Used Chevrolet Silverado 1500 Custom Trail Boss 4wd in Connecticut (CT) For Sale (17 results)
Sort by:
Refine search
Sort by:
Year
-
(3)2023
-
(2)2022
-
(1)2021
-
(7)2020
-
(4)2019
Zip
Price
-
(14)under $40,000
-
(17)under $50,000
Mileage
-
(11)0 - 50000
-
(4)50000 - 100000
-
(2)100000 - 150000
Make
-
Chevrolet
Model
Trim
-
(95)lt
-
(51)rst
-
(31)lt trail boss
-
(29)ltz
-
(28)custom
-
(26)1lt
-
(20)high country
-
custom trail boss
-
(12)2lt
-
(9)wt
-
(5)ls
-
(3)notdoor
-
(2)limited
-
(2)lt 2lt
-
(2)lt 4x4 lt
-
(2)work truck
-
(2)zr2
-
(1)lt 4x4
-
(1)lt 4x4 extended cab
-
(1)lt lt1
-
(1)lt w/1lt
-
(1)ltz w/1lz
Transmission type
-
(17)automatic
Color
-
(5)Black
-
(4)Red
-
(3)Blue
-
(2)White
-
(1)Silver
Body
-
(1)
![]()
Pickup truck
Drive
-
4wd
Fuel
-
(17)gasoline
State
City
-
(2)Danbury, CT
-
(2)Milford, CT
-
(2)Waterbury, CT
-
(2)Watertown, CT
-
(1)Bristol, CT
-
(1)East Windsor, CT
-
(1)Enfield, CT
-
(1)Hartford, CT
-
(1)Norwalk, CT
-
(1)Norwich, CT
-
(1)Torrington, CT
-
(1)Vernon Rockville, CT
-
(1)Woodbury, CT
Features
-
(3)Alloy wheels
-
(3)Cloth interior
-
(3)Compass
-
(3)Fully automatic headlights
-
(2)Advanced safety features
-
(2)Apple CarPlay/Android auto
-
(2)Auto high-beam headlights
-
(2)Backup camera
-
(2)Bluetooth
-
(2)Heated door mirrors
-
(2)Low tire pressure warning
-
(1)ABS brakes
-
(1)AM/FM radio
-
(1)Air conditioning
-
(1)Brake assist
-
(1)Delay-off headlights
-
(1)Door locks power
-
(1)Dual exhaust
-
(1)Electronic stability control
-
(1)Remote keyless entry
-
(1)Security system
2022 chevrolet silverado 1500 custom trail boss
This 2022 Chevrolet Silverado 1500 Custom Trail Boss combines capability with modern technology like Apple CarPlay/Android Auto. It's equipped with a clean CARFAX, 6-speaker audio, and advanced safety features
Danbury, CT
43,148 mi.
Blue
automatic
gasoline
Danbury, CT
$37,984
2023 chevrolet silverado 1500 custom trail boss
Experience the rugged capability of the 2023 Chevrolet Silverado 1500 Custom Trail Boss, combining power and style with its striking black exterior and comfortable jet black interior
Torrington, CT
50,040 mi.
Black
automatic
gasoline
Torrington, CT
$41,670
2023 chevrolet silverado 1500 custom trail boss
Experience the power and versatility of the 2023 Chevrolet Silverado 1500 Custom Trail Boss. With features like a 5.3L V8 engine, four-wheel drive, and an array of modern tech, this truck is built for both work and play
Watertown, CT
18,115 mi.
Black
automatic
gasoline
Watertown, CT
$44,947
2022 chevrolet silverado 1500 custom trail boss
This 2022 Chevrolet Silverado 1500 Custom Trail Boss boasts low mileage and a clean CARFAX. Enjoy features like alloy wheels, Apple CarPlay, and safety tech including Automatic Emergency Braking, all in a striking black exterior
Danbury, CT
36,936 mi.
Black
automatic
gasoline
Danbury, CT
$36,890
2023 chevrolet silverado 1500 custom trail boss
This 2023 Chevrolet Silverado 1500 Custom Trail Boss is a powerful truck featuring a 2.7L Turbo engine and equipped with modern conveniences like Apple CarPlay, a 10-way power driver seat, and advanced safety technologies
Watertown, CT
11,297 mi.
Black
automatic
gasoline
Watertown, CT
$41,995
2021 chevrolet silverado 1500 custom trail boss
Experience the rugged capability of this 2021 Chevrolet Silverado 1500 Custom Trail Boss. Featuring a powerful EcoTec3 5.3L V8 engine, this truck is built for adventure with 4WD and advanced safety features. One owner with no accidents!
Waterbury, CT
79,580 mi.
Satin steel metallic
automatic
gasoline
Waterbury, CT
$30,888
2019 chevrolet silverado 1500 custom trail boss
This 2019 Chevrolet Silverado 1500 Custom Trail Boss in Summit White is equipped with new tires and brakes, features a modern infotainment system, and is ready for your next adventure with robust four-wheel drive capabilities
Woodbury, CT
83,895 mi.
White
automatic
gasoline
Woodbury, CT
$28,475
2019 chevrolet silverado 1500 custom trail boss
This 2019 Chevrolet Silverado 1500 Custom Trail Boss in Summit White is a rugged 4WD truck equipped with a powerful EcoTec3 5.3L V8 and a smooth 6-speed automatic transmission. Perfect for both work and play!
Bristol, CT
46,711 mi.
White
automatic
gasoline
Bristol, CT
$31,282
2019 chevrolet silverado 1500 custom trail boss
This striking red 2019 Chevrolet Silverado 1500 Custom Trail Boss offers an impressive 36,205 miles and features a robust EcoTec3 5.3L V8 engine paired with a smooth 6-speed automatic transmission, perfect for any adventure
Milford, CT
36,205 mi.
Red
automatic
gasoline
Milford, CT
$32,416
2020 chevrolet silverado 1500 custom trail boss
Experience the rugged capability of the 2020 Chevrolet Silverado 1500 Custom Trail Boss with just 38,082 miles. Equipped with a powerful V8 engine and a spacious black interior, this truck is perfect for your adventures
Norwalk, CT
38,082 mi.
Silver
automatic
gasoline
Norwalk, CT
$35,950
2020 chevrolet silverado 1500 custom trail boss
This 2020 Chevrolet Silverado 1500 Custom Trail Boss in Northsky Blue Metallic comes equipped with a powerful four-wheel drive system and automatic transmission. However, it has dashboard warning lights indicating a need for service, and is currently parked
![]()
Pickup truck
East Windsor, CT
140,309 mi.
Blue
Pickup truck
automatic
gasoline
East Windsor, CT
$23,788
2019 chevrolet silverado 1500 custom trail boss
Explore the rugged elegance of this 2019 Chevrolet Silverado 1500 Custom Trail Boss in stunning Cajun Red Tintcoat, featuring a powerful EcoTec3 V6 engine and four-wheel drive, perfect for every adventure
![]()
4d crew cab
Vernon Rockville, CT
30,793 mi.
Red
4d crew cab
automatic
gasoline
Vernon Rockville, CT
$35,500
2020 chevrolet silverado 1500 custom trail boss
This rugged 2020 Chevrolet Silverado 1500 Custom Trail Boss offers an impressive four-wheel drive system, making it perfect for tough terrains. With over 103k miles, it is priced at $29,998—ready for your next adventure
Hartford, CT
103,331 mi.
Black
automatic
gasoline
Hartford, CT
$29,998
2020 chevrolet silverado 1500 custom trail boss
This 2020 Chevrolet Silverado 1500 Custom Trail Boss in Satin Steel Metallic boasts 54979 miles and a 6-speed automatic transmission, offering a smooth ride with four-wheel drive capability. Priced below KBB, it comes with warranty and roadside assistance
Enfield, CT
54,979 mi.
Satin steel metallic
automatic
gasoline
Enfield, CT
$33,978
2020 chevrolet silverado 1500 custom trail boss
This certified 2020 Chevrolet Silverado 1500 Custom Trail Boss is a rugged pickup that's equipped with four-wheel drive and features a striking Northsky Blue Metallic exterior. Enjoy the convenience of a 6-speed automatic transmission, Bluetooth connectivity, and advanced safety features
Norwich, CT
40,220 mi.
Blue
automatic
gasoline
Norwich, CT
$35,530
2020 chevrolet silverado 1500 custom trail boss
This striking red 2020 Chevrolet Silverado 1500 Custom Trail Boss combines rugged off-road capability with modern tech. It's equipped with a powerful V8, backup camera, and plenty of advanced features for an exceptional driving experience
Waterbury, CT
40,077 mi.
Red
automatic
gasoline
Waterbury, CT
$32,994
2020 chevrolet silverado 1500 custom trail boss
This stunning red 2020 Chevrolet Silverado 1500 Custom Trail Boss combines style and functionality with its robust 4WD and efficient EcoTec3 5.3L V8 engine, making it a perfect choice for rugged adventures
Milford, CT
42,227 mi.
Red
automatic
gasoline
Milford, CT
$34,998