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1,593 listings
- $21,700good price$1,138 below market
- 41,924 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Greensboro Auto Center (199 mi away)
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Located in Greensboro, NC / 199 miles away from Chesapeake, VA
2 YEARS COMPLIMENTARY MAINTENANCE (for vehicles 100,000 miles or less. See Dealer for details.) COMPLIMENTARY TIRE ROTATIONS FOR LIFE (with any servic...
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: 1C4PJMMX6MD122225
Stock: 3149
Certified Pre-Owned: No
Listed since: 03-19-2025 - $23,590fair price$285 below market
- 36,716 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Indianapolis, IN / 579 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: 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: 1C4PJMDX7MD161194
Stock: 2003833082
Certified Pre-Owned: No
Listed since: 06-26-2025 - $18,999fair price$664 below market
- 73,482 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 24 Hwy MPG
- Westgate Mitsubishi (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
2019 Jeep Cherokee Trailhawk With aggressive styling, signature red tow hooks, and bold fender flares, the Trailhawk turns heads at stoplights and ...
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:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX0KD118767
Stock: M5913XP
Certified Pre-Owned: No
Listed since: 05-13-2025 - $11,995good price$1,175 below market
- 113,742 miles
- 1 accident, 1 owner, personal use
- 5 Seats, 21 City / 29 Hwy MPG
- DMV Auto (138 mi away)
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Located in Stafford, VA / 138 miles away from Chesapeake, VA
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMLBXKD465008
Stock: DMV1535
Certified Pre-Owned: No - Price Drop$22,699fair price$64 below market
- 53,893 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales Virginia Beach (11 mi away)
- Home delivery*
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Located in Virginia Beach, VA / 11 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: 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: 1C4PJMMB1PD114803
Stock: 7W00HN
Certified Pre-Owned: No
Listed since: 05-12-2025 - $14,800good price$1,208 below market
- 122,886 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 24 Hwy MPG
- Len Stoler Chevrolet (199 mi away)
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Located in Westminster, MD / 199 miles away from Chesapeake, VA
Cherokee Trailhawk, 4WD, Granite Crystal Metallic Clearcoat, Black Leather, 7 & 4 Pin Wiring Harness, Apple CarPlay/Android Auto, Auto-Dimming Rear-Vi...
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:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX8KD471211
Stock: V1886A
Certified Pre-Owned: No
Listed since: 07-02-2025 - $25,990fair price
- 15,749 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Dallas, TX / 1,195 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: 1C4PJMDX0MD219517
Stock: 2003778564
Certified Pre-Owned: No
Listed since: 06-04-2025 - $21,441good price$1,284 below market
- 50,771 miles
- 1 accident, 1 owner, rental vehicle
- 5 Seats, 21 City / 29 Hwy MPG
- Hampton Chevrolet (23 mi away)
- Home delivery*
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Located in Hampton, VA / 23 miles away from Chesapeake, VA
CARFAX One-Owner. Diamond Black Crystal Pearlcoat 2023 Jeep Cherokee AltitudeThis vehicle comes complimentary with a 99 DAY OR 3,000 MILE POWERTRAI...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMMBXPD115397
Stock: PT12027
Certified Pre-Owned: No
Listed since: 05-21-2025 - $21,997fair price$528 below market
- 62,663 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 21 City / 29 Hwy MPG
- Southern Ford (33 mi away)
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Located in Newport News, VA / 33 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price!Certified. Bright White Clearcoat 2023 Jeep Cherokee Altitude 9-Speed 948TE Automatic 2.4L I4 Ford Blue Advanta...
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: 1C4PJMMB4PD111782
Stock: XP10664
Certified Pre-Owned: No
Listed since: 05-05-2025 - $12,988good price$1,391 below market
- 119,493 miles
- 1 accident, 1 owner, personal use only
- 5 Seats
- Sexton Auto Sales (148 mi away)
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Located in Raleigh, NC / 148 miles away from Chesapeake, VA
Visit Sexton Auto Sales Inc online at www.sextonautosales.net to see more pictures of this vehicle or call us at 919-873-1800 today to schedule your ...
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:
Listing Information:
VIN: 1C4PJMLX3KD323059
Stock: 8569
Certified Pre-Owned: No - New Listing$21,590fair price$175 below market
- 87,865 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 24 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Oklahoma City, OK / 1,189 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:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBXXMD178297
Stock: 2003818546
Certified Pre-Owned: No
Listed since: 07-09-2025 - New Listing$22,998fair price
- 38,436 miles
- No accidents, 1 owner, personal use
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Garland, TX / 1,187 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: 1C4PJMDX8MD235142
Stock: 27423979
Certified Pre-Owned: No - Price Drop$19,995fair price$276 below market
- 56,091 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 19 City / 27 Hwy MPG
- CL Hyman Auto Wholesale (94 mi away)
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Located in Ashland, VA / 94 miles away from Chesapeake, VA
Very Clean! 1-Owner! Clean Carfax! Leather, Heated Seats, Rear Camera, Remote Start! [ + MORE ] [ - HIDE ]
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: 1C4PJMMX1MD202144
Stock: 202144
Certified Pre-Owned: No
Listed since: 05-30-2025 - $23,000good price$1,062 below market
- 34,726 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Middletown, NY / 340 miles away from Chesapeake, VA
CarFax No Accidents Reported,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Lane Keeping As...
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: 1C4PJMDX3MD193107
Stock: MD193107P
Certified Pre-Owned: No - Price Drop$22,299fair price$851 below market
- 54,576 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales Raleigh (150 mi away)
- Home delivery*
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Located in Raleigh, NC / 150 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: 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: 1C4PJMMB1PD115045
Stock: 7W33HG
Certified Pre-Owned: No
Listed since: 04-15-2025 - $22,590fair price$38 above market
- 43,459 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Charlotte, NC / 277 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: 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: 1C4PJMMX6MD204603
Stock: 2003829371
Certified Pre-Owned: No
Listed since: 06-23-2025 - $22,998fair price
- 39,061 miles
- No accidents, 1 owner, personal use
- 5 Seats, 19 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Denton, TX / 1,204 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: 1C4PJMDX7MD223533
Stock: 27520882
Certified Pre-Owned: No - $22,000fair price$288 below market
- 52,047 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Lexington Park Chevrolet Buick GMC (109 mi away)
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Located in California, MD / 109 miles away from Chesapeake, VA
2021 Jeep Cherokee Limited Bright White Clearcoat 4WD 9-Speed 948TE Automatic 2.0L I4 DOHC 21/29 City/Highway MPGPrice does not include applicable tax...
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: 1C4PJMDN2MD126643
Stock: 0LG0550A
Certified Pre-Owned: No
Listed since: 06-08-2025 - New Listing$16,195fair price$557 below market
- 78,346 miles
- No accidents, 2 owners, personal use
- 5 Seats, 21 City / 29 Hwy MPG
- Koons Annapolis Toyota (156 mi away)
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Located in Annapolis, MD / 156 miles away from Chesapeake, VA
3.734 Axle Ratio, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, Anti-whiplash front head restrai...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMLB5KD254458
Stock: KATP190184
Certified Pre-Owned: No
Listed since: 07-10-2025 - $24,998fair price$126 above market
- 31,012 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- CarMax (In-stock online)
- Transfer available from IL to VA*
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Located in Schaumburg, IL / 730 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: Yes
Features and Specs:
Listing Information:
VIN: 1C4PJMMN6MD151240
Stock: 27596064
Certified Pre-Owned: No - $21,500fair price$182 below market
- 44,530 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 19 City / 27 Hwy MPG
- Safford Chrysler Dodge Jeep Ram of Winchester (199 mi away)
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Located in Winchester, VA / 199 miles away from Chesapeake, VA
2021 Jeep Cherokee Latitude Lux Blind-Spot and Cross-Path Detection, Park-Sense Rear Park-Assist, Full Speed Forward Collision Warning Plus, Lane Keep...
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: 1C4PJMMX0MD109602
Stock: P7224
Certified Pre-Owned: No
Listed since: 05-24-2025
Showing 148 - 168 out of 1,593 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 80th Anniversary Edition 4dr SUV 4WD (3.2L 6cyl 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $17,022 | $19,142 | $21,269 |
| Clean | $16,660 | $18,725 | $20,795 |
| Average | $16,056 | $18,030 | $20,004 |
| Rough | $15,270 | $17,126 | $18,977 |
The average list price of a used 2021 Jeep Cherokee in Chesapeake, Virginia is $20,779. The average mileage on a used Jeep Cherokee 2021 for sale in Chesapeake, Virginia is 59,594. Based on the average mileage of 59,594 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 $16,056.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.