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*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
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Used
Jeep Gladiator trucks
for sale
near
Winter Springs, FL
under $400,000
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.






Used
2020 Jeep Gladiator Rubicon
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Reviews
Great dealership
Just moved to the area and now have a dealership for life! You will not be disappointed with their employees we felt very happy with our deal!
my grandmother sadly traded in this gladiator i wish she
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.






Used
2023 Jeep Gladiator Mojave 4x4
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I went there woth my wife and Gaby took care of us.
I went there woth my wife and Gaby took care of us. She take care of us, she was very good and knowledgeable.
MOST importantly it is a JEEP.
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!






Used
2023 Jeep Gladiator Rubicon
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Reviews
Excellent customer service
Hello Andrea and Jason was great I loved there customer service it was amazing I would recommend them to a customer they where really patient and they answered all questions so you understand. If I have to do it all over again I would really want to deal with them.
Always go to Pilson auto, we always use the same
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!






Used
2020 Jeep Gladiator Sport
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Reviews
Had exactly what I wanted
Without a doubt a good dealership to do business with. They handled my sale professionally in every way. . Absolutely no pressure and they were honest with me unlike the previous dealership I had dealt with. In particular Jeff A. did a great job making us feel comfortable with our purchase. I highly recommend this dealership.
my grandmother sadly traded in this gladiator i wish she
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.






Used
2022 Jeep Gladiator Sport S
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Reviews
Awesome experience
I’ve bought two vehicle from them and have had zero issues with them. They made it very easy to buy a vehicle! I will continue to buy from them.
My Gladiator is 3 years old.
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.






Used
2024 Jeep Gladiator Mojave
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Reviews
Zach Adams was great!
We had the pleasure of working with your salesman Zach Adams today! He was very professional, helpful and made buying our vehicle much easier & faster. Zach handled everything from showing us the truck, personally cleaning it and all financial paperwork. He went above & beyond to make sure we were satisfied customers!!
It’s a Jeep, so people who buy this understand what it’s
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.






Used
2020 Jeep Gladiator Overland
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Reviews
Look for Jose Williams
Jose Williams as always goes above and beyond. My third vehicle purchased with him. If your looking to buy ask for him and Ricky they’ll take care of you.
I have 84,000 miles.
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 !






Used
2022 Jeep Gladiator High Altitude 4x4
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Reviews
My wife and were looking for a vehicle and in process she
My wife and were looking for a vehicle and in process she found a couple. She worked with the salesman, Sunny who was beyond knowledgeable, and very helpful in the process of narrowing down exactly what we wanted. Originally we found a couple that we liked but there was one that my wife really wanted. Long story short Sunny went above and beyond, to help her get exactly what she wanted. Honestly what more can I say, at 54 yrs old this was by far the easiest vehicle purchase I have ever had. I do know when it comes times for me to trade my truck in, I know who will be the first person i call. Thank you Sunny, sincerely.
What’s Not to Like
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.






Jeep Certified
2024 Jeep Gladiator Sport S
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Reviews
Andy was so helpful and made sure I was taken care of he
Andy was so helpful and made sure I was taken care of he has the best customer service and really looks out for his customers.
Reliable and great looking 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






Used
2021 Jeep Gladiator Sport
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Reviews
Great Facility, Great Customer Service
I was impressed with how easy and seamless it was to trade in old vehicle for a newer Lexus. The deal was fair and the customer service was outstanding. Thanks guys...
We special ordered a Jeep Galdiato Rubicon in 2021 and
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






Used
2023 Jeep Gladiator Overland
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Reviews
Robert was absolutely amazing!
Robert was absolutely amazing! Super sweet and caring! Told him exactly what we wanted and now I am the proud owner of a brand new Mirage! Definitely recommending them to friends and family!
Jeep lifestyle
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!!






Used
2023 Jeep Gladiator Sport S
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Reviews
I wouldn’t buy from anyone else other than Napleton of
I wouldn’t buy from anyone else other than Napleton of Clermont! Always great service from beginning to end.
Must Love The Jeep Experience
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".






Used
2021 Jeep Gladiator High Altitude 4X4
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Reviews
Stand Up Crew
This was my third purchase from there. So obviously I am a happy camper. The Salesman Will was amazing and where else can you get concierge service like this, the managing partner drove me back home to grab my title and when I brought up a prior deal issue over a deposit on a vehicle he actually listened and took care of it. I can tell you that the changes at Falcon Motor Group are on point. The owners care and will keep buying cars there. Will walked me through the Bentley Speed over and over, no pressure sales and after extensive driving I realized it was the car for me. Two Lamborghinis and a Bentley from Falcon and I can tell you I feel better today about buying a fourth. They are Stand Up people and surely stand out in the crowd. Thanks again Will and Eric for taking the time and building the relationship.
Have driven Jeeps in the military and loved the
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!!






Used
2020 Jeep Gladiator Sport
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Reviews
I think this dealership helped make a long distance sale
I think this dealership helped make a long distance sale as easy as possible.looking forward to driving my truck
Great Truck/Jeep
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.






Used
2020 Jeep Gladiator Rubicon
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Reviews
Excellent Experience with Chase and David !
Excellent Experience with Chase and David ! My wife and I have been looking at purchasing a new SUV with three rows for our travel and when our grandchildren are visiting. We looked at 4 other brands and test drove just a few of them. Our friends have a two row Grand Cherokee and another a Grand Wagoneer and they spoke very highly of them. As a result we started our search into the Jeep and was pleasantly surprised that the Grand Cherokee had a limited edition with 3 rows. We connected with Chase Firestone a Manager at New Smyrna Chrysler Jeep Dodge Ram and that started the best experience we've had in purchasing a vehicle. Chase along with David Meeks a sales associate provided us with a test drive on our first visit. First we drove the Limited and then the Overland and David came along with us and did a great job in communicating the features along with how Jeep up their game with the three rows and trims. We never felt pressured by Chase or David, in fact the opposite as it was a relaxing environment and communication. We were both pleasantly surprised by how much we liked them and were leaning towards the GC Limited. With that, we wanted more time to test drive and inspect it more thoroughly. Next day they set us up with a plate and ability to test drive by ourselves and we made our decision to go with the GC Limited. The next step in working on price etc. was as my wife said, "one of the most relaxed and pleasant experience we've had in buying a car". Both Chase and David were professional, personable and so easy going to work with and New Smyrna Chrysler Jeep Dodge Ram are fortunate to have both on their team. We will highly recommend New Smyrna Chrysler Jeep Ram to friends and especially that the request Chase and/or David to work with. Dan & Karen Purchased on 9/19/24
Best vehicle I’ve ever owned. And I’ve owned many
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.
Used
2020 Jeep Gladiator Altitude 4X4
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I got into an accident and had to buy another car.
I got into an accident and had to buy another car. Settled on the 2023 RAV 4. Cyril was not pushy. After signing some papers he showed me the Carfax report and I was shocked to see that the used vehicle I bought was involved in a minimal accident. He said everything was repaired like the bumper. I got the vehicle under the premise everything was repaired. I was told I could get my old plate from my wrecked car the next day. It would be ready for me by the time I get there. So, went there the next day, plate still on the car. Had to ask 3 people if they could just unscrew the rusty screws so I could get my plate. No one helped me, so I saw a female employee and she asked Dave from the body shop to help me and he did. He was awesome. Tried all types of tools to unscrew the screw. He got them off with no complaints. Thank you Dave for being very helpful even if it wasn’t your job!






Used
2020 Jeep Gladiator Overland
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Came in to browse and left with a new car, not due to
Came in to browse and left with a new car, not due to pressure from anyone but because of great prices and the absolutely fantastic service of Nelson and the rest of the team at Mullinax Ford. Dealership came highly recommended from friends who had used them before, and they did not disappoint.

Used
2022 Jeep Gladiator Sport S
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They served me super well with all kindness and
They served me super well with all kindness and professionalism and they got me the offer I wanted I recommend them 100 the big boss a professional and very humble
Great vehicle poor local warranty service
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.
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Reviews
Very friendly service.
Very friendly service. I was kept very well informed about the progress of my car repair. It was a comfortable environment to work in on my laptop and sip coffee during the repair time. In fact I stayed a few extra minutes to finish up on some of my work. Most enjoyable.
23 Jeep Gladiator Sport
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! 🤪

Used
2023 Jeep Gladiator Rubicon
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Devon helped me out a lot and save my money from buying
Devon helped me out a lot and save my money from buying unnecessary parts, and helped me find out my engine issue, thank you! All staffs are very friendly and informative
Jeep Gladiator prices by year
Model year | Average price | Deals |
---|---|---|
2025 Jeep Gladiator | $44,452 | |
2023 Jeep Gladiator | $32,518 | 7 Great deals |
2020 Jeep Gladiator | $29,093 | 16 Good deals |
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used Jeep Gladiator by price
Compare the Jeep Gladiator
Jeep Gladiator under $400,000 by city
-
Jeep Gladiator under $400,000 in Winter Springs, FL
15 Great Deals out of 88 listings starting at $21,500
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Jeep Gladiator under $400,000 in Casselberry, FL
13 Great Deals out of 79 listings starting at $21,500
-
Jeep Gladiator under $400,000 in Longwood, FL
14 Great Deals out of 81 listings starting at $21,500
-
Jeep Gladiator under $400,000 in Fern Park, FL
13 Great Deals out of 79 listings starting at $21,500
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Jeep Gladiator under $400,000 in Oviedo, FL
15 Great Deals out of 84 listings starting at $21,500
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Jeep Gladiator under $400,000 in Goldenrod, FL
13 Great Deals out of 80 listings starting at $21,500
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Jeep Gladiator under $400,000 in Black Hammock, FL
15 Great Deals out of 86 listings starting at $21,500
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Jeep Gladiator under $400,000 in Lake Mary, FL
16 Great Deals out of 90 listings starting at $21,500
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Jeep Gladiator under $400,000 in Sanford, FL
14 Great Deals out of 80 listings starting at $21,500
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Jeep Gladiator under $400,000 in Maitland, FL
14 Great Deals out of 80 listings starting at $21,500
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Jeep Gladiator under $400,000 in Winter Park, FL
13 Great Deals out of 79 listings starting at $21,500
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Jeep Gladiator under $400,000 in Altamonte Springs, FL
14 Great Deals out of 81 listings starting at $21,500
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This vehicle is certified pre-owned, backed by a manufacturer warranty, and typically undergoes a rigorous multi-point inspection to ensure quality and reliability.
This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.