80,000 miles.

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.

Kay did a great job - scheduling - complete service - and very timely. I'm totally impressed with every aspect of their service facilities. A job very well done!!

Runs smooth. Very comfortable. Always loved the Jeep brand so this was a natural upgrade. Love the options too. The adaptive cruise control is amazing.

I’ve owned many Jeeps over the years and this year and model has by far been the best in quality and performance The vehicles interior is exceptional in comfort and wear.

Marko Baxter was an amazing resource in helping us purchase our 2020 sprinter van. We are located in California and placed a lot of trust in the dealership, considering we bought the van site unseen. He was extremely responsive and assured us of the process. Julie Budwig expedited the paperwork and helped with getting finances arranged. The shipping company Marko recommended got the van to us in under two days. When the van arrived we were very pleased. There were a couple minor issues that needed repair and both Marko and Aaron Pfeifer in the service department worked with us and our dealership in California. We are so pleasantly surprised with how smooth of a process this was and how professional and trustworthy the people at Zimbrick are. Makes us want to move to Wisconsin (or at least visit)!

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 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.

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.

I needed a car quickly. This was a quick clean deal. Everyone there was helpful and considerate. When I need my next car this is the first place I will look

2022 Grand Cherokee Overland. Beautiful inside and out. Love the extras that the Overland package provide. Beats EPA milage estimates easily. ride comfort is very good, even in the rear seats.