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 Cos Cob, CT

155 results
Cos Cob, CT
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Bomnin Chevrolet Cadillac Buick GMC Nanuet

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,988 miles

$35,990

Good Deal
Nanuet, NY
21 mi away
Year:
2023
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
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
37,988
Stock number:
C123540A
VIN:
3GCPDCEK3PG123540

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,500 miles

$24,800

Good Deal
Linden , NJ
47 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:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
104,500
Stock number:
184422C01
VIN:
1GCPYCEF3LZ184422

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

111,126 miles

$19,995

Great Deal
Selden, NY
32 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:
Jet Black
Transmission:
Automatic
Mileage:
111,126
Stock number:
9718F
VIN:
1GCRYCEF4KZ298680

Sponsored

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,810 miles

$26,602

Good Deal
Stratford, CT
26 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:
83,810
Stock number:
109712
VIN:
3GCPYCEF8KG175553

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,832 miles

$30,990

Good Deal
Riverhead, NY
47 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:
Automatic
Mileage:
53,832
Stock number:
U22935
VIN:
1GCPYCEF7MZ418546

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,438 miles

$29,715

Great Deal
West Islip, NY
28 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
59,438
Stock number:
U12310A
VIN:
1GCPYCEFXMZ301320

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

85,650 miles

$22,977

Great Deal
Medford, NY
35 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:
Automatic
Mileage:
85,650
Stock number:
10324
VIN:
1GCRYCEF9KZ351566

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,159 miles

$33,124

Good Deal
Pawling, NY
33 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
39,159
Stock number:
A604318
VIN:
3GCPDCEK1NG604318

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,267 miles

$24,853

Great Deal
Naugatuck, CT
43 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:
81,267
Stock number:
115249N
VIN:
3GCPYCEF2KG115249

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

43,101 miles

$33,995

Fair Deal
Certified Pre-Owned
Freeport, NY
28 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:
Automatic
Mileage:
43,101
Stock number:
C12024
VIN:
3GCPDCEK5NG660911

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,584 miles

$29,819

Fair Deal
Bay Shore, NY
28 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:
64,584
Stock number:
55171T
VIN:
1GCPYCEF4LZ141708

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

135,085 miles

$20,790

Great Deal
South Hackensack, NJ
28 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:
135,085
Stock number:
349852
VIN:
3GCPYCEF8MG349852

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,251 miles

$35,195

Good Deal
Pawling, NY
33 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:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,251
Stock number:
A605415
VIN:
3GCPDCEK4NG605415

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,159 miles

$33,124

Good Deal
Pawling, NY
33 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
39,159
Stock number:
A604318
VIN:
3GCPDCEK1NG604318

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Connecticut
  6. / Cos Cob
  • Chevrolet Silverado 1500 LT in Cos Cob CT

  • Chevrolet Silverado 1500 RST in Cos Cob CT

  • Chevrolet Silverado 1500 LTZ in Cos Cob CT

  • Chevrolet Silverado 1500 LT Trail Boss in Cos Cob CT

  • Chevrolet Silverado 1500 LT1 in Cos Cob CT

  • Chevrolet Silverado 1500 High Country in Cos Cob CT

  • Chevrolet Silverado 1500 Custom in Cos Cob CT

  • Chevrolet Silverado 1500 Custom Trail Boss in Cos Cob CT

  • Chevrolet Silverado 1500 Work Truck in Cos Cob CT

  • Chevrolet Silverado 1500 in Stamford CT

  • Chevrolet Silverado 1500 in New York NY

  • Chevrolet Silverado 1500 in Holtsville NY

  • Chevrolet Silverado 1500 in Newburgh NY

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in New Brunswick NJ

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Toms River NJ

  • Chevrolet Silverado 1500 in Trenton NJ

  • Chevrolet Silverado 1500 in Cos Cob CT

  • Old Chevy Trucks for Sale in Cos Cob CT

  • Classic Muscle Cars for Sale in Cos Cob CT

  • Chevrolet Trucks For Sale in Cos Cob CT

  • Cheap Muscle Cars for Sale in Cos Cob CT

  • Work Trucks for Sale in Cos Cob CT

  • Reliable Cars For Sale in Cos Cob CT

  • American Made Trucks For Sale in Cos Cob CT

  • Best Pickup Trucks For Sale in Cos Cob CT

  • Best Cars Under $5,000 For Sale in Cos Cob CT

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Cos Cob CT

  • 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

  • Atlantic Chevrolet Cadillac

  • Richard Chevrolet

  • Bomnin Chevrolet Cadillac Buick GMC Nanuet

  • Ingersoll Auto of Pawling

  • Richard Lucas Chevrolet

  • New Rochelle Chevrolet

  • Chevrolet of Smithtown

  • Bical Auto Mall

  • Hawthorne Chevrolet

  • East Hills Chevrolet of Roslyn

  • LaSorsa Chevrolet

  • Karl 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.