CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Georgetown, FL

154 results
Georgetown, FL
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Starling Chevrolet of Orlando

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,701 miles

$36,449

Good Deal
Orlando, FL
70 mi away
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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
29,701
Stock number:
672607T
VIN:
3GCPDCED5NG672607

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,811 miles

$23,945

Great Deal
Jacksonville, FL
66 mi away
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
104,811
Stock number:
4931
VIN:
1GCPYCEFXKZ244064

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

915 miles

$45,598

Fair Deal
Lake City, FL
86 mi away
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:
8-Speed Automatic
Mileage:
915
Stock number:
R176060A
VIN:
3GCUKCED7SG113256

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,701 miles

$36,449

Good Deal
Orlando, FL
70 mi away
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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
29,701
Stock number:
672607T
VIN:
3GCPDCED5NG672607

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,035 miles

$29,300

Great Deal
Daytona Beach, FL
36 mi away
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
55,035
Stock number:
S080959R
VIN:
1GCPYCEF7KZ428801

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,628 miles

$25,499

Good Deal
Certified Pre-Owned
Brooksville, FL
78 mi away
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
99,628
Stock number:
KZ351072
VIN:
1GCPYCEF7KZ351072

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,420 miles

$29,998

Good Deal
Dade City, FL
81 mi away
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:
Silver Ice Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
74,420
Stock number:
C610083A
VIN:
1GCPYCEF1MZ266697

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,228 miles

$39,963

Good Deal
Wesley Chapel, FL
90 mi away
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:
20,228
Stock number:
N608940A
VIN:
3GCUDCED4RG229082

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,262 miles

$35,984

Good Deal
Ocala, FL
36 mi away
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:
Black
Transmission:
Automatic
Mileage:
52,262
Stock number:
A094456A
VIN:
3GCUDCED2PG279444

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

88,211 miles

$23,498

Good Deal
Orlando, FL
66 mi away
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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
88,211
Stock number:
Z388924
VIN:
1GCRYCEF7KZ388924

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$27,382

Great Deal
Orlando, FL
66 mi away
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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
59,544
Stock number:
Z129755
VIN:
1GCPYCEK8NZ129755

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,954 miles

$42,000

Fair Deal
Daytona Beach, FL
36 mi away
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:
Summit White
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
6,954
Stock number:
U690516A
VIN:
3GCPDCEK4RG306190

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,885 miles

$39,971

Great Deal
Certified Pre-Owned
Mount Dora, FL
38 mi away
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:
Black
Transmission:
8-Speed Automatic
Mileage:
5,885
Stock number:
T25412A
VIN:
3GCPKCEK0SG323144

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

915 miles

$45,598

Fair Deal
Lake City, FL
86 mi away
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:
8-Speed Automatic
Mileage:
915
Stock number:
R176060A
VIN:
3GCUKCED7SG113256

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

123,205 miles

$21,495

Good Deal
Dade City, FL
79 mi away
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
123,205
Stock number:
14883
VIN:
1GCRYCEF1KZ314883

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

116,457 miles

$27,000

Good Deal
Jacksonville, FL
63 mi away
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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
116,457
Stock number:
20623
VIN:
3GCPDCED7NG500143

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,237 miles

$31,881

Good Deal
Jacksonville, FL
66 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Summit White
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
60,237
Stock number:
AY22879
VIN:
3GCPYCEK2NG147393

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,031 miles

$44,500

Fair Deal
Atlantic Beach, FL
68 mi away
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:
Cypress Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
5,031
Stock number:
T6656
VIN:
3GCPKCEK8SG329371

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Florida
  6. / Georgetown
  • Chevrolet Silverado 1500 LT in Georgetown FL

  • Chevrolet Silverado 1500 RST in Georgetown FL

  • Chevrolet Silverado 1500 LTZ in Georgetown FL

  • Chevrolet Silverado 1500 LT Trail Boss in Georgetown FL

  • Chevrolet Silverado 1500 LT1 in Georgetown FL

  • Chevrolet Silverado 1500 Custom in Georgetown FL

  • Chevrolet Silverado 1500 High Country in Georgetown FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Georgetown FL

  • Chevrolet Silverado 1500 Work Truck in Georgetown FL

  • Chevrolet Silverado 1500 in Ocala FL

  • Chevrolet Silverado 1500 in Daytona Beach FL

  • Chevrolet Silverado 1500 in Saint Augustine FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in Gainesville FL

  • Chevrolet Silverado 1500 in Orlando FL

  • Chevrolet Silverado 1500 in Jacksonville FL

  • Chevrolet Silverado 1500 in Crystal River FL

  • Chevrolet Silverado 1500 in Brooksville FL

  • Chevrolet Silverado 1500 in Georgetown FL

  • Old Chevy Trucks for Sale in Georgetown FL

  • Classic Muscle Cars for Sale in Georgetown FL

  • Chevrolet Trucks For Sale in Georgetown FL

  • Cheap Muscle Cars for Sale in Georgetown FL

  • Work Trucks for Sale in Georgetown FL

  • Reliable Cars For Sale in Georgetown FL

  • American Made Trucks For Sale in Georgetown FL

  • Best Pickup Trucks For Sale in Georgetown FL

  • Best Cars Under $5,000 For Sale in Georgetown FL

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Georgetown FL

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Carroll Chevrolet

  • Tom Gibbs Chevrolet, Inc.

  • Palm Chevrolet

  • Vann Gannaway Chevrolet

  • Garber Automall

  • Seminole Chevrolet

  • Jon Hall Chevrolet, Inc.

  • George Nahas Chevrolet

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.