Used Jeep Grand Cherokee for sale near Blue Hills, CT under $100,000

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.

I am a returning customer who bought several Jeeps from Barry Pinto. Barry is not only a true professional but also very approachable, friendly, attends to requests promptly and always returns a call. Everyone at Bolles is helpful, providing a stress-free experience. Their service department over the years has been beyond reproach; the customer service is excellent. It is refreshing to know there is a caring car dealership that has kept car buying stress free with confidence. I shall never go anywhere else and hope Barry Pinto will be there as long as I'm buying cars.

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.

I bought mine ( 04 overland) w/ 250k miles on it, in great condition. Owner had carfax for both his big diesel pusher and matching Jeep - it was towed the majority of its travels. It’s record of maintenance matched by almost half of motor homes service records. it has never had a single issue other than standard maintenance- I jokingly said ‘I’d drive it till it dies”. And. It looks like I’ll be doing just that- I think about it’s not so good ‘gas Guzzling’. But it’s a second vehicle, fits my grandkids,tows most of our toys and is comfortable and sure beats being stuck with 💰

Sarah was really helpful with purchasing a car. I had a very pleasant experience with and would recommend others to visit her for purchasing a car!

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!

Excellent customer service from both Vilkas and Terence. Highly recommend checking out this awesome dealership where they really take care of the customer! Great lot of awesome sports cars!

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 !

Excellent service. Monica kept me totally updated throughout the process, both in terms of service and price.

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.

Columbia Ford/Kia was awesome. Everyone I met there bent over backwards to be helpful. They gave me the information I needed to find the car I wanted. Then they helped me arrange financing. It was the best car buying experience I have ever had.

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.

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.

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.

Great dealer. No hassle. In my new vehicle the same day. Smooth transaction. Very happy with whole experience.

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).

Well, my car beginning of April beginning of September was time for my oil change synthetic went in at my appointment time came out within an hour 100% satisfaction got a car wash touchless I just dried it off when I left Very happy I recommend this service to anyone who buys a car there very clean very nice experience five star

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.

Great overall experience. I have bought three vehicles from this dealership and it has always gone well. Rich D. Has been who I have worked with and everyone else has Ben helpful as well.

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.

Well I came 31/2 hours to see a car and it’s gone yesterday I wanted it I was buying it because i recked mine i wanted the same thing

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 had an outstanding experience purchasing my Cadillac Lyriq from Blasius Cadillac. Despite having researched the vehicle extensively through YouTube videos, sales representative Rich Noble took the time to thoroughly explain every detail during my test drive, ensuring I fully understood all the features. When I arrived late due to travel delays from Boston and a previous dealership appointment, the team was incredibly accommodating and flexible with my schedule. The pricing process was refreshingly transparent—we negotiated the complete out-the-door price entirely through email with no hidden fees or last-minute surprises. Most impressively, they coordinated with the Massachusetts RMV and delivered my vehicle directly to my home with plates and registration paperwork already completed, saving me an additional trip back to the dealership. Blasius Cadillac demonstrated professionalism, transparency, and genuine customer care throughout the entire process. Highly recommended!

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.

Every person I dealt with were very professional and good communicators. This was a factor in my decision to purchase my car. It was a positive experience. Definitely recommend.

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.

What a pleasure to deal with salesman manager number one Would definitely buy another car from them in the future

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.

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

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.

Josh and Marcus made everything very easy and were extremely helpful while helping me find a truck. They made the whole process simple and smooth. i would highly recommend going to Roberts Dodge for your next vehicle.

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

on 3/3/2021All of what my Used Land Range Rover needed was performed with Great precision I would have damage my vehicle if the facility system were not functioning appropriately . I found out upon entering the facility that my car needed a alignment both front and back, And the service director Michael Laurie and Paul Cardoso did a wonderful Job with seeing that safety and customer satisfaction with regards to the service requested I'm Very HAPPY!

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.

Today, purchased the 2013 Nissan Juke, 112,600 mile for $9,995 today. It will be ready Wednesday or Thursday this coming week. My sales person Amy was excellent. She knew I had a firm budget (retired) and she found two great vehicles to test. The Jeep I could have taken home today with less milage... a little older, however, Jeep mph versus the Juke..., Nissan won even with higher mileage. So far, I'm "a HAPPY CAMPER"! I can't foresee any problems from now until pick-up. So, I'd say, if you need a reliable used car, Amy is knowledgeable and, in spite of the packed waiting room with eager customers, we were never abandoned. Note; yes, the sales people had to multi-task at times. Understand, at these reduced prices, compared to any dealerships for used cars... Patience, just a little patience - and you'll be treated right too. All the best to customers in need of a new used vehicle!

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.

Picked up my new lease, 2021 4Runner, on Friday, Aug 13,2021. The service was exceptional from the team at Toyota of Wallingford, specifically Jimmy Ballough, Dan Roberts as well as the general manager, Steve Jr. Because they knew I was in a time crunch, they had my vehicle ready and credit application already processed. Jimmy was great showing me all the upgrades on this vehicle as I was trading in my 2018 4Runner. Dan pushed the paperwork through, which was done electronically in record time. I couldn't be happier with the vehicle and the amazing customer service I received. Will definitely go back!!! Thank you Toyota of Wallingford Theresa Pierson

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.