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 Englewood, FL

127 results
Englewood, FL
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Gator Ford

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,255 miles

$40,323

Good Deal
Seffner, FL
71 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

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,109 miles

$36,891

Fair Deal
Sarasota, FL
21 mi away
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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
32,109
Stock number:
FS82997A
VIN:
1GCPYCEL4MZ261869

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,497 miles

$33,999

Fair Deal
Certified Pre-Owned
Lake Wales, FL
80 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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
52,497
Stock number:
3T26219A
VIN:
3GCPDCEK0NG518272

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,208 miles

$23,586

Great Deal
Dade City, FL
94 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:
108,208
Stock number:
A531106A
VIN:
3GCPYCEF0KG304160

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,720 miles

$37,487

Good Deal
Certified Pre-Owned
Punta Gorda, FL
20 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:
Red Hot
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
25,720
Stock number:
GP2471
VIN:
3GCPDCEK2RG153731

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,659 miles

$29,954

Good Deal
Tampa, FL
74 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:
White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
74,659
Stock number:
G157937A
VIN:
1GCPYCEF7MZ262380

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,255 miles

$40,323

Good Deal
Seffner, FL
71 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

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,497 miles

$33,999

Fair Deal
Certified Pre-Owned
Lake Wales, FL
80 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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
52,497
Stock number:
3T26219A
VIN:
3GCPDCEK0NG518272

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,419 miles

$31,397

Fair Deal
Dade City, FL
93 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:
74,419
Stock number:
C610083A
VIN:
1GCPYCEF1MZ266697

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,546 miles

$25,548

Great Deal
Store transfer to Brandon, FL
119 mi away • Price includes $50 shipping Price includes $50 shipping
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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
72,546
Stock number:
G151037
VIN:
3GCPYCEF0LG151037

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,246 miles

$25,999

Good Deal
Lake Wales, FL
80 mi away
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:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
101,246
Stock number:
5K26045B
VIN:
1GCPYCEF5LZ143001

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
96 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:
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

32,109 miles

$36,891

Fair Deal
Sarasota, FL
21 mi away
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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
32,109
Stock number:
FS82997A
VIN:
1GCPYCEL4MZ261869

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,228 miles

$42,887

Fair Deal
Wesley Chapel, FL
87 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

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

91,352 miles

$25,555

Great Deal
Brandon, FL
66 mi away
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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
91,352
Stock number:
P129231
VIN:
1GCPYCEF7LZ129231

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$27,548

Great Deal
Store transfer to Brandon, FL
119 mi away • Price includes $50 shipping Price includes $50 shipping
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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,653 miles

$33,990

Fair Deal
Punta Gorda, FL
21 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:
Red
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
55,653
Stock number:
A7098-T
VIN:
1GCPYCEF0MZ410787

Sponsored

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

  • Chevrolet Silverado 1500 LT in Englewood FL

  • Chevrolet Silverado 1500 RST in Englewood FL

  • Chevrolet Silverado 1500 LTZ in Englewood FL

  • Chevrolet Silverado 1500 LT Trail Boss in Englewood FL

  • Chevrolet Silverado 1500 LT1 in Englewood FL

  • Chevrolet Silverado 1500 Custom in Englewood FL

  • Chevrolet Silverado 1500 High Country in Englewood FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Englewood FL

  • Chevrolet Silverado 1500 Work Truck in Englewood FL

  • Chevrolet Silverado 1500 in North Port FL

  • Chevrolet Silverado 1500 in Sarasota FL

  • Chevrolet Silverado 1500 in Fort Myers FL

  • Chevrolet Silverado 1500 in Sebring FL

  • Chevrolet Silverado 1500 in Naples FL

  • Chevrolet Silverado 1500 in Tampa FL

  • Chevrolet Silverado 1500 in Lakeland FL

  • Chevrolet Silverado 1500 in Okeechobee FL

  • Chevrolet Silverado 1500 in Brooksville FL

  • Chevrolet Silverado 1500 in Englewood FL

  • Old Chevy Trucks for Sale in Englewood FL

  • Classic Muscle Cars for Sale in Englewood FL

  • Chevrolet Trucks For Sale in Englewood FL

  • Cheap Muscle Cars for Sale in Englewood FL

  • Work Trucks for Sale in Englewood FL

  • Reliable Cars For Sale in Englewood FL

  • American Made Trucks For Sale in Englewood FL

  • Best Pickup Trucks For Sale in Englewood FL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Englewood 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

  • Cox Chevrolet

  • Jenkins Chevrolet of Venice

  • Sunset Chevrolet Buick GMC

  • Arcadia Chevrolet Buick

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.