Used Jeep Gladiator trucks for sale near Yorkville, WI under $599,984

My experience with Mark and Virgil made the trip to Milwaukee worth it. Virgil was kind, made the deal work, and then explained everything about my new Jeep. He took his time with me and I never felt rushed or pressured. I would definitely buy from Griffin Hub again and have Virgil as my salesman.

My Gladiator is 3 years old. Driving in Alaska and what a great vehicle. Starts every morning with no issues. Drives great in deep snow thanks to the ground clearance. The ride is stiff-it’s a Jeep.

Ritchie Sutton.. 3 years later and still on top of his game. Grade A salesman, thank you for all your hard work and dedication, to my Honda needs!

my grandmother sadly traded in this gladiator i wish she would have kept it . It is very comfortable,reliable,it look great on the outside,it has enough power,and its value is very good.

My husband went into the dealership this afternoon and worked with a member of the sales team named Victor. He was able to work with our credit and our trade in to get us into a reliable vehicle that we could afford. He was thorough and efficient and we were well taken care of. We appreciate his help and couldn't be happier with the experience.

my grandmother sadly traded in this gladiator i wish she would have kept it . It is very comfortable,reliable,it look great on the outside,it has enough power,and its value is very good.

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!!!

MOST importantly it is a JEEP. If you want a luxury vehicle, buy one, if you want a full-size truck, buy one, if you want a sports car, buy one, the Jeep Gladiator is none of these. It is designed to be a mid-sized pick-up yet still be a Jeep, it does this PERFECTLY. I have owned 9 Jeeps over the years, as early as 1978 up through 2006; the Jeeps today are full of more amenities and comfort than they ever have been in history. I have 2 Gladiators; a '23 Mojave, and a '23 Diesel Overland, both of them are INCREDIBLE vehicles on and off road, and MORE than fit the bill for a light duty pick-up, superseding most others on the market, and I am even comparing to any of the 5 Tacoma's I have owned. If you are in the market for a light duty pick-up, you can't beat it; whether it is a loaded up graded model, or even the base model, it is still a truck with 4WD, straight axles, and still available with a manual transmission. VERY happy with both of mine!

Visited Raymond Chevrolet on 10/10/25 after texting with Blake. When I arrived I was greeted immediately by Drew and he seemed to immediately know exactly why I was there. Pulled the car around that I wanted to look at and off we went on a test drive. Drew had more of a consultative approach rather than a high pressure approach which was definitely appreciated. The car drove great, yet my hopes weren’t high due to the fact that I have bad credit because of some stupid mistakes I made when I was young and haven’t spent the time/effort to repair yet. After a quick discussion with Drew upon our arrival back at the dealership, Jerry, the Used Car General Manager, came over to sit with me and he answered every single question I had written down (and there were around 15 of them!). At this point, they already knew my credit situation since I made them aware pretty early on. Instead of just going through the motions, EVERY single employee at Raymond Chevrolet took the time to make sure my questions were answered and ensure I had a great experience and I never felt less than or judged because of my credit situation. After Jerry answered all my questions, I wanted the car! I had previously been denied for an auto loan through a local credit union (even with offering a higher down payment than I did at the dealership). It didn’t take long at all and after a very short wait Jerry came over and approached me with his thumbs up, “we got you approved.” I was literally shocked….Sure, I didn’t get the best interest rate possible, but with my credit, simply getting an approval at all was amazing. At this time it was around 9:30 PM and the dealership closes at 9:00 PM. If there was an employee that was needed to make this happen for me that night, they hung tight and worked late to make sure I was taken care of. I want to give a special shout out to Janelle, the Customer Experience Manager. Janelle walked me through some very important Tesla specific topics and was very patient with me. The entire time I felt like I was being HELPED, not SOLD. Any “add-ons” were throughly explained and literally each one made sense with my situation (kids, first time Tesla owner, Chicago winters, etc.)… They offered me what I really needed, not just what they could make extra money on. Janelle made sure that I was clear on everything and then I wrapped up the process with the Sales Manager Cooper. Cooper made the signing process extremely easy and went above and beyond to make sure that what needed to get done, got done that night regardless of the time or any obstacles we encountered. At this point, I was extremely happy with my experience & it was time to head out at which time Jerry (manager) and Drew (sales person) escorted me from Antioch to Pleasant Prairie just so that I could take the vehicle home THAT NIGHT. Keep in mind, by the time we arrived in Pleasant Prairie, WI, it was at least 1:30 AM. My plan was to check out a vehicle so that I could then go look for a co-signor because I didn’t think I stood a chance of getting an approval; however, the folks at Raymond Chevrolet made it possible for me to make ONE trip to the dealership, purchase the vehicle ai wanted AND take it home that same day… All while going above an beyond to make sure that I was taken care of and having a great experience which I 100% did. IF YOU ARE AFRAID THAT YOUR CREDIT WILL PREVENT YOU FROM BUYING A CAR FROM A DEALERSHIP, I URGE YOU TO VISIT MY NEW FRIENDS AT RAYMOND CHEVROLET AND JUST GIVE THEM A CHANCE TO DO WHAT MANY PLACES JUST AREN’T ABLE TO - ON MANY DIFFERENT LEVELS (non-judgement environment, friendly and extremely helpful staff and even the ability to obtain an approval for financing for someone with POOR credit). Every aspect of the experience was on point and I highly recommend visiting Raymond Chevrolet if you’re in the market for a new vehicle and you want to avoid the high pressure sales tactics that we see too often at dealerships! Thanks for everything, guys!

I have 84,000 miles. I don’t hit rod it. I keep it below 2500 rpm unless a must pass happens (rarely). Zero issues with transmission brakes electronics heat or AC. Overland model. It has been a wonderful rig with 19 to 25 mpg. I’m 64 and hoping this and my XJ are my last rides. Both rigs are exceptional. I had a scrambler and loved it, had to have the Gladiator and my 2020 has been far better than expected !

My wife and I found the slightly-used Nissan Leaf at Cars.com and were sure that's what we wanted. But we didn't want to drive to Waukesha from West Bend, so we went to the WB Nissan dealership, also part of the Russ Darrow empire, and people communicated and cooperated and the next day the Leaf showed up in West Bend, we took it for a spin, and we're now its happy owners. So a big Kudos for the friendly and helpful sharing of resources. Beats defending your turf(s) anytime.

Love this truck/Jeep! I moved from a SUV to this Gladiator and have never looked back! I have not found anything that I cannot do! If you have any sort of lift, have the fasteners checked every 30,000 miles. Just a FYI, I speak from experience.

This dealership is Awesome and easy to work with Will be back! Make sure you get your floor mats.

This is a.rock solid vehicle that defines “utility” better than all the rest. You have tons of ways to configure the vehicle every day. Open air roof, doors off, entire top off, pick-up truck uses, off roading, climbing, travel, snowshoeing, skiing, snow driving, trails and dirt roads, hiking, carry bed loads, trailering, ATVs, etc, etc, etc. No way to ever find it boring. Plus, the extra bonus of the culture, friendliness, the wave, jeep groups, and the way it promotes and nurtures getting outdoors and getting active. No issues. Alpine stereo is great. Nav is great. Heat is great. comfort great, carrying fun loads great, towing to 4K lbs great. No complaints.

Excellent dealership experience. Miller Motors added a lot of value to the vehicle both in warranty and repair/recon work done. Mike Asencio, George, and Brandon were wonderful to work with.

Reliable and great looking truck! Love the way it rides and how many options they have to customize this great mid size vehicle. Love the color options

Went for a scheduled oil change. Waited about 1 hour, which is pretty normal. Was treated with respectful & courteous service from the service adviser. Have been going to this dealership for a long time. I would recommend them for your service needs.

I think my 2022 Gladiator is one of the top vehicles I have owned The only drawback is the lack of warranty service from my local Jeep dealer.

The Boucher team has always made us feel like family whenever we do business with them. Mike Hanson, Scott Foote, and Mike Garrett all went above and beyond to make sure we were taken care of. 5+ star service. We will be a life long customer for sure!

Great vehicle for enjoying the outdoors in being able to explore new places other vehicles could not go. Looks like a vehicle that can take you into areas safely.

Did a wonderful job for me I would recommend this place for everybody great organization

Have driven Jeeps in the military and loved the performance and easy maintenance. Have 2 Jeeps now and looking to replace one of my Jeep with another one. Love Jeeps!!

From choosing our vehicle, picking it up, finalizing paperwork, our experience is always seemless. We have our cars serviced here as well because their expertise continues the duration. We will only use Uptown Motors!

I have a jeep gladiator mojave, 2021, great vehicle , the best i have ever owned, great for offroading and the suspension is great, designed for higher speed offroading and it does a great jjob at this and just regular off roading. also fun just to drive around town. Highly recommend this vehicle, i also love the xtras, led lights, safety features, (blind spot and ADC, etc), aux swithes . This just a great vehicle.

Hands down, one of the best dealers in the area. 10/10, highly recommend. The customer service was amazing. Everything about the buying process was awesome.

I am a old school jeep owner, what they have come up with in the Gladiator is a hit. The ride along with rugged styling and performance and a usable pickup bed is fantastic.

My husband and I bought a 2018 Toyota Highlander XLE and could not be more pleased with our purchase. They were extremely knowledgeable and answered every question we had regarding both the vehicle and financing. We are so glad we bought from Car Corral and we will be back again!

Went to the dealership in August of 2020 to get a 2 door Willy. They did not have any and due to COVID did not know when they were getting any in. I had just purchased a grand Cherokee from same dealership about a year prior but needed a jeep wrangler as I previously owned one. They had a 2020 Jeep Gladiator sport on the showroom floor with a ton of extras (2 inch lift kit, all Fox shocks, coated bed liner, custom bed cover (hard shell), 34” all terrain tires, Matt black 18” wheels, led light bar mounted right in front of the front windshield, 2 led lights at front on either side, custom soundproofing on the inside hard shell top and I think the beefed up tow package but not sure. Within the first 2000 miles loaded a 35’ tv weighing 5800 pounds and headed out to Utah from Chicago driving through Colorado. The thing was phenomenal towing this heavy rv up and down the mountain pass on I 70. At a gas station some guy with a fifth wheel and a Ford F350 asked me what I was doing towing such a big rv with such a small truck. Kinda laughed. Saw him on the road later going up a mountain pass and blew right past him in my small truck. This truck has been nothing short of amazing. The dealership I purchased from is the best I’ve ever dealt with (Fields Chrysler/Jeep in Glenview, Il). They always have a loaner if needed. They are awesome. I bought in August of 2020 and today I have just shy of 70k miles on it and still running strong. I do not know why everyone says these things top off at 97 mph. I have gotten mine up to 110mph with a bit of room to spare. Gets to over a 100mph rather quickly. Maybe I just lucked out on a good one. I’ve read a lot of people complaining about a little water run off from the front door design. They are not wrong but you bought a freakin jeep, you’re not going to melt. Grow a set. Best vehicle I have ever owned. Best part with all the extras that came with it I got it for 49k with 15 miles on it. That same gladiator was there when I bought my grand Cherokee. I guess they were sick of it sitting on their showroom floor because back then it was listed for a tad over 60k.

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.

I bought my 2021 Overland new. I love it!!! It is fun to drive. Handles well in the snow. This is a well made vehicle. I love the leather seating. The best heated seats and steering wheel I have owned. I’m definitely a fan!!

Worked with Johnny very professional, kind and helpful. Give him a big raise!!! He us great 10 all across the board.

Mojave trim gives a smooth ride. A big improvement over the 2012 Rubicon Unlimited that I had. 17-18 mpg around suburbs and 20-21 on trips. At 13,000 miles no reliability issues. 8-Speed transmission coupled with the 3.6 v6 works well. Great in SNOW. Recommend the AWD optional transfer case.

My salesperson Kevin Klemz was a great salesperson. Understood what I wanted and was patient while I completed the deal.

Always go to Pilson auto, we always use the same salesman. Always have a good experience! The salesman always answers calls and texts even if he is not at work! Everyone there has always been extremely friendly and helpful!

My new jeep Grand Cherokee had a turn signal problem. As you know technology can be a problem! What sounds doesn't always work that way. Anyway it took 2 appointment. Steven Fee kept me up to the minute with what was going on. He was friendly and very nice. Even with the service area being very busy, his mood never changed. I have been a Jeep owner since early 80s. All my cars have come from here because I appreciate the staff. Thanks again Steven!!

We got the Honda Accord. Ken, the Sales Consultant knows his field. It’s just frustrating because there’s a long wait for the financing office. We stayed 5 hours in the dealership & it’s mostly waiting for the financial office to process our papers.

This is my 3rd Gladiator, I really enjoy the Jeep lifestyle, the Gladiator has been a great addition to my family and we have a ton of fun with it. It’s very versatile we use it for pulling our boat and Travel trailer and for everything else!!