Used Jeep Grand Cherokee for sale near Bayside, WI under $1,000,000

After much copious research I bought a 2019 Malibu LT from Diamond Jim’s, my first experience with the dealership. Joe and Perry were knowledgeable, fair, and easy to work with—no high pressure tactics. No need to haggle and browbeat the staff, either, for a deal. The price of the car was previewed on Carfax, given “a good price” rating for its overall specs, and proved so upon inspection with no hidden after-market products to jack up the published price. Too bad there was no Diamond Jim’s when I bought my first used car way back in the 20th Century from a different dealership that filled the transmission case with sawdust to make it run smooth for a month.

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.

Recently bought a used car with low miles and a good price for my teenage daughter. Employees were helpful and we were very happy with the price of the car.

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.

This Car Dealership is a Wheel-y Good Time -- and So's Their Salesman Brandon! I recently had the pleasure of working with Brandon at the car dealership and let me tell you, this guy is the real deal! He's got more car knowledge in his pinky finger than most people have in their entire brain. Plus, he's got the charm and friendliness of a golden retriever. If you're in the market for a new ride, skip the other guys and hit up Brandon at this dealership. He'll treat you like a dear friend (and maybe even sneak in some car jokes).

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.

Great service. Straightforward and easy process. Would highly recommend to anyone. Will buy again here.

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.

Impeccable Serice Jeremy Simonson, Brandon Gilsch were incredible. They handles my issue with the utmost professionalism and speed. They took the time to investigate and take care of my issue.

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.

What an easy and smooth transaction. I can't say enough good things about the dealership and staff. Knowledgeable, professional, helpful.

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).

Lynch and their entire team is amazing. It is very clear that some people here (and on other sites) are more worried about trolling other people / people’s businesses than they are worried about themselves. If you actually understand that dealers have to make a little money to stay in business, then all is well. If you are one of the miserable “whiny” customers out there then just work on it yourself or buy it on-line!

THIS WAS AN OFF SITE WAREHOUSE SALE. I LOOKED AT A USED TRUCK. IT WASN'T WHAT I WAS LOOKING FOR. THE SALES PEOPLE WERE VERY POLITE AND FRIENDLY. AND NO HIGH PRESSURE. IT WAS A PLEASANT EXPERIENCE MORE THAN AT MOST USED CAR SALES.

It felt like family while purchasing my vehicle. Everyone was so friendly and we all were telling family stories from buying vehicles to our kids talking driving lessons or learning to walk. The salesperson was great, the finance person was great, the receptionist was great. I love the pecks that come with the vehicle and I love my Corsair, it's perfectly lovely!

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.

When I got there, I was told that the asking price for the car had been increased by $2500 because of some work they had done with the safety systems. I could obtain no more detailed explanation. I ended up buying it based on the originally posted price. I was a bit disturbed, but I know it wasn't the idea of the salesman, but more the idea of the sales manager who knew I was very interested in the car. But the salesman was wonderful, as was the financing guy. (I ended up not getting the extended maintenance or their financing, but he never pushed a thing.) It's too far away for service but I'd go back there for a car1

Gary Smith was wonderful to work with and very knowledgeable about my vehicle. I will be recommending and using his services in the future. The staff at Russ Darrow made car buying easy!

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.

Only dealership in milwaukee that had the car i was looking for and was patient enough with me to ensure i pulled off in the vehicle of my choice. as a first time buyer, i was very satisfied with their service.

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 bought my 2022 Wagoneer this week and could not have been happier with the entire experience. Joe, Brian, Chris, Krissy, and the finance team we’re all phenomenal. I have a lot of vehicle purchases under my belt and this team has without a doubt been the best. They have earned our business for years to come. Thanks to everyone on the team for making us feel like more than just a sale.

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.

Knowledgeable, attentive, honest folks. I appreciate the fact they are a locally owned, family dealership. They have earned my trust.

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.

Spike was very helpful and understood my needs Got me setup with the perfect vehicle for my situation. Would highly recommend him and the dealership

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.

Tyler, He treated me with respect and answered all my questions. I love my new RAV4 I got today. Thank you for everything!

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.

I always bring my car here for service- they are honest and good at doing the work that needs to be 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.

Our salesperson, Elijah, did a great job. When picking up our purchase, he spent as much time with us on a used Jeep GC as a new one. Demonstrating the vehicle features and connecting our phones to uConnect. Patiently and without being overbearing, I was impressed and would recommend him and the dealership.

Because it a great car because the car has 118k miles on it and its only 15,371 dollars and its used and works very well

Dealt with Ryan in Sales and Jeana in financing. Two of the best people I've ever worked with. Ryan went well above and beyond trying to make my experience pleasurable. He is the hardest, most sincere salesperson I've ever had the privilege of dealing with. I wish all sales people had his character and work ethic! Jeana was an absolute sweetheart in financial. She didn't try to sell me anything extra, just the basics to keep me covered. You can tell she loves just helping people get only what they need. High quality character and an absolute pleasure to "work" with!

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 !

Bob Groover is amazing, he is an authority on ram trucks and I truly appreciate his expertise. Ewald is a great dealership, and I plan to come back!

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.