Used Jeep Grand Cherokee for sale near Woodbury Center, CT under $50,000

My experience at Northwest Hills Chevrolet was exceptional. I was treated with the utmost kindness and respect, and accommodations for my special needs were made willingly, and in some cases, without my even needing to ask. My salesman, Phil Musmacker, made everything incredibly easy for me throughout the entire process (honorable mention goes to Brendan Elrick, who followed up on my initial request for info on the Equinox EV, and connected me with Phil). In addition, I never found any reason to question the pricing on the purchase order; everything was straightforward and exactly as I had been told, which is incredible considering my previous experiences with dealerships, where I had to fight to keep extras from being added to my order. Truly remarkable! I've already recommended Northwest Hills Chevy to a couple of friends! Thank you for a most wonderful experience (and I also really love my car)!

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.

Easily one of the smoothest & most trustworthy transactions I’ve ever experienced with a car purchase! Will never go anywhere else moving forward. Dejon N. was kind, knowledgeable, and very patient as I asked a ton of questions. Financing staff equally as lovely & incredibly helpful. Highly recommend this location! Thank you!

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.

I am Very happy with the work they did and highly recommend them. Very professional.

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.

Thanks to Mark, Hector and Tony for making my first Porsche purchase an excellent experience. It was a pleasure working with you guys. Let’s do it again someday.

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 !

Just purchased a 2025 KIA Sportage. Everything went really well and smooth thanks to the help of Lila Bubier. ⭐️⭐️⭐️⭐️⭐️ service!

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.

I didn’t end up buying a car from here, but Dan was a pleasure to work with and very professional. Very comfortable at atmosphere.

This is third Jeep I have leased and best yet. Summit Reserve Trim is amazing. Great performance and many comfort features. Performance from the v8 Hemi is amazing.

Louis was excellent on follow up and information. He kept in touch throughout the entire process with a phone after purchase to make certain I was completely satisfied. Great 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.

Bought a 2015 Dodge Challenger with 5800 miles - great price compared with what the same car is going for today with 40K / 50K more miles. Process was easy. All my friends love the cards and strangers give me compliments. My only complaint was these cars go through an inspection where all problems are fixed. I bought the car in February and by the Summer when I finally turned on the A/C, it did not work. When I went to the repaair shop I was told it would cost me 41000.00 dollars as the hose was broken dehind the instrument panel. In my opinion this should have been caught by CARMAX and fixed before I picked up the car. Otherwise very happy - no problems other than that to date. CARMAX - please fix my A/C??????

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!

The sales staff and the management with above and beyond their duties to make sure that my new vehicle purchase went very smooth. Will definitely come back.

Great,sport utility so far plan too keep it for a very long time.It's,the trailhawk trim the off road performance is amazing and get's great mileage.

I bought a brand new Ram 1500 Warlock from a different dealership 3 weeks ago and the check engine light came on. After being shooed away and essentially given a “not our problem” response, Robert’s welcomed me with open arms. I cannot remember her name, but the service woman was fantastic. She told me they could do a quick diagnostic test even though they didn’t have any service openings. The problem was identified as a simple EVAP leak and She told me that it was a quick 15 minute fix and they’ll take care of it. This is ALL I wanted from my other dealership. Robert’s just gained a new customer in the future for this superb service.

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.

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 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.

Melissa Fusco was friendly patient and more than helpful with the registration of my car. I highly recommend this dealership over the dmv any day!

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).

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.

Did not purchase but had a very transparent and honest experience with the staff at Wallingford Auto Park

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.

Over the past 15 or so years, I've bought 4 trucks from AA (a Chevy K1500, 3 Silverados) and I will do so again when I need another vehicle. My K1500 was a little small but ran great and served its purpose; upgraded to a '04 'Rado which was taken out in an accident by a texter; replacement crew cab too big for my needs but Chris and Dave found me another extend cab. I asked and they more than delivered! The guys are awesome to deal with and provide quality maintenance to all my vehicles, free oil changes and tire rotations. They even service my vehicles not purchased at Action Automotive. I can't say enough good things about these guys! I also enjoy visiting with Echo, the shop dog.

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.

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.

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!

Found a used car on the lot that we were interested in. Spoke originally to Josh and then Justin. Liked the laid back atmosphere without pressure or hype. The transaction was smooth and easy. Asher wrapped up the paperwork and we were out the door in no time. Would definitely recommend this dealership!

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!