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 Spring Hill, FL

138 results
Spring Hill, FL
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Ferman Chevrolet of Brandon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

82,349 miles

$31,988

Fair Deal
Tampa, FL
39 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:
82,349
Stock number:
C261668A
VIN:
1GCPYCEF8MZ299597

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,238 miles

$30,994

Good Deal
Seffner, FL
37 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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
49,238
Stock number:
4572
VIN:
1GCPYCEF7KZ287454

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,228 miles

$43,231

Fair Deal
Wesley Chapel, FL
22 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

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,208 miles

$24,544

Great Deal
Dade City, FL
24 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

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,546 miles

$26,048

Great Deal
Store transfer to Brandon, FL
73 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,502 miles

$40,987

Good Deal
Certified Pre-Owned
Homosassa, FL
25 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:
6,502
Stock number:
1618161CP1344
VIN:
3GCPDCEK6RG364740

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,228 miles

$43,231

Fair Deal
Wesley Chapel, FL
22 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

123,205 miles

$21,495

Good Deal
Dade City, FL
23 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$28,048

Great Deal
Store transfer to Brandon, FL
73 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

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

91,352 miles

$25,555

Great Deal
Brandon, FL
40 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,326 miles

$34,988

Good Deal
Tampa, FL
39 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:
40,326
Stock number:
C261670A
VIN:
1GCPYCEF9MZ243992

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,664 miles

$26,348

Good Deal
Store transfer to Brandon, FL
73 mi away • Price includes $50 shipping Price includes $50 shipping
Year:
2021
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
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
81,664
Stock number:
Z243264
VIN:
1GCPYCEH7MZ243264

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

90,847 miles

$26,998

Good Deal
Clearwater, FL
37 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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
90,847
Stock number:
TLG320070
VIN:
3GCPYCEF0LG320070

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

26,031 miles

$34,520

Good Deal
Certified Pre-Owned
Tampa, FL
31 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:
Glacier Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
26,031
Stock number:
NG678155T
VIN:
3GCPDCEK6NG678155

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

43,510 miles

$38,690

Good Deal
Certified Pre-Owned
Tampa, FL
31 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:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
43,510
Stock number:
RG339125T
VIN:
3GCUDCED9RG339125

Sponsored

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

  • Chevrolet Silverado 1500 RST in Spring Hill FL

  • Chevrolet Silverado 1500 LTZ in Spring Hill FL

  • Chevrolet Silverado 1500 LT Trail Boss in Spring Hill FL

  • Chevrolet Silverado 1500 LT1 in Spring Hill FL

  • Chevrolet Silverado 1500 Custom in Spring Hill FL

  • Chevrolet Silverado 1500 High Country in Spring Hill FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Spring Hill FL

  • Chevrolet Silverado 1500 Work Truck in Spring Hill FL

  • Chevrolet Silverado 1500 in Brooksville FL

  • Chevrolet Silverado 1500 in Crystal River FL

  • Chevrolet Silverado 1500 in Tampa FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in Lakeland FL

  • Chevrolet Silverado 1500 in Ocala FL

  • Chevrolet Silverado 1500 in Orlando FL

  • Chevrolet Silverado 1500 in Sarasota FL

  • Chevrolet Silverado 1500 in Gainesville FL

  • Chevrolet Silverado 1500 in Spring Hill FL

  • Old Chevy Trucks for Sale in Spring Hill FL

  • Classic Muscle Cars for Sale in Spring Hill FL

  • Chevrolet Trucks For Sale in Spring Hill FL

  • Cheap Muscle Cars for Sale in Spring Hill FL

  • Work Trucks for Sale in Spring Hill FL

  • Reliable Cars For Sale in Spring Hill FL

  • American Made Trucks For Sale in Spring Hill FL

  • Best Pickup Trucks For Sale in Spring Hill FL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Spring Hill 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

  • Ferman Chevrolet of Brandon

  • Stingray Chevrolet

  • Regal Chevrolet

  • Ferman Chevrolet of Tarpon Springs

  • 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

© 2025 CarGurus, Inc., All Rights Reserved.