Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearWindermere, FL
148 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 22,873
- Stock #:
- 402210
- VIN:
- 3GCPDCEK4RG402210
Sponsored by Winter Park Auto Exchange Inc
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,873 mi
Orlando, FL
18 mi away
Fair Deal
$42,387
- 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)
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 108,823
- Stock #:
- KZ265479
- VIN:
- 1GCPYCEF1KZ265479
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
108,823 mi
Winter Park, FL
18 mi away
Great Deal
$23,294
- 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
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,937
- Stock #:
- Z106884
- VIN:
- 1GCPYCEL2NZ106884
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,937 mi
Orlando, FL
13 mi away
Great Deal
$33,097
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 72,167
- Stock #:
- P13994
- VIN:
- 3GCPYCEF5KG238723
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
72,167 mi
Orlando, FL
18 mi away
Good Deal
$29,770
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,069
- Stock #:
- DP038
- VIN:
- 3GCPDCEK2RG191105
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,069 mi
Deland, FL
38 mi away
Good Deal
$39,912
- 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 $1,455 shipping
Good Deal
$29,673
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 22,873
- Stock #:
- 402210
- VIN:
- 3GCPDCEK4RG402210
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,873 mi
Orlando, FL
18 mi away
Fair Deal
$42,387
- 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)
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 108,823
- Stock #:
- KZ265479
- VIN:
- 1GCPYCEF1KZ265479
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
108,823 mi
Winter Park, FL
18 mi away
Great Deal
$23,294
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5,703
- Stock #:
- 9217
- VIN:
- 3GCPKCEK9SG334188
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
5,703 mi
Home delivery from Excelsior Springs, MO
Price includes $1,302 shipping
Good Deal
$42,202
- 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:
- Cypress Gray
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 27,061
- Stock #:
- SG210355T
- VIN:
- 3GCUKCED1SG210355
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
27,061 mi
Home delivery from Albany, GA
Price includes $394 shipping
Fair Deal
$44,522
- 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:
- Gray
- Fuel type:
- Gasoline
- Mileage:
- 16,222
- Stock #:
- P12998
- VIN:
- 3GCPKCEK5SG301317
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
16,222 mi
Orlando, FL
10 mi away
Good Deal
$44,246
- 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
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,937
- Stock #:
- Z106884
- VIN:
- 1GCPYCEL2NZ106884
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,937 mi
Orlando, FL
13 mi away
Great Deal
$33,097
- 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:
- 104,480
- Stock #:
- 4164132A
- VIN:
- 1GCPYCEF0LZ179663
Price drop
-$500
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,480 mi
Home delivery from Miami, FL
Price includes $400 shipping
Great Deal
$24,389
$23,889
- 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 $1,130 shipping
Good Deal
$31,775
- 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 $59 shipping
Great Deal
$34,551
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 17,522
- Stock #:
- 41261875A
- VIN:
- 3GCPDCEK1RG438923
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
17,522 mi
Orlando, FL
22 mi away
Fair Deal
$42,982
- 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
Home delivery from Jacksonville, FL
Price includes $129 shipping
Fair Deal
$46,289
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 77,562
- Stock #:
- 26DC0634A
- VIN:
- 3GCPYCEL1MG483205
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
77,562 mi
Home delivery from Lewisville, TX
Price includes $1,452 shipping
Fair Deal
$34,290
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,446
- Stock #:
- 268208A
- VIN:
- 3GCPDCEK3RG424618
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,446 mi
Home delivery from Daytona Beach, FL
Price includes $188 shipping
Good Deal
$42,061
- 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
Price drop
-$1,000
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,108 mi
Home delivery from Linden , NJ
Price includes $1,402 shipping
Good Deal
$26,202
$25,202
- 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:
- 104,500
- Stock #:
- 184422C01
- VIN:
- 1GCPYCEF3LZ184422
Price drop
-$1,000
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
104,500 mi
Home delivery from Linden , NJ
Price includes $1,402 shipping
Great Deal
$25,202
$24,202
- 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
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
6,488 mi
Home delivery from Jacksonville, FL
Price includes $186 shipping
Fair Deal
$49,754
- 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:
- 33,293
- Stock #:
- MX4598
- VIN:
- 1GCPYCEF4MZ232253
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
33,293 mi
Home delivery from Michigan Center, MI
Price includes $1,732 shipping
Fair Deal
$36,772
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,069
- Stock #:
- DP038
- VIN:
- 3GCPDCEK2RG191105
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,069 mi
Deland, FL
38 mi away
Good Deal
$39,912
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Windermere, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,815.84. The average price has decreased by -0.6% since last year. The 149 for sale near Windermere, FL on CarGurus, range from $19,385 to $68,056 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Windermere, FL have no reported accidents or damage?
138 out of 149 for sale near Windermere, 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.
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