Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWindham, CT
150 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:
- 112,673
- Stock #:
- 330377
- VIN:
- 1GCPYCEF1KZ330377
Sponsored by Suffield Auto LLC
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,673 mi
Suffield, CT
33 mi away
Good Deal
$23,339
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,919
- Stock #:
- 26133C
- VIN:
- 3GCPYCEF0MG332852
New arrival
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,919 mi
Mendon, MA
41 mi away
Fair Deal
$30,967
- 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:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,520
- Stock #:
- LAW6481
- VIN:
- 3GCPDCEK1PG158111
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,520 mi
Auburn, MA
36 mi away
Fair Deal
$37,797
- 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:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 91,830
- Stock #:
- 20528MK1
- VIN:
- 1GCRYCEH0LZ287789
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
91,830 mi
North Haven, CT
41 mi away
Fair Deal
$25,495
- 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
22 mi away
Good Deal
$27,194
- 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
49 mi away
Good Deal
$29,730
- 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
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,418 mi
Home delivery from St James, NY
Free home delivery
Fair Deal
$42,996
- 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:
- 88,289
- Stock #:
- F78041B
- VIN:
- 3GCPYCEKXNG174177
Price drop
-$1,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
88,289 mi
East Providence, RI
41 mi away
Great Deal
$28,415
$27,415
- 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:
- 63,090
- Stock #:
- SI1924A
- VIN:
- 1GCPYCEK6NZ109889
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,090 mi
Brooklyn, CT
14 mi away
Good Deal
$31,787
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 72,828
- Stock #:
- HM761
- VIN:
- 3GCPDCEK0PG240055
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
72,828 mi
Milford, MA
45 mi away
Great Deal
$31,795
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 50,780
- Stock #:
- 5N00012A
- VIN:
- 1GCPYCEH9MZ295351
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,780 mi
Johnston, RI
34 mi away
Good Deal
$31,546
- 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:
- 51,751
- Stock #:
- CL2008A
- VIN:
- 3GCPDCED2NG680728
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,751 mi
Brooklyn, CT
14 mi away
Fair Deal
$36,787
- 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:
- 84,919
- Stock #:
- 26133C
- VIN:
- 3GCPYCEF0MG332852
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,919 mi
Mendon, MA
41 mi away
Fair Deal
$30,967
- 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, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 25,488
- Stock #:
- WP4039A
- VIN:
- 3GCPDCEK4NG625566
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,488 mi
Wakefield, RI
38 mi away
Good Deal
$35,887
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 60,733
- Stock #:
- ZR64242A
- VIN:
- 1GCPYCEF7LZ123588
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,733 mi
East Hartford, CT
27 mi away
Good Deal
$31,798
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 46,820
- Stock #:
- 16017
- VIN:
- 3GCPKCEKXSG328917
Price drop
-$1,600
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,820 mi
Home delivery from Smithfield, NC
Price includes $1,088 shipping
Good Deal
$39,187
$37,587
- 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
40 mi away
Good Deal
$43,044
- 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:
- Cypress Gray
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 30,594
- Stock #:
- F60084H1
- VIN:
- 3GCUKCED4SG211452
Price drop
-$1,020
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,594 mi
Home delivery from Doylestown, PA
Price includes $450 shipping
Great Deal
$40,970
$39,950
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 79,749
- Stock #:
- U1200390B
- VIN:
- 1GCPYCEFXMZ315251
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
79,749 mi
Home delivery from Tilton, NH
Price includes $246 shipping
Fair Deal
$31,490
- 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
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,590 mi
Home delivery from Euless, TX
Price includes $2,244 shipping
Fair Deal
$30,687
- 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 $184 shipping
Good Deal
$41,080
- 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:
- 8-Speed Automatic
- Mileage:
- 34,003
- Stock #:
- PV26086A
- VIN:
- 3GCPDCEKXRG398597
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,003 mi
Chicopee, MA
40 mi away
Fair Deal
$40,508
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 25,300
- Stock #:
- 28820972
- VIN:
- 1GCPYCEH3MZ283468
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,300 mi
Store transfer to Hartford, CT
Price includes $649 shipping
Fair Deal
$36,647
- 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:
- 8-Speed Automatic
- Mileage:
- 50,413
- Stock #:
- CT2328A
- VIN:
- 3GCPDCEK4NG614132
New arrival
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
50,413 mi
Putnam, CT
19 mi away
Fair Deal
$35,020
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Windham, CT?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,270.08. The average price has decreased by -3.6% since last year. The 150 for sale near Windham, CT on CarGurus, range from $19,997 to $65,614 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Windham, CT have no reported accidents or damage?
150 out of 150 for sale near Windham, 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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