Used Jeep Gladiator trucks for sale near Webster, FL under $899,990

We want to thank Tod Featherstone and Travis for all their hard work getting us our 2024 gmc terrain,we love it . Also all the other people that helped .

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.

I am new to The Villages, so I was unaware of Bill Bryan Subaru service center‘s excellent reputation. Several weeks ago, I was at an early morning medical appointment in Orlando and came out to my car to find my 5 year old battery dead as a door nail. I was able to get a “jump,” but I was very shaky about heading home and perhaps not being able to start my car later in the day. From Orlando, I randomly looked up Subaru dealers near TV. I called Bill Bryan Subaru service at about 8:30 in the morning...probably every service departments busiest time...and a very nice scheduler realized my panic and said “bring it on in”. As soon as I pulled in, I was greeted by Alejandro Rosar. Not only did he have a new battery installed, he also had an oil change, much needed, added on to the service. The technician also performed a wonderful multi-point inspection. Alejandro went over that report with me and, I have to say, his attention and the new battery, the oil change, and the inspection gave me a very satisfied and secure feeling about my car. AND on top of all that, the service department gave my car the BEST wash my car has ever had! I highly recommend Bill Bryan Subaru Service Center and Alejandro and I will return.

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

Great dealership with friend employees. Got me in a truck in my payment range and helped repair the tire that had a nail in it when I bought the truck.

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

One thing I could say , they are very responsive. I wish I was able to make a deal if it wasn’t for my down payment amount I would taken that car so bad . I need it too .

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!!

Good service, great team of sales people and managers. 100% Recommend this dealer ship and special thanks to dale and everyone that works there and i’m grateful.

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.

Mr. Jenkins, Salesmen/ladies (Brady)and (Robert) and employees it was rewarding to drive over 180 miles to review a Toyota Rav4 that I wanted. After a test drive, we discussed a price. With little negiotation I got it for a less cost than posted and happy purchase. Your men Brady/Robert worked to fix my vehicle so I could drive it home. It was a class purchase. I have had experiences before, but this was the BEST one in my life. You are praised for running a satisifying business for your customer. I am happy I drove down to your dealership.

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 the best experience ever in purchasing a new 2025 Lincoln Nautilus. The sales person Hunter Graf was exceptional. He did a super job in getting me acquainted with the new controls on the Nautilus.

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!!

I bought my car on 8/16/2025 and had the pleasure of working with Mathew Andrade. He’s an excellent salesman—very professional, kind, and easy to work with. I recommend asking for him if you’re looking to purchase a car. On the finance side, I had to switch the car from my business name to my personal name, and both the sales manager and finance department made the process smooth. Even when I pushed hard on my interest rate and monthly payment, they stayed patient, professional, and willing to work with me. Great overall experience!

Eddie and the team were great. They worked hard to get my deal done!!! I was not at the dealership too long.

We brought our car in for service today 8/16/25 our service advisor John Kidd was wonderful, he kept us informed on everything, John is very knowledgeable and an asset to your company. Thank you John,for all your hard work.see you next visit Doreen Gaeta

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.

Was in to see Ty, a service guy! He was very pleasant and had my kia soul checked out after we bought it second hand. Would recommend him,as he explained things to us, had it ready for us on time ,etc. And trust the check up was well done. Truly a great guy and will see him again Sandra Lewis

Thanks to Carlos we were able to purchase a certified used Sonata and also received a fair trade in on our old car. This is only the 2nd time I've traded in a vehicle in my long life.

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 !

Great crew. Adrian went out of his way to help us. They have a great selection of cars.

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.

I was recommended by a coworker. The process was smooth. They gave me the same deal as my coworker. An outstanding experience. Highly recommend Jacobs Mitsubishi in Wesley Chapel

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.

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.

I will always take my vehicle to Jim Browne for service, repairs, and body work.

Bought my Jeep from Stephen . Pleasant professional guy . Good experience . Would not hesitate To recommend this dealer .

My husband and I are very pleased with the service we received. Buying a new car is not an easy task. Thankfully we met awesome sales man. Thank you so much James and Paul you guys took your time and answered all of sour questions.

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!

Kristen in the service department was very thorough, friendly, great personality. I spoke to "Gator" from service several times and he was always helpful, patient and courteous. Great place!

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!