Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearMiddlebury, CT
138 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 125,117
- Stock #:
- CU378338
- VIN:
- 1GCPYCEF0KZ378338
Sponsored by Key Chevrolet
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
125,117 mi
Middletown, CT
24 mi away
Fair Deal
$24,492
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- White Sands
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 102
- Stock #:
- A227475
- VIN:
- 3GCUKCE82TG227475
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
102 mi
Danbury, CT
18 mi away
Good Deal
$49,997
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 70,302
- Stock #:
- 17332
- VIN:
- 1GCPYCEF2LZ169720
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,302 mi
Ansonia, CT
13 mi away
Fair Deal
$32,988
- 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:
- Automatic
- Mileage:
- 25,595
- Stock #:
- GB0401
- VIN:
- 3GCPDCEK8PG340310
Price drop
-$1,001
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,595 mi
Carmel, NY
30 mi away
Good Deal
$39,168
$38,167
- 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
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
56,969 mi
Home delivery from Belford, NJ
Price includes $230 shipping
Fair Deal
$29,205
- 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 $897 shipping
Fair Deal
$41,896
$40,896
- 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 $1,124 shipping
Good Deal
$36,612
- 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:
- 125,117
- Stock #:
- CU378338
- VIN:
- 1GCPYCEF0KZ378338
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
125,117 mi
Middletown, CT
24 mi away
Fair Deal
$24,492
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 63,623
- Stock #:
- 51283A
- VIN:
- 3GCPYCEFXKG221125
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,623 mi
Enfield, CT
43 mi away
Good Deal
$29,989
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 75,222
- Stock #:
- 6320A
- VIN:
- 1GCPYCEF5MZ219396
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
75,222 mi
Waterbury, CT
6 mi away
Fair Deal
$32,490
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 102,783
- Stock #:
- 5211
- VIN:
- 3GCPYCEF9MG436837
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
102,783 mi
Old Saybrook, CT
41 mi away
Fair Deal
$28,543
- 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
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 116,316
- Stock #:
- 380599
- VIN:
- 1GCPYCEF5KZ380599
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
116,316 mi
Home delivery from Pembroke, MA
Price includes $188 shipping
Good Deal
$23,682
- 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:
- Blue
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 57,412
- Stock #:
- CT12064
- VIN:
- 1GCRYCEF4KZ223400
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
57,412 mi
Manchester, CT
33 mi away
Good Deal
$28,994
- 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 $215 shipping
Good Deal
$36,904
- 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
- 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
16 mi away
Good Deal
$38,369
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 113,737
- Stock #:
- 275538
- VIN:
- 3GCPYCEF6LG275538
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
113,737 mi
Windsor Locks, CT
36 mi away
Good Deal
$24,794
- 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 $548 shipping
Good Deal
$29,748
- 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 $276 shipping
Great Deal
$34,726
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 60,104
- Stock #:
- N6402A
- VIN:
- 1GCPYCEF7LZ219561
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,104 mi
Cheshire, CT
12 mi away
Good Deal
$32,117
- 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:
- White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 87,056
- Stock #:
- U23623
- VIN:
- 1GCPYCEF6LZ124313
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
87,056 mi
Riverhead, NY
47 mi away
Fair Deal
$28,690
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Red Hot
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $751 shipping
Good Deal
$33,316
- 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:
- 104,108
- Stock #:
- 332395C01
- VIN:
- 1GCPYCEF2KZ332395
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,108 mi
Home delivery from Linden , NJ
Price includes $128 shipping
Good Deal
$25,926
- 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:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 16,913
- Stock #:
- R87954
- VIN:
- 3GCUKCED9SG358155
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
16,913 mi
Home delivery from Herculaneum, MO
Price includes $1,882 shipping
Fair Deal
$47,498
- 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:
- Dark Ash Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,307
- Stock #:
- Z4575
- VIN:
- 3GCPDCEK0RG141805
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,307 mi
Brookfield, CT
16 mi away
Good Deal
$38,369
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Middlebury, CT?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,065.50. The average price has decreased by -1% since last year. The 138 for sale near Middlebury, CT on CarGurus, range from $20,699 to $56,781 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Middlebury, CT have no reported accidents or damage?
138 out of 138 for sale near Middlebury, 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 (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
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