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1,688 listings
- Price Drop$26,590fair price$288 above market
- 25,960 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 6cyl automatic
- Carvana (In-stock online)
- Home delivery*
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Located in Cleveland, OH / 440 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX4MD252622
Stock: 2003697326
Certified Pre-Owned: No
Listed since: 05-08-2025 - $20,875fair price$526 above market
- 67,743 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Felton Holly Kia (160 mi away)
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Located in Felton, DE / 160 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX9MD199892
Stock: F25-259A
Certified Pre-Owned: No
Listed since: 04-25-2025 - 55,610 miles
- No accidents, 1 owner, rental vehicle
- 4cyl automatic
- i.g. Burton Chrysler Dodge Jeep Ram of Smyrna (181 mi away)
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Located in Smyrna, DE / 181 miles away from Chesapeake, VA
Cherokee Altitude, 4D Sport Utility, 2.4L I4, 9-Speed 948TE Automatic, 4WD, Bright White Clearcoat, Black Leather, Quick Order Package 2BT. 2023 Jeep ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMMB5PD114111
Stock: NP25065
Certified Pre-Owned: No
Listed since: 04-14-2025- New Listing$24,998fair price$314 below market
- 29,754 miles
- 6cyl automatic
- CarMax (In-stock online)
- Transfer available from IL to VA*
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Located in Hillside, IL / 717 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMMX7MD238064
Stock: 27436287
Certified Pre-Owned: No - New Listing$25,990fair price$394 above market
- 29,055 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 6cyl automatic
- Carvana (In-stock online)
- Home delivery*
Close
Located in Columbus, OH / 430 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX3MD234416
Stock: 2003714070
Certified Pre-Owned: No
Listed since: 05-06-2025 - 68,125 miles
- No accidents, 1 owner, corporate fleet vehicle
- 6cyl automatic
- Fayetteville DriveTime (193 mi away)
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Located in Fayetteville, NC / 193 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJLLX1KD353641
Stock: 1190213766
Certified Pre-Owned: No
Listed since: 04-15-2025- Price Drop$24,990fair price$555 above market
- 32,094 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 6cyl automatic
- Carvana (In-stock online)
- Home delivery*
Close
Located in Cleveland, OH / 440 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX4MD239062
Stock: 2003661740
Certified Pre-Owned: No
Listed since: 04-23-2025 - $19,999fair price$144 above market
- 55,084 miles
- 1 accident, 1 owner, personal use only
- 6cyl automatic
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Milwaukie, OR / 2,454 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX7MD235496
Stock: 8DTHMD
Certified Pre-Owned: No
Listed since: 02-18-2025 - New Listing
- 40,944 miles
- 1 accident, 1 owner, personal use only
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from AZ to VA*
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Located in Gilbert, AZ / 2,013 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLLB8MD114286
Stock: 27356828
Certified Pre-Owned: No - New Listing$24,998fair price
- 33,480 miles
- 1 accident, 1 owner, personal use
- 6cyl automatic
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Fort Worth, TX / 1,217 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX1MD229022
Stock: 27425514
Certified Pre-Owned: No - 7,718 miles
- No accidents, 1 owner, corporate fleet vehicle
- 6cyl automatic
- CarMax (In-stock online)
- Transfer available from NC to VA*
Close
Located in Hickory, NC / 291 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX3MD229586
Stock: 27286323
Certified Pre-Owned: No- 22,611 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- Don White's Timonium Chrysler Jeep Dodge Ram (191 mi away)
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Located in Cockeysville, MD / 191 miles away from Chesapeake, VA
Dealer Billet Silver Metallic Clearcoat 2021 Jeep Cherokee Latitude Lux 4WD 9-Speed 948TE Automatic 3.2L V6 Lifetime Oil Changes, Lifetime Tire Rotat...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMMX8MD246836
Stock: 4298
Certified Pre-Owned: No
Listed since: 03-13-2025- Price Drop
- 107,514 miles
- No accidents, 2 owners, personal use only
- 6cyl automatic
- Chesapeake DriveTime (4 mi away)
Close
Located in Chesapeake, VA / 4 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX0KD476383
Stock: 1630091686
Certified Pre-Owned: No
Listed since: 04-25-2025 - New Listing
- 11,626 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- CarMax (In-stock online)
- Transfer available from OH to VA*
Close
Located in Columbus, OH / 438 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX6MD226052
Stock: 27327801
Certified Pre-Owned: No - 71,244 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- CarMax Virginia Beach (10 mi away)
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Located in Virginia Beach, VA / 10 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLLB0KD129698
Stock: 27431207
Certified Pre-Owned: No- New Listing
- 34,390 miles
- No accidents, 2 owners, personal use
- 4cyl automatic
- CarMax Newport News (34 mi away)
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Located in Newport News, VA / 34 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJMDNXKD158379
Stock: 27248673
Certified Pre-Owned: No - New Listing
- 37,813 miles
- 6cyl automatic
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Fort Worth, TX / 1,222 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX0MD228816
Stock: 27242592
Certified Pre-Owned: No - New Listing
- 37,877 miles
- 6cyl automatic
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Fort Worth, TX / 1,217 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX0MD223700
Stock: 27425513
Certified Pre-Owned: No - $23,496fair price$48 below market
- 43,941 miles
- 2 accidents, 1 owner, corporate fleet vehicle
- 6cyl automatic
- Driveway (In-stock online)
- Home delivery*
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Located in Orchard Park, NY / 438 miles away from Chesapeake, VA
CarFax 1-Owner,Rare Find,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Lane ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMMX5MD137993
Stock: MD137993P
Certified Pre-Owned: No - Price Drop
- 28,279 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Carvana (In-stock online)
- Home delivery*
Close
Located in Phoenix, AZ / 2,024 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLCB4MD168510
Stock: 2003708346
Certified Pre-Owned: No
Listed since: 05-08-2025 - 39,911 miles
- 1 accident, 2 owners, personal use
- 6cyl automatic
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Lakewood, WA / 2,444 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX8MD227309
Stock: 8GHNSP
Certified Pre-Owned: No
Listed since: 04-21-2025
Showing 316 - 336 out of 1,688 listings
Consumer Reviews for the Jeep Cherokee
Read recent reviews for the Jeep Cherokee
My new Jeep
bmwcharlie, 02/01/2021
2021 Jeep Cherokee Limited 4dr SUV (3.2L 6cyl 9A)
Time for a new lease as my Tiguan went back. I looked at a new Tiguan, Subaru Outback, Jeep Cherokee and the Volvo X 40. I chose the Jeep Cherokee.
The Jeep felt the most substantial by far. I was surprised by the cheap plastic center in the Subaru and the Volvo. The Tiguan was all plastic but for 289.00 a month all in (including all taxes and fees) the Tiguan Se was the least … expensive vehicle I have ever leased. The same equipped Tiguan was 370.00 a month. I really missed the heated steering wheel from my previous BMW so it was a must for my new lease. A Tiguan with a heated steering wheel was 407.00 a month. I set out for a new compact SUV for 350.00 a month. I never thought of leasing a Jeep but in my budget it kept coming up so I test drove it. I knew instantly this would be my next vehicle. I leased a Jeep Cherokee V6 Limited with Elite Pkg. for 381.00 a month including taxes and all fees. This was the most equipped car I ever had. Cooled seats front and back it even can parallel park. I love the remote start which automatically turns on the heated seats and steering wheel. This Jeep is on par with my X3. Which was 500.00 a month a new one 700. a month to lease. Value wise this is the best vehicle you will find. It took months of tracking prices and negotiating for me to get this price.
The Jeep ride is great, acceleration is great too. The Volvo was slightly better but the Jeep was pretty close. It rides more like the X3. The info entertainment is easy to use intuitive and fast which really makes for a great driving experience. The Jeep is compact unlike the Tiguan which felt like you had so much space in the cabin. Handling is sharp seats are comfortable. Since it mainly me and one other person most of the time I can live with the snug cabin. I took Delivery at the end of November and have had no problems. Fit and finish is great so I am thinking it should be pretty reliable.
Update: I still love my Cherokee. The Adaptive cruise control is amazing. Life changing feature. The stop and go really takes the sting out of heavy traffic. The automatic high beams are amazing. The ride is great it really takes any size pot hole no problem. Well not quite the razor sharp handle of a BMW it’s much more comfortable. The ride, handling, and acceleration strike a great balance. The lane keep assist is the cars big down fall. It’s will pull slightly at the wheel for no reason. Less on the highway than around town. It feels like you hit a piece of ice. I doesn’t bother me as much now but at first it was annoying as hell. I tried to disable it but couldn’t. I just put it on the lowest setting. Hopefully they will use a lane centering on the next update. The car feels so high tech it’s quite unexpected.. I am so glad I got this Jeep. I would have never considered it, if not for the chip shortage. Inventories were starting to get tight and they had the inventory. I got this lease at such a great deal.I am so grateful as prices are skyrocketing on leases. Blown away by the luxury driving experience from a Jeep, Who knew!
Used 2021 Jeep Cherokee in Chesapeake, VA Values
Estimated values
2021 Jeep Cherokee Trailhawk 4dr SUV 4WD (3.2L 6cyl 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $19,834 | $22,133 | $24,438 |
| Clean | $19,412 | $21,651 | $23,893 |
| Average | $18,708 | $20,847 | $22,985 |
| Rough | $17,793 | $19,802 | $21,804 |
The average list price of a used 2021 Jeep Cherokee in Chesapeake, Virginia is $23,597. The average mileage on a used Jeep Cherokee 2021 for sale in Chesapeake, Virginia is 41,942. Based on the average mileage of 41,942 for used 2021 Jeep Cherokee for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Jeep Cherokee 2021 in Chesapeake, Virginia to be $18,708.
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