Used Jeep Grand Cherokee for sale near Winchester, WI under $40,000

The dealership and staff were prompt and friendly. Issue fixed and delivered on time. My only negative is that in making the appointment, I was unable to get in for over two weeks!

Have owned Jeeps for 35 years. This is the most comfortable ever. Altitude 4x2 L, V6, avg. 19-24 MPG. Tow up to 8,000. 6 passenger with 2 fold downs in back. Paid 34k with 18k miles

After my car came from the body shop, it was spotless inside and out. Will be looking for a new car in the spring and I will be going to Bergstroms we have always got our cars from Bergstroms.

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.

Issac, the Nissan technician, was so helpful! He maintained excellent communication with me through the whole process of obtaining approval from the warranty company to cover the cost of a new transmission. The process took a few weeks during which he was calm and courteous through it all which helped me so much! We didn't purchase the vehicle at Bergstrom, but were treated with such respect! Thank you!

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.

Great experience with representative Joseph Hawley. Fast, professional, and polite. I do recommend if you are looking for a good deal and a good vehicle.

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 !

There are many things to mention. To begin, I've been looking for for a vehicle, new or used, the last two months throughout eastern WI. Mine was totaled in an accident, so this wasn't an impulse purchase by any means. The car market is crazy, and not in a good way. I was greeted at the door, door opened, and referred to a sales person, Kara Homan. No exaggeration, I wasn't greeted at any dealership the last two months, but instead had to hunt people down to inquire about purchasing. I wanted to test drive a Chevy Spark and was in a car within 15 minutes. No sale was made at that time, wanting to visit a few more places. After pondering over dinner, I went back to Bergstrom Appleton to buy the vehicle. The final price was acceptable and Kara started the paperwork process. I think it took 30-45 minutes and done. A new Chevy Spark owner was born. Maybe I should have started with Bergstrom first and it wouldn't have taken two months! In addition, my vehicle was delivered to my home in my driveway 70 miles from the dealership. The drivers were very nice and professional. Overall, this was the best experience with buying a vehicle - ever.

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.

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.

Great service! The owners are very friendly and have a lot of experience. This is where I will always take my vehicles.

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.

Everything went smoothly and work-to-be-done was explained. I am an elderly woman and they do their best to be sure I understand what they are doing and what they feel should be taken care of with my older car. They are always very helpful.

I initially leased my Grand Cherokee Limited but ended up buying it outright at lease end. It has been an awesome vehicle for the 6 years I've had it. I have only had two minor things that have needed work, one was AC needed more coolant and leaking rear strut which must be a fairly common issue as my mom's Durango has had the same problem. Super comfortable ride and plenty of room. My only beef is the halogen factory lights are horrendous but swapping the bulbs out for LED made a big difference for under $200. I normally don't keep a vehicle for longer than 2 years, but after 6 I love this vehicle just as much today as did the day I ordered it!

Hue was fantastic, very responsive and took the time to answer all questions. We never felt pressured or rushed to make a decision. Hue worked with us to find a car as we are over 4 hours away form the dealership. Hue went out and took specific photos of the vehicle for us. Highly recommend Hue and the 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.

Nick did a great job of getting my truck in after I forgot my appointment,. Mechanic did a great job on it. Will use dealership again

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).

Quick and courteous service. They even had the car driven from Madison to Neenah. Sam is an excellent car salesperson! She listened and was kind and understanding.

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.

Service department is great, people nice, clean, they even clean my jeep. The service writers are very helpful. Service was very quick and complete, thanks

Bought the vehicle with 30,000 miles. Turned over 100,000 this week after four years. ZERO unplanned visits to the dealership. Just normal oil, filters, wipers. Since we tow a 3500-pound boat, decided to replace the brakes at 80,000 miles, turns out there was still plenty of material left. Infotainment screen developed minor delamination this spring. Was still working fine but decided to replace it anyway. Easy replacement job for $350 with YouTube help. Lowest maintenance vehicle we have ever owned.

Anti-Freeze and oil leak discovered during routine servicing. Called my SD, Nick, at Kolosso Dodge in Appleton to have it repaired. He got me in as quickly as possible based on repairs needed. All repairs completed in one day, to my satisfaction. Nick, as always, was polite, efficient and prompt. They are the best.

This is my 2nd Jeep Grand Cherokee (previous one was a 2016), and I absolutely love it. Gives a very smooth ride. The vehicle feels very sturdy and solid, which to me is another plus. Disappointed that it didn't come with a cargo cover though!

I was very satisfied with the service and the friendly people who helped me. Very customer oriented facility. Knowledgeable and competent staff. No further requests or recommendations.

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.

Highly recommend. Staff was excellent and very good service. Vehicle was as nice as advertised. Traveled from out of town and they made it a very easy transaction.

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.

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!

I used the shuttle service after dropping my car off for an oil change. Doug the driver went above and beyond with the drive home. I forgot my keys at the dealership. He was understanding and very friendly. Excellent service. He was wonderful.

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.

I did not get the feeling of pressure, more guiding through the process. I appreciate the direct don't give me a line approach and that is how I prefer to shop. I don't like to waste peoples time or mine. And that is how it went. I have been very happy with the process, I have already made recommendations to people, some looking for a Jeep specifically to go to you and I have specifically told them that it is a laid back approach and not pressured. I also appreciate what appeared to me what was a good fit for me, not lets get you in a bigger more pricier model to make more. It was what was working for me best.

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.

Mike Boll was very prompt in returning phone calls/emails and very knowledgeable about the vehicle I was purchasing. I have bought several vehicles from here and will continue.

bought a new 2022 GC Summit. I wanted the hemi, only found it in Summit pkg at the time. Overall love the vehicle interior is as nice as anything out there. Real wood, lots of leather and nice materials overall on interior. Kicking stereo. Had a 2016 Overland with hemi. Wanted one more new hemi before quit making them. Easy 20-22 mpg at 70 mph. Plenty of power, very quiet and smooth. Biggest complaint all the plastic trim on the outside. First time i shut the door sounded like a rattle or something, not as solid as the 2016, when i shut the door it sounded solid. Nothing i could find wrong just pieces seeming to make a noise. Overall love it. Looks great, rides great, descent mileage, and very nice interior. Did i mention messaging seats are real sweet. Also plenty of towing power which i needed. Excellent in the snow as well.

The staff at VHB is very helpful John communicates well and makes sure that you are comfortable with the work being done. The technicians do a great job of servicing my truck I have never had an issue with the work they have done.

New Jeep GC owner…about a month in. Bought a ‘23 Grand Cherokee Summit after admiring the looks of it. Was nervous to purchase because I usually drive foreign. I also own a ‘22 Audi and have to say that the quality of my Jeep is comparable. I am pleasantly surprised by the drive as well as the quality of the finishes. The ride is quiet and smooth. The 6 cylinder has plenty of pep and has no trouble getting down the highway. It even has a bit of a growl when you step down on it. I legit smile every time I drive my Jeep.