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

I recently visited Udrive USA and had an outstanding experience. The customer service was exceptional, with knowledgeable and friendly staff. Their selection of vehicles is impressive, offering something for everyone. The office space is modern and inviting, and the check-out process was incredibly fast and efficient. I highly recommend stopping by Udrive USA before purchasing a car—you won't be disappointed!

Car was perfect and price was under budget for what I was looking for love the feel of the ride and the seats are very comfortable for a woman, my husband is a big guy and he does not fit too good.

This was the quickest process that I’ve ever been in, and I have bought several vehicles. I need this management team to come work for me.

I love my little JEEP compass! It’s runs well and is perfect for me and my needs! Holds all the baseball gear and more in the trunk!

When looking for a reasonably priced used cars I was so excited when I ran across 518 Auto Sales and the large selection of cars they had!!! The staff including Alex, Wendy, Kyle and Scott were awesome and made me feel right at home!! I will spread the word about this place!!!

In my many years of car driving and ownership, I have rarely had a better vehicle than my 2019 Jeep Compass Latitude. It has been reliable, comfortable, fun to drive and, for its' size and type, very good on gas. In April, I will have been driving "Lattie"for 5 years. My upkeep has been minimal. She is pretty and still looks new. This vehicle is such a pleasure to drive. Handling and response are excellent. Controls are super easy to manage and absolutely love the heated seat and steering wheel. On a long trip, it is very comfortable (yes, I have ridden in the back seat, too) and fuel economy was just great...fully loaded with air-conditioner on and travelling at highway speeds gave me 30+ mpg. Really can't complain. My Neon didn't do any better. This is a great vehicle. Oh, and I had leased it new, and purchased it when the lease was up..that's how good this car is!

Today while on a business trip in Eureka, my car began to have problems. I was near Courtesy Used Cars and asked for assistance. Was told they’re not a repair shop but would take a look to see what the problem might be. It was a problem with the alternator. They said they could make the repairs and suggested I have lunch at the restaurant while the repairs were being made. The part was ordered at cost and no charges for the repair. Over Joyed From San Francisco, Ca.

Great little SUV, nice options as good as a more expensive luxury car. Smooth ride and very comfortable. I'd recommend this Jeep to anyone wanting a smaller SUV

Wonderful experience with the manager of Auto City. The Chesapeake location was closed on Sunday but I was able to text him on his cell and he was prompt but without being pushy. We scheduled a test drive and everything was smooth with no pressure. He was firm on his price but the price was good so I cant blame him. My wife loves the car and thats the most important thing! Our phones were not connected to the internet so he even allowed us to use his desktop computer to do a application for financing ( and leave this review LOL ). Great spot to shop for cars and a wonderful group of folks to work with. I also enjoyed the cars.com site too.

Vehicle is beautiful, but has cracks on the rims and heated seat features do not work or the spotlights Oil change was not done, this is why I wanted to go through a dealer than a private party, for maintenance

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.

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.

This vehicle will always be available. I’ve had 3 other vehicles that came and gone, and the Jeep is still here with 140k. I guess I’m a Jeep Geek

This is the best Jeep Wrangler model ever made. The past YJ, TJ, JK models are great, but this Jeep JL 2018 Wrangler Sahara Automatic V6 is the best one yet. The comfort and modern amenities are top of the line. The 8” infotainment head unit and Alpine sound system is out of this world. The interior fits my family of four and has enough cargo space for a stroller, scooter, Onewheel XR and beach chairs. The exterior needs no introduction with its iconic round headlights and seven slot grill. Followed by a three piece removable top, which I managed to take off and put back on by myself. FYI, don’t try doing this by yourself. My final favorite thing about my Jeep JL is the ability to customize the Jeep with all of the amazing aftermarket parts and pieces. This allows you to take the best looking car on the road and make it your own.

Don’t go anywhere else!!! Streamline auto is the best dealer in hampton roads. Once you go here you won’t want to go anywhere else! This company is the real deal!! We are forever grateful! Robby is the bomb!!! Very informative with the step by step process, no xx!! This company by far is the best we have been too. We have been to other dealers before we met streamline auto and the experience was horrible! I was doing a google search and came across this company at night! They open at 9am, I got a text no sooner after they opened. Robby helped me and my husband get vehicles. Best trade in value as well!! You go here you won’t want to go anywhere else ever!!! We have found our new home to purchase our vehicles and will never go anywhere else!! They are consistent the whole way through the process!! If you can’t get approved by the bank, this is where you wanna go for sure!!! Robby and Randy provide the best customer service ever!!

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

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.

Great place to buy a car. Professional staff. Great selection. Service was beyond my expectations!

I never thought I'd own a Jeep in my lifetime, then five years ago I bought a used 2014 Jeep Patriot and was amazed by its fuel economy and reliability for a mid-size SUV. Then three months ago my sister needed a car, and I passed the Patriot along to her, so I began doing research to buy another used car for myself and found the 2014 Jeep Compass. Now I'm the proud owner of not one but two Jeeps! I fell in love with it because of its looks as it is "less boxy" than the Patriot and the interior is basically a replica of a car I'm already used to driving. Find it a little bit roomier than the Patriot, love the top of the gate spoiler and the headlights design as well as the focused (foglights?). I can carry a ton of stuff in the back specially since I added the retractable cargo cover for privacy and safety. I definitely recommend this crossover SUV, it delivers a ton for its value. Definitely money well invested.

Unbelievable dealer! The only dealership to purchase from in the Va Beach area. Staff is kind and professional, inventory is clean and well serviced, and they have very fair and competitive interest rates. I highly recommend visiting Adam and the rest of the staff if you are in the market. I am a customer for life!

I have a 2021, 2 door, Jeep Wrangler Rubicon. Is it a decent vehicle - yes. Is it for everyone? Probably not. But if you like to drive with the roof off, don't mind bouncing around on the road a little bit....and it is bouncing around, ok with the wind noise, then this is the vehicle for you. The V6 engine is decent. Do the maintenance and it will be fine long term. I have the manual transmission. Works fine and makes it more enjoyable to drive. It is a very nimble vehicle, no problem on the highway, comfortable, and the noise is not that bad when travelling. Is it a vehicle I would drive in bitterly cold winters and icy roads - I am in Canada where winter is winter and -40 is real....nope I would not. However there are thousands of people around here that do. This vehicle is an acquired taste with a variety of uses, applications, and lots of strengths. Does it have many weaknesses - no not really. But you need to be sure why you have it, accept its nuances - which are not that bad, and enjoy it!! It is a fun vehicle to have especially in the summer when the sun is blazing!!!

My wife and I have been car shopping for the last couple of months, and we recently came across Udrive. Let me tell you, they are FAST! We had all our questions answered and left there in less than half an hour with exactly what we wanted. The staff was knowledgeable, efficient, and made the process incredibly smooth. We highly recommend Udrive to everyone looking for a hassle-free car buying experience!

The '03 TJ's hit the sweet spot in the '97-'06 line. They were the last major revision, especially with the 'TUPY' cylinder head, and parts revisions in '04-'06's, well, have issues. 'TJ' means (last) True Jeep. The 4.0L '03's are special. You ride in a car, you drive in a Jeep.

Bought one for my son for college. Had 108K, now as 190K. Can't complaint. Safe, reliable and very comfortable. Did have to replace the oil cooler assembly, but that's a given on a 3.6. Other than that, tires, brake pads, the usual. It's been a winner.

I purchased it used in 2022, it had 76k and now has 96 in 2025. It's 4wd with the 5.7 Hemi in the Overland trim. It hasn't given me any trouble.

I bought my 2016 Ford Escape in Feb 2019 from Wynne Ford and have had it in for routine maintenance. From the buying process to maintenance, the experience has been very positive. They also repaired the vehicle after I was in an accident. It came back to me looking and running like brand new. Wynn is excellent in repairs and maintenance, and has superb customer service.

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.

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.

Hey, I got a 2007 jk wrangler with 380000km still running perfectly, off course I did some refreshing. But still reasonable and good car even daily use.

If I could give them 10 stars I would! TJ and the staff are extremely professional, honest and down to earth. They have assisted me with the purchase of not 1, but 2 vehicles on the same day! I am so glad to have met TJ and the staff here. I am telling any and everyone I know to come here. The process was quick and the service was outstanding! If you are in need of a nice vehicle, don't look any further....I PROMISE YOU WILL NOT BE DISAPPOINTED.

Owning my 2020 Jeep Renegade Limited has been an absolute joy. This SUV strikes the perfect balance between style, comfort, and capability. From the moment I got behind the wheel, I was impressed by its smooth ride, responsive handling, and surprisingly spacious interior. The premium features—like the leather-trimmed seats, intuitive Uconnect infotainment system, and advanced safety technology—make every drive comfortable and convenient. Whether I’m commuting in the city or taking a weekend getaway, the Renegade Limited handles it all with ease. What really stands out is its versatility. The 4x4 capability gives me confidence in any weather condition, and the fuel efficiency is great for an SUV of its size. Plus, the unique design turns heads wherever I go—Jeep really nailed the balance between rugged and modern. If you're looking for a compact SUV that delivers reliability, technology, and a sense of adventure, the 2020 Jeep Renegade Limited is a fantastic choice. I couldn’t be happier with mine!

Chris was great. Honest and accommodating. He stayed late to help get paperwork done and was easy, not pushy at all. Although, the check wngine light did come on during the drive home, it was expected and discussed ahead of time as they were able to work on the price with me a little. Would do business with Supreme Auto again.

We purchased our 2014 Grand Cherokee Overland new and after 11 years and almost 150,000 miles it easily the BEST vehicle we have ever owned. It is comfortable, delivers reasonable mileage, is quiet, well built, incredibly durable and looks as good today as the day we took delivery.