Used Jeep Grand Cherokee for sale near Milton, WI under $25,000

Follow up review on 2015 online Suburban purchase. Dealership went above and beyond to make things right and actually took responsibility for the items that needed attention. I went from never going back there to being their number one fan. Great customer service after the sale! Great working with you all!

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.

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.

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.

How friendly everyone is and how fast the service is. I have not had a problem here in the 14 years I have come here for service.

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).

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 !

Highly recommend this dealership! They are friendly. They took the time to explain all the car features and how they worked and answered all our questions completely. Would most certainly recommend them to family and friends. Will buy from them again. Great customer service!

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.

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.

I bought a 2004 Audi S4 from A to Z and I am very happy with the transaction. We quickly came to a fair price for the car, the car was exactly as described and the customer service and interaction was excellent. The sales rep, Abe Sarhan, was very helpful and quick to return calls or txt msg. I would highly recommend this dealership.

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.

Autoland Outlets service is second to none. I have bought 2 trucks from them and had great experiences. There is no high pressure sales, and there vehicles are all high quality. I can't recommend them enough.

We bought Bob the Burro new in 1992 for delivery early '93, prior to the first model changes. Bob worked well for us ( my wife Cathy included) over 263,000 miles before we gave him to our nephew, Shawn. Bob traveled pavement mostly, but had seasons of heavy snow in Michigan & Idaho, & mud in Louisiana, Indiana & both substances in Pennsylvania. Bob made Targee pass into Wyoming, in Jan. 2001, Wolf Creek pass CO Feb. 1998, & a unnamed pass between somewhere & Leadville CO in 1995. His other achievements include several white-out blizzards along I-70, I-80, I-90 & Malad pass Idaho over a road closed for 3 ft. show after entry (they thought we were lost). Bob did everything we asked, except stay air-conditioned & keep his radio on, for a quarter century. I easily fixed the air-conditioning & didn't need the radio. He used up 3 fuel pumps, one radiator, 5 sets of tires, 3 sets of shocks, 2 headlights, one fog light, 2 windshields, a couple skid plates & one seat cover. Bob carried lots of aftermarket lights, a cargo carrier, exterior tire mount, grille brush guard & overhead spot & warning lights (Police reserve & Chaplain duty). He was loved by 2 dogs. He pulled several heavy loads, including a mobile home & horse trailer. He was only hit once during his first week out of dealer, that in the rear which puckered his plastic bumper, a wound he kept for life. Our nephew drives Bob to work every day, takes him out in the snow & mud whenever available, keeps him in a warm garage (something he never had with us). We still love Bob & check on him occasionally. His successor, Larry, a Wrangler JK-US, called "Lizard Leader" is taking after Bob's record. Check with us in about 20 years for a similar Larry story. If you can find a "Bob", buy one; it's the ultimate vehicle for everything including the Apocalypse.

The Cool Car Guys treated me like family with a no pressure buying experience! Drew the owner was awesome to deal with and helped me get into the vehicle I wanted!

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.

Anytime I call and let them know that there’s a problem with my vehicle I bring it in and they take care of it. Found out yesterday that there’s something wrong with my transmission. Thank God for their warranties. I have a special needs son and I need a bigger vehicle and because of them I have that bigger vehicle.

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.

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

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.

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!

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

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

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.

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

Love my GC 80th Anniversary Edition. A little over 15K miles and she’s been in the shop 2 times now with a squeaking coming from the engine. Tensioner rod and idle sensor were replaced first, they had it for almost a month. alternator was just replaced, they had it for a week. Picked her up last night, drove her this morning and it’s still squeaking! Very frustrated but hoping to get her fixed!

Great family owned dealer. Easy to deal with and you can actually talk to someone that knows what they are talking about.

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!

Very good repairs were done correctly and a timely manner

I’ve owned many Jeeps over the years and this year and model has by far been the best in quality and performance The vehicles interior is exceptional in comfort and wear.

As I read, don't buy unless you can work on it. Plenty of things broke, but the parts are cheap if you can work on it. All four interior door handles broken, but all four replacements were $40, I put them in. Starter motor bad, $160 and very difficult to install, but did it. Exhaust manifold to engine gasket bad. $20 and very difficult to install. Rubber gators over CV joints, cheap, but very hard to install. Advice: watch Youtube video's, take your time, and don't get aggravated, I told you its difficult...Plus all the plastic fasteners and parts are dry and brittle after 17 years.

Robert delivered great service and I appreciated that they were able to transfer the vehicle to the Stoughton location for easier pick up.

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.

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.

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!

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!!

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