Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearMidway, KY
239 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Cypress Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,979
- Stock #:
- PP331639
- VIN:
- 3GCPKCEK1SG331639
Sponsored by McFarland Chevrolet Buick
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
27,979 mi
Maysville, KY
60 mi away
Good Deal
$40,598
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 8,704
- Stock #:
- P6923
- VIN:
- 3GCUDCED2PG295840
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,704 mi
Lebanon, OH
94 mi away
Fair Deal
$42,439
- 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
- Fuel type:
- Gasoline
- Mileage:
- 11,805
- Stock #:
- P6862
- VIN:
- 3GCPKCEK6SG164808
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,805 mi
La Grange, KY
40 mi away
Fair Deal
$44,242
- 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:
- Red Hot
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,875
- Stock #:
- R6460
- VIN:
- 3GCPDCEK9PG137006
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,875 mi
Lexington, KY
15 mi away
Good Deal
$33,626
- 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:
- 42,114
- Stock #:
- MG311737
- VIN:
- 3GCPYCEF5MG311737
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
42,114 mi
Home delivery from Corsicana, TX
Price includes $1,170 shipping
Good Deal
$32,986
- 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:
- Brown
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,888
- Stock #:
- 215172
- VIN:
- 1GCPYCEH5MZ215172
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,888 mi
Lebanon, KY
49 mi away
Great Deal
$30,199
- 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:
- 1,535
- Stock #:
- 260136A
- VIN:
- 3GCUDCED4PG334766
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,535 mi
Lebanon, OH
94 mi away
Good Deal
$43,039
- 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:
- 60,685
- Stock #:
- MZ321296
- VIN:
- 1GCPYCEF7MZ321296
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,685 mi
Cincinnati, OH
82 mi away
Good Deal
$31,848
- 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:
- 52,743
- Stock #:
- P10012
- VIN:
- 3GCPYCEKXNG110012
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
52,743 mi
Nicholasville, KY
20 mi away
Great Deal
$30,137
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 182,786
- Stock #:
- F16587
- VIN:
- 1GCPYCEF4KZ234422
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
182,786 mi
Louisville, KY
49 mi away
Good Deal
$17,949
- 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:
- 41,790
- Stock #:
- NG204699
- VIN:
- 3GCPYCEL4NG204699
Price drop
-$1,294
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,790 mi
Cincinnati, OH
82 mi away
Great Deal
$34,526
$33,232
- 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:
- 48,835
- Stock #:
- P224269
- VIN:
- 1GCPYCEK3NZ224269
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
48,835 mi
Home delivery from Hendersonville, NC
Free home delivery
Great Deal
$31,425
- 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:
- 51,557
- Stock #:
- T260968A
- VIN:
- 3GCPDCED9NG525917
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,557 mi
Cincinnati, OH
82 mi away
Good Deal
$35,763
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,297
- Stock #:
- 270102
- VIN:
- 1GCPYCEF8MZ270102
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $3,852 shipping
Fair Deal
$33,815
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 66,314
- Stock #:
- R7594
- VIN:
- 3GCUDCED5RG291378
Price drop
-$1,080
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
66,314 mi
Lexington, KY
15 mi away
Fair Deal
$38,506
$37,426
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 20,987
- Stock #:
- 30079
- VIN:
- 3GCPKCEKXSG270842
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
20,987 mi
Home delivery from Lexington, NC
Price includes $290 shipping
Good Deal
$39,545
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $762 shipping
Fair Deal
$31,137
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 23,178
- Stock #:
- T1616
- VIN:
- 3GCPDCEK4PG172875
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,178 mi
Home delivery from Shelby, NC
Price includes $399 shipping
Fair Deal
$40,598
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,055
- Stock #:
- 26-2836A
- VIN:
- 3GCPYCEK3NG124818
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,055 mi
Louisville, KY
47 mi away
Great Deal
$30,415
- 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:
- 89,302
- Stock #:
- 269833
- VIN:
- 3GCPYCEF0LG269833
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,302 mi
West Chester, OH
85 mi away
Fair Deal
$29,247
- 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:
- 39,306
- Stock #:
- AT6263
- VIN:
- 1GCPYCEFXMZ368466
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,306 mi
West Chester, OH
82 mi away
Fair Deal
$35,392
- 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 $1,558 shipping
Fair Deal
$44,259
- 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:
- Cypress Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,979
- Stock #:
- PP331639
- VIN:
- 3GCPKCEK1SG331639
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
27,979 mi
Maysville, KY
60 mi away
Good Deal
$40,598
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 29,901
- Stock #:
- 129514A
- VIN:
- 3GCPDCED9NG588404
New arrival
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
29,901 mi
Paris, KY
26 mi away
Fair Deal
$39,186
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Midway, KY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,117.38. The average price has decreased by -4.4% since last year. The 216 for sale near Midway, KY on CarGurus, range from $18,999 to $62,856 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Midway, KY have no reported accidents or damage?
194 out of 216 for sale near Midway, KY 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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