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

Our sales person, Mike, went above and beyond to assure that we were very satisfied with our purchase. And we really enjoy our new ride. I highly recommend this dealership!

We bought it in 2023 just off lease as a CPO. It’s been a great vehicle. We love it would buy another one in a minute.

Very professional dealership. Jeremiah was wonderful to work for and not pushy towards the sale. I bough a used vehicle but it was in nearly perfect condition. Will definately be looking to purchase antoher jeep from them.

  I have the Trailhawk trim, the serious off-road version.  Finally, a car that I can confidently drive in and out of rough construction sites, and not be afraid that I'll break it or get it stuck.   It is possessed by a powerful spirit of wanderlust, and frequently demands that I take it on drives just to see places it hasn't yet been, preferably places that normal cars cannot go.   If Don Quixote de La Mancha lived in our time, he would surely drive a vehicle like this one; a vehicle truly fit for a modern Knight Errant.   I didn't know until a few days after I bought it, and I don't think the dealership knew either, but this one has about a 2" aftermarket lift, and slightly larger tires than stock.

The staff was friendly and knowledgeable.Jose answered every question I asked him. He is a good salesman He’s pretty funny to

I have a 2018 Cherokee latitude plus. More than 140k miles. Very nice SUV. I think most of this bad reviews are not fair. I will buy a new one in the near future.

They were able to get me an appointment very quickly. Their Service Department staff are very friendly and knowledgeable. Everything was explained to me very clearly and the billing was exactly what they said it would be.

Like the look and has plenty of power we have the v6 option The interior is very comfortable with all the bells and whistles you can appreciate. We traded in a Liberty and the ride is so much smoother.

I was very impressed with the quick response I received from both Jeff Meadows and Matt Borsecnik when I had inquired about the CX-5 SUV. After my initial conversation with Jeff, Matt called me back within 15 minutes to let me know they had the vehicle I was interested in and it had been pulled off the floor waiting for my arrival! Matt was accommodating to my schedule for a test drive. He answered all of my questions, was knowledgeable about the vehicle and offered me the special financing that was available for the CX-5. Within 3 days of our first conversation I was the proud owner of a new shiny red Mazda CX-5!

I drive a lot my car is a 2014 and it has currently 277,400 miles and still ticking. I’ve had very few maintenance issues overall the basic wear and tear as expected! I didn’t expect it would last as long as it has but I am being pleasantly surprised. It is great on gas compared to most SUVs and overall a comfortable car !

Very responsive about the questions I had on the car Michael, Michelle, Tara all very helpful

I love my Cherokee overall. This is my 3rd one. Sadly I've noticed the quality slipping. Jeep no longer provides a spare tire - WHAT? The floor mats are now of lesser quality and no longer have the Jeep emblem embroidered on them. The transmission is still a little iffy but not as bad as my '15. The tail lights fill with condensation but the dealership tells me it is normal to do so - WHAT? Additionally you're never gonna be able to find a V6 anymore. I had to go down a year to a '22 in order to get one. They are pushing EVs and Hybrids. All this being said I'm still Jeep girl and still love my Cherokee.

We have purchased 4 Mercedes-Benz and absolutely love the sales team (Tony!) and the service team (Jody, Cathi, Sam). I've been to other dealers and service places, and Zimbrick European is light years better! You never have to worry or second guess what they are saying. They also keep you super informed on how you car is doing with super detailed reports. I love the text communication and payment options-makes picking car up so convenient. We had an older car with high miles that developed issues, and they helped us out going above and beyond to minimize the stress...and eventually taking that one on trade for a new one! I don't trust anyone with our cars, except the folks here!

Overall, pretty decent car. As professional reviews will note, the transmission is a little finicky, but nothing over the top. Learn to work with it, it works with you. Bought this car used last year with 68k and I drive a lot, so I've already put 30k on it. Handling wise, this works great, even in the snow (FWD, not 4x4). Good cargo room, and room for the kiddo's carseat. Now, this is a Jeep, and hasn't been without issue. The front struts have been replaced, probably as part of my driving style and the rough roads in my area. Part of the bumper got pulled off a while back, not a big deal. Mechanically, decently sound, the car has thrown a few check engine lights but for non-issues. It had an issue a while back where it would turn off or restart on its own when stopping (not to be confused with the auto-stop, which is annoying but can be turned off, this car would just flat out turn off), but that fixed itself. Developed an engine tick that does appear in Jeeps, but that has also righted itself. As such, no major maintenance has needed to be done besides my struts. So all in all, it works. If you're in a situation like mine, yeah, buy the 2019.

A great looking car. We will probably never learn all of the features the car has. Dealer was excellent and no problems working with them. Only one thing not to like was the location of the Emergency Brake lever. Things seem to get set there, and locking the lever.

I was looking for something good but reasonable and found it at the Used Car Factory. I found a great newer model Jeep at a very reasonable price. Jay was very helpfull and accomodating and made our overall experience a great one. If you need a used car, you have to check this place out!

A few years ago I bought a 2014 Jeep Cherokee Latitude, at the time it had 24,000 miles. Today it has 68,000, at the time it was a really good upgrade from my last vehicle, a 2005 Dodge Grand Caravan. I loved the comfortable cloth seats, the V6 engine had tons of power for commuting and good gas mileage (I've gotten over 30 on the highway). After 5 years of owning my Cherokee it has never let me down, it has only gone into the shop for a CV Axle, which Chrylser had paid for most of, and tires. Now that my Jeep is going on 7 years old, I'm in the market for another car, I've not even considered anything other than a 2021 Jeep Cherokee, especially because I am considering leasing and lease deals are awesome with Jeep / Chysler.

Great cars, even better people. Highly recommend for anyone interested in buying or selling a vehicle.

I bought my 2019 Cherokee new in July 2019. I have had it for 4 and a half years now and I have had no problems at all. I have over 61k miles on it. I do worry about the warranty being up that something might happen but it has not given me any issues so I shouldn't really be letting it bother me. This is the longest I have had a vehicle. I usually keep a car and trade it in around 3 years but I have loved driving this car so much that I have no desire in letting it go. I hate that Jeep is no longer producing more of these.

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!

Was at dealership shopping and this new Jeep Cherokee Lattitude came in on transport. Wanted it the minute I saw it. Jeep dealership had ordered it custom with every option I wanted. Blackout package, V6 a true dual exhaust, sport, power everthing, 4x4 etc. The 4x4 is excellent and never failed me! Its been flawless, aftermarket tuning has turned it into a screaming black speed machine. 112,000 miles so far. No issues with anything! Would buy another if they still made this Cherokee Latitude Special! One very satisfied customer!!!

Would recommend this vehicle. Overall very good value and has proven very reliable. Sorry to hear it is being discontinued Jeep had a winner and what I thought was a great tweeter between the Compass and Grand Cherokee.

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 recently a used 2020 Cherokee Limited and it has turned out excellent, I have no problems or issues. The only minor issue that I have is the location of the cup holderss.

After having an oil and filter change, we noticed a swishing sound. My husband pulled the air cleaner and discovered that some 'tabs' were not place properly. He fixed the problem and the swishing sound diminished. Not a big deal, but it would be nice if it wasn't there.

Great SUV...BOUGHT in 2017...good on gas penalty of zip with V6 engine. The start stop stop working last year and found out why.I needed a new battery as went dead this year...now start stop feature works 100 percent. Have low milage 30000 miles or 50000 kms here in Canada. .

Out of town my breaks went out, after aging them replaced at a different dealership. This dealership was the closest to my location. They were able to fine the part and repair the damage hose. Which my exteded warranty did not cover . But still good service. The only thing is that some went through my glove box pulled just about everything out and left it I. The front set. So disappointed

Go with the 3.2 V 6 it has plenty of power. The Auto engine stop/start is terrible even if it does save gas it is too jerky

After a disappointing day shopping at other dealerships I was very happy to find Bryden. Friendly low pressure sales staff. Was able to take time to review all numbers and they stayed late to complete the sale!

We worked with Kyle on our purchase, very knowledgeable, and we ended up getting the car that we wanted at a fair price. Met many of the staff, all very friendly. The only improvement opportunity, was the process took a long time. They seemed to be very busy, and somewhat understaffed, so they were dong their best, but it made for about a 7 hour event over two days. RB

the car is largest enough to haul baseball equipment around, yet easy parking and handling. i like the interior and the room. the seats are very comfortable

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

I have been looking at new Jeeps for awhile was needing a new vehicle was driving a 2005 dodge grand caravan sxt drove it everywhere kid's learned how to drive in it. But I'm a jeep guy have a 1979Jeepcj7 since brand new drive it daily. Seen the jeep cherokee trailhawk at my local dealership talked to them about it took it for a test drive and fell in love with it. Had to take it home. Very comfortable all the buttons are in the right places. Display screen is very simple to navigate easy-to-use app's phone linked right up no need to look at it. Mics are in right places above head everyone I call or calls me has no problem hearing me. Has alot of safety features to get use to but not hard. I have had other cherokee in the past but love this one. If you are interested in a Jeep check out the Cherokee line like I said I'am a Jeep guy test drive and you will see what I mean.

Fast, courteous, personable, professional, a great experience— thx! Will recommend to others! Work was excellent.

Purchased new in 2015. Have only done 1 repair in 129k, which was fixing oil leak at oil filter housing. Solid car, great in rain and snow. Thoroughly enjoy this car