Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearO Brien, FL
156 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 15,757
- Stock #:
- SG168938
- VIN:
- 3GCPKCEK6SG168938
Price drop
-$1,397
Sponsored by AutoNation Ford Jacksonville
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
15,757 mi
Jacksonville, FL
84 mi away
Good Deal
$45,820
$44,423
- 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:
- Gray
- Transmission:
- Automatic
- Mileage:
- 109,885
- Stock #:
- 26220
- VIN:
- 3GCPDCEK4PG294877
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
109,885 mi
Live Oak, FL
19 mi away
Good Deal
$29,784
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 95,688
- Stock #:
- 26221
- VIN:
- 3GCUDCED0PG361351
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
95,688 mi
Live Oak, FL
19 mi away
Good Deal
$33,368
- 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:
- 88,681
- Stock #:
- G199121T
- VIN:
- 3GCPYCEF9LG199121
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
88,681 mi
Home delivery from Deland, FL
Price includes $216 shipping
Great Deal
$25,992
- 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:
- Slate Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 46,774
- Stock #:
- S19825A
- VIN:
- 3GCUDCED7RG267941
Price drop
-$1,000
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,774 mi
Home delivery from Newton, NC
Price includes $597 shipping
Good Deal
$40,596
$39,596
- 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:
- 19,818
- Stock #:
- G399240A
- VIN:
- 3GCUDCEDXRG445180
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,818 mi
Jacksonville, FL
80 mi away
Great Deal
$44,290
- 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:
- 8,331
- Stock #:
- 26S401A
- VIN:
- 3GCUDCED5RG367925
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
8,331 mi
Jacksonville, FL
75 mi away
Fair Deal
$46,724
- 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:
- 8-Speed Automatic
- Mileage:
- 51,065
- Stock #:
- 22696A
- VIN:
- 3GCPDCEK3PG106074
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,065 mi
Home delivery from Tampa, FL
Price includes $149 shipping
Great Deal
$35,128
- 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:
- 53,768
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,768 mi
Home delivery from Pleasantville, NJ
Price includes $1,672 shipping
Fair Deal
$37,117
- 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:
- Silver
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 133,123
- Stock #:
- 374625
- VIN:
- 1GCRYCEF4KZ374625
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
133,123 mi
Home delivery from Brandon, FL
Price includes $231 shipping
Great Deal
$21,112
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 100,359
- Stock #:
- KG234924T
- VIN:
- 3GCPYCEF6KG234924
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
100,359 mi
Saint Augustine, FL
98 mi away
Good Deal
$27,269
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Black
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 7,021
- Stock #:
- S5221
- VIN:
- 3GCUDCE80RG406004
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,021 mi
Home delivery from Palm Coast, FL
Price includes $549 shipping
Good Deal
$44,191
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,948
- Stock #:
- LZ244870C
- VIN:
- 1GCRYCEF1LZ244870
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
89,948 mi
Jacksonville, FL
73 mi away
Fair Deal
$29,415
- 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:
- 62,775
- Stock #:
- 5019
- VIN:
- 1GCPYCEF0LZ168095
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $893 shipping
Great Deal
$29,893
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 24,034
- Stock #:
- TRG431087
- VIN:
- 3GCUDCED5RG431087
Price drop
-$1,669
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
24,034 mi
Home delivery from Cleveland, TN
Price includes $1,472 shipping
Good Deal
$43,223
$41,554
- 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:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $980 shipping
Good Deal
$33,215
- 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:
- 60,683
- Stock #:
- PZ378921
- VIN:
- 1GCPYCEF7KZ378921
Price drop
-$1,600
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,683 mi
Home delivery from Cordele, GA
Price includes $207 shipping
Good Deal
$33,202
$31,602
- 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:
- Automatic
- Mileage:
- 32,335
- Stock #:
- MZ292172
- VIN:
- 1GCPYCEF7MZ292172
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,335 mi
Home delivery from Roswell, GA
Price includes $572 shipping
Good Deal
$37,736
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Summit White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2,843
- Stock #:
- TG124399T
- VIN:
- 3GCUKCE81TG124399
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,843 mi
Saint Augustine, FL
98 mi away
Great Deal
$47,092
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 58,880
- Stock #:
- TT4758A
- VIN:
- 3GCPKCEK9SG249335
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,880 mi
Ocala, FL
76 mi away
Fair Deal
$39,641
- 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:
- Slate Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,105
- Stock #:
- P9991
- VIN:
- 3GCUKCED5SG215235
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
14,105 mi
Jacksonville, FL
88 mi away
Good Deal
$47,219
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 104,108
- Stock #:
- 332395C01
- VIN:
- 1GCPYCEF2KZ332395
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,108 mi
Home delivery from Linden , NJ
Price includes $1,318 shipping
Good Deal
$26,118
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 28,885
- Stock #:
- 26H039B
- VIN:
- 3GCUDCED3RG433940
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,885 mi
Ocala, FL
76 mi away
Fair Deal
$43,837
- 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:
- 61,092
- Stock #:
- BY24546
- VIN:
- 3GCPYCEK1NG202836
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
61,092 mi
Jacksonville, FL
88 mi away
Fair Deal
$35,172
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in O Brien, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,073.80. The average price has decreased by -0.7% since last year. The 141 for sale near O Brien, FL on CarGurus, range from $21,065 to $63,762 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in O Brien, FL have no reported accidents or damage?
141 out of 141 for sale near O Brien, 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 (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
Relevant articles
CarGurus Editorial Team
Car Deals with 0% APR in July 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
CarGurus Editorial Team
Best Truck Lease Deals in July 2026
Leasing a truck can be a great way to get into one of the latest models, with the best technology, at a more affordable monthly price. Here are the best deals we've found this month.
CarGurus Editorial Team
Best Car Deals in July 2026
In the market for a new or used car this year? Whether you’re looking to buy or lease, we’ve collated a list of the best car deals available this month.
Chevrolet Silverado 1500 LT in O Brien FLChevrolet Silverado 1500 RST in O Brien FLChevrolet Silverado 1500 LTZ in O Brien FLChevrolet Silverado 1500 LT Trail Boss in O Brien FLChevrolet Silverado 1500 LT1 in O Brien FLChevrolet Silverado 1500 Custom in O Brien FLChevrolet Silverado 1500 High Country in O Brien FLChevrolet Silverado 1500 Custom Trail Boss in O Brien FLChevrolet Silverado 1500 Work Truck in O Brien FL
Chevrolet Silverado 1500 in Lake City FLChevrolet Silverado 1500 in Gainesville FLChevrolet Silverado 1500 in Valdosta GAChevrolet Silverado 1500 in Ocala FLChevrolet Silverado 1500 in Jacksonville FLChevrolet Silverado 1500 in Crystal River FLChevrolet Silverado 1500 in Thomasville GAChevrolet Silverado 1500 in Tallahassee FLChevrolet Silverado 1500 in Moultrie GA
Chevrolet Silverado 1500 in O Brien FLOld Chevy Trucks for Sale in O Brien FLClassic Muscle Cars for Sale in O Brien FLChevrolet Trucks For Sale in O Brien FLCheap Muscle Cars for Sale in O Brien FLWork Trucks for Sale in O Brien FLReliable Cars For Sale in O Brien FLAmerican Made Trucks For Sale in O Brien FLBest Pickup Trucks For Sale in O Brien FLBest Cars Under $5,000 For Sale in O Brien 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 O BrienUsed SUVs / Crossovers for Sale with Low Mileage in O BrienUsed Hatchbacks for Sale with Low Mileage in O BrienUsed Convertibles for Sale with Low Mileage in O BrienUsed Vans for Sale with Low Mileage in O BrienUsed Minivans for Sale with Low Mileage in O BrienUsed Pickup Trucks for Sale with Low Mileage in O BrienUsed Coupes for Sale with Low Mileage in O BrienUsed Wagons for Sale with Low Mileage in O Brien
