Used Jeep Grand Cherokee for sale near Watertown, WI under $20,000

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!

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.

Jason Archimede came to us as soon as we walked in answered all our questions and after explaining what we were interested in quickly found us the car we were wanting within our budget. He kept us comfortable and entertained our toddler making it as smooth as possible and made sure we were 100% satisfied and setup before driving off the lot

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 found Phil Aleio to be very responsive to questions and Kaifer Zulesdorf especially enjoyable to work with. I trust him and plan to trade cars back and purchase future special vehicles. Great experience from a Wisconsin dealership!

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.

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.

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.

The best experience I have ever had buying a car. Tom was so nice and helpful, and talking with him was like talking with one of my good friends. The van I bought is still running great and I just love it.

Purchased my 2007 Grand Cherokee Laredo with 87,200 miles and am proud to say this Jeep is the best vehicle I’ve ever owned. At 192,500 miles and it still runs beautifully and has withstood New England weather.

i did my homework prior to our recent purchase of a low mileage used Mercedes. One of my primary information sources was Cars.Com. and the other was Car Max. We visited the Kenosha Car Max and found everyone we had contact with to be professional and informative. We ultimately bought a car from a Mercedes dealer but did sell our trade to Car Max Waukesha. The experience was handled quickly and pleasantly. I would definitely recommend Car Max and their staff.

This is the best car we've ever had! Before my wife passed away, we bought this car (pre-owned), she fell in love with it and insisted on driving everywhere! Since she passed in Sept, 2021, I've been driving it and I LOVE IT TOO! I have some issues with programming/memory, but the dealer assures me they can fix this problem

I was extremely happy that Stuart, my service representative took the time to listen to my concerns. Once the inspection was complete, he explained each line item. I made the decision to only do 2 or the 7 recommendations at this time. I never once felt pressured to get all done immediately. He even highlighted the items that would be wise for me to do next. I will definitely go back for the additional recommendations to this location

I bought my used 2017 limited around christmas of 2022. Its now may of 23 and i cannot believe how much i like this thing. Always been a ford truck guy but for a great all arounder....this jeep cannot be beat. I got the 3.6L V6, has alot more giddy up then you would expect, tows my 4200lb trailer with ease, and in my daily driving i average around 22mpg. Snow/off road performance is excellent...its not a 78 Bronco but for a modern SUV its very capable. 10inches of slushy snow riding on street tires it ate it up and asked for more. Its comfortable, drives good, and ive put 7000mi on since december with not so much as a hiccup. Reccommend to anyone looking for an SUV.

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!!!

Bought this SUV last week. My "new" 2012 JGC had 227,000 miles on it. The salesperson didn't know much about the Jeep, as it was a Ford dealership I had gone to. Two days later, I had to go for preparations to bury my son, over 800 miles away. I was very fearful, because I had this JGC that I had never driven before, and I was on this journey alone. I have seen so many cars with temp plates sitting on the side of the road, and was fearful mine could just be another one. Needless to say, the only 2 things I haven't liked about my vehicle transaction, is that there is no owners manual, and evidently the sensor for low fuel doesn't work. I knew about the owners manual before the purchase, but not the low fuel indicator. I will just fill up at 1/4 tank asI always have. LOVE, LOVE this vehicle.....stylish, comfy, and all the perks. Auto start and heated seats will surely be welcomed as winter can hit hard here in the midwest. So far, the best car I've had, and I've had a lot over the last 55 years!

I had been looking for a while was having trouble getting financed I did have some money to put down New 2 You in Waukesha sales team worked hard to get me taken care of it wasn't smooth because of my part they made up for it and got me into exactly what I wanted thanks guys

Even though throughout the 18 years that I've owned her, I have put quite a bit of money into her, I feel that she's a dream!!

Great family friendly people and would recommend Select Auto to any family member or friend. If you want a great buying experience this is the place to go to buy all of your vehicles!!!

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!

Alan Z made magic happen for me! No pressure, no run around, just a great deal! Best car buying experience yet!

I already owned this vehicle when I took it in for service. But. I love the vehicle. I haven't had any major problems with my Jeep Summit

This vehicle met all of my needs. Excellent handling in the snow with the Snow setting. It’s a great car to drive in the summer as well. Dual sunroof and cooled seats.

I went in for an oil change and came out with a new vehicle. The sales staff are amazing. Friendly, accomodating and efficient. The manager in the service department pays attention to the details. He has been very friendly and accomidating.

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.

Everything about my experience was top notch. From the salesperson, Justin, the manager, Maik, and the finance manager, Mo. I truly felt like I was in the most capable hands. The best car buying experience I have ever had.

This car served me very well for a number of years. It was able to transport a heavy load with minimal effort. It was extremely comfortable to ride. Only downside was limited acceleration.

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.

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.

Love the vehicle Very clean and well-maintained excellent history Love the air suspension the jeep Overland Grand Cherokee is a great vehicle Would recommend this vehicle to anyone

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!

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!

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

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.