Used Jeep cars for sale near Gloucester Point, VA under $50,000

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!

What a great look. I have bought several cars and trucks over the past few years, from 2 trucks for me and helped the family with other cars. I wanted to get something for looks and the 2025 Grand Cherokee fit the bill. Style and looks, 10 out of 10 in my opinion. Good on the mileage and performance. Great dealership and people at Ray's CDJR in Fox Lake. They treat you like you should be, with respect through the entire process.

I thank you from the bottom of my heart for the service you provided me and I hope that everyone who comes to the same place with the purpose of buying a new car will help you just like they did to me so that they never change and always continue to be the best of all. Dealer that I have known and we will always recommend them to more people who want to buy a new one, especially family and friends, do not doubt that we will reach you in that same place.

I’ve had my ‘15 latitude, for a year. T-bones a car, last week, and they crumple like a beer can… In other words: had my wife get a ‘16 75th edition TODAY!! Yes, ramen diet, for a few years, + her “special edition” doesn’t have heated seats, or a heated wheel 😖 My latitude does!! I wouldn’t look at different 💯

The best car buying experience ever! I will go back! I've told all my friends about this dealership! Great customer experience with no hassle!

I initially leased my Grand Cherokee Limited but ended up buying it outright at lease end. It has been an awesome vehicle for the 6 years I've had it. I have only had two minor things that have needed work, one was AC needed more coolant and leaking rear strut which must be a fairly common issue as my mom's Durango has had the same problem. Super comfortable ride and plenty of room. My only beef is the halogen factory lights are horrendous but swapping the bulbs out for LED made a big difference for under $200. I normally don't keep a vehicle for longer than 2 years, but after 6 I love this vehicle just as much today as did the day I ordered it!

I purchased this Jeep brand new in 2012 as a 2013 Model, I have since put 150,000 miles on. It is a Jeep and can get a little uncomfortable on long highway drives. I took this on a 3 week coast to coast road trip across the US I would know. It does a great job towing my 20foot i/o boat to and from the lake, but wouldn't recommend long trips with that much to tow. Maintenance has been astonishingly low, the only things I needed was regular oil changes, brakes, and a radiator leak that was covered under warranty. This is one of the best all around vehicles, top down cruising in the summer and 4x4 for the snowy PA winters.

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.

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

This has been an amazing vehicle! Super comfortable and will buy again. Loved all of the tech and comfort features to make each trip the best. I have owned a lot of cars and this one has the most intuitive features by far.

Nice hellcat red eye jeep Chrysler ram good drive suspension engine and supercharger. Great exhaust 6 seconds on track and review 5 star safety rating

driving now 1 1/2 years. still love it. 59,000 mi. rec. chang rear end oil. mine had broken bits of gear. much better now. leaks from windsheld area, gotta work on that. overall still jeep'n--- please stop putting ducks on my jeep

Purchased new in 2015. Have only done 1 repair in 129k, which was fixing oil leak at oil filter housing. Solid car, great in rain and snow. Thoroughly enjoy this car

Dante was great. He was able to work out a great deal and got everything that I needed for the vehicle. Incredible customer service. Ask for Dante!!!

The 2019 Grand Cherokee Limited was the Jeep I had my eye on for a while. I've owned a 2012 Laredo X, and a 2018 Limited Anniversary/Heritage Edition. I was specifically looking for Limited trim without the 20" rims, although, I love the look of the Altitude versions, I just didn't really care/want to deal with less side-wall, nicer-looking rims. I avoided the Overland and Trailhawk because of the air-suspension. Overall the interior is fine, it's comfortable and familiar for me, since I've owned them before, but that's also the only issue/complaint I would have. The interior is updated from the 2012, however, basically it's a very light update, U-Connect, Gauges, Shifter, and possibly a few other items here and there. But essentially, the dashboard is the same dashboard I've seen since 2012. While owning the previous (2) I never experienced any mechanical issues that left me stranded. One had a weird issue with blowing lights in the tailgate, but it would just randomly decide to burn out, replace one it would blow another. No other major issues. The 2019 leather on the steering wheel feels smooth and buttery like they always have. The suspension feels great, still solid and tight. Brakes are strong and grippy, pedal feel is nice and firm. So far I'm super satisfied with this Jeep, I got the perfect combination of all the features I wanted, Memory Seats, Sunroof, power trunk, heated-seats and wheel. Not sure if I'd be willing to sell this one and get a newer model, but, I'd possibly get another WK2.

Myron couldn’t have been more helpful. Had a great experience with my recent purchase and look forward to buying from here again. Thanks for the help

I have been wanting a Jeep for a while and very happy that I was finally able to purchased the Jeep and it seems like a nice car.

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.

I bought my Jeep Grand Cherokee limited in 2018 I love jeeps this is my 3rd one it is now 2022 the only problems I have really encountered with the car are mostly run of the mill the water pump went out which is normal and I had a starter go out which is also a normal for a vehicle with a 100,000 plus miles The only problem I had that kind of sucked was the transmission speed sensor when out when me and my girlfriend were on vacation in Michigan The car will go into safe mode which only allows you to go about 27 miles an hour, I would caution anybody that would be buying one for Winter driving that these cars drive so nice in the Winter that you can get overconfident and drive too fast because they handle excellent in the snow My basic philosophy is drive it like it's only 2 wheel drive One other issue I have recently had is that I have a check engine light on I read the code on it and it says that a temperature in variance was detected I am thinking about getting a different car as the different car as this car has now 201,000 miles on it I may get another Jeep I'm not sure I'm looking the other sensor that has triggered is electronic throttle control the car is not behaving funny it's not overheating so I'm not really going to worry about it

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 special ordered my 2021 4 dr Sahara in Feb of 2022 and received it 4/1. I have previously owned 4 JK models over the yrs. The 2021 I just love. the interior appts, the dash layout with the nav. I got the upgraded leather seats and paint color white with One Touch Skyview top. Got the 3.6 with E torque for powerplant. They improved on the brakes vs JK. Much stronger!