Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Connecticut
166 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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
Sponsored by Middletown Chevrolet
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,931 mi
Middletown, CT
16 mi away
Fair Deal
$40,489
- 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:
- 112,673
- Stock #:
- 330377
- VIN:
- 1GCPYCEF1KZ330377
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,673 mi
Suffield, CT
15 mi away
Good Deal
$21,339
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 79,305
- Stock #:
- T422755
- VIN:
- 1GCPYCEF3MZ422755
Price drop
-$1,000
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
79,305 mi
Danbury, CT
46 mi away
Good Deal
$30,000
$29,000
- Year:
- 2026
- 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:
- 11,602
- Stock #:
- S1560A
- VIN:
- 3GCUKCED1TG144617
Price drop
-$1,560
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,602 mi
Stafford Springs, CT
22 mi away
Good Deal
$46,360
$44,800
- 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:
- Shadow Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 41,350
- Stock #:
- 21180-03
- VIN:
- 1GCRYCEF4LZ286594
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
41,350 mi
Vernon, CT
10 mi away
Fair Deal
$32,441
- 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
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,931 mi
Middletown, CT
16 mi away
Fair Deal
$40,489
- 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:
- 17,155
- Stock #:
- 31316
- VIN:
- 3GCPDCEK0RG174125
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
17,155 mi
West Springfield, MA
23 mi away
Fair Deal
$41,195
- 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
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,178 mi
Thomaston, CT
22 mi away
Good Deal
$28,283
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 103,145
- Stock #:
- U1683MA
- VIN:
- 1GCPYCEL8NZ172209
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
103,145 mi
Cheshire, CT
19 mi away
Fair Deal
$28,958
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 97,071
- Stock #:
- 5564
- VIN:
- 3GCPYCEF2LG198182
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
97,071 mi
Feeding Hills, MA
21 mi away
Great Deal
$24,394
- 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:
- 29,816
- Stock #:
- PV26115A
- VIN:
- 3GCUDCE87RG153960
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,816 mi
Chicopee, MA
28 mi away
Fair Deal
$41,349
- 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
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,903 mi
Home delivery from Gorham, NH
Price includes $382 shipping
Great Deal
$31,271
- 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:
- 112,673
- Stock #:
- 330377
- VIN:
- 1GCPYCEF1KZ330377
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,673 mi
Suffield, CT
15 mi away
Good Deal
$21,339
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Silver Ice Metallic
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 63,514
- Stock #:
- 00047981
- VIN:
- 1GCRYCEF8LZ233610
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
63,514 mi
North Windham, CT
25 mi away
Good Deal
$28,098
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 80,410
- Stock #:
- 26-846A
- VIN:
- 3GCPYCEFXLG346014
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
80,410 mi
Torrington, CT
23 mi away
Fair Deal
$29,176
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 58,128
- Stock #:
- DC26250
- VIN:
- 1GCPYCEF6KZ273870
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,128 mi
Home delivery from Delphos, OH
Price includes $761 shipping
Fair Deal
$30,356
- 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:
- 23,895
- Stock #:
- 26S0349
- VIN:
- 3GCUDCED3PG221438
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,895 mi
Home delivery from Norwich, NY
Price includes $156 shipping
Great Deal
$37,752
- Year:
- 2026
- 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:
- 12,471
- Stock #:
- 2CT7026
- VIN:
- 3GCUKCED7TG347026
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,471 mi
Home delivery from Reidsville, NC
Price includes $741 shipping
Good Deal
$44,590
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,391
- Stock #:
- P010376
- VIN:
- 3GCPDCEK5RG292882
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,391 mi
Home delivery from Zumbrota, MN
Price includes $1,534 shipping
Fair Deal
$37,380
- 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:
- 57,493
- Stock #:
- XPA2415
- VIN:
- 1GCPYCEK8NZ146975
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
57,493 mi
Milford, CT
44 mi away
Fair Deal
$31,792
- 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:
- 30,863
- Stock #:
- U301A
- VIN:
- 3GCPDCEKXPG273791
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,863 mi
Home delivery from Oswego, NY
Price includes $448 shipping
Fair Deal
$37,408
- 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:
- Blue
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,625
- Stock #:
- 70139418
- VIN:
- 3GCPDCEK0PG123320
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,625 mi
Store transfer to Hartford, CT
Price includes $1,599 shipping
Fair Deal
$35,597
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 63,747
- Stock #:
- 23079
- VIN:
- 1GCPYCEK4NZ172683
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,747 mi
Home delivery from Tampa, FL
Price includes $1,150 shipping
Fair Deal
$32,129
- 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:
- 17,155
- Stock #:
- 31316
- VIN:
- 3GCPDCEK0RG174125
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
17,155 mi
West Springfield, MA
23 mi away
Fair Deal
$41,195
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Connecticut?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $25,697.77. The average price has decreased by -5.5% since last year. The 166 for sale near Connecticut on CarGurus, range from $18,510 to $56,863 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Connecticut have no reported accidents or damage?
141 out of 166 for sale near Connecticut 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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