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Used Jeep Trucks for Sale in Chesapeake, VA

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Items 1 to 2 of 12.
    Sponsored by Matthew Sessoms Chrysler Dodge Jeep Ram
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    New 2026 Jeep Gladiator Sport
    53,944
    MSRP$50,765
    Dealer Fees Included
    Similar Match
    Matthew Sessoms Chrysler Dodge Jeep Ram
    (252) 802-8443
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    Used 2026 Jeep Gladiator Rubicon
    Used

    2026 Jeep Gladiator

    • Rubicon
    • 12K mi
    45,479
    No Accidents
    Sponsored by Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
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    Used 2021 Jeep Gladiator Overland w/ Cold Weather Group
    Used

    2021 Jeep Gladiator

    • Overland
    • 56K mi
    28,490
    Sponsored by Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
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    Used 2025 Jeep Gladiator Rubicon w/ Safety Group
    Used

    2025 Jeep Gladiator

    • Rubicon
    • 2K mi
    45,998
    No Accidents
    Sponsored by Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
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    Based on 4.5% APR for mos.
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    Used 2020 Jeep Gladiator Rubicon

    2020 Jeep Gladiator

    • Rubicon
    • 37K mi
    29,938
    Great Price
    Dealer Fees Included
    No Accidents
    Cavalier Ford Greenbrier
    • 2.63 mi. away
    Call
    Used 2020 Jeep Gladiator Sport w/ Quick Order Package 24S
    Used

    2020 Jeep Gladiator

    • Sport
    • 83K mi
    22,982
    Great Price
    Dealer Fees Included
    No Accidents
    Little Joe's Mitsubishi
    • 2.45 mi. away
    • Online Paperwork
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    Price Drop
    Used 2020 Jeep Gladiator Rubicon w/ Dual Top Group
    Used

    2020 Jeep Gladiator

    • Rubicon
    • 73K mi
    32,348
    Dealer Fees Included
    No Accidents
    Priority Ford Norfolk
    • 8.98 mi. away
    Call
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    Used 2023 Jeep Gladiator Rubicon w/ Cold Weather Group
    Used

    2023 Jeep Gladiator

    • Rubicon
    • 21K mi
    37,000
    No Accidents
    Southern Chrysler Dodge Jeep Ram Greenbrier
    • 2.77 mi. away
    Call
    Sponsored
    Price Drop
    Item 1 of 4.
    Certified 2025 Jeep Gladiator Sport
    Price Reduced!
    Certified

    2025 Jeep Gladiator

    • Sport
    • 4K mi
    38,750
    No Accidents
    Call
    Price Drop
    Used 2021 Jeep Gladiator Overland
    Used

    2021 Jeep Gladiator

    • Overland
    • 57K mi
    32,499
    Good Price
    Dealer Fees Included
    No Accidents
    Beach Auto Brokers
    • 11.14 mi. away
    Call
    Used 2020 Jeep Gladiator Sport w/ Quick Order Package 24S
    Used

    2020 Jeep Gladiator

    • Sport
    • 81K mi
    26,992
    Dealer Fees Included
    No Accidents
    Little Joe's Mitsubishi
    • 2.45 mi. away
    • Online Paperwork
    Call
    Used 2024 Jeep Gladiator Sport

    2024 Jeep Gladiator

    • Sport
    • 25K mi
    37,563
    Dealer Fees Included
    No Accidents
    Priority Ford Norfolk
    • 8.98 mi. away
    Call
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    Used 2026 Jeep Gladiator Rubicon
    Used

    2026 Jeep Gladiator

    • Rubicon
    • 18K mi
    43,697
    Great Price
    Dealer Fees Included
    No Accidents
    Cavalier Mazda
    • 2.47 mi. away
    • Online Paperwork
    Call
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    Used 2020 Jeep Gladiator Rubicon w/ Dual Top Group
    Used

    2020 Jeep Gladiator

    • Rubicon
    • 48K mi
    34,000
    No Accidents
    Southern Chrysler Dodge Jeep Ram Greenbrier
    • 2.77 mi. away
    Call
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    Used 2022 Jeep Gladiator Overland
    Used

    2022 Jeep Gladiator

    • Overland
    • 8K mi
    36,895
    No Accidents
    Southern Buick GMC Greenbrier
    • 3 mi. away
    Call
    Newly Listed
    Used 2024 Jeep Gladiator Sport
    Used

    2024 Jeep Gladiator

    • Sport
    • 20K mi
    34,696
    Good Price
    Dealer Fees Included
    No Accidents
    Elizabeth City GMC
    • 33.34 mi. away
    • Online Paperwork
    Call
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    Used 2024 Jeep Gladiator Sport
    Used

    2024 Jeep Gladiator

    • Sport
    • 17K mi
    37,329
    Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
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    Used 2021 Jeep Gladiator Rubicon
    Used

    2021 Jeep Gladiator

    • Rubicon
    • 14K mi
    38,770
    No Accidents
    Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
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    Used 2025 Jeep Gladiator Rubicon w/ Safety Group
    Used

    2025 Jeep Gladiator

    • Rubicon
    • 2K mi
    45,998
    No Accidents
    Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
    Newly Listed
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    Used 2023 Jeep Gladiator Mojave w/ LED Lighting Group
    Used

    2023 Jeep Gladiator

    • Mojave
    • 42K mi
    37,759
    Great Price
    Dealer Fees Included
    No Accidents
    Southern Ford Newport News
    • 31.27 mi. away
    Call
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    Used 2022 Jeep Gladiator Sport
    Used

    2022 Jeep Gladiator

    • Sport
    • 58K mi
    28,300
    No Accidents
    Southern Chrysler Dodge Jeep Ram Greenbrier
    • 2.77 mi. away
    Call
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    Used 2021 Jeep Gladiator Mojave
    Used

    2021 Jeep Gladiator

    • Mojave
    • 67K mi
    33,545
    No Accidents
    Southern Chrysler Dodge Jeep Ram Greenbrier
    • 2.77 mi. away
    Call
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    Used 2020 Jeep Gladiator Sport w/ Quick Order Package 24S
    Used

    2020 Jeep Gladiator

    • Sport
    • 50K mi
    26,488
    No Accidents
    Southern CDJR Chesapeake
    • 12.19 mi. away
    Call
    Newly Listed
    Used 2020 Jeep Gladiator Overland
    Used

    2020 Jeep Gladiator

    • Overland
    • 39K mi
    30,999
    Good Price
    Dealer Fees Included
    No Accidents
    Southern CDJR Fiat Newport News
    • 30.09 mi. away
    Call
    Used 2021 Jeep Gladiator Overland w/ Popular Equipment Package

    2021 Jeep Gladiator

    • Overland
    • 137K mi
    25,413
    Dealer Fees Included
    No Accidents
    Priority Ford Norfolk
    • 8.98 mi. away
    Call
    Price Drop
    Used 2024 Jeep Gladiator Sport
    Used

    2024 Jeep Gladiator

    • Sport
    • 15K mi
    36,000
    No Accidents
    CarDirect, LLC
    • 11.59 mi. away
    Call
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    Used 2021 Jeep Gladiator Overland w/ Cold Weather Group
    Used

    2021 Jeep Gladiator

    • Overland
    • 56K mi
    28,490
    Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
    360°
    Used 2026 Jeep Gladiator Rubicon
    Used

    2026 Jeep Gladiator

    • Rubicon
    • 12K mi
    45,479
    No Accidents
    Southern Dodge Chrysler Jeep Ram Alfa Romeo Fiat Norfolk
    • 8.69 mi. away
    Call
    Price Drop
    360°
    Used 2025 Jeep Gladiator Mojave
    Used

    2025 Jeep Gladiator

    • Mojave
    • 18K mi
    45,000
    No Accidents
    Southern Chrysler Dodge Jeep Ram Greenbrier
    • 2.77 mi. away
    Call
    Price Drop
    Used 2020 Jeep Gladiator Sport w/ Quick Order Package 24S
    Used

    2020 Jeep Gladiator

    • Sport
    • 98K mi
    24,499
    Dealer Fees Included
    No Accidents
    Beach Auto Brokers
    • 11.14 mi. away
    Call
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