Used Jeep Grand Cherokee for sale near Chesapeake, VA under $40,000

David was amazing customer service and treated me very well I always love coming to Casey Chevrolet

My dream car since a teenager was a grand Cherokee and when I finally got one in 2021, I’ve loved it the same ever since. They are bold in appearance and look like a strong vehicle. It has always run beautifully and I have had no issues thus far since 2021 and now it’s 2024. Very comfortable interior and attractive to the eye. Love love love my car.

This experience was excellent. I can't speak highly enough about Southern Norfolk, Justin Cannady and Katie Rose. They were topnotch in understanding and making sure that I got the best car for me. They made me feel like family which alleviated all of my anxiety and tension when buying a car. After all of my, "I want this and not that" they were still nice and professional, compassionate, open and honest. They went above and beyond. Thank you all for you patience and time dealing with me.

I HATE is the warning 'Place Two Hands On Wheel' as it goes off even when I have both hands on the wheel - No matter where I place my hands on the wheel it goes off. Since it is connected to the Lane Departure feature in order to not have to hear a constant warning alarm for Two Hands on Wheel I have to turn off the Lane Departure feature (which I love).

Outstanding service! Fast and friendly. I had an issue and couldn?t get help from Hall so we reached out here and they took care of the problem!

Have owned Jeeps for 35 years. This is the most comfortable ever. Altitude 4x2 L, V6, avg. 19-24 MPG. Tow up to 8,000. 6 passenger with 2 fold downs in back. Paid 34k with 18k miles

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

This is my first Jeep I have ever owned. I always liked the looks of the Grand Cherokee. I’m happy with the vehicle. No complaints except it does like to drink gasoline. My previous 4 vehicles were all 8 cylinder full size pickup trucks. The Jeep being a 6 cylinder eats more gas. The Other than that, I’m very happy with my purchase of my 2022 Jeep Grand Cherokee. Good looks, drives well, comfortable and safe.

My representative was outstanding. She is very personable, knowledgeable and is a great representative of your dealership. Thank you for an amazing experience. This dealership is lucky to have you.

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 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!!

This is my 2nd Jeep Grand Cherokee (previous one was a 2016), and I absolutely love it. Gives a very smooth ride. The vehicle feels very sturdy and solid, which to me is another plus. Disappointed that it didn't come with a cargo cover though!

This dealership is by far one of the best I've been to, great attention to detail and great customer service. Also they're taking very good measures in this though time with the Corona Virus in maintaining social distance a much a posible.

Bought my first Jeep Grand Cherokee in January of 2022. I was in a wreck where another vehicle hit me and threw me off the road into a ditch. I went airborne and came down hard. It was a miracle I did not flip. All of my driver-side airbags deployed (front and back) and I walked away with minor injuries. This vehicle kept me safe and I will have another one to replace the totaled Jeep from my wreck.

I wouldn’t shop at any other dealership. They made me feel comfortable right away. I never felt pressure. They put me with a great Lender for my loan. I’m taking my son here when it comes time for him to purchase. Thanks so much to Sullivan Auto Trading for helping me!

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 just love everything about my 2021 80th anniversary edition G/C! I purchased new but now has 81000km. So much enjoy all the style comfort with no issues. So much more reliable and better looking than the new body style that was released later in 2021.

Great service, good selection and staff is easy going and very helpful. I also appreciate all the different loan options.

This car has everything we need and more. 4x4, looks, performance, can be towed behind an RV. Includes sun roof, rear camera, safety braking, more. Rides great.

Martin Gross was awesome very friendly and helped me get a car with no money down definitely will recommend to my people. Thanks martin your great

My Grand Cherokee Laredo E just turned 50,000 miles a few days ago. Other than routine maintenance, the only money that I have invested in it was for 4 tires last month. Extremely comfortable, capable and reliable. While not delivering Prius-like gas mileage, given the performance it provides in all types of weather.............NO COMPLAINTS !

It was a pleasure working with Nate. He is very professional at his job. This was my third vehicle I've purchased from him. I'm very happy with all the vehicles I've purchased from him. I would definitely call him again!

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.

I cannot say enough about my salesmen (David). I will be remised if I do not share one of the best experiences that I ever had while buying my 2024 Denali Ultimate 1500. David contacted me months before I knew I would be purchasing this vehicle. David and I created a build for a 2024 Denali Ultimate 3500 Dually. My experiences with him were so grand, that my wife wanted to deal with him in finding her the 1500 Denali Ultimate. We gravitate toward genuinely ?good people?, and David is one-of-a-kind. He answered all calls day/night. He has taken my calls even when he was off duty. Truth be told, David, was off the day I came to pick up my vehicle. He is extremely personable. He knows how to genuinely deal with people. I have been a Chevy/GMC man my entire life, and I have tried to test his knowledge even when it was not to my best interest; he stayed honest. He delivers not-so-good news like warm rain. We, as consumers, get so caught up in believing that we can ask for anything with the expectation that we are going to get it because WE ARE THE CUSTOMER. Some things are indeed out of a salesmen control. Some things may even be out of the control of the dealership and the General Motors Corporation itself, but David remained honest even when things could not go my way. He does so with class, and I admire that. Wherever he works, wherever he is selling automobiles, I WILL ONLY PURCHASE FROM DAVID. If he is selling Toyota, then I will buy a Tundra. If he is selling Dodge, then I will buy a RAM. If he is selling Ford, then I will buy the F series truck. Why, because David has taken the time to know what I need and what I like. That means something to me. I am certain that if David is selling it, then I will surely want to buy it! I especially like the way he trained his young apprentice (I can?t remember his name), but this young man called my wife and I twice during our 7-hr. drive home to ensure that we were traveling ok. Thank you, David. Thank you for being there for my wife and I. Thank you always taking my calls to answer the same questions repeatedly. Thank you for picking us up from the airport on your day off and providing us transportation to the dealership. Thank you for finding our truck, which was surely a needle in the haystack. Thank you giving my wife the experience of a lifetime ? this is her first brand new truck. Thank you for giving us one heck of a deal ? one that we can be proud of. I can?t wait until my 3500 Dually is ready for pickup. It would be my pleasure to treat you to a meal and break bread with you like family, because this is what real people do for others that we hold in the highest regard. David for President!

2017 GC Limited 4WD. Bought it 3 years ago with 53k miles and now approaching 108k miles. When we bought it, we went to fill the tank for the first time and the gas pump kept shutting off. Turns out there was a known issue with the fuel filler neck assembly. The selling dealer replaced it under warranty and we literally didn't have another issue until 100k miles. At 100k miles took it in for new spark plugs, which is normal maintenance, and found the radiator leaking. The new radiator was not cheap. Have not had any other issues, just replaced the factory original brakes, they made it almost to 108k! We live in Minnesota and this vehicle is an absolute beast in the snow. Put it in snow mode and it is very stable and feels unstoppable. It is a comfortable long distance cruiser and gets decent mileage on the highway, between 24-27mpg. The UConnect system is very easy to use, and the nav is pretty good, but the whole system operates quite slowly. That's a minor complaint I think. Overall we are pretty happy with our WK2.

This is at least the 6th car I have purchased from this dealership. Have always gone to same salesperson. Test drove the car I wanted, found one in another color on the lot which was less expensive and purchased the vehicle. Had an overall pleasant experience.

We are very happy with our '21 GC Limited. It is well appointed, with many options, drives nice, comfortable and still sits higher, unlike a lot of other "car" SUV's. We use this as our only vehicle, and flat tow behind our motorhome. Jeeps are the best vehicles made to flat tow!! We have climbed dirt trails in the West and cruised coastal waterways. Love it.

This was the best experience I have had while buying a vehicle ( 12 over 40 years). Lucas Giles made the process easy and stress free. While reviewing the vehicle (Tacoma) a number of issues of concern were raised and Lucas assured me that each would be addressed and resolved to my satisfaction. True to his word, the finished product exceeded my expectations. I could not be happier with the results. Kudos to Lucas and the various service departments that made this happen.Checkered Flag rates high marks because of people like Mr. Giles and all the conscientious service techs that contributed. Thanks.

Love my GC 80th Anniversary Edition. A little over 15K miles and she’s been in the shop 2 times now with a squeaking coming from the engine. Tensioner rod and idle sensor were replaced first, they had it for almost a month. alternator was just replaced, they had it for a week. Picked her up last night, drove her this morning and it’s still squeaking! Very frustrated but hoping to get her fixed!

Dion the salesman was easy to deal with...no pressure...did not try to hide anything...did what he said he was going to do. Great overall experience.

Bought my 2017 Overland 2WD preowned with 74k miles. It’s now Feb of 2024 my Jeep’s got 135k on the odometer and I’ve never once had an issue. I occasionally get car fever, start looking at cars online, but the second I jump behind the wheel of my Grand Cherokee I smile and decide to keep it for a little longer. I still love the look, it’s super comfortable, has plenty of power, all the bells and whistles I want (and beyond), and I love the fact not every single thing is touch screen as most modern vehicles. I love I can turn up the volume, operate the AC and many features with good ‘ole KNOBS without taking my eyes off the road.

Bought the vehicle with 30,000 miles. Turned over 100,000 this week after four years. ZERO unplanned visits to the dealership. Just normal oil, filters, wipers. Since we tow a 3500-pound boat, decided to replace the brakes at 80,000 miles, turns out there was still plenty of material left. Infotainment screen developed minor delamination this spring. Was still working fine but decided to replace it anyway. Easy replacement job for $350 with YouTube help. Lowest maintenance vehicle we have ever owned.

This is the 3rd Jeep product we have owned over the years, first was a Grand Cherokee Laredo, then most recently a 2012 Jeep Liberty Sport. We just purchased the 2019 Jeep Grand Cherokee Ltd in Febrary 2023. This Jeep is the most luxuary we've ever had in a vehicle, it has everything but the cooling seats which would be nice as we live in FL. This will be a dinghy towed vehicle behind our Class A motorhome. We also towed the Liberty Sport.

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.

Purchased brand new after totalling out my Santa Fe XL. This has by far been one of the best vehicles I've owned. For as large as it is, its incredibly fuel efficient yet has plenty of power to tow my parents fish/ski boat. My only complaints are the factory Michelin's were trash in Minnesota and the interior "Cargo" area is significantly smaller than my previous Santa Fe's, but thats more of a personal opinion versus any design flaw. Ironically quite a few of my coworkers have JGC's as well and almost all of them have over 200k on them, I'm still at 65k. Not sure why they have a bad reputation in the auto world, but I'm certainly glad pleased with my choice, even 6 years later!