Used Jeep Grand Cherokee for sale near Windham, CT under $99,980

Jacob, Sean and the team made me feel like my business was the most important thing they were working on and the finance guy, John was very efficient and explained everything perfectly. Would definitely recommend them for the selection and the buying experience

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.

Overall, a good honest dealership. I had a predefined monthly spending limit and Josh worked his magic and got me the monthly payment to meet that number. His can-do attitude made this deal happen and got us the car. The finance manager Alex was also a pleasure to work with and made our car buying experience much less painful that I have experienced in past years with other dealers. There is no pressure from the sales team to buy and were up front with everything. No hidden agenda. I would recommend buying new or used vehicles from this dealer without hesitation and for that I’m giving them 5 out of 5 stars.

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.

Beginning with John Tapio, who responded to an inquiry then Cameron, Jillian, Matt! Jay, and (apologies, can?t remember name) Finance guy, this whole process was the best ever. Best Kudos go to Cameron and Jillian! The both were a breath of fresh air in a position that had previously filled by (not at Monaco) people who seemed to only care about commission. It seems Monaco has gotten away from that, so no dog eat dog cut throat games. Mary Jo and I are very pleased with your awesome sss ad Les team.

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.

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.

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 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.

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.

Sam was awesome, other saff are awesome too ,,very informative, and helpful to meet my needs

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.

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

New Jeep GC owner…about a month in. Bought a ‘23 Grand Cherokee Summit after admiring the looks of it. Was nervous to purchase because I usually drive foreign. I also own a ‘22 Audi and have to say that the quality of my Jeep is comparable. I am pleasantly surprised by the drive as well as the quality of the finishes. The ride is quiet and smooth. The 6 cylinder has plenty of pep and has no trouble getting down the highway. It even has a bit of a growl when you step down on it. I legit smile every time I drive my Jeep.

Went in for oil change and tire rotation. The friendliness of the service people and the quality of work is why I keep going back!

Besides the hefty amount of recalls in the first year, overall has been the best Jeep I’ve owned. Super comfortable, very reliable in weather conditions. Can sit in it for 6+ hours a day without my back hurting (I have a rod in my back). Traded a hellcat for more comfort. It was worth it. Probably best adult decision I’ve made. Does pretty well on gas. (3.6L) I get about 584 range, sometimes 598 depending on how traffic is. However the interior could have been constructed of better materials. (Steering wheel stitching came lose but covered under warranty). Had it since end of March 23 with 25k miles already. No huge issues, never had to worry about screen issues (like what I’ve heard about 21-22 models). I would recommend this vehicle to anyone who is looking for an upgrade from previous body style GC, bigger suv with legroom, and enjoyable drive. I test drove a RAV4, CR-V. Ended up buying a 23 Jeep. Most vehicles in the market don’t have the technology the Jeep has. Toyota is a few years behind (& the road noise is unbearable), CR-V doesn’t have enough pep in its step ( Also the interior gives off impoverished/ barely any enjoyable features and buttons. Jeep is perfect. I love how a lot of options are in the screen but also below the screen. Not too cluttered.

Highly recommend! Purchase was easy and seamless. Josh went above and beyond. Purchased over the phone today and was delivered tonight. Vehicle is pristine, like new!

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 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.

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 !

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.

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 brought my 14 Echo Diesel in for warranty work and Avery Brown the service rep was awesome, very knowledgeable, and courteous. Awesome place 👍

Very good the cars were good and the goodness of the level of good was so good I was like dang. The overall experience was very good

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!

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.

Tom was my sales man for my gladiator. I had a great experience up front with everything part of the sale. Listen to what I wanted. Everyone was great to work with could not ask for more. I would definitely buy from them again.

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!

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.

OMG !!! This was my 3rd time there. I had a very pleasant experience. Keep up the good work and wonderful staff. Not more to say.

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.

I found a Ford F250 that had the options I was looking for on cars.com that Blasius of Middletown had in stock. Contacted Edwin (salesman) to confirm truck was still there and set up an appointment. The truck was detailed and ready to go when I arrived after a 3 hour drive to the dealership. I liked the truck, so I made the purchase. We negotiated a little on my trade and came to a deal we could both agree to. Overall had a smooth transaction.

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).

Really enjoyed this car buying experience. When the car started acting up they were all over it and fo t it to a Ford dealership for diagnostics. Literally refused to let them send the car back until they were satisfied that my car is tip top. Can't say enough about Dave in sales, Phil their awesome mechanic who advocated for me like it was his own car. Then the GM met with me to talk about the experience and stand behind the car if the same problem recurs. Jessica at the desk made a rough week much nicer. So pleased to work with Blasius of Middletown and will be a repeat customer for sure!!

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

Called to make an appt to diagnose my car. I did NOT know what was wrong with my Audi. My car had no power. I dropped it off to European motorcars they called me within an hr and half and had figured it out! 10/10 recommend staff are so professional, work is done with precise and good timing. You guys have a forever customer thank you!

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!!