Used Jeep Gladiator trucks for sale near Chesapeake, VA

I get a lot anxiety when buying a car. Fredie went above and beyond to make my buying process easy and calm. Fredie is very friendly and patient. Thank you Fredie for being awesome!

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

Cinna was a great help with clear communication and follow through. She was able to assist even over the weekend and even brought the vehicle to me.

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!

Bill and Cameron both were ABSOLUTELY amazing and went out of their way to help me find a vehicle for my son. They even went above and beyond to prepare everything in their off hours just to make a pleasant surprise for our kid. Absolute respect for these guys. Highly recommend!

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!!

Great service, nice staff, they didn?t have a lot of staff that day but they got me out quickly. I will recommend them to anyone that needs service done to their 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.

David was amazing customer service and treated me very well I always love coming to Casey Chevrolet

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.

Julian, Jasmin and the rest of the staff have been nothing but excellent! Best competitive prices in the Hampton Roads area….definitely recommend! Will be back.

The best vehicle that I've ever owned! It's never needed to go back to the dealer for any work or new vehicle adjustments. I will get another Gladiator after this one!

The sale people were very knowledgeable , and was a pleasure to do business with. She had the service department clean the car prior to delivery and they did not half clean anything. The windows, interior seats, and carpet was not cleaned as good as previous car dealers had done. Overall Sale personnel are fine, Service personnel are not as good.

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.

Bought a new 2025 Ford Explorer from Cavalier Ford yesterday and hands down this was the smoothest experience buying a vehicle. Georgy’s attention to detail from beginning to end was phenomenal. I highly recommend you see him first if buying a vehicle is in your future!!

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 !

Jim Bowman, retired US Marine, sold us a 2007 Chevy Silverado. He was a nice, no-pressure salesman. Great sense of humor, very friendly guy, will definitely see him again if we ever need another car.

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!

This place is New < but the Staff is very knowledgeable. They responded right back to me as soon as I inquired about a car. Frank helped arrange financing for me and I was in and out with my new MUSTANG. I had a great experience and would recommend them to others.

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!!

I recently bought a Mercedes from udrive, and I couldn't be happier! Initially, I had doubts – after all, this isn't just a dress, but a car for my family and our beloved dog. udrive eased my worries and even included a complimentary 3-month warranty with my purchase. Their exceptional service and support have made me a loyal customer. Highly recommended!

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.

Outstanding service! Fast and friendly. I had an issue and couldn?t get help from Hall so we reached out here and they took care of the problem!

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.

This experience was excellent. I can't speak highly enough about Southern Norfolk, Justin Cannady and Katie Rose. They were topnotch in understanding and making sure that I got the best car for me. They made me feel like family which alleviated all of my anxiety and tension when buying a car. After all of my, "I want this and not that" they were still nice and professional, compassionate, open and honest. They went above and beyond. Thank you all for you patience and time dealing with me.

Ecodiesel gladiator is fun to drive and getting good MPG. My second gladiator and no issues. Jeeps aren't for everyone as they are boxy, heavy, noisy in cab at high speeds and not as luxurious as a Lexus. But these things are tanks with body on frame build, Dana 44 axles, real transfer case and mega offroad capability. Plus its easy to modify suspension and its a "jeep thing".

I had a wonderful experience today! Everything went smoothly. The Managers and staff were extremely supportive and a delight to work with.

With the prices of the Gladiator coming way down (because of incentives), it made it an affordable choice. Black on Black, with a tone of options. I love it, and most importantly so does my wife! 🤪

I had a great experience working with Cynthia Adams, her customer service and assistance with me purchasing my new vehicle was outstanding. I truly appreciated how she made me feel comfortable about purchasing a new vehicle seeing that it was a major purchase for me. Her knowledge and expertise on the vehicle were exceptional and she made sure I how to operate all my new electronic gadgets, & etc. before I departed. I'm loving my new vehicle and my decision to purchase one. I am 100% satisfied with her professionalism and knowledge and would highly recommend her and Southern Kia Greenbrier to all my friends and family members looking to buy a vehicle. Thank again Cynthia for your help. Patricia

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!!

This dealership is by far one of the best I've been to, great attention to detail and great customer service. Also they're taking very good measures in this though time with the Corona Virus in maintaining social distance a much a posible.

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.

Josh was one of the best customer service representatives I have ever encountered. He was totally thorough and knowledgeable. I had a wonderful experience and would recommend him personally to anyone.

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.

Great service. Keyshawn Brown was awesome. Thank you again for all your hard work. Thank u 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.

Everything is good to go. Service is good. Not a long time to fix car. I would recommend this dealer ship to anyone.thanks again

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

I had an appointment and was taken on time. My wait for service to complete was what I expected.