Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearMidway, FL
163 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 30,500
- Stock #:
- P501583
- VIN:
- 3GCPDCEK5RG193804
Price drop
-$1,337
Sponsored by Prince Chevrolet GMC of Albany
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,500 mi
Albany, GA
76 mi away
Fair Deal
$41,498
$40,161
- 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 Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 95,686
- Stock #:
- TZ388614
- VIN:
- 1GCPYCEF4KZ388614
Price drop
-$1,572
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
95,686 mi
Sylvester, GA
80 mi away
Good Deal
$28,566
$26,994
- 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:
- 100,861
- Stock #:
- G300917A
- VIN:
- 1GCPYCEF7MZ255199
Price drop
-$1,800
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
100,861 mi
Valdosta, GA
71 mi away
Fair Deal
$31,498
$29,698
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,297
- Stock #:
- 270102
- VIN:
- 1GCPYCEF8MZ270102
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,297 mi
Home delivery from Bend, OR
Price includes $4,406 shipping
Fair Deal
$34,369
- 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:
- 86,352
- Stock #:
- 9010A
- VIN:
- 3GCPYCEL9NG144497
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
86,352 mi
Home delivery from Brewton, AL
Price includes $278 shipping
Fair Deal
$32,884
- 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 $590 shipping
Fair Deal
$31,075
- 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:
- 129,857
- Stock #:
- 119868
- VIN:
- 1GCPYCEL3NZ119868
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
129,857 mi
Home delivery from Orlando, FL
Price includes $351 shipping
Good Deal
$25,339
- 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 $232 shipping
Good Deal
$24,931
- 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:
- 100,861
- Stock #:
- G300917A
- VIN:
- 1GCPYCEF7MZ255199
Price drop
-$1,800
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
100,861 mi
Valdosta, GA
71 mi away
Fair Deal
$31,498
$29,698
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 36,687
- Stock #:
- 26444U
- VIN:
- 3GCUDCED7RG139750
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
36,687 mi
Ashburn, GA
97 mi away
Great Deal
$39,900
- 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 Ice Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 95,686
- Stock #:
- TZ388614
- VIN:
- 1GCPYCEF4KZ388614
Price drop
-$1,572
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
95,686 mi
Sylvester, GA
80 mi away
Good Deal
$28,566
$26,994
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 54,020
- Stock #:
- 93822
- VIN:
- 3GCPKCEK2SG193822
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,020 mi
Home delivery from Nashville, TN
Price includes $723 shipping
Fair Deal
$36,703
- 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 $1,136 shipping
Good Deal
$29,578
- 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 $864 shipping
Good Deal
$29,764
- 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:
- 73,178
- Stock #:
- Z240465
- VIN:
- 1GCPYCEF4MZ240465
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
73,178 mi
Home delivery from Port Richey, FL
Price includes $499 shipping
Good Deal
$31,797
- 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
Price drop
-$956
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
6,488 mi
Home delivery from Jacksonville, FL
Price includes $248 shipping
Good Deal
$47,372
$46,416
- 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:
- 30,673
- Stock #:
- P2692
- VIN:
- 3GCUKCED5SG351347
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,673 mi
Home delivery from Griffin, GA
Price includes $300 shipping
Fair Deal
$43,013
- 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:
- 32,017
- Stock #:
- 8T617F
- VIN:
- 3GCUDCED3RG201855
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,017 mi
Home delivery from Scottsboro, AL
Price includes $448 shipping
Fair Deal
$42,908
- Year:
- 2026
- 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:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 1,112
- Stock #:
- P6707
- VIN:
- 3GCUKCED6TG236399
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
1,112 mi
Home delivery from Alpharetta, GA
Price includes $249 shipping
Good Deal
$47,189
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 44,970
- Stock #:
- CC14512T
- VIN:
- 3GCUKCED0SG214512
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
44,970 mi
Home delivery from Chatom, AL
Free home delivery
Fair Deal
$41,377
- 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:
- 30,500
- Stock #:
- P501583
- VIN:
- 3GCPDCEK5RG193804
Price drop
-$1,337
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,500 mi
Albany, GA
76 mi away
Fair Deal
$41,498
$40,161
- 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:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 28,052
- Stock #:
- J109637A
- VIN:
- 3GCPDCEK7RG214944
Price drop
-$1,995
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,052 mi
Home delivery from Cumming, GA
Price includes $396 shipping
Great Deal
$38,186
$36,191
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Blue
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 91,910
- Stock #:
- 29141548
- VIN:
- 1GCPYCEK0NZ179999
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
91,910 mi
Store transfer to Tallahassee, FL
Price includes $1,799 shipping
Fair Deal
$29,797
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 58,192
- Stock #:
- RG294923
- VIN:
- 3GCPDCEK3RG294923
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
58,192 mi
Home delivery from Saint Augustine, FL
Price includes $382 shipping
Fair Deal
$36,281
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Midway, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,372.53. The average price has decreased by -2.8% since last year. The 171 for sale near Midway, FL on CarGurus, range from $20,948 to $64,970 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Midway, FL have no reported accidents or damage?
164 out of 171 for sale near Midway, 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
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 Midway FLChevrolet Silverado 1500 RST in Midway FLChevrolet Silverado 1500 LTZ in Midway FLChevrolet Silverado 1500 LT Trail Boss in Midway FLChevrolet Silverado 1500 LT1 in Midway FLChevrolet Silverado 1500 Custom in Midway FLChevrolet Silverado 1500 High Country in Midway FLChevrolet Silverado 1500 Custom Trail Boss in Midway FLChevrolet Silverado 1500 Work Truck in Midway FL
Chevrolet Silverado 1500 in Tallahassee FLChevrolet Silverado 1500 in Bainbridge GAChevrolet Silverado 1500 in Thomasville GAChevrolet Silverado 1500 in Marianna FLChevrolet Silverado 1500 in Moultrie GAChevrolet Silverado 1500 in Valdosta GAChevrolet Silverado 1500 in Dothan ALChevrolet Silverado 1500 in Panama City FLChevrolet Silverado 1500 in Albany GA
Chevrolet Silverado 1500 in Midway FLOld Chevy Trucks for Sale in Midway FLClassic Muscle Cars for Sale in Midway FLChevrolet Trucks For Sale in Midway FLCheap Muscle Cars for Sale in Midway FLWork Trucks for Sale in Midway FLReliable Cars For Sale in Midway FLAmerican Made Trucks For Sale in Midway FLBest Pickup Trucks For Sale in Midway FLBest Cars Under $5,000 For Sale in Midway 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 MidwayUsed SUVs / Crossovers for Sale with Low Mileage in MidwayUsed Hatchbacks for Sale with Low Mileage in MidwayUsed Convertibles for Sale with Low Mileage in MidwayUsed Vans for Sale with Low Mileage in MidwayUsed Minivans for Sale with Low Mileage in MidwayUsed Pickup Trucks for Sale with Low Mileage in MidwayUsed Coupes for Sale with Low Mileage in MidwayUsed Wagons for Sale with Low Mileage in Midway
