Used Jeep Gladiator trucks for sale near Winsted, CT under $40,000

This was my first Jeep Wrangler purchase and it was very pleasant and my salesman Henry went above and beyond! I was astonished with how much Henry really cared about me and how much he actively assisted me with purchasing my vehicle.

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 have bought many cars and this was the best experience I’ve ever had,Gerald made my buying experience smooth and easy.I would recommend this dealership and this salesman to anyone.I changed my decision on the car I came in for and switched to the one I bought and Gerald made the sale effortless for me,and remarkably fast,can’t thank them enough

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.

Worked with Steve, didn't end up buying but he was super nice and upfront with us. A much better experience than some of the dealers we talked to on this journey.

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!

Came to thrifty in a pickle and Mike helped me out tremendously! He went above and beyond to get me into the car I really wanted! The finance manager went above and beyond to help me with a payment as well! I definitely recommend thrifty to anyone!

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!

It was a pleasure to deal with Zach, Patrick and Mike. The car was as Zach described, and I am very happy with it. The purchase was made easy by these guys and they were very accommodating:)

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.

Great sales person Tyler used car sales manager never met could’ve came out and introduced himself, but could not say enough about the sales person Tyler thank you again

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.

Great sales and excellent service departments! Have leased two jeeps and have always been happy going here. I would recommend to go here to others!

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.

Kyle and Richard thanks again you guys are the best. Proud owner of a 2025 navigator

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!!

Fantastic sales team at CDJR. Cassandra walked me through the process and made purchase of my new Jeep simple and easy. Highly recommend Shaker and ask for Cassandra for great service buying a new car.

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.

just purchased my second car everyone waall are great there s great and very Mo is the best , the very best honest, knows his work very well , just a great person all around with a big heart and looks out for you the customer , i would buy 10 cars if i could thank you Mo selena smyth

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.

Service is always tops Sales department the best Would recommend to anyone looking for a new, used car or service. Blasius Chevrolet is, by far, the best dealership in Connecticut

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!!

Got my answer in very short time just what I needed ok fine job but

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.

There was a mishap during a transmission service. Artioli took care of all problems and in the end I received an excellent service. Wonderful people, great business!

Very good customer service, very good support throughout the process. Shout out to John in sales.... thank you so much for your time and patience!

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 a great experience with this dealership. Straightforward and efficient, backed by a great team aiding in finding and purchasing the exact car for me. I would entirely recommend to others, through and through.

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 !

Tori from sales was great!!! Please commend her and the dealership for excellent customer service Made me feel relaxed and comfortable Highly recommended will definitely be back!!

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.

From start to finish a 5 star experience leasing a new Velar from Land Rover Hartford. Thanks to Sean, I’ve never felt more comfortable and confident with a sales process. It was actually fun. Also want to thank Brian, who made my virtual experience the best I’ve encountered from any dealer.

It was very easy with them. I bought a Ford transit 250 from them, and when I saw that my odometer was not working, they quickly repaired it. Thank you.

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!!