Used Jeep cars for sale near Winchester, MA under $25,000

Brought my car in for regular maintenance and all went well. Quick service. Mathew was able to hook me up with a discount helped me out.

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.

Robert was great through the car buying process. I bought an x5 and did an inspection . Robert made sure everyone from the inspection was fixed. So great to experience! Thanks

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.

Nothing big, just having regular maintenance. This has been a great car. I leased then purchased it from Colonial and have been happy that I did. All set now.

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!!

I took my daughter to Toyota of Braintree to check out Toyota Camry's. This was her first time looking to purchase a car. We ran into salesman Gerry Gorham who could not have been more helpful. We were just there to browse, however, we walked away in one hour with the purchase of a new SE Camry that exceeded our expectations. Gerry and the team were so helpful guiding my daughter through the process to complete a very fair deal. They even got us the recent grad rebate. We highly recomment Gerry and Toyota of Braintree!

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 service very friendly and professional. No stress with test driving or even "talking numbers" it was a great experience and will go back there again.

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.

I had an excellent experience at Woburn Toyota, especially with my salesperson, Ken Ouen, and the service team. The quality of service and the personalized attention were outstanding, and I truly appreciated it. I highly recommend them!

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!

Great service last three years Lisa is truly special and I appreciate it. Their hospitality is great . will continue to have a relationship with them👍🏾.

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.

My wife and I have had wonderful experience buying the new RAV4 XLE 2022 from Westboro Toyota. Ricky was the first salesperson with whom we discussed the need for a new car. He is very professional, knowledgeable, and respectful and explained everything that we need to know about the new car buying process very patiently. We had to wait for more than 2 months to get the car with the color of our choice. Whenever I called him or texted him, we have received responses which encouraged us to wait patiently. 3 days ago, we have received a call from BB, a genuinely nice, knowledgeable, and respectful salesperson or manager who explained to us the availability of the Car with the color of our choice. We have had friendly conversation with BB and the Finance Manager, and we got the car in 2 days after completing all works related to Car buying. It has been a wonderful experience. Also, we would like to let you know that we have been getting excellent service from the Service team for other Toyota vehicles for 11 years. We would highly recommend Westboro Toyota for great buying and service experience.

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 !

Rodman Ford made purchasing my used car so easy. The service is outstanding, and for anyone who does not like buying cars, this experience was exceptional!! Great service, great price and friendly people!

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.

Jake was super helpful. Knew his stuff. Got a fair price on trade in and then also drive me home. Well done I was quite pleased

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.

One of the absolute best buying experiences I have ever had! The team is awesome and Bill was fantastic and engaged from the moment we met until we drove off wi the our new truck! I will be back for next vehicle!❤️🚙🛻

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.

Excellent salesman Scott. Dealership impeccable. Everyone professional and courteous. Explained every detail of buying process. Finance staff Kendra extremely professional and explained every process of leading my vehicle

The turning radius is the best for the size of this suv. The brakes are quick to respond. The 4x4 is a must. The only downside is that they aren't all standard with a trailer hitch. Love the sunroof, the all leather interior.

This is my 3 Volvo. After leaving to buy another make of a car was an experience in itself. Working with Ronnie and Gavin from beginning to the end....in the dealership or over the phone was a pleasure. From the minute you walk in and until you leave you are taken care of. Glad to be back fantastic staff.

Hands down the best Jeep ever.. would take it over the Santa Fe any day of the week.. there’s no comparison.. performance is excellent.. have 70,000 miles on a 2018 and a 2019.. ac went out on one but warranty covered it🙂🙂

Thank you to Brian and auto factory for selling my 2019 Chevy Silverado it was very stress free and made the experience wonderful. -Justin E.

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.

The process was very simple, seamless, and the vehicle was ready when they said it was going to be ready. The buying process was stress-free in dealing with Autumn was a real pleasure.

Low to no pressure sales. Good prices and inventory. I enjoyed the buying process (as much as one can). Thanks George!

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).

Nice clean cars a pleasure to deal with and if anything major goes wrong with the vehicle you can bring it back to them and they will fix it

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.

Excellent as always. The team in Rockland is always helpful and goes above and beyond to get the job done. I was very pleased with the service provided and would recommend them to friends and family

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?

I worked with Camari and everything went smooth! I was originally in the market for a used telluride but I ended up going with the 2025 telluride and it was perfect. Camari never made me feel pressured even though I visited 3 separate times before making my purchase! I love my new car - however I find it really weird that the passenger front seat is not electronic. My old 2013 ford both seats were electronic ! But regardless I am very happy with my purchase and the entire process that went along with it !!

Purchased brand new after totalling out my Santa Fe XL. This has by far been one of the best vehicles I've owned. For as large as it is, its incredibly fuel efficient yet has plenty of power to tow my parents fish/ski boat. My only complaints are the factory Michelin's were trash in Minnesota and the interior "Cargo" area is significantly smaller than my previous Santa Fe's, but thats more of a personal opinion versus any design flaw. Ironically quite a few of my coworkers have JGC's as well and almost all of them have over 200k on them, I'm still at 65k. Not sure why they have a bad reputation in the auto world, but I'm certainly glad pleased with my choice, even 6 years later!

Waiting room is small and not conducive to doing work while you wait. Fortunately, I didn't have to wait very long.

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.