Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearPrincess Anne, MD
185 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 28,523
- Stock #:
- 267516A
- VIN:
- 3GCUDCE89RG387033
Sponsored by R. K. Chevrolet
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,523 mi
Virginia Beach, VA
96 mi away
Good Deal
$42,899
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Cypress
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 6,898
- Stock #:
- CU63439
- VIN:
- 3GCUKCE85SG173717
Price drop
-$1,407
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
6,898 mi
Newport News, VA
88 mi away
Good Deal
$47,699
$46,292
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Blue
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 113,256
- Stock #:
- 121643
- VIN:
- 1GCPYCEF1LZ121643
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
113,256 mi
Townsend, DE
84 mi away
Fair Deal
$26,995
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 4.3L V6 Flex Fuel Vehicle
- Exterior color:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 107,204
- Stock #:
- B261571A
- VIN:
- 1GCPYCEH9LZ140605
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
107,204 mi
Berlin, MD
29 mi away
Good Deal
$26,194
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Summit White
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 81,723
- Stock #:
- 260491B
- VIN:
- 3GCPYCEF8MG101391
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
81,723 mi
Milford, DE
55 mi away
Good Deal
$31,798
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 19,896
- Stock #:
- 800269A
- VIN:
- 3GCUKCE82SG143350
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,896 mi
Home delivery from Summersville, WV
Price includes $420 shipping
Great Deal
$43,316
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- SAND DUNE METALLIC
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $1,143 shipping
Fair Deal
$31,938
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 4.3L V6 Flex Fuel Vehicle
- Exterior color:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,509
- Stock #:
- BC0904A
- VIN:
- 1GCPYCEHXMZ386323
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,509 mi
Baltimore, MD
88 mi away
Good Deal
$29,300
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Slate Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,116
- Stock #:
- 1261950E
- VIN:
- 3GCUKCED5SG275645
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,116 mi
Milford, DE
54 mi away
Fair Deal
$41,493
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Blue Metallic
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 33,288
- Stock #:
- E266452A
- VIN:
- 3GCPYCEF1MG119277
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,288 mi
Elkton, MD
98 mi away
Fair Deal
$36,796
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Sterling Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2,485
- Stock #:
- 269379A
- VIN:
- 3GCPKCEK1TG248813
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,485 mi
Fort Washington, MD
79 mi away
Good Deal
$44,749
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Blue
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 113,256
- Stock #:
- 121643
- VIN:
- 1GCPYCEF1LZ121643
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
113,256 mi
Townsend, DE
84 mi away
Fair Deal
$26,995
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 66,548
- Stock #:
- 144310
- VIN:
- 3GCPDCED6NG650163
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
66,548 mi
Norfolk, VA
97 mi away
Good Deal
$35,495
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5,703
- Stock #:
- 9217
- VIN:
- 3GCPKCEK9SG334188
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
5,703 mi
Home delivery from Excelsior Springs, MO
Price includes $1,796 shipping
Good Deal
$41,696
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- Jet Black
- Mileage:
- 54,367
- Stock #:
- BF2479
- VIN:
- 1GCPYCEL8NZ133782
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,367 mi
Williamsburg, VA
81 mi away
Fair Deal
$37,099
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,586
- Stock #:
- G1288
- VIN:
- 1GCPYCEF1LZ379791
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,586 mi
Home delivery from Butler, PA
Price includes $1,172 shipping
Fair Deal
$36,662
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 28,523
- Stock #:
- 267516A
- VIN:
- 3GCUDCE89RG387033
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,523 mi
Virginia Beach, VA
96 mi away
Good Deal
$42,899
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 70,388
- Stock #:
- 313046
- VIN:
- 3GCUDCED8PG313046
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,388 mi
Home delivery from Euless, TX
Price includes $2,259 shipping
Good Deal
$34,530
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 117,261
- Stock #:
- 303419
- VIN:
- 1GCPYCEFXKZ303419
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
117,261 mi
Norfolk, VA
94 mi away
Fair Deal
$25,799
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Gray
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 99,700
- Stock #:
- KWMTMZ374480
- VIN:
- 1GCPYCEF1MZ374480
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
99,700 mi
White Marsh, MD
90 mi away
Good Deal
$28,300
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 62,775
- Stock #:
- 5019
- VIN:
- 1GCPYCEF0LZ168095
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $531 shipping
Great Deal
$29,431
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Slate Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 20,987
- Stock #:
- 30079
- VIN:
- 3GCPKCEKXSG270842
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
20,987 mi
Home delivery from Lexington, NC
Price includes $300 shipping
Good Deal
$40,399
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 49,954
- Stock #:
- P35037
- VIN:
- 1GCPYCEF3MZ377848
Price drop
-$822
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,954 mi
Norfolk, VA
96 mi away
Good Deal
$36,610
$35,788
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 13,242
- Stock #:
- X33968
- VIN:
- 3GCPDCEK0RG422454
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,242 mi
Norfolk, VA
96 mi away
Good Deal
$41,497
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Princess Anne, MD?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,456.54. The average price has decreased by -2.2% since last year. The 166 for sale near Princess Anne, MD on CarGurus, range from $20,687 to $65,760 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Princess Anne, MD have no reported accidents or damage?
151 out of 166 for sale near Princess Anne, MD have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG/MPGe.
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
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