Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearJennings, FL
178 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Red Hot
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 6,488
- Stock #:
- 26C1373A
- VIN:
- 3GCUKCE80TG120733
Sponsored by Nimnicht Chevrolet
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
6,488 mi
Jacksonville, FL
86 mi away
Good Deal
$48,868
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 125,361
- Stock #:
- IT11270A
- VIN:
- 3GCPDCED7NG658319
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
125,361 mi
Gainesville, FL
78 mi away
Fair Deal
$28,558
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,035
- Stock #:
- WOP2030
- VIN:
- 3GCPKCEK8SG332030
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,035 mi
Jacksonville, FL
92 mi away
Good Deal
$42,766
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,035
- Stock #:
- WOP2030
- VIN:
- 3GCPKCEK8SG332030
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,035 mi
Jacksonville, FL
92 mi away
Good Deal
$42,766
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Sterling Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,088
- Stock #:
- 269191
- VIN:
- 3GCUKCE82SG218192
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,088 mi
Home delivery from Winter Haven, FL
Price includes $591 shipping
Fair Deal
$40,327
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 20,909
- Stock #:
- 330654T
- VIN:
- 3GCPKCEK3SG330654
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
20,909 mi
Home delivery from Orlando, FL
Price includes $500 shipping
Fair Deal
$40,786
- 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:
- Aluminum
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 100,391
- Stock #:
- 6496
- VIN:
- 1GCRYCEF0KZ260301
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
100,391 mi
Jacksonville, FL
87 mi away
Fair Deal
$24,698
- 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 $1,179 shipping
Good Deal
$32,294
- 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:
- Lakeshore Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 32,430
- Stock #:
- P501583
- VIN:
- 3GCPDCEK5RG193804
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,430 mi
Albany, GA
93 mi away
Fair Deal
$39,699
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 93,534
- Stock #:
- CCATLG1777
- VIN:
- 3GCPYCEF8LG177711
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,534 mi
Jacksonville, FL
99 mi away
Good Deal
$28,539
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,538
- Stock #:
- 5UT4850
- VIN:
- 3GCPDCEK1RG226779
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,538 mi
Home delivery from Hattiesburg, MS
Price includes $566 shipping
Fair Deal
$37,878
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 92,655
- Stock #:
- 152740
- VIN:
- 1GCPYCEK0NZ152740
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,655 mi
Home delivery from Monroe, LA
Price includes $546 shipping
Fair Deal
$29,936
- 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:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 41,657
- Stock #:
- 20325
- VIN:
- 1GCPYCEF4MZ289181
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,657 mi
Home delivery from Mesa, AZ
Price includes $1,686 shipping
Fair Deal
$34,681
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 121,622
- Stock #:
- UT4177B
- VIN:
- 1GCRYCEF1KZ419956
Price drop
-$1,705
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
121,622 mi
Douglas, GA
65 mi away
Good Deal
$24,999
$23,294
- 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:
- 93,992
- Stock #:
- 144813B
- VIN:
- 1GCPYCEK5NZ144813
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,992 mi
Home delivery from Dallas, TX
Price includes $819 shipping
Fair Deal
$27,544
- 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
- Transmission:
- Automatic
- Mileage:
- 125,634
- Stock #:
- 10014
- VIN:
- 3GCPYCEF1KG144161
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
125,634 mi
Tallahassee, FL
65 mi away
Fair Deal
$24,590
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 99,802
- Stock #:
- 160815
- VIN:
- 3GCPYCEH1LG262679
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
99,802 mi
Home delivery from Orlando, FL
Price includes $177 shipping
Fair Deal
$24,876
- 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:
- Automatic
- Mileage:
- 6,289
- Stock #:
- APSG292772
- VIN:
- 3GCUKCED9SG292772
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
6,289 mi
Home delivery from Pinellas Park, FL
Price includes $378 shipping
Fair Deal
$45,641
- 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:
- 37,230
- Stock #:
- R10624A
- VIN:
- 3GCPDCEK5PG194044
Price drop
-$1,537
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
37,230 mi
Home delivery from Buford, GA
Price includes $864 shipping
Good Deal
$38,226
$36,688
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 86,176
- Stock #:
- AN12101A
- VIN:
- 1GCPYCEL2MZ144453
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
86,176 mi
Valdosta, GA
24 mi away
Fair Deal
$33,989
- 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:
- Red
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 32,641
- Stock #:
- MX5558
- VIN:
- 1GCPYCEF3MZ296638
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,641 mi
Home delivery from Louisville, TN
Price includes $661 shipping
Fair Deal
$36,016
- 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:
- 6-Speed Automatic Overdrive
- Mileage:
- 70,808
- Stock #:
- U2223
- VIN:
- 1GCPYCEF6LZ216473
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
70,808 mi
Tifton, GA
66 mi away
Fair Deal
$32,187
- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 61,843
- Stock #:
- 3U1795
- VIN:
- 1GCPYCEF3MZ358300
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
61,843 mi
Home delivery from Lenoir, NC
Price includes $403 shipping
Fair Deal
$33,382
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 121,622
- Stock #:
- UT4177B
- VIN:
- 1GCRYCEF1KZ419956
Price drop
-$1,705
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
121,622 mi
Douglas, GA
65 mi away
Good Deal
$24,999
$23,294
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Jennings, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $25,962.55. The average price has decreased by -5.2% since last year. The 157 for sale near Jennings, FL on CarGurus, range from $18,923 to $62,615 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Jennings, FL have no reported accidents or damage?
129 out of 157 for sale near Jennings, FL 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
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
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.
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 Jennings FLChevrolet Silverado 1500 RST in Jennings FLChevrolet Silverado 1500 LTZ in Jennings FLChevrolet Silverado 1500 LT Trail Boss in Jennings FLChevrolet Silverado 1500 LT1 in Jennings FLChevrolet Silverado 1500 Custom in Jennings FLChevrolet Silverado 1500 High Country in Jennings FLChevrolet Silverado 1500 Custom Trail Boss in Jennings FLChevrolet Silverado 1500 Work Truck in Jennings FL
Chevrolet Silverado 1500 in Valdosta GAChevrolet Silverado 1500 in Lake City FLChevrolet Silverado 1500 in Thomasville GAChevrolet Silverado 1500 in Moultrie GAChevrolet Silverado 1500 in Douglas GAChevrolet Silverado 1500 in Tallahassee FLChevrolet Silverado 1500 in Gainesville FLChevrolet Silverado 1500 in Jacksonville FLChevrolet Silverado 1500 in Bainbridge GA
Chevrolet Silverado 1500 in Jennings FLOld Chevy Trucks for Sale in Jennings FLClassic Muscle Cars for Sale in Jennings FLChevrolet Trucks For Sale in Jennings FLCheap Muscle Cars for Sale in Jennings FLWork Trucks for Sale in Jennings FLReliable Cars For Sale in Jennings FLAmerican Made Trucks For Sale in Jennings FLBest Pickup Trucks For Sale in Jennings FLBest Cars Under $5,000 For Sale in Jennings FL
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 JenningsUsed SUVs / Crossovers for Sale with Low Mileage in JenningsUsed Hatchbacks for Sale with Low Mileage in JenningsUsed Convertibles for Sale with Low Mileage in JenningsUsed Vans for Sale with Low Mileage in JenningsUsed Minivans for Sale with Low Mileage in JenningsUsed Pickup Trucks for Sale with Low Mileage in JenningsUsed Coupes for Sale with Low Mileage in JenningsUsed Wagons for Sale with Low Mileage in Jennings
