Used Jeep cars for sale near Winchester, CT under $100,000

I’m very loyal to the Acura and Honda brand, and with good reason. The cars and SUV’s I’ve purchased have all been great quality and they hold their value! I’ve now purchased 5 vehicles from Acura of Berlin and will continue to do so because of the professionalism of their staff, their commitment to their customers and the quality of vehicles they continue to sell! Erica was my salesperson; she’s very knowledgeable and worked with me to get the deal and car I wanted. Larissa, the Sales Manager, continued to check in with me throughout the finalizing of my purchase! Tony, the General Manager, accommodated my request to push up the timeline of when I was able to pick up my vehicle due to me and my family’s vacation. He does a great job running the dealership. Tom in finance worked hard, and overtime, to make sure that all of my paperwork and financing was all set to finalize the sale! I also need to give a shout out to Keith who manages the service department! Him and his staff are awesome! I highly recommend Acura of Berlin!

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.

This is my 2nd HRV that I am buying from Hoffman Honda!!! Kim the sales person was wonderful!! Love everything about this dealership!!! Very happy!!!

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 !

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.

Bought my used 2 door at about a year old, with 17,000 miles. Had a couple issues initially: passenger seat got stuck, and airbag light was on. But once I had those fixed, the car has been completely reliable. And I found out that the 2 problems were related. So really it was only 1 problem. The stuck seat has impacted the air bag sensor or something. Loads of fun driving this thing through the snow. 1 foot, 2 feet. Fluffy, or packed by the snow plow. It didn’t matter. Shift it into 4wd and point it where you want it to go. It just went over all of it, and without any drama. Nice and slow. No need for momentum. It just went right through the snow . Can’t wait to take it off road with some friends. As for everyday driving, I love it. You just have to know what you’re getting into. It’s not designed to be a comfortable or sporty car. It’s loud, rather uncomfortable on the bumps, the 2 liter engine sounds like a dish washer, etc. But, those are also all the quirks I love about it. It’s not pretending to be something it’s not. I would’ve gotten the manual roll down windows if I had the choice. It’s just the opposite of my other car, a Macan turbo. It’s just a good old fashioned, honest vehicle. The engine and transmission combo make for a pretty quick team. I’d say 0-60 in about 6 seconds. That’s pretty xxxx quick for a 4000 pound truck designed to go off road. Rarely do I push it that fast of course. I like to drive nice and slow in this car. This is my car to go slow and smell all the roses. I love it. I’m averaging just under 20 mpg driving mostly in NYC. Not bad. Best mpg I’ve had from all my suvs. The hardtop only takes 10 minutes to take off. But it’s still a pain in the xxx. It’s definitely a 2 person job. And then there the issue of where to store this big thing. It’s not like NYC houses have big garages. We’ll see how often I take it off once the summer comes around.

I recently purchased a 2022 BMW X3 m40 from BMW of Waterbury. It was a very smooth process and thoroughly enjoyed my experience. I worked with the Dennis Smith and can’t say enough about his professional manner.It was pleasure doing business with both him and Courtney Gale the finance manager.

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.

Easy, friendly, and low pressure buying experience. Offered a good price and then was open to an even better price. Delivered car to my home.

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 staff in the service department are friendly, prompt, and knowledgeable. I have been going to them since I bought my first car with them and this is my second car. I will keep going there for the service of my car.

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.

If I could give more stars than 5, I definitely would! Lila Bubier, Mark Deal, trade checker and Kia Finance went above and beyond to get me out of my negative equity from my Hyundai Ioniq 5. I am so grateful to have a new 2025 Kia Sorento Plug-In Hybrid. I had originally went in February, but did not come away with a deal. Lila has consistently reached out to me asking if I was interested and provided many different options to get me at the price point that I wanted. It was not easy, but we made it to the end goal. My growing family and I are so grateful to have this amazing team working at Kia and I hope to continue this new relationship with them at Blasius for years to come! Thank you so much!!!!

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.

Vinny at Sullivan's Northwest Hills was great to work with and to buy a car from. It was truly a good experience. He was very knowledgeable and let you lead the conversation. I will buy my next vehicle from Vinny the next time I need one.

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've bought 2 cars here and am headed in soon to buy another. THE BEST.

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.

Great Experience. Very attentive, quick responses to questions, no surprises. A pleasure to deal with and would buy from again.

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.

everything was great and quick friendly no one try to sell me anything and had free coffee very clean dealership waiting room. Manager ask how I was doing and how my Escape was. IT WAS 95 DEGREES OUT AND STRONG ac

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.

Awesome people to buy from and just could not be more helpful. Will return with family and friends..AAA+ dealership in my book.Thanks again John Clemons

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.

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.

10 out of 5 stars! Charlie is beyond amazing! He was professional, trustworthy, down to earth, and communicative. He estimated a financial deal that was great and then beat it! Next time we want a vehicle, we're going to Charlie! HIGHLY RECOMMENDED!

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 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.

It was a pleasure to deal with Zach, Patrick and Mike. The car was as Zach described, and I am very happy with it. The purchase was made easy by these guys and they were very accommodating:)

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.

i have a 2017 wrangler unlimited sport with a 6 speed ..at 18 000 miles they had to drop the tranny ..now at 49 000 they will need to do it again and its pissing me off. Plastic parts in a tranny is stupid . And a reverse gear too pointy and too thin ..Seriously ? You know its an issue and still no recall?

Love my jeep. They have come a long way baby!! I am now a Jeep girl for life and recommend them highly. No matter the weather my Grand Cherokee gets me there in comfort and safety.

Jerry is amazing! I really enjoyed finding my car online, and when I left a message about the one I was interested in, Jerry responded that same night. He even followed up with a text the next morning to let me know he’d check to make sure the car wasn’t already sold. Jerry—and everyone else at the dealership—treated us with genuine kindness and respect. I absolutely love my Rogue, and the color is beautiful! If you’re looking for a used car, I highly recommend coming here and asking for Jerry!

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!

Great sales and excellent service departments! Have leased two jeeps and have always been happy going here. I would recommend to go here to others!

I love my jeep Sahara I put a 2in lift in it and 20 in rims with 35 in wide tires , I took it on a 5000 mile road trip it did great on the highway and over the mountains of Colorado I hit a lot of snow and rain on the trip to the west coast and back to Oklahoma I loved the drive it does not drive like a sport car but better then my work truck does , for the whole trip I avg 20 miles to the gal even with the over size tires on it and the off road is just what you think a jeep would be , if you want a good on and off road then I say this is a good jeep for you