Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearChester, MD
145 vehicles found
See the total price upfront.
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:
- 355 hp 5.3L V8
- Exterior color:
- Lakeshore Blue
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 34,727
- Stock #:
- T627569
- VIN:
- 3GCUDCED4RG219779
New arrival
Sponsored by Ourisman Chevrolet of Marlow Heights
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,727 mi
Marlow Heights, MD
36 mi away
Fair Deal
$43,800
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 112,979
- Stock #:
- R1E0034A
- VIN:
- 1GCPYCEF1LZ125823
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,979 mi
Baltimore, MD
27 mi away
Good Deal
$26,638
- 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:
- Black
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 47,860
- Stock #:
- P4361
- VIN:
- 3GCPYCEF7MG325378
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
47,860 mi
Jarrettsville, MD
47 mi away
Good Deal
$35,201
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 67,307
- Stock #:
- C260235B
- VIN:
- 3GCPDCED9NG628755
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
67,307 mi
Baltimore, MD
28 mi away
Good Deal
$35,615
- 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:
- Mosaic Black Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,771
- Stock #:
- 5048
- VIN:
- 1GCPYCEL5NZ100710
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,771 mi
Home delivery from Seffner, FL
Price includes $873 shipping
Great Deal
$31,867
- Year:
- 2024
- 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
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 46,774
- Stock #:
- S19825A
- VIN:
- 3GCUDCED7RG267941
Price drop
-$1,000
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,774 mi
Home delivery from Newton, NC
Price includes $534 shipping
Fair Deal
$41,533
$40,533
- 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:
- Black
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 47,860
- Stock #:
- P4361
- VIN:
- 3GCPYCEF7MG325378
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
47,860 mi
Jarrettsville, MD
47 mi away
Good Deal
$35,201
- 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:
- Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 26,322
- Stock #:
- 48208
- VIN:
- 3GCUDCED4PG360459
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
26,322 mi
Home delivery from Arlington, TX
Price includes $1,864 shipping
Good Deal
$39,084
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 39,202
- Stock #:
- B4976A
- VIN:
- 3GCPYCEH3MG250079
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,202 mi
Home delivery from Culpeper, VA
Free home delivery
Fair Deal
$35,994
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 56,969
- Stock #:
- 3927
- VIN:
- 1GCRYCEF9KZ249670
Price drop
-$2,010
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
56,969 mi
Home delivery from Belford, NJ
Price includes $385 shipping
Fair Deal
$31,370
$29,360
- 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 $475 shipping
Great Deal
$29,675
- 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:
- Silver Ice Metallic
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 81,862
- Stock #:
- BR01505
- VIN:
- 1GCPYCEH7LZ136357
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
81,862 mi
Randallstown, MD
41 mi away
Fair Deal
$29,549
- 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:
- Cherry Red Tintcoat (gsk)
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black (h1t)
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 157,606
- Stock #:
- U6766
- VIN:
- 1GCPYCEF9MZ173359
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
157,606 mi
Glen Burnie, MD
24 mi away
Fair Deal
$23,198
- 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:
- Red
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 89,913
- Stock #:
- G5959A
- VIN:
- 3GCPYCEF3MG123248
Price drop
-$831
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,913 mi
Bel Air, MD
39 mi away
Good Deal
$31,422
$30,591
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 112,979
- Stock #:
- R1E0034A
- VIN:
- 1GCPYCEF1LZ125823
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,979 mi
Baltimore, MD
27 mi away
Good Deal
$26,638
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,703
- Stock #:
- DT546A
- VIN:
- 3GCUKCED9SG221121
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
24,703 mi
Home delivery from White Hall, WV
Price includes $314 shipping
Good Deal
$44,388
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 62,288
- Stock #:
- 62895A
- VIN:
- 3GCPDCED0NG658324
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,288 mi
Home delivery from Danville, PA
Price includes $500 shipping
Fair Deal
$36,486
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3,560
- Stock #:
- P25761
- VIN:
- 3GCPKCEK0TG160125
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
3,560 mi
Home delivery from Scottsdale, AZ
Price includes $2,814 shipping
Fair Deal
$46,413
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,768
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,768 mi
Home delivery from Pleasantville, NJ
Price includes $230 shipping
Great Deal
$34,970
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,501
- Stock #:
- 7007182A
- VIN:
- 3GCPDCEK1NG607137
Price drop
-$1,060
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,501 mi
Home delivery from Sanford, NC
Price includes $286 shipping
Good Deal
$37,576
$36,516
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,065
- Stock #:
- 22696A
- VIN:
- 3GCPDCEK3PG106074
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,065 mi
Home delivery from Tampa, FL
Price includes $874 shipping
Fair Deal
$35,868
- 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 $1,201 shipping
Fair Deal
$44,701
- 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:
- Cypress Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,640
- Stock #:
- T2443A
- VIN:
- 3GCPKCEK1SG189857
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,640 mi
Home delivery from Charlottesville, VA
Price includes $213 shipping
Fair Deal
$41,356
- 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:
- Black
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 103,022
- Stock #:
- 61383A
- VIN:
- 1GCPYCEF9MZ382052
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
103,022 mi
Glen Burnie, MD
24 mi away
Fair Deal
$29,797
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Chester, MD?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,084.80. The average price has decreased by -1.2% since last year. The 145 for sale near Chester, MD on CarGurus, range from $21,783 to $66,094 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Chester, MD have no reported accidents or damage?
145 out of 145 for sale near Chester, 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 (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
Relevant articles
Jill Ciminillo
2027 Chevrolet Silverado 1500 Pricing, Specs, and Release Date
The 2027 Chevrolet Silverado 1500 is all-new, entering its fifth generation with new tech, a ground-up redesign, and two new V8 engines.
CarGurus Editorial Team
The Best Pickup Trucks of 2026, Ranked
Pickup truck competition is fierce and change is in the air. Electric trucks and compact pickups are hitting the market, providing new choices for both small businesses and weekend adventurers. But which truck suits your needs best?
CarGurus Editorial Team
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Chevrolet Silverado 1500 LT in Chester MDChevrolet Silverado 1500 RST in Chester MDChevrolet Silverado 1500 LTZ in Chester MDChevrolet Silverado 1500 LT Trail Boss in Chester MDChevrolet Silverado 1500 LT1 in Chester MDChevrolet Silverado 1500 Custom in Chester MDChevrolet Silverado 1500 High Country in Chester MDChevrolet Silverado 1500 Custom Trail Boss in Chester MDChevrolet Silverado 1500 Work Truck in Chester MD
Chevrolet Silverado 1500 in Baltimore MDChevrolet Silverado 1500 in Washington DCChevrolet Silverado 1500 in Dover DEChevrolet Silverado 1500 in Newark DEChevrolet Silverado 1500 in Salisbury MDChevrolet Silverado 1500 in Manassas VAChevrolet Silverado 1500 in Hanover PAChevrolet Silverado 1500 in Lancaster PAChevrolet Silverado 1500 in Fredericksburg VA
Chevrolet Silverado 1500 in Chester MDOld Chevy Trucks for Sale in Chester MDClassic Muscle Cars for Sale in Chester MDChevrolet Trucks For Sale in Chester MDCheap Muscle Cars for Sale in Chester MDWork Trucks for Sale in Chester MDReliable Cars For Sale in Chester MDAmerican Made Trucks For Sale in Chester MDBest Pickup Trucks For Sale in Chester MDBest Cars Under $5,000 For Sale in Chester MD
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in ChesterUsed SUVs / Crossovers for Sale with Low Mileage in ChesterUsed Hatchbacks for Sale with Low Mileage in ChesterUsed Convertibles for Sale with Low Mileage in ChesterUsed Vans for Sale with Low Mileage in ChesterUsed Minivans for Sale with Low Mileage in ChesterUsed Pickup Trucks for Sale with Low Mileage in ChesterUsed Coupes for Sale with Low Mileage in ChesterUsed Wagons for Sale with Low Mileage in Chester
Ourisman Chevrolet of RockvilleKoons White Marsh ChevroletKoons Clarksville Chevrolet GMCJBA ChevroletOurisman Chevrolet Buick GMC of AlexandriaOurisman Chevrolet of BowieAutoNation Chevrolet TimoniumAdams ChevroletWillis ChevroletLexington Park Chevrolet Buick GMCi.g. Burton Chevrolet of Milfordi.g. Burton Chevrolet of Seaford
