Used Jeep cars for sale near Windsor, VA under $899,990

We just bought a 2021 RAV4 and couldn’t be happier. Ozzie Reece was our salesman and he was such a pleasure to work with he did everything he promised. It was a great experience dealing with him and the finance department. There was no pressure and I would recommend Pearson to anyone. I will definitely go back when I purchase another vehicle.

It’s currently summer 2025, I’ve owned my 2020 Wrangler Sahara since spring 2021. I LOVE my jeep and have had ZERO issues with it. This is my 2 nd Wrangler, first one was 2915 New. No issues with it at either. Mine is a 4 cl turbo. I didn’t want that I wanted a 6 cl. My husband convinced me to buy it and I’m glad I did. I have 59,000. Miles currently and I haven’t had to replace anything besides general maintenance.

I’ve been coming to Casey Kia in Newport News Va since 2019 and they are very good at what they do in the service department. I get expeditious professional and quality service every time. I always let them know they are appreciated too.

i recently had a 2023 for explorer it was a good truck never a problem but not a comfortable as the jeep grand Cherokee l front seating is amazing no issues at all i did my research and made sure i bought one with the German transmission its a good idea to check that only thing i can say on the down side seam to be a little under powered but i can live with it decent milage 20 around town.

The first this I want people to know is the salesman, Omar was fantastic and very helpful finding a car for me. The first week of December I totaled my 2019 Highlander Platinum, and the most important thing was that nobody was hurt. So when we discussed replacement car, I wanted another Platinum Highlander, but a new one. Little did I know how rare they were a this point. Omar at Pearson Toyota was able within a few minutes found me one to look.at. It was a Grand Highlander Platinum and had under 5000 miles, and was beautiful. It had everything I wanted and had never been sold to anyone. Omar and the entire staff at Pearson worked so hard and now less than 48 hours later it is sitting in my driveway. They made what for me is usually a very stressful situation very easy,plus everyone was so very kind. I would recommend Omar to anyone looking for a car. He went over and above for us and I think that's just his normal thing, and Pearson Toyota was a great place to do business. Thans to all of you that made my day possible.

I love my vehicle. It's a 2023 model year Jeep Grand Cherokee L in the Summit Reserve trim with the 5.7 liter HEMI V8 engine. Overall sleek exterior design of the vehicle is nice. As for the interior, it's great! Nice and comfortable interior. Palermo leather seats, massaging front seats and power folding rear seats. Heated/ventilated seats for both the first and second rows. Front passenger infotainment screen, interior camera, night vision camera, ambient lighting and a 19-speaker premium audio system. More importantly is the excellent performance. This V8 engine comes with 357 horsepower and 390 pound feet of torque. It'll go from 0-60 in 6.1 seconds. Very good acceleration for sure. A recommended vehicle for performance, enjoying features, hauling passengers and carrying big loads when seats are folded. 👍👍

I went in looking at a used Tucson but ended up leaving in a 2019 Tucson Night.. Chris,Jimmy and the finance manager went above and beyond to get me exactly what I wanted at the price I needed .. this car shopping experience exceeded all of my expectations. I am so in love with my new baby!!!!

Love my 2023 Jeep Grand Cherokee L Overland Reserve for hauling kids / traveling on vacation with dog included. All safety features work as expected and provide the extra level of comfort / safety we expect from a next generation vehicle.

Very professional, they handled everything very well. Would use them again if I needed to.

  I have the Trailhawk trim, the serious off-road version.  Finally, a car that I can confidently drive in and out of rough construction sites, and not be afraid that I'll break it or get it stuck.   It is possessed by a powerful spirit of wanderlust, and frequently demands that I take it on drives just to see places it hasn't yet been, preferably places that normal cars cannot go.   If Don Quixote de La Mancha lived in our time, he would surely drive a vehicle like this one; a vehicle truly fit for a modern Knight Errant.   I didn't know until a few days after I bought it, and I don't think the dealership knew either, but this one has about a 2" aftermarket lift, and slightly larger tires than stock.

Responding back quickly with information that I requested. They still continue to keep in touch and provide updates on my request.

I love my new Wagoneer Series II in white with sea salt interior. It has a big punch from the twin turbos, the ride is like my Cadillac Deville. It raises and lowers it's own height based on speed and road conditions. My only complaint is that the seams on the trim at the two back windows don't seem to be sealed properly so the water after washing it continues to drip down leaving a calcium line down the vehicle. I'd would also love it if you could add more apps to the infotainment center. Overall I'd buy it again. I've had two Gukon XL Denalis and the amenities on the Wagoneer at a lower price point far surpasses the GM vehicles.

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.

Our 22 Wagoneer Series II is awesome. So quiet and the ride quality is like there's a layer of cream cheese between the road and the tires. Totally reliable, nothing but oil/filter changes. Super roomy and comfy interior.

Salespeople we?re courteous and friendly. I have several vehicles from this dealership in the past.

It is a GOOD Jeep and I LOVE everything about it the color and EVERYTHING it have in it and the drive and the performance

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.

We have a 2022 Wagoneer Series II rear-wheel drive. It's got nearly 47,000 miles on it now. We absolutely love it. "Silver Zenith" exterior and the two-tone black/Baltic salt interior. It is SO roomy and comfortable, and quiet! Ride quality is smooth as the suspension absorbs just about anything. The exhaust note has an amazingly deep note to it. We love this Wagoneer.

This dealership has an amazing selection of inventory and great prices. If you are looking for a new or used vehicle they will satisfy your needs. The staff is amazing and they treat you with care.

I’ve owned a Sahara unlimited for 2 years then purchased a 2019 sport unlimited, hands down the two best cars I ever drove, they don’t exceed in any one category besides getting you where you need to be in style!! I’ve loved every minute of my jeep wrangler!!

So I cannot express the amazing experience I had at Courtesy Auto Sales, Jason and Justin were both truly amazing and made my car buying experience smooth and easy. They listened to my needs, and applied the pressure.

Owning a Jeep is more than just having a car — it’s a lifestyle. The rugged capability, the open-road freedom, and that unmistakable Jeep spirit make every drive an adventure. Whether it’s tackling trails or cruising through town, my Jeep delivers power, comfort, and pure fun every time. Once a Jeeper, always a Jeeper!

My buying process was quick the price was reasonable the facility was clean and I didn’t feel pressured into buying. I referred two more family members who will be buying this year!!!!!!

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!

I love my new car! Matt the manager was great. The cars were nice. The price was good. I will be back

The dealer and sales people everyone was amazing. G was awesome! He stayed late and worked with me through everything! I could not have asked for a better experience with everything that happened this day.

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 was honestly in need of a vehicle today I went in to Winners Circle Chrysler dealer today. I just knew I won’t going to get a vehicle due to my credit score. Eric and Julian was upfront & honest with me ! I am walking out with a 2020 Nissan Altima baby !!!!! Thank you so much!! My new family !!!!!!!! Ps! If you looking for honesty & someone who going to work with your credit they are the best in Hampton roads !!!! You guys are the best !!! Thank you two brothers Eric and Julian!!

I’ve owned this for 2.5 years, I bought it because it was as jeep and allowed me to drive it in electric mode. Few problems. I drive it almost exclusively in electric mode. Yes, there are times when electric is unavailable but that is due to not putting gas in for a long time. Once I even put in 2-3 gals. good to go.

Had a very good experience working with John and staff at Courtesy Auto Sales. People are very laid back with no real pressure to buy, although they make that process very easy. Walked away with a nice vehicle at a fair price, with a good interest rate and a fair value for my trade-in. I'd recommend giving them a visit when interested in purchasing another vehicle.

Needs oil filter conversion so oil doesn't drain back, Google it..good power, goes anywhere , better than the 2 door for smoother ride,, I would buy again

I recently purchased a Subaru Forester a commuter car. The car was exceptionally clean and the lowest mileage unit within 20m miles. The purchase was seamless from the test ride to the closing. I did however have an issue with the AC, which was covered immediately. My wife also purchased her 3rd vehicle for them, a 2021 Toyota Rav4. She traded a RC350 getting above book because of mileage and condition. I wouldn't buy a used vehicle from anyone other than Sullivan Auto Trading in the Mid Atlantic area.

There is a lot of new technology working together in this car so i recommend a extended service plan. That being said this hybrid Wrangler has more power, quieter (got hard top insulation), and smoother riding (I have a Sahara High Altitute) than the Rubicon ICE previously owned. So far at 19k miles no mechanical issues.

Great experience, wonderful working with Jason and everyone at the dealership,very friendly. Love the new car.

Hello, my review is positive. I'm happy with my jeep compass limited. Stylish body design. I, like having fuel efficiency mileage. Pretty good performance and awd suspension. Comfortable heated seats. Plenty of cargo area for my items. Very cool ride, reliable fun to drive.

Service advisor Lindsey Givens was/is very professional and extremely competent. Same/same for Ashley House and Canon Hughes.

I have had my 22 High Altitude for about 4 months now and the only issue(s) I find are the following: MPG is not as advertised, it's not that great. It's around 24 average, I am about 50/50 city/highway driving - It's fine. It DOES ride like a Jeep - so it's not as "luxurious" as your higher end cars, but YOU BOUGHT A JEEP - The last snow storm we had in Cleveland was about 10" in 2 hours - No problem, even with 235/45/19 tires - Would be way better with not so wide tires. It's slow. Who cares? Are you driving in the F1? Nah - It's plenty. Interior is baller. Infotainment is great, comfortable. Heated steering wheel is a plus. IDK - I read these reviews and everyone is so picky - It's a nice ride. If you find you like it, give it a shot.

A great looking car. We will probably never learn all of the features the car has. Dealer was excellent and no problems working with them. Only one thing not to like was the location of the Emergency Brake lever. Things seem to get set there, and locking the lever.