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 River Ranch, FL

129 results
River Ranch, FL
2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Ferman Chevrolet of Brandon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

19,780 miles

$42,988

Fair Deal
Tampa, FL
71 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:
Automatic
Mileage:
19,780
Stock number:
C262747A
VIN:
3GCPKCEK0SG247411

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,604 miles

$39,995

Great Deal
Spring Hill, FL
99 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

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,022 miles

$43,888

Fair Deal
Tampa, FL
71 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:
Automatic
Mileage:
7,022
Stock number:
C262413B
VIN:
3GCPKCEK8SG332030

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,608 miles

$28,809

Fair Deal
Certified Pre-Owned
Mount Dora, FL
78 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:
104,608
Stock number:
185411A
VIN:
3GCPYCEF8MG352914

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,604 miles

$39,995

Great Deal
Spring Hill, FL
99 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

160,293 miles

$17,995

Fair Deal
Brooksville, 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:
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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,091 miles

$38,236

Good Deal
Fruitland Park, FL
86 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:
Dark Ash Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
27,091
Stock number:
N225297B
VIN:
3GCPDCEK2RG334635

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,837 miles

$32,998

Good Deal
Lakeland, FL
52 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
51,837
Stock number:
28013158
VIN:
3GCPYCEF8MG343680

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

125,591 miles

$26,356

Fair Deal
New Smyrna Beach, FL
87 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:
Gray
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
125,591
Stock number:
G137059B
VIN:
1GCPYCEF2MZ393197

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,089 miles

$29,392

Fair Deal
Tampa, FL
79 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
89,089
Stock number:
L549410B
VIN:
1GCPYCEF7MZ160769

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,490 miles

$40,497

Fair Deal
Store transfer to Melbourne, FL
623 mi away • Price includes $499 shipping Price includes $499 shipping
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:
Black
Transmission:
Automatic
Mileage:
34,490
Stock number:
28011249
VIN:
3GCUDCED2PG312359

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

76,923 miles

$25,999

Good Deal
Vero Beach, FL
51 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,923
Stock number:
2S25609C
VIN:
1GCRYCEF1KZ198083

Preparing for a close up...

Photos coming soon

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,773 miles

$51,000

Good Deal
Daytona Beach, FL
100 mi away
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:
Cypress Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
6,773
Stock number:
X330650B
VIN:
3GCUKCED3TG108637

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,536 miles

$33,984

Fair Deal
Cape Coral, FL
88 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
70,536
Stock number:
W260309441T1
VIN:
3GCPYCEL1MG440466

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

99,227 miles

$29,984

Fair Deal
Punta Gorda, FL
78 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:
Northsky Blue Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
99,227
Stock number:
T382594B
VIN:
1GCPYCEF3MZ288796

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,745 miles

$35,950

Fair Deal
Brooksville, FL
90 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:
Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
66,745
Stock number:
STK163303
VIN:
3GCUDCED7PG163303

Sponsored

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

  • Chevrolet Silverado 1500 RST in River Ranch FL

  • Chevrolet Silverado 1500 LTZ in River Ranch FL

  • Chevrolet Silverado 1500 LT Trail Boss in River Ranch FL

  • Chevrolet Silverado 1500 LT1 in River Ranch FL

  • Chevrolet Silverado 1500 Custom in River Ranch FL

  • Chevrolet Silverado 1500 High Country in River Ranch FL

  • Chevrolet Silverado 1500 Custom Trail Boss in River Ranch FL

  • Chevrolet Silverado 1500 Work Truck in River Ranch FL

  • Chevrolet Silverado 1500 in Sebring FL

  • Chevrolet Silverado 1500 in Melbourne FL

  • Chevrolet Silverado 1500 in Okeechobee FL

  • Chevrolet Silverado 1500 in Lakeland FL

  • Chevrolet Silverado 1500 in Orlando FL

  • Chevrolet Silverado 1500 in Titusville FL

  • Chevrolet Silverado 1500 in Fort Pierce FL

  • Chevrolet Silverado 1500 in Tampa FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in River Ranch FL

  • Old Chevy Trucks for Sale in River Ranch FL

  • Classic Muscle Cars for Sale in River Ranch FL

  • Chevrolet Trucks For Sale in River Ranch FL

  • Cheap Muscle Cars for Sale in River Ranch FL

  • Work Trucks for Sale in River Ranch FL

  • Reliable Cars For Sale in River Ranch FL

  • American Made Trucks For Sale in River Ranch FL

  • Best Pickup Trucks For Sale in River Ranch FL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in River Ranch 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 in River Ranch

  • Used SUVs / Crossovers for Sale with Low Mileage in River Ranch

  • Used Hatchbacks for Sale with Low Mileage in River Ranch

  • Used Convertibles for Sale with Low Mileage in River Ranch

  • Used Vans for Sale with Low Mileage in River Ranch

  • Used Minivans for Sale with Low Mileage in River Ranch

  • Used Pickup Trucks for Sale with Low Mileage in River Ranch

  • Used Coupes for Sale with Low Mileage in River Ranch

  • Used Wagons for Sale with Low Mileage in River Ranch

  • Starling Chevrolet of Orlando

  • Starling Chevrolet GMC

  • Dyer Chevrolet Lake Wales

  • AutoNation Chevrolet Airport

  • Regal Chevrolet

  • Stingray Chevrolet Bartow

  • Huston 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.