Used Jeep Grand Cherokee for sale near West Simsbury, CT under $40,000

I was pleased with the whole process of buying a new Grand Cherokee from Executive Jeep in Wallingford. I worked with Tim Harris throughout the process. He devoted a lot of time to helping me compare and understand all the models/trim levels, figure out the financial details, and make a good decision. I would definitely return to this dealership.

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've bought 4 vehicles from this dealership as a return customer die the the (CPR) - Courtesy - Respect - Professionalism I live in Delaware and make the journey for these three requirements for me to purchase. Ask for Lou 😉

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!

Jon Bryant and team were highly professional and made my recent purchase a pleasant experience.

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.

A1 service clean and customer service was great and have to say the restroom was spotless.

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).

Just purchased a car from them. Very professional sales people and service department. Even after we agreed on a price, the service department decided to put new tires on the car before giving it to me

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.

The dealer knew their product, fair and let you make your own decision. The sales person was wonderful.

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.

Kristina in customer service is exceptional she kept me informed about everything that was happening and always does when I’m there. She goes above and beyond. Great job.

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 !

Todd helped us buy our new car. After seeing other cars and dealerships coming to Highline was refreshing. He was so pleasant and very prompt during the testing of vehicles. Cars were pulled up right away back to back with zero down time. I love this. Considering they had a busy day with many customers in the office we still received great care. We closed on a 2022 Honda Accord and are in love. The manager closed the deal and experienced was everything as he too was great

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.

I was very satisfied with work done to resolve recall on our 2013 Honda Accord. Everyone was friendly and helpful. I would definitely recommend Sullivan auto repair.

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.

I bought my car here 8 years ago and have only brought it here for service. Andrew has been such a good service advisor, they are all great of course, but he was very helpful and caring during my recent appointments for brakes and oil change. I will be scheduling with him in the future.

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!

Erin the service advisor was very sweet, got a recall done really fast and was able to enjoy my day, made sure to send me reminders for my appointment

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.

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)!

We special ordered the 2021 Jeep Grand Cherokee Trailhawk. The vehicle is all black inside and out. The paint is a Diamond Gloss Black Metalic. The day after delivery we had the entire finish done with Ceramic Coating. We've had this vehicle for a year and the fit and finish is like new. The Ride is tight and still handles great. Fuel mileage is now 21 City. We're sorry to see they will no longer produce this vehicle!!

This was our second time working with Derrick Buccacio and finding a vehicle we love. Derrick is always personable and professional. He doesn’t pressure you into things and is honest. One thing that stands out with me about him is he always gets back to you whether he thinks he’s making a sale or not. A lot of salesmen I notice only care to contact you back if they think they’re making money off you. Derrick always gets back to our questions and concerns regardless. To us that says a lot about his character and makes us always wants to go through him to get a vehicle. We highly recommend Derrick to anyone.

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

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

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.

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

Rodney was great! Bought a 2013 Nissan Altima and couldn't be happier with it. Sale was smooth and easy and overall a pleasant experience. Would buy again from them in the future.

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.

Very friendly and helpful from Kevin D in sales to Nate in finance! Everything went very smoothly and I am very happy with my purchase!

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.

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.