Save your search and get notified when new inventory arrives.
Contact seller
Customize your budget
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
About your privacy: Cars.com is asking for your ZIP and credit rating because it helps us to make an educated guess at your sales tax and loan interest. These two factors can greatly change your monthly payment.
Used
Jeep cars
for sale
near
Windsor, VA
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used
2025 Jeep Grand Cherokee L Laredo
Used
2020 Jeep Wrangler Unlimited Sport
Used
2025 Jeep Grand Cherokee Limited
Vehicle information
Features
Reviews
Dominic, Derrick and Alex made the car buying experience
Dominic, Derrick and Alex made the car buying experience a smooth one. They were very accommodating and a pleasure to work with. A couple days after I bought the car, Dominic and Derrick both reached out to me via text message to make sure I was loving the car and to contact them if I needed anything.
What a great look.
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.
Used
2018 Jeep Grand Cherokee Upland
Vehicle information
Features
Reviews
Very professional, they handled everything very well.
Very professional, they handled everything very well. Would use them again if I needed to.
Because it a great car because the car has 118k miles on
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
Used
2025 Jeep Grand Cherokee Altitude
Vehicle information
Features
Reviews
Nice hellcat red eye jeep Chrysler ram good drive
Nice hellcat red eye jeep Chrysler ram good drive suspension engine and supercharger. Great exhaust 6 seconds on track and review 5 star safety rating
Used
2018 Jeep Grand Cherokee Limited
Vehicle information
Features
Reviews
This experience was excellent.
This experience was excellent. I can't speak highly enough about Southern Norfolk, Justin Cannady and Katie Rose. They were topnotch in understanding and making sure that I got the best car for me. They made me feel like family which alleviated all of my anxiety and tension when buying a car. After all of my, "I want this and not that" they were still nice and professional, compassionate, open and honest. They went above and beyond. Thank you all for you patience and time dealing with me.
I initially leased my Grand Cherokee Limited but ended up
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!
Used
2024 Jeep Wrangler Rubicon
Vehicle information
Features
Reviews
2004 jeep wrangler sport s 2 door.
2004 jeep wrangler sport s 2 door. So far it is wonderful. Bought it just as a fun beach jeep but it has turned into our daily driver. Only problem is my wife wants to drive it all the time. She has claimed it as HER car. Guess I will need to just buy MY jeep.
Used
2024 Jeep Wrangler Sport
Vehicle information
Features
Reviews
Great service.
Great service. Keyshawn Brown was awesome. Thank you again for all your hard work. Thank u again.
I purchased a special ordered Jeep Wrangler RubiconX with
I purchased a special ordered Jeep Wrangler RubiconX with the 3.6 engine from our local Dealership! When I first drove this this vehicle I knew it may be rough riding, but after having this for for over 6 months it now is our main vehicle for getting around town. I get 17.1-18.3mpg. It's a 4dr and we enjoy it every day for shopping and other chores. We had it on the main highway and do between 65 and 70mph. It handles great and the ride is actually pretty good. Has great passing power as it has 4:56 gearing! We just recently took our vehicle to Keene Dodge/Jeep to have the tires rotated and were very impressed with the service and the entire staff as they treated us very special.
Used
2019 Jeep Wrangler Sport S
Vehicle information
Features
Reviews
Responding back quickly with information that I
Responding back quickly with information that I requested. They still continue to keep in touch and provide updates on my request.
2019 Jeep Wrangler Sport S
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!!
Used
2022 Jeep Grand Cherokee Summit
Vehicle information
Features
Reviews
Vehicle purchase
Cinna was a great help with clear communication and follow through. She was able to assist even over the weekend and even brought the vehicle to me.
My opinion of 2022 Jeep Grand Cherokee
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.
Used
2018 Jeep Grand Cherokee Limited
Vehicle information
Features
Reviews
Matt and Catalina were impressive and professional
Matt and Catalina were very professional and friendly. They did not stop until i was satisfied due to my bad experience in servicing with my Touareg. They made sure i was happy and drove away in a brand new Tiguan. Thanks to Matt Seyfert for giving me V.I.P. treatment, and many thanks to Catalina Dizon for being thoughtful friendly and very professional by getting Matt involved when she learned the situation.
Bought the vehicle with 30,000 miles.
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.
Used
2015 Jeep Grand Cherokee Laredo
Vehicle information
Features
Reviews
Matt Hanson was amazing helped me through every step of
Matt Hanson was amazing helped me through every step of the process and I could not have done it without him!
I purchased it used in 2022, it had 76k and now has 96 in
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.
Used
2021 Jeep Wrangler Rubicon
Vehicle information
Features
Reviews
I recently purchased a Subaru Forester a commuter car.
I recently purchased a Subaru Forester a commuter car. The car was exceptionally clean and the lowest mileage unit within 20m miles. The purchase was seamless from the test ride to the closing. I did however have an issue with the AC, which was covered immediately. My wife also purchased her 3rd vehicle for them, a 2021 Toyota Rav4. She traded a RC350 getting above book because of mileage and condition. I wouldn't buy a used vehicle from anyone other than Sullivan Auto Trading in the Mid Atlantic area.
I have a 2021, 2 door, Jeep Wrangler Rubicon.
I have a 2021, 2 door, Jeep Wrangler Rubicon. Is it a decent vehicle - yes. Is it for everyone? Probably not. But if you like to drive with the roof off, don't mind bouncing around on the road a little bit....and it is bouncing around, ok with the wind noise, then this is the vehicle for you. The V6 engine is decent. Do the maintenance and it will be fine long term. I have the manual transmission. Works fine and makes it more enjoyable to drive. It is a very nimble vehicle, no problem on the highway, comfortable, and the noise is not that bad when travelling. Is it a vehicle I would drive in bitterly cold winters and icy roads - I am in Canada where winter is winter and -40 is real....nope I would not. However there are thousands of people around here that do. This vehicle is an acquired taste with a variety of uses, applications, and lots of strengths. Does it have many weaknesses - no not really. But you need to be sure why you have it, accept its nuances - which are not that bad, and enjoy it!! It is a fun vehicle to have especially in the summer when the sun is blazing!!!
Used
2019 Jeep Grand Cherokee Overland
Vehicle information
Features
Reviews
The 2019 Grand Cherokee Limited was the Jeep I had my eye
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.
Used
2019 Jeep Grand Cherokee Limited
Vehicle information
Features
Reviews
We love our new Jeep
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.
Used
2023 Jeep Grand Cherokee Limited
Vehicle information
Features
Reviews
Best car buy experience
Martin Gross was awesome very friendly and helped me get a car with no money down definitely will recommend to my people. Thanks martin your great
Natural upgrade choice
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.
Used
2020 Jeep Grand Cherokee Altitude
Vehicle information
Features
Reviews
I wouldn’t shop at any other dealership.
I wouldn’t shop at any other dealership. They made me feel comfortable right away. I never felt pressure. They put me with a great Lender for my loan. I’m taking my son here when it comes time for him to purchase. Thanks so much to Sullivan Auto Trading for helping me!
Snow commuter
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.
Used
2018 Jeep Grand Cherokee Limited
Vehicle information
Features
Reviews
Great dealership and smooth easy experience!
Great dealership and smooth easy experience! Would go back here again to purchase another car.
Purchased brand new after totalling out my Santa Fe XL.
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!
Used
2022 Jeep Wrangler Unlimited Sport S
Vehicle information
Features
Reviews
Read the Owners Manual, Often.
Visibility and size are what I need. 4WD, clearance for snow. Rather tight interior, not suitable for more than two. Auto Park is very confusing. Not auto parallel Park. Car will stop while backing out of parking space, won't move if a somewhat complex procedure is not followed.
Used
2018 Jeep Grand Cherokee High Altitude
Vehicle information
Features
Reviews
Sullivan Auto Trading has the Best Cars for the Best
Sullivan Auto Trading has the Best Cars for the Best Prices, Its that simple. We love our Van!
Jeep Cheerokee
So I got a Jeep from The Chrysler,Dodge, Jeep dealership in Deland. Jean was my salesman and he was great! Got me the vehicle I wanted for a great price! I’m very satisfied with my overall experience. 👍🏾
Used
2022 Jeep Grand Cherokee Overland
Vehicle information
Features
Reviews
Outstanding dealership!
Julian, Jasmin and the rest of the staff have been nothing but excellent! Best competitive prices in the Hampton Roads area….definitely recommend! Will be back.
2022 Grand Cherokee Overland. great car.
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.
Used
2018 Jeep Wrangler Sport S
Vehicle information
Features
Reviews
I was honestly in need of a vehicle today I went in to
I was honestly in need of a vehicle today I went in to Winners Circle Chrysler dealer today. I just knew I won’t going to get a vehicle due to my credit score. Eric and Julian was upfront & honest with me ! I am walking out with a 2020 Nissan Altima baby !!!!! Thank you so much!! My new family !!!!!!!! Ps! If you looking for honesty & someone who going to work with your credit they are the best in Hampton roads !!!! You guys are the best !!! Thank you two brothers Eric and Julian!!
Jeep passing jobs have been corroding at welds & hinges
Jeep passing jobs have been corroding at welds & hinges due to 2 diff. Metals built together. Issue for 15+ years!, recalled opens need to be addressed, my 3 rd wrangler and loved it! Great freedom ride, sport driven, outdoorsy attitude, love Jeep Wrangler the makers need to fix this cheap paint job causing our jeeps to rust prematurely!
About Jeep
What is the cheapest Jeep vehicle available?
The Jeep Liberty is the cheapest available vehicle by average Cars.com listing price in Jeep's lineup, with an average listing price of $6,276.
Which Jeep vehicle has the best MPG?
The hybrid Jeep Wrangler can reach up to 22 MPG city and 24 MPG highway for a combined rating of 23 MPG. The Jeep Compass with traditional internal combustion engine offers up to 24 MPG city and 32 MPG highway for a combined rating of 27 MPG.
These figures are based on EPA mileage ratings and are for comparison purposes only. The actual mileage will vary depending on the selected vehicle model year, trim, driving conditions, driving habits, vehicle maintenance, and other factors.
Which Jeep vehicle has the longest range?
The electric Jeep Wagoneer S can travel up to 300 miles on a single charge depending on electric motor and battery options. The plug-in hybrid Jeep Grand Cherokee 4xe can travel up to 26 electric-only miles before the gas engine kicks on.
EPA-estimated range is the distance, or predicted distance, a new plug-in vehicle will travel on electric power before its battery charge is exhausted. Actual range will vary depending on model year, driving conditions, driving habits, elevation changes, weather, accessory usage (lights, climate control), vehicle condition and other factors.
Which Jeep vehicle has the most deals?
The Jeep Grand Cherokee has the most available deals on Cars.com with 5200 great deals out of 14366 listings starting at $1,000.
Where can I find the most Jeep deals?
The most Jeep deals can be found near Carrollton, VA with 143 great deals out of 431 listings starting at $3,999.
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
Used Jeep by price
- Jeep for sale under $7,000 in Windsor, VA
- Jeep for sale under $8,000 in Windsor, VA
- Jeep for sale under $9,000 in Windsor, VA
- Jeep for sale under $10,000 in Windsor, VA
- Jeep for sale under $15,000 in Windsor, VA
- Jeep for sale under $20,000 in Windsor, VA
- Jeep for sale under $25,000 in Windsor, VA
- Jeep for sale under $30,000 in Windsor, VA
- Jeep for sale under $40,000 in Windsor, VA
- Jeep for sale under $50,000 in Windsor, VA
- Jeep for sale under $100,000 in Windsor, VA
Used Jeep by city
-
Used Jeep in Suffolk, VA
108 Great Deals out of 316 listings starting at $3,999
-
Used Jeep in Camptown, VA
25 Great Deals out of 60 listings starting at $5,735
-
Used Jeep in Benns Church, VA
141 Great Deals out of 425 listings starting at $3,999
-
Used Jeep in Smithfield, VA
136 Great Deals out of 411 listings starting at $3,999
-
Used Jeep in Franklin, VA
13 Great Deals out of 29 listings starting at $12,000
-
Used Jeep in Carrollton, VA
143 Great Deals out of 431 listings starting at $3,999
-
Used Jeep in Courtland, VA
13 Great Deals out of 28 listings starting at $13,455
-
Used Jeep in Rushmere, VA
77 Great Deals out of 231 listings starting at $3,999
-
Used Jeep in Portsmouth, VA
135 Great Deals out of 413 listings starting at $3,999
-
Used Jeep in Newport News, VA
131 Great Deals out of 395 listings starting at $3,999
-
Used Jeep in Waverly, VA
9 Great Deals out of 27 listings starting at $8,995
-
Used Jeep in Chesapeake, VA
119 Great Deals out of 355 listings starting at $3,999
Used Jeep in Windsor, VA by model
-
Jeep Grand Cherokee in Windsor, VA
24 Great Deals out of 79 listings starting at $3,999
-
Jeep Wrangler Unlimited in Windsor, VA
14 Great Deals out of 64 listings starting at $9,495
-
Jeep Cherokee in Windsor, VA
17 Great Deals out of 37 listings starting at $4,995
-
Jeep Compass in Windsor, VA
14 Great Deals out of 34 listings starting at $4,800
-
Jeep Wrangler in Windsor, VA
9 Great Deals out of 32 listings starting at $6,500
-
Jeep Gladiator in Windsor, VA
10 Great Deals out of 27 listings starting at $20,990
Used Jeep by body style
- ${price_badge()}
- ${ami_badge()}
- ${battery_badge()}${ev_report_link()}
- ${hot_car_badge()}
- ${award_badge()}
- ${cpo_badge()}
${price_badge_description}
${ami_badge_description}
The EV Battery Rating is based on this vehicle's current expected range relative to the vehicles expected range when new. ${battery_badge_text}
This vehicle is certified pre-owned, backed by a manufacturer warranty, and typically undergoes a rigorous multi-point inspection to ensure quality and reliability.
This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.
