Skip to FiltersReport abuse
2,743 listings
- $31,289great price$3,743 below market
- 43,193 miles
- No accidents, 1 owner, personal use
- 5 Seats
- Crossroads Chrysler Dodge Jeep Ram Fiat of Henderson (126 mi away)
Close
Located in Henderson, NC / 126 miles away from Chesapeake, VA
Get ready for open-air adventure with this 2021 Jeep Wrangler Unlimited Willysa trail-ready legend with serious personality and premium upgrades. Powe...
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: 1C4HJXDGXMW711689
Stock: PU420
Certified Pre-Owned: No
Listed since: 04-29-2025 - New Listing
- 76,930 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Crossroads Ford of Sanford (185 mi away)
Close
Located in Sanford, NC / 185 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:
Listing Information:
VIN: 1C4HJXFN3LW156756
Stock: T09272A
Certified Pre-Owned: No
Listed since: 06-19-2025 - New Listing
- 79,661 miles
- No accidents, 4 owners, personal use
- 5 Seats
- Exclusive Motor Cars (186 mi away)
Close
Located in Randallstown, MD / 186 miles away from Chesapeake, VA
This 2020 Granite Crystal Metallic Clearcoat Jeep Wrangler Unlimited Sport S 4WD is well equipped and includes these features and benefits:. 4WD Cle...
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: 1C4HJXDN8LW149613
Stock: W149613
Certified Pre-Owned: No
Listed since: 06-19-2025 - Price Drop$31,233great price$5,296 below market
- 92,828 miles
- No accidents, 1 owner, personal use
- 5 Seats
- John Hiester Chrysler Dodge Jeep Ram of Sanford (185 mi away)
Close
Located in Sanford, NC / 185 miles away from Chesapeake, VA
CLEAN CARFAX, ONE OWNER, LOCAL TRADE, 4WD, FAST AND EASY FINANCING, THE NEW PRICE OUTLET, 1-Year SiriusXM Guardian Trial, 240 Amp Alternator, 4G LTE W...
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: 1C4JJXFM5MW823515
Stock: SJ3687A
Certified Pre-Owned: No
Listed since: 05-31-2025 - $26,500great price$4,096 below market
- 85,637 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Farrish Chrysler Dodge Jeep Ram (158 mi away)
Close
Located in Fairfax, VA / 158 miles away from Chesapeake, VA
**LOCAL TRADE IN** 1 OWNER CLEAN CARFAX NO ACCIDENTS** BEST COLOR COMBO!! 2021 JEEP WRANGLER UNLIMITED WILLYS 4X4** STING GRAY W/ BLACK INTERIOR** CUS...
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: 1C4HJXDGXMW544234
Stock: PZ12741B
Certified Pre-Owned: Yes
Listed since: 06-02-2025 - 62,237 miles
- Frame damage reported, 2 owners, corporate fleet vehicle
- 5 Seats, 17 City / 23 Hwy MPG
- Kargar Motors (155 mi away)
Close
Located in Manassas, VA / 155 miles away from Chesapeake, VA
BUYING A CAR HAS NEVER BEEN THIS EASY.We specialize in 100% GUARANTEED APPROVAL. BAD CREDIT, NO CREDIT, BANKRUPTCY, REPO, FORECLOSURE...NO PROBLEM. NO...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
19 Combined MPG (17 City/23 Highway)
Listing Information:
VIN: 1C4HJXEN0LW209527
Stock: KMM12883
Certified Pre-Owned: No- $24,995great price$3,799 below market
- 104,746 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 21 City / 24 Hwy MPG
- Virginia Auto Trader Co (156 mi away)
Close
Located in Arlington, VA / 156 miles away from Chesapeake, VA
2021 JEEP WRANGLER 4 WHEEL DRIVE with powerful 2.0L I4 DOHC DI TURBO W/ESS engine and driven only 104746 miles! Fully loaded and much more! CARFAX CER...
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 (21 City/24 Highway)
Listing Information:
VIN: 1C4HJXKN2MW619283
Stock: 2607
Certified Pre-Owned: No - 37,512 miles
- 1 accident, 2 owners, personal use only
- 4 Seats, 17 City / 25 Hwy MPG, Manual
- Hyman Bros Kia (93 mi away)
Close
Located in Midlothian, VA / 93 miles away from Chesapeake, VA
Black Clearcoat exterior and Black interior. Brake Actuated Limited Slip Differential, Keyless Start, Bluetooth®, iPod/MP3 Input, 4x4, ENGINE: 3.6L V6...
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:
20 Combined MPG (17 City/25 Highway)
Listing Information:
VIN: 1C4GJXAGXLW282715
Stock: N732041
Certified Pre-Owned: No
Listed since: 08-23-2024- New Listing
Photos not available- Not provided
- No accidents, 1 owner, personal use only
- 5 Seats, 21 City / 22 Hwy MPG
- Len Stoler Chrysler Dodge Jeep Ram (199 mi away)
Close
Located in Westminster, MD / 199 miles away from Chesapeake, VA
2020 Jeep Wrangler Unlimited Rubicon Black Clearcoat 8-Speed Automatic 4WD 2.0L I4 DOHCRecent Arrival! CARFAX One-Owner. Clean CARFAX. Odometer is 250...
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 (21 City/22 Highway)
Listing Information:
VIN: 1C4HJXFN3LW138807
Stock: BJ1295AA
Certified Pre-Owned: No
Listed since: 06-21-2025 - $33,998great price$4,381 below market
- 59,091 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- CarMax Dulles (170 mi away)
Close
Located in Sterling, VA / 170 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: 1C4HJXFN1MW612061
Stock: 27275761
Certified Pre-Owned: No - Price Drop$29,500great price$4,207 below market
- 74,791 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Ourisman Chrysler Dodge Jeep Ram Fiat of Baltimore (177 mi away)
Close
Located in Baltimore, MD / 177 miles away from Chesapeake, VA
CARFAX One-Owner. Recent Arrival! This 2021 Hydro Blue Pearl Coat Jeep Wrangler Unlimited Sahara Altitude 4WD is well equipped and includes these feat...
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: 1C4HJXEG3MW669896
Stock: B4668
Certified Pre-Owned: No
Listed since: 06-12-2025 - $27,995great price$3,996 below market
- 93,409 miles
- No accidents, 2 owners, personal use only
- 5 Seats, 17 City / 23 Hwy MPG
- Carvault of Chantilly (165 mi away)
Close
Located in Chantilly, VA / 165 miles away from Chesapeake, VA
Visit CarVault of Chantilly to shop our great deals. You can call 571-585-7830 to schedule your test drive today.
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:
19 Combined MPG (17 City/23 Highway)
Listing Information:
VIN: 1C4HJXFG6KW591044
Stock: CVLC1044
Certified Pre-Owned: No - Price Drop$31,690great price$3,945 below market
- 54,163 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Farrish Chrysler Dodge Jeep Ram (158 mi away)
Close
Located in Fairfax, VA / 158 miles away from Chesapeake, VA
**SKY ONE TOUCH** 1 OWNER CLEAN CARFAX NO ACCIDENTS** OFF LEASE** BEST COLOR!! **SNAZBERRY PEARLCOAT** DEALER SERVICED AND WELL MAINTAINED** ONLY 54K ...
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: 1C4HJXDG5MW583670
Stock: PZ12875
Certified Pre-Owned: Yes
Listed since: 05-19-2025 - Price Drop$40,500good price$4,815 below market
- 12,408 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Hall Chrysler Dodge Jeep RAM Virginia Beach (11 mi away)
Close
Located in Virginia Beach, VA / 11 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Black Clearcoat 2021 Jeep Wrangler Unlimited Rubicon 4WD 8-Speed Automatic 3.0L V6 Turbodiesel Wrangler Unlimited Rubi...
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: 1C4JJXFM5MW697169
Stock: 18251010A
Certified Pre-Owned: No
Listed since: 05-31-2025 - Price Drop$25,702great price$3,096 below market
- 92,984 miles
- No accidents, 1 owner, personal use
- 5 Seats
- Nissan of Hampton (23 mi away)
Close
Located in Hampton, VA / 23 miles away from Chesapeake, VA
Vehicle DetailsDiscover the adventurous spirit of the 2021 Jeep Wrangler Unlimited Sahara, a vehicle engineered for those who refuse to be con...
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: 1C4HJXEN5MW613831
Stock: UP613831
Certified Pre-Owned: No
Listed since: 05-23-2025 - New Listing$23,805great price$3,259 below market
- 71,844 miles
- No accidents, 2 owners, personal use only
- 5 Seats, 17 City / 23 Hwy MPG
- McLaren Washington (170 mi away)
Close
Located in Sterling, VA / 170 miles away from Chesapeake, VA
Bright White Clearcoat 2021 Jeep Wrangler Unlimited Willys 4WD 8-Speed Automatic 2.0L I4 DOHC. Customer Preferred Package 22K.Prices do not include...
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:
19 Combined MPG (17 City/23 Highway)
Listing Information:
VIN: 1C4HJXDN4MW594805
Stock: MW594805Z
Certified Pre-Owned: No
Listed since: 11-08-2024 - New ListingPhotos not available
- 93,950 miles
- 1 accident, 1 owner, personal use only
- 5 Seats
- Johnson Lexus of Raleigh (144 mi away)
Close
Located in Raleigh, NC / 144 miles away from Chesapeake, VA
Take on any terrain in this rugged and reliable 2020 Jeep Wrangler Unlimited Willys, built for adventure with authentic Jeep performance and unmistaka...
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: 1C4HJXDN0LW194156
Stock: 54622A
Certified Pre-Owned: No
Listed since: 06-19-2025 - $25,000great price$3,115 below market
- 92,240 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 17 City / 23 Hwy MPG, Manual
- Koons Ford of Falls Church (156 mi away)
Close
Located in Falls Church, VA / 156 miles away from Chesapeake, VA
2021 Jeep Wrangler Unlimited Freedom Edition 4D Sport Utility 6-Speed Manual Priced below KBB Fair Purchase Price! 17/23 City/Highway MPG 2021 Clean C...
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:
19 Combined MPG (17 City/23 Highway)
Listing Information:
VIN: 1C4HJXDG7MW654318
Stock: FB53315A
Certified Pre-Owned: No
Listed since: 05-03-2025 - $21,990great price$2,732 below market
- 78,555 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5 Seats, 17 City / 23 Hwy MPG
- Sanford Imports (187 mi away)
Close
Located in Sandford, NC / 187 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price!2019 Jeep Wrangler Unlimited Sport S Bright White Clearcoat Carfax Accident Free, Bluetooth, Multi Point Inspect...
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:
19 Combined MPG (17 City/23 Highway)
Listing Information:
VIN: 1C4HJXDG7KW505551
Stock: 7005791
Certified Pre-Owned: No
Listed since: 04-14-2025 - Price Drop$28,250great price$3,089 below market
- 68,262 miles
- No accidents, 1 owner, personal use
- 5 Seats
- Impex Chevrolet GMC (192 mi away)
Close
Located in Reidsville, NC / 192 miles away from Chesapeake, VA
Clean CARFAX.2021 Jeep Wrangler Unlimited Willys Sky One Touch® Power Top 4WD 8-Speed Automatic Black Clearcoat 2.0L I4 DOHCTHIS VEHICLE INCLUDES THE ...
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: 1C4HJXDN3MW575128
Stock: 2JT5128
Certified Pre-Owned: No
Listed since: 03-06-2025 - Price Drop$30,500great price$2,599 below market
- 39,711 miles
- No accidents, 1 owner, personal use
- 5 Seats
- Koons Tysons Chrysler Dodge Jeep Ram (160 mi away)
Close
Located in Vienna, VA / 160 miles away from Chesapeake, VA
*** 2021 JEEP WRANGLER UNLIMITED SPORT ALTITUDE *** SNAZZBERRY W/ BLACK INTERIOR *** LOADED W/ TECHNOLOGY GROUP *** APPLE CARPLAY *** ANDROID AUTO **...
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: 1C4HJXDN9MW586540
Stock: 00JB1286
Certified Pre-Owned: No
Listed since: 06-12-2025
Showing 64 - 84 out of 2,743 listings
Consumer Reviews for the Jeep Wrangler
Read recent reviews for the Jeep Wrangler
Capable but not for everyone
Thom Mills, 03/17/2020
2020 Jeep Wrangler Sport S 2dr SUV 4WD (3.6L 6cyl 6M)
The 2-door Wrangler (Sport S trim, 3.6l, manual, with limited slip rear diff in my case) is really capable off road, though it’s not without at least one flaw: the engine. You don’t normally want an engine that comes into its own at higher RPM if you are off road. The lack of low end torque in this engine, especially with the manual gear box, is less than ideal.
With that said, there’s … a lot of people griping about the cost of one of these things compared to other 4x4 SUVs. These days there are no purpose built off road vehicles that are designed specifically for the most challenging situations. Not at this price point. Even unmodified the Wrangler is more capable than anything else out there. The “vague” steering? Enjoy the benefits of that solid front axle. The “road noise?” Enjoy the light top that keeps the center of gravity low for off road tracks. Many complaints are actually highlighting what is good about the Wrangler.
Although the seats are surprisingly comfortable (I enjoy the lower lumbar adjustment) you aren’t paying for high end interior trim or “soft touch” materials. You’re paying for sealed electronics, the ability to spray out the interior, the Dana axles and everything else that you won’t see on a normal 4x4 SUV.
I bought this thing to go wherever I want, to have the ability to add things like a winch, a lift kit beyond 2” (good luck doing that with an independent front suspension) for hunting and camping trips. It’s so I have very few geographical limits.
If that’s not what you want, maybe you should look elsewhere.
If you want a cool looking little SUV with an independent front suspension, and all that entails, wait for the new Bronco. If you actually want an extremely capable solid axle vehicle designed specifically for going off road pick a Wrangler. You won’t be disappointed.
Used 2021 Jeep Wrangler in Chesapeake, VA Values
Estimated values
2021 Jeep Wrangler Unlimited Willys 4dr SUV 4WD (3.6L 6cyl gas/electric mild hybrid 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $20,907 | $22,750 | $24,607 |
| Clean | $20,414 | $22,183 | $23,961 |
| Average | $19,592 | $21,239 | $22,885 |
| Rough | $18,525 | $20,011 | $21,486 |
The average list price of a used 2021 Jeep Wrangler in Chesapeake, Virginia is $29,088. The average mileage on a used Jeep Wrangler 2021 for sale in Chesapeake, Virginia is 67,341. Based on the average mileage of 67,341 for used 2021 Jeep Wrangler 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 Wrangler 2021 in Chesapeake, Virginia to be $19,592.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.