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Work Pickup Trucks for Sale near Windermere, Florida

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95,227 results

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Condition

Body Type
Pickup
95,227
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Less than $400,000
Any
Chevrolet
24,652
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Ford
48,268
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Freightliner
1
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GMC
11,224
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Ram
10,651
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Cadillac
1
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Dodge
46
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Hummer
2
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Nissan
145
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Toyota
237
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Avalanche
11
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C/K 1500
3
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C/K 2500
1
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Canyon
2
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Dakota
6
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Escalade EXT
1
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Explorer Sport Trac
3
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F-150
11,229
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F-250
21,492
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F-350
13,842
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F-450
1,694
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F-550
5
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F-650
1
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F-750
2
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H2
1
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H2 SUT
1
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M2 106
1
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Ram 1500
7,579
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Ram 1500 Classic
64
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Ram 2500
2,823
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Ram 3500
225
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Sierra 1500
5,155
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Sierra 2500
4,688
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Sierra 3500
1,379
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Silverado 1500
12,996
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Silverado 1500 LTD
28
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Silverado 2500
9,700
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Silverado 3500
1,905
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Silverado 4500
1
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Silverado 5500
1
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SSR
6
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Titan
117
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Titan XD
28
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Tundra
237
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1794
12
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1LT
3
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2LT
3
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4x4
1
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AT4
1,929
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AT4X
606
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Base
86
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Big Horn
1,884
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Classic
1
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Custom
2,220
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Denali
2,218
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Denali Ultimate
1,314
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Denali Unlimited
4
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Elevation
884
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FL
2
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High Country
2,057
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King Ranch
2,851
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Laramie
2,051
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Lariat
12,946
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Limited
554
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Limited Longhorn
12
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Lobo
4
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Lone Star
2,077
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Longhorn
54
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LS
28
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LT
8,165
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LT1
2
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LTZ
2,561
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Night
9
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P700
1
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Platinum
5,098
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Platinum Reserve
16
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Platinum+
143
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Power Wagon
232
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Premium
1
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Pro
1,906
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PRO-4X
32
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Raptor
306
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Raptor R
57
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Rebel
778
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Reserve
1
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RHO
2
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RST
3,996
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S
10
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SC
5
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SE
2
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Shelby
86
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SL
11
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SLE
491
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SLE2
1
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SLT
1,885
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Sport
54
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SR
10
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SR5
138
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SRT
1
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SSV
7
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ST
35
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STX
516
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Styleside
1
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Supercharged
19
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SV
67
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Tradesman
2,460
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Trail Boss
12
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Trail Boss Custom
5
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Trail Boss LT
3
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TRD Pro
9
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Tremor
544
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TRX
268
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Warlock
268
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Work Truck
4,266
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XE
1
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XL
12,020
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XL STX
25
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XLT
11,036
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Z71
14
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ZR2
1,303
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Chassis Options
Conventional
11
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Club
1
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Conventional
1
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Crew
75,294
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CrewMax
80
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Double
1,585
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Extended
93
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Extra
2
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King
5
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Large
3
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Mega
11
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Quad
204
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Regular
4,397
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Super
3,319
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SuperCrew
10,184
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Cab Chassis
391
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Pickup
94,836
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2WD/4x2/RWD
6,394
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4WD/4x4/AWD
88,818
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Dual Rear Wheel
5,104
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Single Rear Wheel
12,377
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CNG/LPG
1,482
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Diesel
36,733
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Electric
1
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Gas/E85
1,559
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Gasoline
55,362
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Hybrid
88
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Chrysler
8
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Cummins
19
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Fiat Chrysler Automobiles
2,336
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Ford
48,160
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General Motors
92
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Isuzu
18
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Navistar
64
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Toyota
95
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Warren
6
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Engine Cylinders
8
95,227
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Automatic
91,721
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Manual
34
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Black
17,745
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Blue
4,559
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Brown
1,193
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Gold
72
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Gray
17,914
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Green
617
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Orange
24
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Red
4,948
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Silver
3,451
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White
40,063
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Yellow
24
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Light
40,831
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Medium
31,276
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Heavy
1
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1
3
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2
40,828
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3
31,263
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4
5
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5
7
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6
1
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7
1
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140"
7
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141"
50
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146"
3
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158"
1
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161"
3
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162"
41
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164"
3
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169"
12
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170"
1
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172"
56
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176"
13
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177"
6
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Body Options
Knapheide
14
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Reading
8
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Royal
4
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Bedrock
1
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Black Widow
4
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BOSS
1
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Cadet Truck Bodies
1
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CM Trailers
4
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Fox Factory Truck
1
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Harbor
2
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Norstar
1
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Roush Perfomance
6
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Scelzi
2
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Weather Guard
1
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Western
1
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8'
1
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8' 2"
2
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Steel
4
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Air Compressor
5
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Camper Shell
25
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Ladder Rack
17
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Lift Gate
3
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Refrigeration
1
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Snowplow
8
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Toolbox
27
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Winch
1
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Alabama
2,658
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Alaska
130
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Arizona
3,090
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Arkansas
456
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California
6,807
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Colorado
2,272
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Connecticut
965
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Delaware
74
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Florida
7,935
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Georgia
4,649
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Hawaii
132
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Idaho
1,864
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Illinois
2,004
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Indiana
1,931
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Iowa
1,677
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Kansas
670
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Kentucky
732
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Louisiana
696
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Maine
255
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Maryland
2,284
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Massachusetts
1,658
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Michigan
2,346
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Minnesota
805
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Mississippi
453
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Missouri
1,026
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Montana
436
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Nebraska
340
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Nevada
753
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New Hampshire
461
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New Jersey
1,311
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New Mexico
521
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New York
2,143
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North Carolina
4,059
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North Dakota
776
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Ohio
3,836
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Oklahoma
558
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Oregon
1,070
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Pennsylvania
3,190
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Rhode Island
71
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South Carolina
2,012
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South Dakota
95
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Tennessee
2,282
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Texas
15,845
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Utah
1,624
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Vermont
23
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Virginia
2,486
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Washington
1,664
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West Virginia
442
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Wisconsin
1,608
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Wyoming
52
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Used 2017 Ford F-350 Lariat Super Cab

$32,021
speed 114,105 mi
sell
Key features
  • Diesel
  • 4WD
  • SRW
location_on
Mercedes-Benz of South Orlando
Orlando, FL (8.4 mi)

Used 2023 GMC Sierra 1500 Denali Ultimate Crew Cab

$55,251
speed 28,672 mi
sell
Key features
  • Gasoline
  • 4WD
  • Denali Ultimate
location_on
Mercedes-Benz of South Orlando
Orlando, FL (8.4 mi)

Used 2018 Toyota Tundra Limited Crew Cab

$34,021
speed 109,106 mi
sell
Key features
  • Gasoline
  • 4WD
  • Limited
location_on
Mercedes-Benz of South Orlando
Orlando, FL (8.4 mi)

New 2026 Chevrolet Silverado 2500 LT Crew Cab

$77,534
sell
Key features
  • Diesel
  • 4WD
  • LT
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 RST Crew Cab

$60,524
sell
Key features
  • Gasoline
  • 4WD
  • RST
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 RST Crew Cab

$58,474
sell
Key features
  • Gasoline
  • 4WD
  • RST
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 Work Truck Crew Cab

$47,565
sell
Key features
  • Gasoline
  • 4WD
  • WT
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Ford F-250 XLT Crew Cab

$70,465
sell
Key features
  • Gasoline
  • 4WD
  • XLT
location_on
Tropical Ford Inc
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 RST Crew Cab

$74,064
sell
Key features
  • Gasoline
  • 4WD
  • RST
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Ford F-150 XLT SuperCrew Cab

$68,815 MSRP
$63,488
sell
Key features
  • Gasoline
  • 4WD
  • XLT
location_on
Tropical Ford Inc
Orlando, FL (9.2 mi)

New 2026 Ford F-350 XL Super Cab

$62,405 MSRP
$60,245
sell
Key features
  • Gasoline
  • 4WD
  • SRW
location_on
Tropical Ford Inc
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 2500 LT Crew Cab

$75,134
sell
Key features
  • Diesel
  • 4WD
  • LT
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 Custom Crew Cab

$53,499
sell
Key features
  • Gasoline
  • 4WD
  • Custom Trail Boss
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 LT Crew Cab

$61,379
sell
Key features
  • Gasoline
  • 4WD
  • LT Trail Boss
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 LT Crew Cab

$61,379
sell
Key features
  • Gasoline
  • 4WD
  • LT Trail Boss
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 RST Crew Cab

$56,539
sell
Key features
  • Gasoline
  • 4WD
  • RST
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 RST Crew Cab

$56,839
sell
Key features
  • Gasoline
  • 4WD
  • RST
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Ford F-350 XL Super Cab

$71,185
sell
Key features
  • Diesel
  • 4WD
  • SRW
location_on
Tropical Ford Inc
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 2500 LT Crew Cab

$76,769
sell
Key features
  • Diesel
  • 4WD
  • LT
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 Custom Crew Cab

$55,549
sell
Key features
  • Gasoline
  • 4WD
  • Custom Trail Boss
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 2500 LT Crew Cab

$78,114
sell
Key features
  • Diesel
  • 4WD
  • LT
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 RST Crew Cab

$56,539
sell
Key features
  • Gasoline
  • 4WD
  • RST
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 LT Crew Cab

$61,379
sell
Key features
  • Gasoline
  • 4WD
  • LT Trail Boss
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Ford F-250 XLT Crew Cab

$83,165
sell
Key features
  • Diesel
  • 4WD
  • XLT
location_on
Tropical Ford Inc
Orlando, FL (9.2 mi)

New 2026 Ford F-250 XL Super Cab

$67,230
sell
Key features
  • Diesel
  • RWD
  • XL
location_on
Tropical Ford Inc
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 Custom Crew Cab

$53,499
sell
Key features
  • Gasoline
  • 4WD
  • Custom Trail Boss
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 Custom Crew Cab

$53,499
sell
Key features
  • Gasoline
  • 4WD
  • Custom Trail Boss
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 2500 LT Crew Cab

$77,534
sell
Key features
  • Diesel
  • 4WD
  • LT
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)

New 2026 Ford F-250 Lariat Crew Cab

$87,160
sell
Key features
  • Diesel
  • 4WD
  • Lariat
location_on
Tropical Ford Inc
Orlando, FL (9.2 mi)

New 2026 Chevrolet Silverado 1500 RST Crew Cab

$54,919
sell
Key features
  • Gasoline
  • RWD
  • RST
location_on
Starling Chevrolet of Orlando
Orlando, FL (9.2 mi)