Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearBridgeport, CT
160 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:
- 310 hp 2.7L I4
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,307
- Stock #:
- Z4575
- VIN:
- 3GCPDCEK0RG141805
Sponsored by Blasius Mitsubishi
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,307 mi
Brookfield, CT
22 mi away
Good Deal
$35,992
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 21,405
- Stock #:
- BU2554A
- VIN:
- 3GCUDCED7PG364215
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
21,405 mi
Poughkeepsie, NY
48 mi away
Fair Deal
$42,025
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,491
- Stock #:
- XPA2415
- VIN:
- 1GCPYCEK8NZ146975
New arrival
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,491 mi
Milford, CT
7 mi away
Good Deal
$31,792
- 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:
- 10,418
- Stock #:
- U20778T
- VIN:
- 3GCPKCEK4SG326516
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,418 mi
St James, NY
23 mi away
Fair Deal
$41,168
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 80,543
- Stock #:
- 184095
- VIN:
- 1GCRYCEF4KZ184095
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
80,543 mi
Home delivery from Peabody, MA
Price includes $296 shipping
Fair Deal
$27,796
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black, Cloth seat trim
- Transmission:
- Automatic
- Mileage:
- 68,302
- Stock #:
- 66644A
- VIN:
- 3GCPDCEK5RG328277
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,302 mi
Englewood, NJ
45 mi away
Good Deal
$33,190
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 21,405
- Stock #:
- BU2554A
- VIN:
- 3GCUDCED7PG364215
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
21,405 mi
Poughkeepsie, NY
48 mi away
Fair Deal
$42,025
- Year:
- 2022
- 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:
- 8-Speed Automatic
- Mileage:
- 28,769
- Stock #:
- XPA2047
- VIN:
- 1GCPYCEL7NZ128900
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,769 mi
Milford, CT
7 mi away
Fair Deal
$37,359
- 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
-$2,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,903 mi
Home delivery from Gorham, NH
Price includes $478 shipping
Good Deal
$35,367
$33,367
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 60,733
- Stock #:
- ZR64242A
- VIN:
- 1GCPYCEF7LZ123588
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,733 mi
East Hartford, CT
50 mi away
Good Deal
$30,498
- 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:
- 25,375
- Stock #:
- C13575
- VIN:
- 3GCPDCEK8RG179069
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,375 mi
Freeport, NY
41 mi away
Fair Deal
$39,170
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 17,400
- Stock #:
- C13559
- VIN:
- 3GCPDCED3NG638892
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
17,400 mi
Freeport, NY
41 mi away
Fair Deal
$38,670
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,307
- Stock #:
- Z4575
- VIN:
- 3GCPDCEK0RG141805
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,307 mi
Brookfield, CT
22 mi away
Good Deal
$35,992
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 92,992
- Stock #:
- CU4125B
- VIN:
- 1GCPYCEF0KZ223191
Price drop
-$828
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,992 mi
Beacon, NY
45 mi away
Good Deal
$26,531
$25,703
- 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:
- GRY
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 62,918
- Stock #:
- 11258
- VIN:
- 3GCPDCED1NG673222
Price drop
-$1,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,918 mi
Home delivery from Blackwood, NJ
Free home delivery
Good Deal
$33,782
$32,782
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 13,957
- Stock #:
- 113812
- VIN:
- 3GCUDCED5RG113812
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,957 mi
Home delivery from Irving, TX
Price includes $2,850 shipping
Fair Deal
$45,551
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,178
- Stock #:
- C9068209A
- VIN:
- 3GCPYCEF1MG344184
Price drop
-$781
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,178 mi
Thomaston, CT
34 mi away
Good Deal
$29,064
$28,283
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 57,550
- Stock #:
- KZ370333T
- VIN:
- 1GCRYCEF4KZ370333
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
57,550 mi
Home delivery from Egg Harbor Township, NJ
Price includes $218 shipping
Good Deal
$28,456
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Blue
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 25,960
- Stock #:
- CS125892
- VIN:
- 3GCUDCED5PG125892
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,960 mi
Bethany, CT
19 mi away
Good Deal
$40,798
- 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 $2,168 shipping
Fair Deal
$35,658
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 29,931
- Stock #:
- CU360721
- VIN:
- 3GCUDCED2PG360721
Price drop
-$3,000
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,931 mi
Middletown, CT
38 mi away
Fair Deal
$43,989
$40,989
- 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:
- Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,046
- Stock #:
- 10T2450
- VIN:
- 3GCPDCEK7NG676916
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,046 mi
Home delivery from Albany, NY
Price includes $160 shipping
Fair Deal
$32,410
- 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:
- Automatic
- Mileage:
- 73,718
- Stock #:
- 47682C
- VIN:
- 1GCRYCEF8KZ178395
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
73,718 mi
Home delivery from St Albans, VT
Price includes $251 shipping
Good Deal
$24,978
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Blue
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 25,960
- Stock #:
- CS125892
- VIN:
- 3GCUDCED5PG125892
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,960 mi
Bethany, CT
19 mi away
Good Deal
$40,798
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Bridgeport, CT?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,096.69. The average price has decreased by -4.5% since last year. The 160 for sale near Bridgeport, CT on CarGurus, range from $19,204 to $64,008 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Bridgeport, CT have no reported accidents or damage?
149 out of 160 for sale near Bridgeport, CT 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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