Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Middleton, MA
126 results
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,532
- Stock #:
- TP6940
- VIN:
- 3GCPKCEK4SG347138
Sponsored by Imperial Toyota
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
24,532 mi
Milford, MA
39 mi away
Fair Deal
$43,467
- 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:
- Blue
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 110,821
- Stock #:
- 330394
- VIN:
- 1GCRYCEH7LZ330394
Sponsored Listing
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
110,821 mi
North Reading, MA
5 mi away
Fair Deal
$23,690
- 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:
- Red Hot
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 23,379
- Stock #:
- 5800
- VIN:
- 3GCUKCED6SG177255
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,379 mi
Fitchburg, MA
39 mi away
Fair Deal
$46,999
- 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:
- 16,847
- Stock #:
- 101543C
- VIN:
- 1GCPYCEK7NZ101543
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
16,847 mi
Framingham, MA
30 mi away
Great Deal
$36,495
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 103,015
- Stock #:
- 260777A
- VIN:
- 3GCPYCEF6MG379657
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
103,015 mi
Epping, NH
30 mi away
Good Deal
$28,125
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 6.2L V8
- Exterior color:
- Silver Ice Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 36,239
- Stock #:
- C48717
- VIN:
- 1GCPYCEL8MZ365958
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
36,239 mi
Mendon, MA
40 mi away
Fair Deal
$39,967
- 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:
- Cajun Red Tintcoat
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic
- Mileage:
- 102,937
- Stock #:
- 183013
- VIN:
- 1GCRYCEF4KZ183013
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
102,937 mi
Rochester, NH
45 mi away
Fair Deal
$24,675
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Transmission:
- Automatic
- Mileage:
- 79,727
- Stock #:
- N355141
- VIN:
- 1GCRYCEH4LZ355141
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
79,727 mi
Home delivery from Barre, VT
Price includes $198 shipping
Good Deal
$26,492
- 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:
- Blue
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 110,821
- Stock #:
- 330394
- VIN:
- 1GCRYCEH7LZ330394
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
110,821 mi
North Reading, MA
5 mi away
Fair Deal
$23,690
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 67,825
- Stock #:
- G293416
- VIN:
- 3GCPYCEH5KG293416
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
67,825 mi
Home delivery from West Palm Beach, FL
Price includes $1,824 shipping
Great Deal
$27,718
- 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:
- 12,621
- Stock #:
- P10485
- VIN:
- 3GCUDCED5RG332205
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,621 mi
Norwood, MA
30 mi away
Fair Deal
$44,449
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 65,257
- Stock #:
- S3971B
- VIN:
- 3GCPYCEH3MG246873
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
65,257 mi
Woonsocket, RI
49 mi away
Fair Deal
$33,394
- 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:
- Glacier Blue Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 13,870
- Stock #:
- T1916
- VIN:
- 3GCPDCEK7RG192735
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,870 mi
Nashua, NH
24 mi away
Great Deal
$39,095
- 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
- Transmission:
- Automatic
- Mileage:
- 76,277
- Stock #:
- 640376
- VIN:
- 3GCPDCEK8NG640376
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
76,277 mi
Peabody, MA
5 mi away
Fair Deal
$32,500
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 32,756
- Stock #:
- W8788AA
- VIN:
- 1GCPYCEHXMZ298467
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,756 mi
Andover, MA
8 mi away
Fair Deal
$35,444
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,561
- Stock #:
- 26183
- VIN:
- 1GCPYCEF3MZ373198
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,561 mi
Uxbridge, MA
48 mi away
Fair Deal
$34,769
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,915
- Stock #:
- A25720A
- VIN:
- 3GCPDCEK7NG684420
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
88,915 mi
Acton, MA
22 mi away
Good Deal
$29,594
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,681
- Stock #:
- MK2813
- VIN:
- 3GCPYCEF8KG281307
Price drop
-$1,000
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,681 mi
Epsom, NH
45 mi away
Good Deal
$29,698
$28,698
- 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:
- Red
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 82,000
- Stock #:
- 11-9371
- VIN:
- 1GCRYCEF1KZ248562
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
82,000 mi
West Bridgewater, MA
39 mi away
Good Deal
$26,396
- 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 $2,364 shipping
Good Deal
$41,366
- 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:
- 56,316
- Stock #:
- T12317
- VIN:
- 3GCPYCEL4NG212317
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
56,316 mi
Concord, NH
47 mi away
Fair Deal
$37,683
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Red
- Fuel type:
- Diesel
- Interior color:
- Black
- Mileage:
- 110,590
- Stock #:
- 301317
- VIN:
- 3GCUDCE84PG301317
New arrival
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,590 mi
Home delivery from Euless, TX
Price includes $2,354 shipping
Good Deal
$31,348
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 68,889
- Stock #:
- 23805
- VIN:
- 1GCPYCEH4MZ379691
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,889 mi
South Easton, MA
40 mi away
Fair Deal
$33,494
- 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:
- 43,500
- Stock #:
- T11219A
- VIN:
- 3GCPDCEDXNG611219
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,500 mi
Concord, NH
47 mi away
Fair Deal
$39,183
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