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

I like how Omar the seller was helping me out on getting the perfect truck for me thanks to Omar because I?m very happy with my new truck

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.

Great people who follow through and work hard to make a customer feel appreciated. The car I was interested in wasn't the color my wife wanted or I would have purchased it on the spot. This is a dealer I felt I could 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.

The part i really appreciated about it was the fact that of the fine gentleman i worked with, Tim, Matt and Teddy, they understood that the 1 truck they had on the lot I liked but had one feature that I did not want to have on a truck I would buy for the future. I had said feature, Ramboxes, on the truck I traded and I think they was a great creation by Ram. I like the Ramboxes and the way they create extra storage on the outside of the truck for ease of access. However with my current and expanding family situation, I was going to need a standard bed. After I explained this to all 3 of them, they were polite and receptive of my request and worked hard to find a truck they could do a truck for truck swap that was on my wheelhouse of options. They were able to accomplish just that and I am very appreciative as the truck I purchased will hopefully be a lifelong vehicle turned into a collector's item since it is a special edition truck.

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!

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!

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.

Ayinde Garry is genuine and passionate about customer satisfaction. He’s very knowledgeable and professional. I would refer him to many others because he’s really detailed when explaining each question that’s asked without being misleading.

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.

A fantastic honest dealer, a breath of fresh air to deal with. Well trusted. Most important great price! Very knowledgeable and answered all my questions.

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.

Excellent customer service and great prices compared to other dealers with a Wide selection of vehicles. bought my first car from here and definitely coming back when its time to replace it.

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).

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.

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.

Sales staff professional. All questions answered. History of interest vehicle reviewed. Nice experience. But, a better price was not offered to me. So I lost some interest. This visit was the initial phase of my research, so everything was expected.

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.

We bought a Toyota Sequoia and noticed a couple of things that were a little off like the mirror the motor was out. They also did an inspection and found the back window did not go down so they ordered all the parts right away. Customer service is excellent! We worked with Jairo and is always willing to answer our questions at anytime taking our worries away. I work in sales and can see the Hussle they put in.

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.

Friendly and accommodating. Our salesman was Jeff Schultz and he was helpful and answered our questions. The car had been cleaned up great and what needed fixing was done. Our first purchase of a used car and it was 5 star!!

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.

Had a great experience buying 2 new cars from Stevie Weed! It was an easy going experience that I would recommend to anyone looking!

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!

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

I had an awesome experience at this dealership. Everyone I dealt with was very friendly and helpful. There was no need to haggle over pricing, they were upfront and fair in not only the cost of the vehicle I purchased but the trade in I had was priced more then fair. I live in Milwaukee and it was well worth the trip to Waukesha!!!

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 !

Tyler was very easy to work with. My girlfriend stopped by to look at a rav4, she and Tyler came to my place and took a test drive, deal was made at work, came into the see Tyler at the dealership after work. Came to good terms and closed on the deal. Appreciated not having to take off work to do the test drive. Tyler, thanks for everything

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.

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.

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.

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.

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.

Very pleasant auto buying experience. Great people to talk with and fair in their negotiations. I pointed out a scrape on the vehicle and they made a fair adjustment. It was the perfect buying experience … until I woke up this morning. I went out to wash the bugs off from driving home the night before and found several breaks and cracks in the grill and fender that I didn’t notice when I bought it the night before. They of course didn’t point them out to me. All I can say is, “Shame on me,”. My responsibility for not looking it over more closely. My bad not them. Buyers Beware! Look over every inch, twice. Everything is made of plastic these days.

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.

Had an awesome experience with sales representative Roy Visor. He was very helpful and knowledgeable towards my needs. Although I did not find exactly what I was looking for at the time, Roy was very patient with me. I look forward to doing business with Roy.

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.

Ours sales person was excellent, without Cecilia I don?t think we would of made it through the long process. Getting a trade in for our car took way to long. They need speed up the process! Also the finance part was backed way up and also need to speed that up!

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.