Skip to main content
Best match Lowest price Highest price Lowest mileage Highest mileage Nearest location Best deal Newest year Oldest year Newest listed Oldest listed
Skip to Filters
  • Summit White 2024 Chevrolet Silverado 1500 Custom Trail BossSummit White 2024 Chevrolet Silverado 1500 Custom Trail BossSummit White 2024 Chevrolet Silverado 1500 Custom Trail BossSummit White 2024 Chevrolet Silverado 1500 Custom Trail BossSummit White 2024 Chevrolet Silverado 1500 Custom Trail BossSummit White 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $42,497

    $500
    4,651 mi.
    Est. $799/mo

    Sunrise Volkswagen of Fort Pierce

    4.4
    Check Availability
    Fort Pierce, FL (1,085 mi)

    Quick view
  • Summit White 2021 Chevrolet Silverado 1500 Custom Trail BossSummit White 2021 Chevrolet Silverado 1500 Custom Trail BossSummit White 2021 Chevrolet Silverado 1500 Custom Trail BossSummit White 2021 Chevrolet Silverado 1500 Custom Trail BossSummit White 2021 Chevrolet Silverado 1500 Custom Trail BossSummit White 2021 Chevrolet Silverado 1500 Custom Trail Boss

    $35,472

    49,912 mi.
    Est. $667/mo

    AutoNation USA Phoenix

    4.2
    Check Availability
    Phoenix, AZ (1,447 mi)

    Quick view
  • Red 2024 Chevrolet Silverado 1500 Custom Trail BossRed 2024 Chevrolet Silverado 1500 Custom Trail BossRed 2024 Chevrolet Silverado 1500 Custom Trail BossRed 2024 Chevrolet Silverado 1500 Custom Trail BossRed 2024 Chevrolet Silverado 1500 Custom Trail BossRed 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $46,445

    29,216 mi.
    Est. $873/mo

    Smedley's Chevrolet

    4.6
    Check Availability
    Vandalia, OH (226 mi)
    Quick view
  • Dark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail Boss

    $39,593

    $401
    38,421 mi.
    Est. $744/mo

    Bob Allen Motor Mall

    4.7
    Check Availability
    Danville, KY (329 mi)
    Quick view
  • Summit White 2020 Chevrolet Silverado 1500 Custom Trail BossSummit White 2020 Chevrolet Silverado 1500 Custom Trail BossSummit White 2020 Chevrolet Silverado 1500 Custom Trail BossSummit White 2020 Chevrolet Silverado 1500 Custom Trail BossSummit White 2020 Chevrolet Silverado 1500 Custom Trail BossSummit White 2020 Chevrolet Silverado 1500 Custom Trail Boss

    $30,000

    110,706 mi.
    Est. $564/mo

    Strosnider Chevrolet

    4.8
    Check Availability
    Hopewell, VA (635 mi)
    Quick view
  • Northsky Blue Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossNorthsky Blue Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossNorthsky Blue Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossNorthsky Blue Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossNorthsky Blue Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossNorthsky Blue Metallic 2021 Chevrolet Silverado 1500 Custom Trail Boss

    $33,900

    $350
    49,606 mi.
    Est. $637/mo

    Westgate Chevrolet of Burgaw

    Check Availability
    Burgaw, NC (732 mi)
    Quick view
  • Slate Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSlate Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSlate Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSlate Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSlate Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSlate Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $42,810

    12,320 mi.
    Est. $805/mo

    North County Kia

    2.9
    Check Availability
    Escondido, CA (1,715 mi)
    Quick view
  • Lakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $40,510

    $322
    15,254 mi.
    Est. $761/mo

    Auto Gallery Chevrolet GMC, Inc.

    4.9
    Check Availability
    LaGrange, GA (628 mi)

    Quick view
  • Ash 2024 Chevrolet Silverado 1500 Custom Trail BossAsh 2024 Chevrolet Silverado 1500 Custom Trail BossAsh 2024 Chevrolet Silverado 1500 Custom Trail BossAsh 2024 Chevrolet Silverado 1500 Custom Trail BossAsh 2024 Chevrolet Silverado 1500 Custom Trail BossAsh 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $45,488

    $500
    16,855 mi.
    Est. $855/mo

    Daytona Dodge Chrysler Jeep & RAM

    4.3
    Check Availability
    Daytona Beach, FL (949 mi)
    Quick view
  • Black 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail Boss

    $31,975

    $675
    84,288 mi.
    Est. $601/mo

    Troncalli Chrysler Dodge Jeep RAM

    4.9
    Check Availability
    Cumming, GA (565 mi)
    Quick view
  • Lakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossLakeshore Blue Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $33,633

    $251
    76,318 mi.
    Est. $632/mo

    Corwin Ford of Spokane

    4.5
    Check Availability
    Spokane Valley, WA (1,499 mi)
    Quick view
  • Sterling Gray Metallic 2026 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2026 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2026 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2026 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2026 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2026 Chevrolet Silverado 1500 Custom Trail Boss

    $44,988

    429 mi.
    Est. $846/mo

    Ferman BMW

    4.8
    Check Availability
    Palm Harbor, FL (995 mi)
    Quick view
  • Black 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail BossBlack 2020 Chevrolet Silverado 1500 Custom Trail Boss

    $28,990

    68,237 mi.
    Est. $545/mo

    Lorenzo Buick GMC

    4.4
    Check Availability
    Miami, FL (1,188 mi)
    Quick view
  • Red Hot 2019 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2019 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2019 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2019 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2019 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2019 Chevrolet Silverado 1500 Custom Trail Boss

    $31,495

    71,626 mi.
    Est. $592/mo

    Rudolph Chevrolet

    4.2
    Check Availability
    El Paso, TX (1,251 mi)

    Quick view
  • Black 2019 Chevrolet Silverado 1500 Custom Trail BossBlack 2019 Chevrolet Silverado 1500 Custom Trail BossBlack 2019 Chevrolet Silverado 1500 Custom Trail BossBlack 2019 Chevrolet Silverado 1500 Custom Trail BossBlack 2019 Chevrolet Silverado 1500 Custom Trail BossBlack 2019 Chevrolet Silverado 1500 Custom Trail Boss

    $29,631

    $337
    93,071 mi.
    Est. $557/mo

    Rick Hendrick Chevrolet Buick GMC

    4.7
    Check Availability
    Richmond, VA (606 mi)
    Quick view
  • Satin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail Boss

    $29,988

    110,228 mi.
    Est. $564/mo

    Freedom Dodge Chrysler Jeep Ram by Ed Morse

    4.8
    Check Availability
    Duncanville, TX (815 mi)
    Quick view
  • Black 2026 Chevrolet Silverado 1500 Custom Trail BossBlack 2026 Chevrolet Silverado 1500 Custom Trail BossBlack 2026 Chevrolet Silverado 1500 Custom Trail BossBlack 2026 Chevrolet Silverado 1500 Custom Trail BossBlack 2026 Chevrolet Silverado 1500 Custom Trail BossBlack 2026 Chevrolet Silverado 1500 Custom Trail Boss

    $49,500

    $400
    5,303 mi.
    Est. $930/mo

    Toyota of Colorado Springs in Motor City

    4.8
    Check Availability
    Colorado Springs, CO (928 mi)
    Quick view
  • Summit White 2023 Chevrolet Silverado 1500 Custom Trail BossSummit White 2023 Chevrolet Silverado 1500 Custom Trail BossSummit White 2023 Chevrolet Silverado 1500 Custom Trail BossSummit White 2023 Chevrolet Silverado 1500 Custom Trail BossSummit White 2023 Chevrolet Silverado 1500 Custom Trail BossSummit White 2023 Chevrolet Silverado 1500 Custom Trail Boss

    $38,995

    55,629 mi.
    Est. $733/mo

    Simpson Chevrolet

    4.6
    Check Availability
    Garden Grove, CA (1,737 mi)
    Quick view
  • Black 2024 Chevrolet Silverado 1500 Custom Trail BossBlack 2024 Chevrolet Silverado 1500 Custom Trail BossBlack 2024 Chevrolet Silverado 1500 Custom Trail BossBlack 2024 Chevrolet Silverado 1500 Custom Trail BossBlack 2024 Chevrolet Silverado 1500 Custom Trail BossBlack 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $44,000

    29,819 mi.
    Est. $827/mo

    Metro Ford

    4.5
    Check Availability
    Schenectady, NY (705 mi)
    Quick view
  • Red Hot 2020 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2020 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2020 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2020 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2020 Chevrolet Silverado 1500 Custom Trail BossRed Hot 2020 Chevrolet Silverado 1500 Custom Trail Boss

    $30,000

    86,544 mi.
    Est. $564/mo

    Toyota of Gastonia

    4.5
    Check Availability
    Gastonia, NC (579 mi)

    Quick view
  • Red 2025 Chevrolet Silverado 1500 Custom Trail BossRed 2025 Chevrolet Silverado 1500 Custom Trail BossRed 2025 Chevrolet Silverado 1500 Custom Trail BossRed 2025 Chevrolet Silverado 1500 Custom Trail BossRed 2025 Chevrolet Silverado 1500 Custom Trail BossRed 2025 Chevrolet Silverado 1500 Custom Trail Boss

    $48,975

    23,379 mi.
    Est. $921/mo

    Colonial West Chevrolet

    4.9
    Check Availability
    Fitchburg, MA (812 mi)
    Quick view
  • Silver Ice Metallic 2019 Chevrolet Silverado 1500 Custom Trail BossSilver Ice Metallic 2019 Chevrolet Silverado 1500 Custom Trail BossSilver Ice Metallic 2019 Chevrolet Silverado 1500 Custom Trail BossSilver Ice Metallic 2019 Chevrolet Silverado 1500 Custom Trail BossSilver Ice Metallic 2019 Chevrolet Silverado 1500 Custom Trail BossSilver Ice Metallic 2019 Chevrolet Silverado 1500 Custom Trail Boss

    $30,881

    93,031 mi.
    Est. $580/mo

    Tom Bell Chevrolet

    4.3
    Check Availability
    Redlands, CA (1,689 mi)
    Quick view
  • Summit White 2022 Chevrolet Silverado 1500 Custom Trail BossSummit White 2022 Chevrolet Silverado 1500 Custom Trail BossSummit White 2022 Chevrolet Silverado 1500 Custom Trail BossSummit White 2022 Chevrolet Silverado 1500 Custom Trail BossSummit White 2022 Chevrolet Silverado 1500 Custom Trail BossSummit White 2022 Chevrolet Silverado 1500 Custom Trail Boss

    $43,141

    29,388 mi.
    Est. $811/mo

    Phillips Buick GMC

    4.5
    Check Availability
    Fruitland Park, FL (954 mi)
    Quick view
  • Satin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2021 Chevrolet Silverado 1500 Custom Trail Boss

    $33,543

    $354
    96,574 mi.
    Est. $630/mo

    Sapaugh GM Country

    4.8
    Check Availability
    Herculaneum, MO (291 mi)
    Quick view
  • Satin Steel Metallic 2020 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2020 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2020 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2020 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2020 Chevrolet Silverado 1500 Custom Trail BossSatin Steel Metallic 2020 Chevrolet Silverado 1500 Custom Trail Boss

    $27,895

    $2.1K
    110,130 mi.
    Est. $524/mo

    Trent Cadillac Buick GMC

    4.9
    Check Availability
    New Bern, NC (742 mi)
    Quick view
  • Dark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail BossDark Ash Metallic 2023 Chevrolet Silverado 1500 Custom Trail Boss

    $34,997

    $1K
    42,425 mi.
    Est. $658/mo

    Fairway Ford, Inc.

    4.6
    Check Availability
    Greenville, SC (565 mi)

    Quick view
  • Sterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail BossSterling Gray Metallic 2024 Chevrolet Silverado 1500 Custom Trail Boss

    $40,960

    33,041 mi.
    Est. $770/mo

    Stingray Chevrolet

    4.6
    Check Availability
    Plant City, FL (1,006 mi)
    Quick view
  • Summit White 2026 Chevrolet Silverado 1500 Custom Trail BossSummit White 2026 Chevrolet Silverado 1500 Custom Trail BossSummit White 2026 Chevrolet Silverado 1500 Custom Trail BossSummit White 2026 Chevrolet Silverado 1500 Custom Trail BossSummit White 2026 Chevrolet Silverado 1500 Custom Trail BossSummit White 2026 Chevrolet Silverado 1500 Custom Trail Boss

    $49,299

    $185
    7,726 mi.
    Est. $927/mo

    Gettel Nissan

    4.4
    Check Availability
    Sarasota, FL (1,049 mi)
    Quick view
Skip to Listings
Best match Lowest price Highest price Lowest mileage Highest mileage Nearest location Best deal Newest year Oldest year Newest listed Oldest listed

Chevrolet Silverado 1500 Custom Trail Boss by popular city

Chevrolet Silverado 1500 Custom Trail Boss by year

Chevrolet Silverado 1500 by trim