Used Jeep Grand Cherokee for sale near Winchester, MA under $99,994

6 months ago, today, I bought a truck from Chelmsford Street Auto Sales. As I'm approaching my first oil change, I believe the verdict is out on how everything has gone. The experience I had here was very good. Ross was very accommodating to me when I purchased the truck and he made things very easy for me. He took care of just about everything I needed and was very thorough on the test drive/vehicle walk through/paperwork process. This place is definitely not the stereotypical sleazy used car dealership, and the environment is very low pressure. The first week I had the truck, I had a few minor problems come up with it. However, they were very prompt to fix these issues for me immediately. So far, I have not had any problems since that initial speed bump. Other than that, the truck had been looked over pretty well by their shop and several wearable parts were replaced prior to me getting it. I paid a little more than I think I should have for the truck, but that being said, I did end up with a pretty good vehicle. This isn't a dealer where you go to buy an old beater car. If you're looking for a quality used vehicle, and want to be treated like a decent human being, I highly recommend this place.

The 2012 Gran Cherokee Overland has been my car for over 12 years. I’ve enjoyed every minute of driving it. Have made several road trips with it and never a complaint. It’s plush with features and luxury items. Love the looks, love the ride, love the comfort and love the low cost of ownership. Jeep lives up to its name and fame.

The most stress free and enjoyable buying experience ever! Shant (our Salesperson) was upfront about everything. No games here, and we purchased a truck we are most happy with. And, it checked out perfectly with our Mechanic.

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.

One of the best vehicles I have ever owned! Dependable, lots of features, stylish, fun to drive on and off road. A vehicle you can enjoy and be proud of!

I already owned this vehicle when I took it in for service. But. I love the vehicle. I haven't had any major problems with my Jeep Summit

I am very happy with the SUV I bought from Truck World. Everyone was very welcoming and helpful. Brian made the financing process really easy and they made sure it was cleaned and ready for pick up

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.

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.

Having a limited amount of funds to use, I still want a reliable SUV because my grandchildren and daughter live with me. As such, I've had to contact a lot of dealerships. Unfortunately, not all cared to continue after hearing my budget. Some hung up immediately, a few others actually scoffed before hanging up. These are actual large dealerships that make a lot of money. I was beginning to get quite discouraged . Then I emailed Bobby at Advanced Auto Sales. I left him a list of questions, not realizing that he wasn't the one to ask. However, he answered each one. Without complaining and without directing me to someone else. This is the kind of dealership everyone needs. Where you're able to get a truthful answer. I've not yet bought my vehicle here, but will soon.

This vehicle met all of my needs. Excellent handling in the snow with the Snow setting. It’s a great car to drive in the summer as well. Dual sunroof and cooled seats.

Found 2014 Audi A4 Quattro manual transmission on Saugus Auto Mall website and called after hours to set up a test drive for the next day. Car was in great condition and was really fun to drive. Though the car's price was very competitive for the market (we shopped around for a few weeks) it was just slightly outside of our price range and they were able to meet us in the middle. We test drove the car for a second time the next day. Both times there was no hassling or pressure from Ali or the Saugus team. We decided to buy the car cash and everything went so smoothly. When we got home we realized it was one of those unicorn car buying experiences. The DMV is super slow right now during the pandemic so we had to wait for a full week for our paper plates and registration to come through. The car was fully detailed and everything was in order when we came to pick it up. Also, we had asked for one of the tires to be replaced because it was damaged and they ended up replacing ALL four tires! Great experience buying a used Audi! Thank you to Ali, Mike, Jason and the whole team.

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 was in a car accident in the middle of April (not my fault). The other driver was an uninsured motorist. It was taking to long for my own insurance company to cut me a check for my vehicle that they had declared totaled. I needed a vehicle immediately so I started searching on the internet. I found the perfect vehicle at Padula Auto, the only problem was that it was 75 miles from my house and I was low on cash waiting for the insurance check. I talked with Cam and he set me up with financing. This was the quickest and easiest car buying experience I have ever had. The car was originally owned by an older couple and sat in their garage for a number of years. Cam told me not to worry, they would take care of any issues I had due to the vehicle not being driven, literally, for years. I drove the car home and it passed the NH Safety and Emissions Inspections with flying colors. Two days later I noticed smoke coming from the engine, the rubber boot on my axle shaft assembly had split and grease was leaking onto the motor. My mechanic replaced it and true to his word, sight unseen, Cam sent me a check to cover the cost. Three days after that I got two flat tires. The sidewalls of those two tires had blown out because the car sat so long. I went to the mechanic and had four brand new tires installed, sent Cam the bill and, once again, he took care of the bill sight unseen. My car has run great since the first time I drove it. I can't say enough good things about Cam and the employees at Padula Auto. I do know this, the next time I'm looking for a vehicle the first place I'm checking is Padula Auto, even if it is 75 miles from home.

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.

I recently purchased a Jeep Wrangler from Dan at Drive Automotive, and I couldn’t be happier with the experience. Dan has a great eye for quality vehicles in the market, and his no-pressure sales approach made the process smooth and stress-free. Not only did I get a fantastic deal, but he was also a great resource in navigating everything from start to finish. You can tell how passionate he is about cars and his customers—he went above and beyond to ensure the vehicle was fully detailed and that I drove off the lot with complete confidence, knowing there was nothing else I needed. I highly recommend working with Dan, and I definitely plan to do business with him again in the future

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 good experience to buy my Acura RDX Technology 2015 at Continental Auto Sales Inc. Good customer service. I will refer my family and my friends to Continental Auto Sales Inc. I love my car , it was a good dealer. Thanks to "Cars.com".

I've been driving for 43 years now and have owned an array of different vehicles, however I've never been financially fortunate to purchase a luxury model - until now! I was looking for a mid size vehicle that would check many boxes for my snowy Michigan commutes, along with distant travel comfort to and from my cabin and some towing capacity. I have only had this for roughly 1500 miles and wow.. My first impression was luxury. So many base options included in a mid sized and mid priced SUV that pleasantly surprised me. Secondly was the ride quality. Both smooth and quiet and handling. I've read other reviews discussing power inadequacy, but not at all. Plenty of passing and get tup to speed power. Next was the snow. I have Michelin defender tires and wow - what have I been missing? The snow 4x4 duaratac features combined with these tires make this a beast in the snow, slush and rain. It definitely gives me a much more safety reassurance while driving in these conditions. I have not tried the towing yet and have not had any "reliable" issues to report, but we are very fortunate with our pick and one very capable snow commuter.

I highly recommend Mike and Route 110 Auto Sales. Mike does not have the "used car dealer" approach. He will provide the information you need but not try a hard close to try and sell you a car. He was incredibly responsive both by phone and text. There were a few extra repairs the Explorer needed but Mike and his mechanic took care of them right away. I appreciated his willingness to make sure the car was ready to go. There are a few negative reviews here but we're buying used vehicles, cars can have issues. I don't believe those reviews should prevent anyone to check out one of his cars and meet him in person. I had a really good experience with Mike and believe you will too.

Because it a great car because the car has 118k miles on it and its only 15,371 dollars and its used and works very well

It was a great low pressure buying experience at Central. I highly recommend Jonathan Levin as your salesman. He is very knowledgeable and is customer focused.

2022 Grand Cherokee Overland. Beautiful inside and out. Love the extras that the Overland package provide. Beats EPA milage estimates easily. ride comfort is very good, even in the rear seats.

Good place and good people to work with. Car was in great shape and process was clear.

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.

Thay got right back to me with all the information I requested. Their price on the car was way above what these cars are trending.

Runs smooth. Very comfortable. Always loved the Jeep brand so this was a natural upgrade. Love the options too. The adaptive cruise control is amazing.

Big thanks to the Alliance Motor Group team. Ali the financial manager was on point in helping me getting an audi since day one. One of the best thing in this process was communication 👏 🙌 he stayed in contact with me the whole time until the end. Bendji Adhemar

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).

Been dealing with this dealership since 2002 when I bought a new Jeep Liberty and now many Jeeps and 22 years later I still go back and get the great customer service and friendly atmosphere since day one. Other dealers need to learn from Kelly, they set the standard and going above and beyond is the normal for them. Look forward to another 22 years!

bought a new 2022 GC Summit. I wanted the hemi, only found it in Summit pkg at the time. Overall love the vehicle interior is as nice as anything out there. Real wood, lots of leather and nice materials overall on interior. Kicking stereo. Had a 2016 Overland with hemi. Wanted one more new hemi before quit making them. Easy 20-22 mpg at 70 mph. Plenty of power, very quiet and smooth. Biggest complaint all the plastic trim on the outside. First time i shut the door sounded like a rattle or something, not as solid as the 2016, when i shut the door it sounded solid. Nothing i could find wrong just pieces seeming to make a noise. Overall love it. Looks great, rides great, descent mileage, and very nice interior. Did i mention messaging seats are real sweet. Also plenty of towing power which i needed. Excellent in the snow as well.

I just got my second car from Avon auto broker they have the best selection and their staff is very knowledgeable and the owner Dana was very helpful. I highly recommend this dealership.

This car has met my needs and want's. Looking forward to comfort and reliability. Once again Lonnie there was no pressure in the buying process. Thank you all at Miller Motor's

Another buyer beat me to the car but I was very impressed by the professionalism, information and great communication provided by this dealership!

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.

the staff is amazing and they are very knowledgeable and i truly trust they are doing what is best for me and my vehicles life! highly recommend to anyone!

New Jeep GC owner…about a month in. Bought a ‘23 Grand Cherokee Summit after admiring the looks of it. Was nervous to purchase because I usually drive foreign. I also own a ‘22 Audi and have to say that the quality of my Jeep is comparable. I am pleasantly surprised by the drive as well as the quality of the finishes. The ride is quiet and smooth. The 6 cylinder has plenty of pep and has no trouble getting down the highway. It even has a bit of a growl when you step down on it. I legit smile every time I drive my Jeep.