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1,184 listings
  • $18,000
    good price
    $1,876 below market
    • 67,211 miles
    • 1 accident, 2 owners, rental vehicle
    • 5 Seats, 18 City / 24 Hwy MPG
    • Koons Tysons Chrysler Dodge Jeep Ram (41 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Vienna, VA / 41 miles away from Windsor Mill, MD

    Recent Arrival! 2019 Jeep Cherokee Trailhawk 4WD Bright White Clearcoat*** LED FOG LAMPS *** JEEP ACTIVE DRIVE II*** APPLE CARPLAY AND ANDROID AUTO ...

    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: 1C4PJMBX7KD360679
    Stock: 00JK6859
    Certified Pre-Owned: No
    Listed since: 04-14-2025

  • $12,500
    good price
    $1,705 below market
    • 96,506 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats
    • Len Stoler Chrysler Dodge Jeep Ram (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Sunroof/Moonroof
    • Keyless Entry/Start
    Close

    Located in Westminster, MD / 21 miles away from Windsor Mill, MD

    2016 Jeep Cherokee 75th Anniversary Edition Brilliant Black Crystal Pearlcoat 9-Speed 948TE Automatic 4WD 3.2L V6CARFAX One-Owner.BLUETOOTH, BACK UP 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: No

    Features and Specs:

    Listing Information:

    VIN: 1C4PJMCS7GW317328
    Stock: J1637A
    Certified Pre-Owned: No
    Listed since: 05-07-2025

  • Price Drop
    $21,900
    fair price
    $264 below market
    • 48,524 miles
    • No accidents, 1 owner, rental vehicle
    • 5 Seats, 21 City / 29 Hwy MPG
    • Ourisman Chrysler Dodge Jeep Ram Fiat of Baltimore (9 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Baltimore, MD / 9 miles away from Windsor Mill, MD

    CARFAX One-Owner. This 2023 Hydro Blue Pearlcoat Jeep Cherokee Altitude 4WD is well equipped and includes these features and benefits:. *** Back Up ...

    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: 1C4PJMMB3PD111370
    Stock: R4553
    Certified Pre-Owned: No
    Listed since: 04-16-2025

  • $19,999
    fair price
    $839 below market
    • 54,700 miles
    • No accidents, 1 owner, rental vehicle
    • 5 Seats, 20 City / 29 Hwy MPG
    • Enterprise Car Sales Marlow Heights (37 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Suitland, MD / 37 miles away from Windsor Mill, MD

    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:

    23 Combined MPG (20 City/29 Highway)

    Listing Information:

    VIN: 1C4PJLMX3ND519659
    Stock: 8DQQ2M
    Certified Pre-Owned: No
    Listed since: 04-22-2025

  • Price Drop
    $19,406
    good price
    $2,183 below market
    • 70,824 miles
    • 1 accident, 1 owner, personal use only
    • 5 Seats
    • BMW of Catonsville (5 mi away)
    • Five Star Dealer
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Baltimore, MD / 5 miles away from Windsor Mill, MD

    Recent Arrival! CARFAX One-Owner.*Your additional costs are sales tax, tag and title fees for the state in which the vehicle will be registered, any d...

    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: 1C4PJMDN6LD555024
    Stock: 450963A
    Certified Pre-Owned: No
    Listed since: 04-12-2025

  • $16,484
    good price
    $885 below market
    • 91,702 miles
    • 1 accident, 3 owners, corporate fleet vehicle
    • 5 Seats, 19 City / 27 Hwy MPG
    • Koons Annapolis Toyota (26 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Annapolis, MD / 26 miles away from Windsor Mill, MD

    10 Speakers, 3.251 Axle Ratio, 4-Wheel Disc Brakes, 8.4" Touchscreen Display, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, Anti-...

    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: 1C4PJMDX5KD359592
    Stock: EE21383
    Certified Pre-Owned: No
    Listed since: 04-17-2025

  • $18,995
    good price
    $1,408 below market
    • 64,378 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 18 City / 24 Hwy MPG
    • Exclusive Motor Cars (8 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Randallstown, MD / 8 miles away from Windsor Mill, MD

    This 2019 Billet Silver Metallic Clearcoat Jeep Cherokee Trailhawk 4WD is well equipped and includes these features and benefits:. 4WD Clean CARFAX....

    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: 1C4PJMBX0KD427252
    Stock: D427252
    Certified Pre-Owned: No
    Listed since: 05-14-2024

  • Price Drop
    $18,895
    fair price
    $199 below market
    • 22,266 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats
    • Len Stoler Hyundai (9 mi away)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    • Power Driver Seat
    Close

    Located in Owings Mills, MD / 9 miles away from Windsor Mill, MD

    CARFAX One-Owner. Clean CARFAX. 2018 Jeep Cherokee Latitude Plus Granite Crystal Metallic Clearcoat FWD 9-Speed 948TE Automatic 2.4L I417" x 7" Alumin...

    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: 1C4PJLLB9JD504020
    Stock: H3230A
    Certified Pre-Owned: No
    Listed since: 05-20-2025

  • Price Drop
    $14,788
    fair price
    $1,043 below market
    • 81,156 miles
    • No accidents, 3 owners, rental vehicle
    • 5 Seats
    • Rich Morton Mazda (15 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Pasadena, MD / 15 miles away from Windsor Mill, MD

    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: 1C4PJMDB9HW515442
    Stock: 515442P
    Certified Pre-Owned: No
    Listed since: 05-01-2025

  • $23,898
    good price
    $1,057 below market
    • 38,712 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 19 City / 27 Hwy MPG
    • Safford Brown CDJR Sterling (46 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Sterling, VA / 46 miles away from Windsor Mill, MD

    CARFAX One-Owner. Clean CARFAX. Bright White Clearcoat 2022 Jeep Cherokee Latitude Lux 4WD 9-Speed 948TE Automatic 3.2L V6 Leather, Sunroof / Moonroof...

    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: 1C4PJMMX8ND523633
    Stock: P880
    Certified Pre-Owned: No
    Listed since: 04-13-2025

  • New Listing
    $17,998
    fair price
    $1,208 above market
    • 48,895 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 21 City / 30 Hwy MPG
    • CarMax Laurel (16 mi away)
    • Back-up camera
    • Bluetooth
    • Upgraded Headlights
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Laurel, MD / 16 miles away from Windsor Mill, MD

    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 (21 City/30 Highway)

    Listing Information:

    VIN: 1C4PJLCB2JD533925
    Stock: 27252295
    Certified Pre-Owned: No

  • $16,598
    good price
    $1,551 below market
    • 79,661 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 19 City / 27 Hwy MPG
    • Dulles Kia (49 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Leesburg, VA / 49 miles away from Windsor Mill, MD

    CLEAN 1 OWNER CARFAX, SXM READY, 3.2L V6, PANORAMIC ROOF, NAVIGATION, SXM, BLIND SPOT, REMOTE START, 18" WHEELS, APPLE CARPLAY/ANDROID AUTO, HEATED ST...

    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: 1C4PJMDX5KD243874
    Stock: 15745A
    Certified Pre-Owned: No
    Listed since: 02-20-2025

  • Price Drop
    $22,500
    good price
    $1,925 below market
    • 47,288 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 24 Hwy MPG
    • Koons Tysons Chrysler Dodge Jeep Ram (41 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Vienna, VA / 41 miles away from Windsor Mill, MD

    Recent Arrival! 2021 Jeep Cherokee Trailhawk 4WD Granite Crystal Metallic Clearcoat**** DUAL PANORAMIC SUNROOF *** BLIND SPOT **** APPLE CARPALY AND...

    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:

    21 Combined MPG (18 City/24 Highway)

    Listing Information:

    VIN: 1C4PJMBX3MD221961
    Stock: 00J16049
    Certified Pre-Owned: No
    Listed since: 05-11-2025

  • Price Drop
    $20,500
    good price
    $1,649 below market
    • 48,587 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 21 City / 29 Hwy MPG
    • Len Stoler Chrysler Dodge Jeep Ram (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Westminster, MD / 21 miles away from Windsor Mill, MD

    2023 Jeep Cherokee Altitude Diamond Black Crystal Pearlcoat 9-Speed 948TE Automatic 4WD 2.4L I4CARFAX One-Owner.BLUETOOTH, BACK UP CAMERA, NAVIGATION,...

    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: 1C4PJMMB1PD114235
    Stock: BJ1445
    Certified Pre-Owned: No
    Listed since: 03-25-2025

  • New Listing
    $17,998
    fair price
    $353 above market
    • 58,472 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 5 Seats
    • CarMax Dulles (46 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Sterling, VA / 46 miles away from Windsor Mill, MD

    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: 1C4PJMDB9JD569390
    Stock: 27282844
    Certified Pre-Owned: No

  • $20,900
    fair price
    $260 below market
    • 34,105 miles
    • 1 accident, 2 owners, corporate fleet vehicle
    • 5 Seats
    • 1 US Motors (22 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Edgewood, MD / 22 miles away from Windsor Mill, MD

    Vehicle Overview: **Vehicles come with complimentary Lifetime Powertrain warranty (with Qualifying purchase) The Eprice does not include state taxes s...

    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: 1C4PJMLX1LD644695
    Stock: 644695
    Certified Pre-Owned: No

  • Price Drop
    $20,496
    good price
    $956 below market
    • 44,793 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 21 City / 29 Hwy MPG
    • Oursiman Nissan (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Laurel, MD / 17 miles away from Windsor Mill, MD

    2021 Jeep Cherokee Altitude Granite Crystal Metallic Clearcoat USB/AUX, BLUE TOOTH, LOCAL TRADE, New Tires!, New Brakes!, New Oil change and New oil f...

    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: 1C4PJMLB4MD225472
    Stock: X029119A
    Certified Pre-Owned: No
    Listed since: 04-29-2025

  • $25,000
    fair price
    $794 below market
    • 30,074 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 24 Hwy MPG
    • Len Stoler Hyundai (9 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Owings Mills, MD / 9 miles away from Windsor Mill, MD

    CARFAX One-Owner. Clean CARFAX. 2021 Jeep Cherokee Trailhawk Spitfire Orange Clearcoat 4WD 9-Speed Automatic 3.2L V63.517 Axle Ratio, 4-Wheel Disc Bra...

    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: 1C4PJMBX5MD220097
    Stock: BH1278
    Certified Pre-Owned: No
    Listed since: 04-10-2025

  • $17,332
    good price
    $1,230 below market
    • 87,554 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 19 City / 27 Hwy MPG
    • Jack Giambalvo Mazda (45 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in York, PA / 45 miles away from Windsor Mill, MD

    "Diamond Black Crystal Pearlcoat 2020 Jeep Cherokee Limited 4WD 9-Speed 948TE Automatic 3.2L V6 8.4""Touchscreen Display Alloy wheels Anti-whiplash fr...

    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: 1C4PJMDX7LD583142
    Stock: 743768B
    Certified Pre-Owned: No
    Listed since: 05-01-2025

  • Price Drop
    $9,900
    fair price
    $530 below market
    • 107,584 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats
    • Manchester Motors (25 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Manchester, MD / 25 miles away from Windsor Mill, MD

    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: 1C4PJMCS0EW311397
    Stock: 7819
    Certified Pre-Owned: No
    Listed since: 05-07-2025

  • $21,998
    fair price
    $441 above market
    • 42,959 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 5 Seats, 21 City / 29 Hwy MPG
    • CarMax Dulles (46 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Sterling, VA / 46 miles away from Windsor Mill, MD

    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:

    24 Combined MPG (21 City/29 Highway)

    Listing Information:

    VIN: 1C4PJMLB4MD157531
    Stock: 27275304
    Certified Pre-Owned: No

Showing 22 - 42 out of 1,184 listings
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.