Used Jeep Gladiator trucks for sale near Wind Lake, WI under $1,000,000

Unexpectedly Surprised! Jim, aka Turk, the 2nd generation owner of Diamond Jim’s is a 10 out of 10 and if the scale was out of 100, he would be a 100 out 100. Here’s my story: I have had over 35 Corvettes and had been looking for a 2015 Corvette - Daytona Sunrise Orange Metallic - convertible - 7 speed manual for 18 months and finally found one and it was at Diamond Jim’s in Milwaukee, WI. I called and spoke with Jim and he suggested that we FaceTime and we did for it a good 20 minutes. Car was great except the tires were a little worn … not a problem … I put a deposit down and scheduled a flight from Southwest Florida to Milwaukee with the plans of driving it back 1,430 miles! 🤪 I have never flown cross country to buy a car before so I was a little nervous to say the least. We arrived at Diamond Jim’s and met Jim … the car was everything he said it was and better (fair price too)! This is when things turned to the unbelievable and quiet frankly, shocking … Jim said he felt uneasy selling me the Corvette with the slightly worn tires so he replaced them with brand new OEM exact factory replacement Michelin tires!! I have another, identical Corvette and recently replaced the tires on that one for a whopping $2,000!! 🫣 Jim apologized for not giving me a full tank of gas (it was 1/2 full) … I said, “Let me see, a full tank of gas or $2,000 worth new tires!!” He laughed and said the construction in front of his dealership prevented him from filling up the tank! He’s a true gentleman. Then, to add to this amazing person that I just met, Jim called us about 2 hours later during our drive home making sure that we were doing OK!! Lastly, we plan on buying another car within the next year and there is no doubt that we will call Jim, take his word for the description of the car, pay for it and ship it to Florida … we drove the 1,430 miles in 28 hours and we don’t plan on doing it again! 😁 I have been buying cars since the late 1970’s and I have never had a better experience than I did with Jim at Diamond Jim’s and I give them the highest recommendation possible!! 👍

We special ordered a Jeep Galdiato Rubicon in 2021 and loved it. Our only problem was it didn't leave much space in the garage. We decided to trade it for a special ordered Jeep Wrangle 4dr. RubiconX. This new vehicle left us with 34 more inches of space in our garage. We still have our 2021 Jeep GrandCherokee Trailhawk as our long trip vehicle. 2 never gave any problems accept with the Aux, battery after 3 years of own

I bought a car from Pete Espinoza. And I had a great experience there at that dealership. He was so patient and kind and moved things right along. I would definitely buy another car from him.

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!

Although I ultimately did not buy a car from this dealership, I was thankful for their assistance during my shopping process. My sales associate, Griffin, was extremely helpful - patiently answering my questions and providing me with information that I was looking for. Hopefully we'll be able to cross paths again sometime!

It’s a Jeep, so people who buy this understand what it’s all about, great off road performance, reliable and fun to drive. The Gladiator is unique because it’s a pickup and gives you more flexibility on abilities to carry more, but doesn’t hamper performance in any way, also, priced well compared to similar vehicles.

Nick K in sales was exceptional! 10/10 customer service! If you need a new or used car, go see Nick! He was extremely professional, and did not pressure me at all!

Tim is an excellent salesman. We haven't closed a deal yet due to other issues not relating to Palmen Even though they are an hour and half away from me, they earned my future business.

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

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.

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!

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!!

Cheryl was great, and the process was quick and painless. A great experience at Serra.

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.