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 Dover, FL

144 results
Dover, FL
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Chevrolet Center Incorporated

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

96,887 miles

$31,000

Fair Deal
Winter Haven, FL
30 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
96,887
Stock number:
261481
VIN:
3GCPYCEL7NG112552

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,171 miles

$39,625

Fair Deal
Seminole, FL
34 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
33,171
Stock number:
PP2359
VIN:
3GCUDCED4RG129810

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

102,920 miles

$25,500

Great Deal
Bradenton, FL
43 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:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
102,920
Stock number:
32961W
VIN:
3GCPYCEF0MG133462

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,255 miles

$38,645

Great Deal
Seffner, FL
6 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:
8,255
Stock number:
G292934
VIN:
3GCPDCEK9RG292934

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,491 miles

$29,993

Great Deal
Tampa, FL
18 mi away
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:
8-Speed Automatic
Mileage:
50,491
Stock number:
W543055A
VIN:
1GCPYCEK6NZ226727

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,193 miles

$42,490

Fair Deal
Wesley Chapel, FL
20 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
15,193
Stock number:
T292127
VIN:
3GCPKCEK8SG292127

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,628 miles

$24,885

Good Deal
Certified Pre-Owned
Brooksville, FL
42 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

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,803 miles

$28,484

Great Deal
Seffner, FL
5 mi away
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:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
48,803
Stock number:
4767
VIN:
1GCPYCEH1LZ221114

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,717 miles

$29,994

Great Deal
Seffner, FL
5 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:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
48,717
Stock number:
4704
VIN:
1GCPYCEF1MZ198692

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

123,205 miles

$21,495

Fair Deal
Dade City, FL
27 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

102,920 miles

$25,500

Great Deal
Bradenton, FL
43 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:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
102,920
Stock number:
32961W
VIN:
3GCPYCEF0MG133462

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

160,293 miles

$17,995

Fair Deal
Brooksville, FL
42 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:
White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
160,293
Stock number:
2928
VIN:
1GCRYCEF1KZ297812

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,930 miles

$42,500

Good Deal
Bradenton, FL
40 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
3,930
Stock number:
D26039A
VIN:
3GCPKCEK3SG329729

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

88,211 miles

$23,548

Good Deal
Store transfer to Brandon, FL
62 mi away • Price includes $50 shipping Price includes $50 shipping
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

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,604 miles

$41,992

Fair Deal
Spring Hill, FL
42 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:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
9,604
Stock number:
P0578
VIN:
3GCPKCEK7SG305594

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,171 miles

$39,625

Fair Deal
Seminole, FL
34 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
33,171
Stock number:
PP2359
VIN:
3GCUDCED4RG129810

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,255 miles

$38,645

Great Deal
Seffner, FL
6 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:
8,255
Stock number:
G292934
VIN:
3GCPDCEK9RG292934

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Florida
  6. / Dover

  • Chevrolet Silverado 1500 LT in Dover FL

  • Chevrolet Silverado 1500 RST in Dover FL

  • Chevrolet Silverado 1500 LTZ in Dover FL

  • Chevrolet Silverado 1500 LT Trail Boss in Dover FL

  • Chevrolet Silverado 1500 LT1 in Dover FL

  • Chevrolet Silverado 1500 High Country in Dover FL

  • Chevrolet Silverado 1500 Custom in Dover FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Dover FL

  • Chevrolet Silverado 1500 Work Truck in Dover FL

  • Chevrolet Silverado 1500 in Tampa FL

  • Chevrolet Silverado 1500 in Lakeland FL

  • Chevrolet Silverado 1500 in Brooksville FL

  • Chevrolet Silverado 1500 in Sarasota FL

  • Chevrolet Silverado 1500 in Sebring FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in Orlando FL

  • Chevrolet Silverado 1500 in North Port FL

  • Chevrolet Silverado 1500 in Crystal River FL

  • Chevrolet Silverado 1500 in Dover FL

  • Old Chevy Trucks for Sale in Dover FL

  • Classic Muscle Cars for Sale in Dover FL

  • Chevrolet Trucks For Sale in Dover FL

  • Cheap Muscle Cars for Sale in Dover FL

  • Work Trucks for Sale in Dover FL

  • Reliable Cars For Sale in Dover FL

  • American Made Trucks For Sale in Dover FL

  • Best Pickup Trucks For Sale in Dover FL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Dover 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

  • Dimmitt Chevrolet

  • Cox Chevrolet

  • Ferman Chevrolet North Dale Mabry

  • Ferman Chevrolet of Brandon

  • Stingray Chevrolet

  • Jim Browne Chevrolet GMC

  • Dyer Chevrolet Lake Wales

  • Regal Chevrolet

  • Stingray Chevrolet Bartow

  • Register Chevrolet

  • Ferman Chevrolet of Tarpon Springs

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.