Used Jeep cars for sale near Simsbury, CT under $99,995

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.

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.

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.

On Saturday, June 7, my daughter and I had an outstanding experience at XXX Chevrolet. While my initial intent was simply to support her in purchasing her first vehicle, I ended up trading in my own car and driving away in a brand-new 2026 Equinox — while she purchased a 2025 Colorado. Both vehicles impressed us during the test drive. The safety features, interior design, storage space, and overall aesthetics sealed the deal for both of us. While comfort and safety were top priorities, what truly set this experience apart was the exceptional service we received. Steven connected us with Brian, an outstanding sales specialist who was both highly knowledgeable and incredibly personable. He built immediate rapport, listened carefully to our needs, and guided us to the right vehicles without any pressure. The process was smooth and efficient — we were both driving off the lot the same day! The dealership itself was clean, welcoming, and even treated us to a delicious lunch during our visit — a thoughtful touch that made the day feel even more special. I’ve purchased several vehicles over the years, but nothing compares to the level of service we received from Steven and Brian. I highly recommend them to anyone looking for a car-buying experience that’s professional, honest, and genuinely enjoyable. Judi and Jackie T.

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.

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).

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

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.

Bought the car here 7 years ago had one minor issue this year Joe did my diagnostic and was great to work with! This is the only place I get my car serviced at

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 !

i think car max got it right when they make you an offer they are serious.it is good for 7 days and the process is rather seamless

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.

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

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 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.

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.

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)!

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.

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.

Great service. Shout out to Tom for always taking care of the customer. He responds promptly and follows through, always with a smile.

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 had an excellent experience at Balise Toyota throughout the entire process. I would highly recommend purchasing a car here. Nick was great from the beginning. We stopped in to test drive the Rav 4 and within 15 minutes we were out on the road! Nick was fantastic start to finish in helping us acquire the proper insurance and banking documents that we needed to purchase the car. He was there at the end to congratulate us and send us on our way. 5 stars! The pick up process was excellent and exceeded our expectations. I love that Balise provided someone to talk us through the features of our vehicle before just letting us drive off to figure it out on our own. Nate was fantastic in doing this. Very calm and thorough. I did not feel rushed. He got my phone connected with apple play, which is super cool! He showed me how all that stuff worked and he answered all of my questions. I love that if I have any future questions about the car or the technology that I can check in without feeling like I am bothering someone. Good vibes!! 5 stars! I love the new car. My first ever new car purchase at age 53 and am super psyched to have joined the Balise Toyota family!! Thank you for your commitment to good service, it shines through in your employees! Dawn Premo

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.

My experience with this dealer could not have been any better. They were professional, honest, and pleasant throughout the process, and they went the extra mile for me on their own in preparing the car. I would recommend them to anyone looking for a good car and a low stress experience.

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.

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!

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.

Metro is the only dealership thats responded to my inquiries and they responded immediately. They’ve always followed up

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.

Even though throughout the 18 years that I've owned her, I have put quite a bit of money into her, I feel that she's a dream!!

This was the best experience I ever had with purchasing a vehicle, David, was very understanding what I needed, he showed me numerous vehicles , helped me with setting up the bank that would finance my car, for the best rate, I wasn’t nervous talking to him, he wasn’t pushy trying to get me to purchase a vehicle, I highly recommend this dealership to anyone looking for a used car, I left there happy with the purchase I made, hats off to Dave and his staff. I gave 5 stars , it they had more stars I would of given all of them, Thank you Dave😊😊😊⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️

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.

Great no stress car buying experience from the beginning to end. Happy with my experience.

I love my 2019 Jeep Wrangler. It looks and drives great and is a good value for the money. Try it…You might like it!! The Jeep Wrangler Sport S is like no other…with the exception of another style of Jeep Wrangler!!