Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearMiddlefield, OH
224 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 104,691
- Stock #:
- D15093A
- VIN:
- 3GCPYCEF5MG131500
Sponsored by Classic Chrysler Dodge Jeep Ram
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,691 mi
Madison, OH
24 mi away
Fair Deal
$27,438
- Year:
- 2026
- 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:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 8,334
- Stock #:
- 26015
- VIN:
- 3GCPKCEK2TG193367
Sponsored Listing
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,334 mi
Canal Fulton, OH
49 mi away
Good Deal
$44,447
- 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:
- 58,117
- Stock #:
- G262814A
- VIN:
- 3GCPDCEK1PG187656
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,117 mi
Medina, OH
46 mi away
Fair Deal
$35,903
- 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:
- 60,985
- Stock #:
- F0140AE
- VIN:
- 1GCPYCEK5NZ128658
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,985 mi
Columbiana, OH
42 mi away
Good Deal
$31,410
- 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:
- 48,518
- Stock #:
- 5153
- VIN:
- 3GCUDCED9PG302640
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
48,518 mi
Home delivery from Seffner, FL
Price includes $979 shipping
Great Deal
$33,871
- 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:
- 28,946
- Stock #:
- 7C5824A
- VIN:
- 1GCRYCEF6LZ288377
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
28,946 mi
Youngstown, OH
28 mi away
Fair Deal
$33,113
- 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:
- Automatic
- Mileage:
- 82,098
- Stock #:
- 26748NCX
- VIN:
- 3GCPYCEFXKG153960
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,098 mi
North Canton, OH
44 mi away
Good Deal
$25,841
- 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:
- 104,691
- Stock #:
- D15093A
- VIN:
- 3GCPYCEF5MG131500
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,691 mi
Madison, OH
24 mi away
Fair Deal
$27,438
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 74,793
- Stock #:
- W3385A
- VIN:
- 3GCPYCEH9MG101160
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
74,793 mi
Alliance, OH
39 mi away
Good Deal
$28,939
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 79,997
- Stock #:
- 256943
- VIN:
- 1GCPYCEF6MZ256943
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
79,997 mi
Home delivery from Monroe, LA
Price includes $866 shipping
Fair Deal
$31,256
- 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:
- Red
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 80,775
- Stock #:
- 5728EUX
- VIN:
- 3GCPYCEH9KG163249
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
80,775 mi
Euclid, OH
28 mi away
Fair Deal
$27,727
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,586
- Stock #:
- G1288
- VIN:
- 1GCPYCEF1LZ379791
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,586 mi
Home delivery from Butler, PA
Price includes $272 shipping
Fair Deal
$35,762
- 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 Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 60,797
- Stock #:
- 16495P
- VIN:
- 1GCRYCEF6KZ263221
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
60,797 mi
Westlake, OH
45 mi away
Good Deal
$26,347
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,773
- Stock #:
- 54173
- VIN:
- 3GCPDCEK6NG533147
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,773 mi
Home delivery from Cambridge, OH
Price includes $76 shipping
Fair Deal
$28,853
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 169,661
- Stock #:
- 34879B
- VIN:
- 3GCPYCEH9KG266221
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
169,661 mi
Randolph, OH
31 mi away
Good Deal
$17,466
- 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:
- 39,132
- Stock #:
- P1107
- VIN:
- 3GCPDCEK2RG372365
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
39,132 mi
Randolph, OH
31 mi away
Fair Deal
$36,966
- 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:
- 128,245
- Stock #:
- 34768A
- VIN:
- 1GCPYCEF4LZ302123
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
128,245 mi
Randolph, OH
31 mi away
Fair Deal
$23,966
- 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:
- 65,801
- Stock #:
- NMBB1774A
- VIN:
- 3GCPYCEK2NG191586
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
65,801 mi
North Canton, OH
46 mi away
Good Deal
$29,348
- 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:
- Automatic
- Mileage:
- 107,956
- Stock #:
- P01245A
- VIN:
- 1GCPYCEH1LZ188423
Price drop
-$1,609
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
107,956 mi
Brunswick, OH
42 mi away
Fair Deal
$25,201
$23,990
- 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:
- Automatic
- Mileage:
- 2,923
- Stock #:
- 6050
- VIN:
- 3GCPDCEK6RG236532
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,923 mi
Canal Fulton, OH
49 mi away
Good Deal
$40,947
- 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:
- 118,487
- Stock #:
- 34988A
- VIN:
- 1GCPYCEF6MZ154140
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
118,487 mi
Randolph, OH
31 mi away
Fair Deal
$25,966
- 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:
- Red Hot
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,496
- Stock #:
- 26961NC
- VIN:
- 3GCPKCEK8SG191704
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,496 mi
North Canton, OH
44 mi away
Good Deal
$41,227
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,000
- Stock #:
- 3015749X
- VIN:
- 3GCPDCEK1NG607137
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,000 mi
Home delivery from Raleigh, NC
Price includes $1,028 shipping
Fair Deal
$36,328
- 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:
- 23,677
- Stock #:
- T260732A
- VIN:
- 3GCUDCED6PG363718
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,677 mi
Warrensville HTS, OH
25 mi away
Fair Deal
$42,488
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Middlefield, OH?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,418.75. The average price has decreased by -2.5% since last year. The 226 for sale near Middlefield, OH on CarGurus, range from $17,466 to $65,263 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Middlefield, OH have no reported accidents or damage?
210 out of 226 for sale near Middlefield, OH 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.
Relevant articles
CarGurus Editorial Team
Best Cars for New Parents
Discover the best family cars for first-time parents in 2025, accounting for door access, car seat compatibility, and other real-world considerations new parents will want to keep in mind.
Drew Johnson
The Cheapest New Trucks on Sale in 2026
Is there such a thing as a cheap new truck any more? Absolutely! Here's our expert guide to the top 10 cheapest new trucks on sale.
CarGurus Editorial Team
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Chevrolet Silverado 1500 LT in Middlefield OHChevrolet Silverado 1500 RST in Middlefield OHChevrolet Silverado 1500 LTZ in Middlefield OHChevrolet Silverado 1500 LT Trail Boss in Middlefield OHChevrolet Silverado 1500 LT1 in Middlefield OHChevrolet Silverado 1500 Custom in Middlefield OHChevrolet Silverado 1500 High Country in Middlefield OHChevrolet Silverado 1500 Custom Trail Boss in Middlefield OHChevrolet Silverado 1500 Work Truck in Middlefield OH
Chevrolet Silverado 1500 in Cleveland OHChevrolet Silverado 1500 in Youngstown OHChevrolet Silverado 1500 in Akron OHChevrolet Silverado 1500 in Boyers PAChevrolet Silverado 1500 in Erie PAChevrolet Silverado 1500 in Mansfield OHChevrolet Silverado 1500 in Pittsburgh PAChevrolet Silverado 1500 in Warren PAChevrolet Silverado 1500 in Greensburg PA
Chevrolet Silverado 1500 in Middlefield OHOld Chevy Trucks for Sale in Middlefield OHClassic Muscle Cars for Sale in Middlefield OHChevrolet Trucks For Sale in Middlefield OHCheap Muscle Cars for Sale in Middlefield OHWork Trucks for Sale in Middlefield OHReliable Cars For Sale in Middlefield OHAmerican Made Trucks For Sale in Middlefield OHBest Pickup Trucks For Sale in Middlefield OHBest Cars Under $5,000 For Sale in Middlefield OH
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in MiddlefieldUsed SUVs / Crossovers for Sale with Low Mileage in MiddlefieldUsed Hatchbacks for Sale with Low Mileage in MiddlefieldUsed Convertibles for Sale with Low Mileage in MiddlefieldUsed Vans for Sale with Low Mileage in MiddlefieldUsed Minivans for Sale with Low Mileage in MiddlefieldUsed Pickup Trucks for Sale with Low Mileage in MiddlefieldUsed Coupes for Sale with Low Mileage in MiddlefieldUsed Wagons for Sale with Low Mileage in Middlefield
