Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearAnnapolis, MD
175 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 13,083
- Stock #:
- H31370A
- VIN:
- 3GCPKCEK4TG170382
Sponsored by Lindsay Chevrolet of Woodbridge
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,083 mi
Woodbridge, VA
50 mi away
Good Deal
$43,395
- 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:
- Silver ICE Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK, CLOTH SEAT TRIM
- Transmission:
- Automatic
- Mileage:
- 57,036
- Stock #:
- P1937
- VIN:
- 3GCPYCEF8LG318325
New arrival
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,036 mi
Easton, MD
28 mi away
Good Deal
$33,478
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 39,177
- Stock #:
- KWMPNG636137
- VIN:
- 3GCPDCED1NG636137
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,177 mi
White Marsh, MD
27 mi away
Fair Deal
$37,300
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,903
- Stock #:
- 610597T
- VIN:
- 3GCPDCED4NG610597
Price drop
-$1,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,903 mi
Home delivery from Gorham, NH
Price includes $920 shipping
Great Deal
$33,809
$32,809
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 121,973
- Stock #:
- G6970A
- VIN:
- 3GCPYCEF2MG162946
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
121,973 mi
Bel Air, MD
37 mi away
Fair Deal
$25,299
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 86,801
- Stock #:
- 261450A
- VIN:
- 1GCPYCEF8KZ341053
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
86,801 mi
Gaithersburg, MD
40 mi away
Fair Deal
$27,795
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 13,083
- Stock #:
- H31370A
- VIN:
- 3GCPKCEK4TG170382
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,083 mi
Woodbridge, VA
50 mi away
Good Deal
$43,395
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,546
- Stock #:
- KP1927
- VIN:
- 3GCPDCEK4RG203674
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,546 mi
Fallston, MD
37 mi away
Fair Deal
$40,795
- 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, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 76,904
- Stock #:
- 12605A
- VIN:
- 3GCUDCED8RG273960
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,904 mi
Home delivery from High Point, NC
Price includes $568 shipping
Good Deal
$35,641
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 112,851
- Stock #:
- 277362
- VIN:
- 3GCPYCEF5LG277362
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,851 mi
Home delivery from Columbus, OH
Price includes $716 shipping
Good Deal
$24,552
- 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 #:
- KBFPMZ374480
- VIN:
- 1GCPYCEF1MZ374480
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
99,700 mi
Baltimore, MD
27 mi away
Good Deal
$27,800
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 93,992
- Stock #:
- 144813B
- VIN:
- 1GCPYCEK5NZ144813
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,992 mi
Home delivery from Dallas, TX
Price includes $1,212 shipping
Fair Deal
$27,937
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 19,054
- Stock #:
- 70253003
- VIN:
- 3GCPDCEKXRG335791
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,054 mi
Store transfer to Laurel, MD
Price includes $149 shipping
Good Deal
$37,147
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 32,641
- Stock #:
- MX5558
- VIN:
- 1GCPYCEF3MZ296638
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,641 mi
Home delivery from Louisville, TN
Price includes $842 shipping
Fair Deal
$36,197
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 47,730
- Stock #:
- G6498A
- VIN:
- 3GCPDCED3NG536055
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
47,730 mi
Bel Air, MD
37 mi away
Fair Deal
$36,787
- Year:
- 2019
- 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:
- Cajun Red Tintcoat
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 83,299
- Stock #:
- G4453CB
- VIN:
- 1GCRYCEH0KZ256086
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
83,299 mi
Home delivery from Tallmadge, OH
Price includes $448 shipping
Good Deal
$25,184
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 28,388
- Stock #:
- 9K8987
- VIN:
- 3GCUKCED8SG248326
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,388 mi
Home delivery from Kernersville, NC
Price includes $556 shipping
Fair Deal
$42,234
- 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 $299 shipping
Good Deal
$39,554
- 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:
- Silver ICE Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK, CLOTH SEAT TRIM
- Transmission:
- Automatic
- Mileage:
- 57,036
- Stock #:
- P1937
- VIN:
- 3GCPYCEF8LG318325
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,036 mi
Easton, MD
28 mi away
Good Deal
$33,478
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 41,657
- Stock #:
- 20325
- VIN:
- 1GCPYCEF4MZ289181
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,657 mi
Home delivery from Mesa, AZ
Price includes $1,992 shipping
Fair Deal
$34,987
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Summit White
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 60,943
- Stock #:
- 29517
- VIN:
- 1GCPYCEKXNZ109832
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,943 mi
Home delivery from Cambridge, OH
Price includes $422 shipping
Fair Deal
$30,398
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 63,448
- Stock #:
- 3652DFX
- VIN:
- 1GCPYCEF5LZ374769
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,448 mi
Home delivery from Du Bois, PA
Price includes $285 shipping
Good Deal
$29,570
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 6.2L V8
- Fuel type:
- Gasoline
- Mileage:
- 97,494
- Stock #:
- AP001168
- VIN:
- 1GCPYCEL9MZ130212
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
97,494 mi
Fairfax, VA
43 mi away
Fair Deal
$29,985
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 6.2L V8
- Fuel type:
- Gasoline
- Mileage:
- 97,494
- Stock #:
- AP001168
- VIN:
- 1GCPYCEL9MZ130212
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
97,494 mi
Fairfax, VA
43 mi away
Fair Deal
$29,985
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Annapolis, MD?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $25,981.00. The average price has decreased by -5.2% since last year. The 175 for sale near Annapolis, MD on CarGurus, range from $18,772 to $63,183 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Annapolis, MD have no reported accidents or damage?
155 out of 175 for sale near Annapolis, 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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