Used Jeep cars for sale near Winchester, MA under $899,990

I couldn’t be happier with my experience at Richards Motorcars, mainly due to the GM I worked with, Joe, who was great. He was prompt and very easy to communicate with over the phone and via texts. He answered a lot of the questions I had before I even made it to the dealership. I made an appointment, checked out the car and was able to do the test drive, fill out all the paperwork, and complete the purchase in a little over an hour. I couldn’t recommend the dealership more.

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.

Top notch dealership. Made buying our son his first car a very simple process. Friendly, helpful staff. If you're looking for a quality used car this is your place.

Because it a great car because the car has 118k miles on it and its only 15,371 dollars and its used and works very well

I only write reviews for truly exceptional businesses. Truly great buying and post-purchase experience. My wife fell in love with this Jeep, and Dan let us take it for a test drive “as long as you want”. We didn’t abuse the offer, but went for a healthy drive. Loved the manual, but you always have to wonder if the prior owner wore out the clutch, but no problem as Dan had already installed a new clutch as well as a couple new tires and a couple other things. We returned it and said we wanted to sleep on it. There was no hard sell at all. I called the next day to see if I could bring it to my regular mechanic. “No problem”, said Dan. I took it to my regular guy half expecting to get a report back about a half dozen things that were either worn out, broken, or just missing. As it turned out, my mechanic came back saying, “we couldn’t find a single thing wrong!” He seemed disappointed, so I know he tried to find anything. Even with that, I was a little nervous about the purchase - you know what I’m talking about, that “Am I just buying someone else’s problem?” feeling. We needed a car, my wife loved the car, it came back with a clean inspection, and the price was very reasonable compared to other options I reviewed online. So we went for it. Dan made sure the car was detailed and handled all the registry stuff. Not two days after we got delivery, the engine light comes on. I’m thinking, “Here we go….this is going to cost me”:( We called, and Dan was genuinely horrified, “Bring it in, I’ll take care of it.” Full stop right there. Awesome! We had already paid for the car, and I was not expecting that response. Dan provided a loaner and took what I would call exceptional care of the car not only fixing the what-ended-up-being-a-minor-issue, but also doing a full check, again, post-purchase, just to make sure it was perfect. I waited a month to write this review just to make sure nothing else happened, and it hasn’t. The car is great; my wife is happy. As I reflect back on the whole buying and post-purchase experience, I am in awe. How many companies these days not only ‘do what they say they will do’ but also add in a few ‘surprises and delights’? If you are a serious buyer, go here and buy from DRIVE and sleep well at night based on your good decision made.

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.

Came in to trade my old van in for a newer version. Kervin was very helpful and made the buying process very easy. Thank you !

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.

Bought a corolla from them last week, the car was in excellent condition and the price was lower than I'd have expected. Gary the owner, and Walter were both helpful and laid back. No pressure for the sale, and both friendly and professional.

There's nothing like a 2 door Jeep Wrangler when it comes to climbing rocks, crawling through mud, and making those tight turns. My other jeep was a soft top which can be noisy on the highway, but this hard top is quiet. I also love that roll cage/soundbar. I can still take the roof and doors off, put it in 4WD and have a blast.

Best car buying experience I’ve ever had. Great price on my new Suburban RST. Very clean truck with no prior damage. Gave me a fair trade-in on my Tahoe. Thanks again!

The 2012 Gran Cherokee Overland has been my car for over 12 years. I’ve enjoyed every minute of driving it. Have made several road trips with it and never a complaint. It’s plush with features and luxury items. Love the looks, love the ride, love the comfort and love the low cost of ownership. Jeep lives up to its name and fame.

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.

Highly recommend this dealership to anyone! Super clean location the staff is very friendly. This was the best place ever to chose for buying my first car. The staff is great to talk to and are so helpful and will make sure that the car is in the best condition it can be before you take it off the lot. They were super understanding when I didn't understand something and had my dad help to explain as well. Overall my dad and I had a great experience and we will go back in the future.

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.

Ali was good. I had the financing secured online as well as a couple others to choose from that Ali provided.. Made sure the car was in tip top shape before delivery and handled everything at the RMV. Extremely satisfied with the process.

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.

Super professional and very helpful through the whole process. Can only recommend to buy a used car at European Engineering, also if you are international and is a first-time buyer in the market, they put a lot of effort to help you through every step of the process.

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!

Have had great experiences here.bought a 2009 Jeep Grand Cherokee 3 years ago that I’ve had no problems with. we just passed it down to my Daughter.A couple months ago we went and bought a 2014 Jeep Grand Cherokee. When we test drove it we mentioned that the rotors looked a little beat up when we went and picked up the jeep it had brand new Pads and rotors on all 4 tires. We only mentioned the front. They go above and beyond to make sure there customers are happy. Defiantly will be going back for a third vehicle next year when my other daughter gets her license

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 have wanted an SUV for quite awhile but could not find one I could afford until I saw a SUV at Boston Auto Cars. It was exactly what I wanted...a low mileage quality car one owner. I purchased the Lexus RX350 and I could not be happier with this car. No high pressure here and Anthony is great with handling the buying process effortlessly.

Great vehicle. mine is a soft top and the noise was expected Have to be aware of oil leak at the oil cooler. Chrysler uses a plastic material that over time will warp and not seal. The after market ones are aluminum and since you have to remove to of intake, the coils and spark plugs are accessible as well on the drivers side. Other than that it is awesome

Staffs were very kind and respectful. They matched the price from other dealership and got my my dream car! Will definitely recommend them to anyone shopping for cars

So beautiful and so comfy and so cute and so speedy and so tough and so perfectly green like kermit the frog or nice fresh lettuce.

I found the brothers who run this dealership genuine and honest. Normally, I assume that even a well priced car has a bit of wiggle room but David would not budge on the price which I found refreshing as opposed to large dealerships who never give you their bottom line price. David gave me his best price first!! The vehicle was well prepared for me and they have been extremely helpful throughout the process. I highly recommend this small and honest place!

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.

Was in search for a reliable used SUV for my daughter’s first car. I searched for months and did my homework and went to a lot of dealerships. I almost ready to give up, but then I found Boston Auto Cars. Anthony went above and beyond to help us. The car was exactly what we were looking for at a great price. My daughter has been driving it for two months now and loves it. It has proven to be a very reliable car. I will be back in a few years for daughter #2’s first car.

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.

I am very happy with the SUV I bought from Truck World. Everyone was very welcoming and helpful. Brian made the financing process really easy and they made sure it was cleaned and ready for pick up

We bought this car for our daughter. Elvis could not have been any better. He was so patient with us and I would recommend anyone looking for a vehicle to go see Elvis. He was a rock star. I was in the car business for 30 years and he exceeded our expectations of how we wanted to be treated. Five Star Dealership and sales person.

Bought my 2017 Overland 2WD preowned with 74k miles. It’s now Feb of 2024 my Jeep’s got 135k on the odometer and I’ve never once had an issue. I occasionally get car fever, start looking at cars online, but the second I jump behind the wheel of my Grand Cherokee I smile and decide to keep it for a little longer. I still love the look, it’s super comfortable, has plenty of power, all the bells and whistles I want (and beyond), and I love the fact not every single thing is touch screen as most modern vehicles. I love I can turn up the volume, operate the AC and many features with good ‘ole KNOBS without taking my eyes off the road.

The most stress free and enjoyable buying experience ever! Shant (our Salesperson) was upfront about everything. No games here, and we purchased a truck we are most happy with. And, it checked out perfectly with our Mechanic.

One of the best vehicles I have ever owned! Dependable, lots of features, stylish, fun to drive on and off road. A vehicle you can enjoy and be proud of!

Great experience all around. This is my 4th Kia and the sale was flawless. Thank you Nashua Kia and Ian and your whole team. Would definitely buy from again.

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.

I was looking for a used Jeep and after looking around, this dealership really took care of their used cars. The jeep that I purchased from here was well maintained and clean! There were some small parts missing from the vehicle and when I purchased the vehicle, the dealer ordered the missing parts for me for no extra cost. Overall experience was great and would highly recommend.

I already owned this vehicle when I took it in for service. But. I love the vehicle. I haven't had any major problems with my Jeep Summit