Skip to main content
Skip to Filters
2,792 listings
  • New Listing
    Stock photo**
    $33,390
    fair price
    $921 above market
    • 11,058 miles
    • No accidents, 1 owner, personal use
    • 5 Seats
    • Whitten Brothers (92 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Richmond, VA / 92 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: 1C4HJXDN9MW831756
    Stock: PL3797
    Certified Pre-Owned: No
    Listed since: 05-16-2025

  • Price Drop
    $39,814
    good price
    $977 below market
    • 36,522 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 17 City / 23 Hwy MPG
    • Safford Chrysler Jeep Dodge Ram of Warrenton (162 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Warrenton, VA / 162 miles away from Chesapeake, VA

    2023 Jeep Wrangler High Tide CARFAX One-Owner.2-Door Passive Entry, Front Door Locks, 220 Amp Alternator, 240 Amp Alternator, 35" Tire Suspension, 4...

    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: 1C4HJXDG0PW635341
    Stock: Z0136
    Certified Pre-Owned: No
    Listed since: 05-01-2025

    • 28,888 miles
    • No accidents, 2 owners, personal use
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from NC to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Winston Salem, NC / 233 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: 1C4HJXEG9MW725081
    Stock: 27122761
    Certified Pre-Owned: No

  • Selling or trading in?

    Know what your car is worth while you shop for your next vehicle.

    See my car’s value
  • New Listing
    $33,998
    good price
    $4,347 below market
    • 52,623 miles
    • 2 accidents, 1 owner, corporate fleet vehicle
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from SC to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Greenville, SC / 367 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: 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: 1C4HJXFN9MW525749
    Stock: 26973741
    Certified Pre-Owned: No

  • New Listing
    $34,998
    fair price
    $796 below market
    • 29,935 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from NY to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Smithtown, NY / 329 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:

    Listing Information:

    VIN: 1C4HJXEN9MW667018
    Stock: 26920994
    Certified Pre-Owned: No

  • New Listing
    • 30,388 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from IL to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Tire Pressure Warnin...
    Close

    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: 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: 1C4HJXDN4MW859805
    Stock: 27345875
    Certified Pre-Owned: No

  • $28,781
    fair price
    $156 below market
    • 65,135 miles
    • No accidents, 3 owners, personal use
    • 5 Seats
    • Sport Durst Mitsubishi (162 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Tire Pressure Warnin...
    Close

    Located in Durham, NC / 162 miles away from Chesapeake, VA

    Clean CARFAX. 2021 Jeep Wrangler Unlimited Sport S Granite Crystal Metallic Clearcoat 4WD 8-Speed Automatic 3.6L V6 24V VVT *LOCAL TRADE*, *INCLUDES 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: 1C4HJXDG0MW518581
    Stock: J9629A
    Certified Pre-Owned: No
    Listed since: 05-02-2025

  • $43,998
    fair price
    $1,488 above market
    • 29,301 miles
    • No accidents, 3 owners, personal use only
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from CO to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Colorado Springs, CO / 1,556 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: 1C4HJXFN0MW664409
    Stock: 27247501
    Certified Pre-Owned: No

  • New Listing
    Stock photo**
    $27,400
    fair price
    $610 below market
    • 53,780 miles
    • No accidents, 1 owner, personal use
    • 5 Seats
    • Bayside Chrysler Dodge Jeep Ram (156 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Annapolis, MD / 156 miles away from Chesapeake, VA

    CARFAX One-Owner. Clean CARFAX.At Bayside, our goal is to build long-term relationships with our customers by providing exceptional service and value ...

    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: 1C4HJXDN0MW784018
    Stock: MW784018
    Certified Pre-Owned: No
    Listed since: 05-15-2025

  • $31,591
    fair price
    $838 above market
    • 42,524 miles
    • No accidents, 1 owner, personal use
    • 5 Seats
    • Don White's Timonium Chrysler Jeep Dodge Ram (191 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Cockeysville, MD / 191 miles away from Chesapeake, VA

    Dealer Billet Silver Metallic Clearcoat 2021 Jeep Wrangler Unlimited Willys 4WD 8-Speed Automatic 2.0L I4 DOHC Lifetime Oil Changes, Lifetime Tire Ro...

    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: 1C4HJXDN8MW721331
    Stock: 4339
    Certified Pre-Owned: No
    Listed since: 04-24-2025

  • Price Drop
    $35,993
    good price
    $4,159 below market
    • 34,930 miles
    • 1 accident, 1 owner, personal use
    • 5 Seats
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Wappingers Falls, NY / 358 miles away from Chesapeake, VA

    CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Leather Seats,Remote Start,Sa...

    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: 1C4HJXFG7MW611448
    Stock: WTP8200
    Certified Pre-Owned: No

  • Price Drop
    • 33,552 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from NC to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Asheville, NC / 365 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:

    Listing Information:

    VIN: 1C4HJXDN8MW669490
    Stock: 27355509
    Certified Pre-Owned: No

  • New Listing
    $29,998
    fair price
    $471 above market
    • 34,522 miles
    • No accidents, 1 owner, personal use
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from OH to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in West Carrollton, OH / 479 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: 1C4HJXDN0MW775562
    Stock: 27329013
    Certified Pre-Owned: No

  • $34,998
    fair price
    $872 above market
    • 32,645 miles
    • No accidents, 1 owner, personal use
    • 5 Seats
    • CarMax (In-stock online)
    • Transfer available from TN to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Memphis, TN / 766 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: 1C4HJXEN1MW707351
    Stock: 27326894
    Certified Pre-Owned: No

  • Price Drop
    • 33,176 miles
    • No accidents, 1 owner, personal use
    • 5 Seats
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Reno, NV / 2,354 miles away from Chesapeake, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,HD Radio,V6...

    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: 1C4HJXDGXMW573782
    Stock: MW573782C
    Certified Pre-Owned: Yes

  • New Listing
    Stock photo**
    • 69,261 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats
    • Ourisman Honda of Frederick (194 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Frederick, MD / 194 miles away from Chesapeake, VA

    2021 Jeep Wrangler Unlimited Sport Sarge Green Clearcoat CARFAX One-Owner.

    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: 1C4HJXDG3MW571243
    Stock: TW571243
    Certified Pre-Owned: No
    Listed since: 05-16-2025

  • New Listing
    $32,998
    fair price
    $447 above market
    • 34,035 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 17 City / 23 Hwy MPG, Manual
    • CarMax (In-stock online)
    • Transfer available from NM to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Santa Fe, NM / 1,657 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:

    19 Combined MPG (17 City/23 Highway)

    Listing Information:

    VIN: 1C4HJXDG9MW731965
    Stock: 27061010
    Certified Pre-Owned: No

  • Price Drop
    $30,400
    good price
    $1,449 below market
    • 43,077 miles
    • 1 accident, 1 owner, personal use only
    • 5 Seats, 21 City / 24 Hwy MPG
    • Ourisman Chrysler Dodge Jeep Ram Fiat of Baltimore (178 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Baltimore, MD / 178 miles away from Chesapeake, VA

    CARFAX One-Owner. This 2023 Sarge Green Clearcoat Jeep Wrangler Sahara 4WD is well equipped and includes these features and benefits:. *** Back Up C...

    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 (21 City/24 Highway)

    Listing Information:

    VIN: 1C4HJXEN1PW693102
    Stock: R4559
    Certified Pre-Owned: No
    Listed since: 04-17-2025

  • Price Drop
    $33,170
    great price
    $4,509 below market
    • 4,632 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 16 City / 22 Hwy MPG
    • Fair Oaks Chrysler Jeep Dodge Ram (164 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Chantilly, VA / 164 miles away from Chesapeake, VA

    Certified. 2024 Jeep Wrangler SportCARFAX One-Owner. Clean CARFAX.Odometer is 3599 miles below market average! FCA US LLC Certified Pre-Owned Cert...

    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 (16 City/22 Highway)

    Listing Information:

    VIN: 1C4PJXDG7RW324312
    Stock: PRW324312
    Certified Pre-Owned: Yes
    Listed since: 04-10-2025

  • New Listing
    $26,990
    fair price
    $792 above market
    • 63,927 miles
    • 4 Seats
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    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 Unavailable.

    Features and Specs:

    Listing Information:

    VIN: 1C4GJXAN5MW647737
    Stock: 2003721720
    Certified Pre-Owned: No
    Listed since: 05-13-2025

  • New Listing
    $35,500
    fair price
    $243 above market
    • 57,103 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats
    • Capital Chevrolet (141 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Wake Forest, NC / 141 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: 1C4HJXFN8MW779646
    Stock: 9C18017A
    Certified Pre-Owned: No
    Listed since: 05-13-2025

Showing 421 - 441 out of 2,792 listings

Consumer Reviews for the Jeep Wrangler

Read recent reviews for the Jeep Wrangler
Overall Consumer Rating
4.4 out of 5 stars57 Reviews
Write a vehicle reviewSee all 57 reviews
  • 5 star
    (81%)
  • 4 star
    (4%)
  • 3 star
    (2%)
  • 2 star
    (2%)
  • 1 star
    (12%)
1 out of 5 stars

Don’t get the 2021 Wrangler!

Heather, 12/19/2022
2021 Jeep Wrangler Unlimited Sport RHD 4dr SUV 4WD (2.0L 4cyl Turbo 8A)
Just don’t!! Custom built Wrangler Sport 2.0 Turbo in 2021. Less than 9 months and 13,500k miles in experienced shaking, loss of acceleration, and overheating. Towed and was diagnosed as engine failure. Almost 7 weeks with a loaner. Get it back from dealer and 2 months in at about 15k, loss of acceleration and shuts down. Told needs new transmission. Reach out finally to Jeep wave … where I’m informed the engine was never actually replaced, only part replacements. This is NOT the experience I was looking for when I purchased a brand new Jeep. Absolute nightmare.
Report abuse

Used 2021 Jeep Wrangler in Chesapeake, VA Values

Estimated values
2021 Jeep Wrangler Unlimited Willys 4dr SUV 4WD (2.0L 4cyl Turbo 8A) with no options
ConditionTrade-InPrivate PartyDealer Retail
Outstanding$26,352$28,685$31,037
Clean$25,731$27,971$30,222
Average$24,695$26,780$28,865
Rough$23,350$25,231$27,100

The average list price of a used 2021 Jeep Wrangler in Chesapeake, Virginia is $33,309. The average mileage on a used Jeep Wrangler 2021 for sale in Chesapeake, Virginia is 39,096. Based on the average mileage of 39,096 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 $24,695.

Filters
Skip to Results

Applied Filters4Active

Select Buying Experience

Location

Search radius200 miles
Search radius

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

Listing Details


* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.