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 Kittery, ME

150 results
Kittery, ME
2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Portsmouth Ford Lincoln

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,539 miles

$32,995

Good Deal
Portsmouth, NH
3 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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
52,539
Stock number:
P57368A
VIN:
3GCPYCEF6LG310000

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

78,964 miles

$28,330

Good Deal
Orleans, MA
100 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:
78,964
Stock number:
KG305851
VIN:
3GCPYCEFXKG305851

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,088 miles

$36,925

Fair Deal
Westborough, MA
72 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:
Northsky Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
45,088
Stock number:
P1801
VIN:
3GCPDCEK4PG128777

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,712 miles

$33,524

Good Deal
Raynham, MA
85 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:
Summit White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
55,712
Stock number:
M0035A
VIN:
3GCPDCEK1PG172722

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,925 miles

$28,500

Great Deal
Plaistow, NH
26 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:
Automatic
Mileage:
74,925
Stock number:
143375
VIN:
1GCPYCEF2LZ143375

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,195 miles

$31,990

Great Deal
Malden, MA
49 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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
44,195
Stock number:
C14811
VIN:
3GCPYCEK3NG116041

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,211 miles

$27,199

Good Deal
White River Junction, VT
88 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:
Silver Ice Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
92,211
Stock number:
W4410A
VIN:
1GCPYCEF6LZ331705

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

38,144 miles

$40,300

Good Deal
Norwood, MA
69 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:
38,144
Stock number:
U2400050
VIN:
3GCUDCED3RG248660

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,662 miles

$19,995

Great Deal
Tilton, NH
48 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:
Silver
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
133,662
Stock number:
75
VIN:
3GCPYCEF2KG141396

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,635 miles

$46,924

Fair Deal
Raynham, MA
85 mi away
Year:
2025
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
1,635
Stock number:
M0131A
VIN:
3GCUKCED8SG339385

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,962 miles

$36,307

Good Deal
Falmouth, ME
49 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:
Black
Transmission:
Automatic
Mileage:
39,962
Stock number:
F91064
VIN:
1GCPYCEL9MZ406453

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

107,990 miles

$21,995

Great Deal
Tilton, NH
48 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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
107,990
Stock number:
0056
VIN:
1GCRYCEF5KZ338197

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,331 miles

$29,758

Fair Deal
Lynn, MA
47 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,331
Stock number:
PC2507
VIN:
1GCPYCEH3LZ189704

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

46,272 miles

$34,400

Fair Deal
Malden, MA
49 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:
Northsky Blue Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
46,272
Stock number:
C15222
VIN:
1GCPYCEF5LZ352058

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,635 miles

$46,924

Fair Deal
Raynham, MA
85 mi away
Year:
2025
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
1,635
Stock number:
M0131A
VIN:
3GCUKCED8SG339385

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Maine
  6. / Kittery
  • Chevrolet Silverado 1500 LT in Kittery ME

  • Chevrolet Silverado 1500 RST in Kittery ME

  • Chevrolet Silverado 1500 LTZ in Kittery ME

  • Chevrolet Silverado 1500 LT Trail Boss in Kittery ME

  • Chevrolet Silverado 1500 LT1 in Kittery ME

  • Chevrolet Silverado 1500 Custom in Kittery ME

  • Chevrolet Silverado 1500 High Country in Kittery ME

  • Chevrolet Silverado 1500 Custom Trail Boss in Kittery ME

  • Chevrolet Silverado 1500 Work Truck in Kittery ME

  • Chevrolet Silverado 1500 in Portsmouth NH

  • Chevrolet Silverado 1500 in Manchester NH

  • Chevrolet Silverado 1500 in Portland ME

  • Chevrolet Silverado 1500 in Boston MA

  • Chevrolet Silverado 1500 in Groton MA

  • Chevrolet Silverado 1500 in Auburn ME

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in Plymouth MA

  • Chevrolet Silverado 1500 in Brattleboro VT

  • Chevrolet Silverado 1500 in Kittery ME

  • Old Chevy Trucks for Sale in Kittery ME

  • Classic Muscle Cars for Sale in Kittery ME

  • Chevrolet Trucks For Sale in Kittery ME

  • Cheap Muscle Cars for Sale in Kittery ME

  • Work Trucks for Sale in Kittery ME

  • Reliable Cars For Sale in Kittery ME

  • American Made Trucks For Sale in Kittery ME

  • Best Pickup Trucks For Sale in Kittery ME

  • Best Cars Under $5,000 For Sale in Kittery ME

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Kittery ME

  • 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

  • Banks Chevrolet Buick GMC

  • Portsmouth Chevrolet

  • Nucar Chevrolet of Woburn

  • Herb Chambers Chevrolet of Danvers

  • Bill Deluca Chevrolet Cadillac

  • Commonwealth Motors

  • Dover Chevrolet

  • Key GMC Of Rochester

  • Pride Chevrolet

  • Amesbury Chevrolet

  • Sudbay Chevrolet Buick Cadillac GMC

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.