Used Jeep Grand Cherokee for sale near Sturbridge, MA under $50,000

I recently bought a car there and the experience was awesome!! The process was very fast and the salesman Matty is great!! Very good service i highly recommend them!!

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.

Had my first oil change and was impressed! They were professional, reliable and efficient! Thank you! Tanya Abram

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.

Mike, Mackey, Dan and Scott were all a pleasure to deal with and provided a pleasurable experience. They worked as a team and answered all my questions.

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.

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

My experience at Imperial chrysler dodge jeep ram was very good. I worked with Ahmad Al-Jallad and Khalil Mansour and both were very attentive and explained everything clearly. They answered all my questions and gave me the best deal possible. If you are looking for a new or used car, I would recommend Imperial dealerships for your next purchase.

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!

Purchased a used 2011 Santa Fe from Gary Jackson Motors and had a great experience. My salesman, Jordan was friendly, knowledgeable and easy to deal with. I saw the vehicle online, noted the good deal and drove over an hour to test drive. Any concerns with the vehicle mechanically were addressed prior to my returning to pick up the vehicle. Jordan made the sales paper work easy and the registration was processed by the staff as well. Super easy transaction.

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 recently purchased a used Subaru from Imperial and had a wonderful experience with Laith. He was kind, courteous and very efficient. Highly recommend.

My husband and I love our Grand Jeep Cherokee we purchased from Chrysler, Dodge, Jeep of Winter Haven. We love everything about this vehicle. Matt is our Salesman, and he did everything he could to get us in a Jeep we would like. I highly recommend this company.

Bob Jeffers provided excellent customer service and helped take the stress out of finding the right used car at a reasonable price, for me. He was very knowledgeable and up front. I would definitely recommend Enfield Street Auto Sales. Thanks again Bob, You Rock!

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 bought three cars from AutoCare in the last 5 years. The owner Frank is a no nonsense car guy. He won't waste my time if I don't waste his. That is to say; when I go to his dealership with the INTENT to purchase a vehicle, he goes out of his way to make it happen. Never an issue with either vehicle I've purchased from him.

I have that car and I’m happy with it. Yes it have some problems, need some care, you can just go to speedway and fuel up it would be your last fuel up with diesel on speedway. To previous review: I bought the car with 185000 miles. After I fuel up at speedway 😁, I sen car to dealership. They replace entire emission system with brand new. No problems after that. Just fuel up at good stations, I prefer Sheetz or BP or shell. About $300 oil changes: I do my oil changes by my self: 2, 5 quart oil canisters and $25 filter and it’s don for $75. I change oil every 5k miles. About fuel filters: I do it by myself too. So 2 filters on Amazon for $17-25 and you have done it for $35-50. I change them every 20k miles.

Great group of guys that answered my questions. Honest without the games. Even though I did not buy a car here I will the next time I am in the market.

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.

We got awesome treatment and a good deal from this place. My salesman, Jonathan Testa was fantastic, honest and accommodating. The Toyota brand itself is an excellent, reliable car to begin with and the salesman I worked with could not be more pleasant and reasonable.

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.

I have been dealing with Bolles Motors since 1987. I purchased 3 Jeeps from them -- a Laredo, Grand Cherokee, Patriot -- and I have leased my last 3, all Grand Cherokee Limited. They are a great dealership and their service is equally outstanding. Brian makes it a point to say hello and check in with me every time I visit the dealership. I have dealt with Barry Pinto several times (sales/leases) and Dan in service is top notch. I wouldn't deal with any other Jeep dealership.

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.

If you are in this area, and have a Ram HD with a Cummins diesel, these guys are the best. Ask for Bob to work on your truck and you won't go wrong!

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 !

There was a mishap during a transmission service. Artioli took care of all problems and in the end I received an excellent service. Wonderful people, great business!

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.

Tori from sales was great!!! Please commend her and the dealership for excellent customer service Made me feel relaxed and comfortable Highly recommended will definitely be back!!

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!

My Jeep Liberty was brought there by the dealer I bought it from for repair of a coolant pressure problem , they had been working on it prior to the fire they had in the service dept and parts of it were in the fire, they were able to put a replacement engine in it and now it’s back on the road, thanks to Leo and Jen and the guys in the service dept for their effort with the main building gone they are working out of small garages and trailers on the property, not the most ideal conditions but they got it done !

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.

Recently completed a purchase with Jordan as my salesman. Hands down the best buying experience I've ever had with a dealer: straight-talking, low-pressure, transparent negotiations. My daughter is looking to replace her car soon and I recommended Gary-Jackson Motors without hesitation.

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.

Darryl Wilson has sold me cars over the past several years. I went in looking for a used vehicle with low mileage. The vehicle I wanted was just sold. He showed me the same car but it was a new 2021 Jeep Renegade Trailhawk, for just about the same price. I looked at the vehicle on Wednesday and purchased the vehicle that Saturday July 31, 2021. I am very happy with the attention given, his professionalism, and he is very courteous. I have recommended my friends and family to buy a car from Darryl. Richard and Katreen Shaver

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.

Workers and establishment is amazing , very smooth process , willing to help you in any way , very professional with a variety of inventory !

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!

Great people very friendly staff was a pleasure doing business with them would reccomend too anyone in the market for a used was quality used car.

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.