Skid Steers For Sale in Virginia

2023 Caterpillar 299D3 Track Skid Steer

Newly Listed

$62,500 USD

2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Flow - Standard Flow, Bucket, Coupler Type - Hydraulic, Emissions Level - EPA - Tier4, Emissions Level - EU - Stage5, Emissions Level -...

Inspection Report

Condition	Used
Usage	1,911 Hours
Drivetrain	Track
Stock Number	5063850
MLS Number	14714850
Category	Skid Steers
Last Updated	11/4/2026
Location	Dulles, VA, US
Sold By	Carter Machinery

2024 Caterpillar 265 Track Skid Steer

Recently Updated

$99,000 USD

2 Speed Travel, Air Conditioner, Auxiliary Hydraulics Flow - Standard Flow, Bucket, Coupler Type - Hydraulic, Emissions Level - EPA - EPA TIER 4f, Emissions Level - EU - EU STAGE V,...

Inspection Report

Condition	Used
Usage	366 Hours
Drivetrain	Track
Stock Number	5063110
MLS Number	14610057
Category	Skid Steers
Last Updated	11/5/2026
Location	Mechanicsville, VA, US
Sold By	Carter Machinery

2026 Caterpillar 255 DCA2 Mini Skid Steer

Recently Updated

$77,500 USD

255 05A COMPACT TRACK LOADER, AIR CONDITIONING, R134A REF, CERTIFICATION ARR, P65, COLD STARTING PACKAGE, 120V, COMFORT PKG, ENCLOSED CAB, HVAC, DOOR, CAB, GLASS, ENGINE AR-GENL, FAN,...

Inspection Report

Condition	Used
Usage	252 Hours
Drivetrain	Track
Stock Number	5063340T0
MLS Number	14594273
Category	Skid Steers
Last Updated	11/4/2026
Location	Winchester, VA, US
Sold By	Carter Machinery

2025 Caterpillar 255 DCA2 Track Skid Steer

Recently Updated

$69,500 USD

*255 05A COMPACT TRACK LOADER, *CERTIFICATION ARR, P65, *COLD STARTING PACKAGE (120V), *COMFORT PKG, ENCLOSED CAB,HVAC, *DOOR, CAB, GLASS, *FAN, COOLING, DEMAND, *HYDRAULICS, PERFORMANCE,...

Inspection Report

Condition	Used
Usage	145 Hours
Drivetrain	Track
Stock Number	5062100
MLS Number	14587275
Category	Skid Steers
Last Updated	11/4/2026
Location	Chesapeake, VA, US
Sold By	Carter Machinery

2023 Caterpillar 299D3 Track Skid Steer

Recently Updated

$72,500 USD

299D CTL, BATTERY, EXTRA HEAVY DUTY, DISC, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, DEBRIS MGMT PKG, NONE, DM0, DOOR, CAB, POLYCARBONATE, Engine, FILM, SELF LEVEL, ANSI, HEATER, ENGINE...

Inspection Report

Condition	Used
Usage	1,359 Hours
Drivetrain	Track
Stock Number	5060180
MLS Number	14558317
Category	Skid Steers
Last Updated	11/4/2026
Location	Richmond, VA, US
Sold By	Carter Machinery

2025 Caterpillar 255 Track Skid Steer

Recently Updated

$76,900 USD

255 05A COMPACT TRACK LOADER, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, COLD STARTING PACKAGE, 120V, COUNTERWEIGHT,MACHINE,EXTERNAL, DOOR, CAB, POLYCARBONATE, ENGINE AR-GENL, FUEL,...

Inspection Report

Condition	Used
Usage	324 Hours
Drivetrain	Track
Stock Number	5061240
MLS Number	14535992
Category	Skid Steers
Last Updated	11/4/2026
Location	Warrenton, VA, US
Sold By	Carter Machinery

2024 ASV VT100F Track Skid Steer

Recently Updated

$79,000 USD

2 Speed Travel, Air Conditioner, ANTI THEFT SYSTEM, ASV-POSITRACK VT100F SKD STR LDR, AUXILIARY HYD FLOW, HIGH, AUXILIARY HYD PRESSURE, HIGH, Coupler Type - Hydraulic, HEATER/DEFROSTER,...

Inspection Report

Condition	Used
Usage	913 Hours
Drivetrain	Track
Stock Number	5059880T0
MLS Number	14449525
Category	Skid Steers
Last Updated	11/4/2026
Location	Sterling, VA, US
Sold By	Carter Machinery

2022 Caterpillar 299D3 XE Track Skid Steer

Recently Updated

$95,500 USD

CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, COUNTERWEIGHT,MACHINE,EXTERNAL, DOOR, CAB, POLYCARBONATE, Engine, FAN,COOLING,DEMAND,REVERSING, FILM, RIDE CONTROL, ANSI, FILM, SELF LEVEL, ANSI,...

Inspection Report

Condition	Used
Usage	762 Hours
Drivetrain	Track
Stock Number	5059670T0
MLS Number	14631774
Category	Skid Steers
Last Updated	11/4/2026
Location	Richmond, VA, US
Sold By	Carter Machinery

2022 Caterpillar 272D3 XE Mini Skid Steer

Recently Updated

$53,500 USD

2 Speed Travel, 272D3 XE SKID STEER LOADER, AIR CONDITINER, Bucket, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, DOOR, CAB, POLYCARBONATE, Engine, FILM, RIDE CONTROL, ANSI, FILM, SELF LEVEL,...

Inspection Report

Condition	Used
Usage	2,287 Hours
Stock Number	5058840
MLS Number	14522006
Category	Skid Steers
Last Updated	11/3/2026
Location	Sterling, VA, US
Sold By	Carter Machinery

2023 Caterpillar 299D3 Track Skid Steer

Recently Updated

$58,000 USD

2 Speed Travel, 299D CTL, Air Conditioner, ANTI THEFT SYSTEM, AUXILIARY HYD FLOW, HIGH, BATTERY,EXTRA HEAVY DUTY,DISC, Bucket, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, DEBRIS MGMT PKG,...

Inspection Report

Condition	Used
Usage	2,748 Hours
Drivetrain	Track
Stock Number	5058200T0
MLS Number	14287582
Category	Skid Steers
Last Updated	11/3/2026
Location	Salem, VA, US
Sold By	Carter Machinery

2023 Caterpillar 289D3 Track Skid Steer

Recently Updated

$85,500 USD

289D3 CTL DCA4B, 289D3 CTLT4F, BATTERY, EXTRA HEAVY DUTY, DISC, CAB AIR, CAB PACKAGE, PRO PLUS, CERTIFICATION ARR, P65, DOOR, CAB, GLASS, Engine, FILM, SELF LEVEL, ANSI, GP BUCKET, HEATER,...

Inspection Report

Condition	Used
Usage	196 Hours
Drivetrain	Track
Stock Number	5057510
MLS Number	14377822
Category	Skid Steers
Last Updated	11/3/2026
Location	Richmond, VA, US
Sold By	Carter Machinery

2024 Caterpillar 299D3 XE Track Skid Steer

Recently Updated

$156,000 USD

2 Speed Travel, Air Conditioner, AUXILIARY HYD FLOW, HIGH, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, COMBINED HYDRAULICS, TWO WAY, DEBRIS MANAGEMENT PKG, DM2, DOOR, CAB, POLYCARBONATE,...

Inspection Report

Condition	Used
Usage	1,163 Hours
Drivetrain	Track
Stock Number	5057360T0
MLS Number	14546821
Category	Skid Steers
Last Updated	11/3/2026
Location	Richmond, VA, US
Sold By	Carter Machinery

2023 Caterpillar 299D3 Track Skid Steer

Recently Updated

$68,000 USD

2 Speed Travel, 299D3 COMPACT TRACK LOADER, Air Conditioner, ANTI THEFT SYSTEM, AUXILIARY HYD FLOW, HIGH, AUXILIARY HYD PRESSURE, HIGH, BATTERY,EXTRA HEAVY DUTY, DISC, Bucket, CAB PACKAGE,...

Inspection Report

Condition	Used
Usage	2,472 Hours
Drivetrain	Track
Stock Number	5056350
MLS Number	14586749
Category	Skid Steers
Last Updated	11/3/2026
Location	Sterling, VA, US
Sold By	Carter Machinery

2023 Caterpillar 299D3 Track Skid Steer

Recently Updated

$82,500 USD

2 Speed Travel, 299D3 COMPACT TRACK LOADER, Air Conditioner, AUXILIARY HYD FLOW, HIGH, BATTERY,EXTRA HVY DUTY, DISC, Bucket, CAB PACKAGE, PRO PLUS, CERTIFICATION AR, P65, DEBRIS MGMT PKG,...

Inspection Report

Condition	Used
Usage	1,245 Hours
Drivetrain	Track
Stock Number	5055840T0
MLS Number	14164602
Category	Skid Steers
Last Updated	11/3/2026
Location	Fisherville, VA, US
Sold By	Carter Machinery

2023 Caterpillar 299D3 Track Skid Steer

Recently Updated

$70,900 USD

2 Speed Travel, 299D CTL, 299D3 CTL DCA4D, Air Conditioner, ANTI THEFT SYSTEM, AUXILIARY HYD FLOW, STANDARD, BATTERY,EXTRA HEAVY DUTY, DISC, Bucket, CAB PACKAGE, PRO PLUS, CERTIFICATION ARR,...

Inspection Report

Condition	Used
Usage	1,761 Hours
Drivetrain	Track
Stock Number	5055690T0
MLS Number	14110103
Category	Skid Steers
Last Updated	11/3/2026
Location	Richmond, VA, US
Sold By	Carter Machinery

2024 Caterpillar 255 Track Skid Steer

Recently Updated

$92,122 USD

2 Speed Travel, 74" BUCKET (SN:A424CBK20184), Air Conditioner, AUXILIARY HYD PRESSURE, HIGH, CERTIFICATION ARR, P65, COMFORT PKG, ENCLOSED CAB, HVAC, COUNTERWEIGHT,MACHINE,EXTERNAL, DOOR,...

Inspection Report

Condition	Used
Usage	154 Hours
Drivetrain	Track
Stock Number	5051750T0
MLS Number	13907168
Category	Skid Steers
Last Updated	11/3/2026
Location	Williamsburg, VA, US
Sold By	Carter Machinery

2023 Caterpillar 289D3 Track Skid Steer

Recently Updated

$68,500 USD

2 Speed Travel, 289D3 CTLT4F, Air Conditioner, AUXILIARY HYD FLOW, STANDARD, BATTERY,EXTRA HEAVY DUTY,DISC, CAB PACKAGE, PRO PLUS, CERTIFICATION ARR, P65, Coupler Type - Hydraulic, DOOR, CAB...

Inspection Report

Condition	Used
Usage	1,115 Hours
Drivetrain	Track
Stock Number	5050760
MLS Number	14108248
Category	Skid Steers
Last Updated	11/3/2026
Location	Warrenton, VA, US
Sold By	Carter Machinery

2019 Caterpillar 289D Track Skid Steer

Recently Updated

$37,622 USD

AUXILIARY HYDRAULIC FLOW, BATTERY, XTRA HVY DUTY, DISC, BELT, SEAT, 2", CERTIFICATION ARR, P65, CONTROL, H/F, PROP, W, CONVERSION ARRANGEMENT, DISPLAY, ADVANCED, LCD, CAMERA, DOOR, CAB,...

Inspection Report

Condition	Used
Usage	4,409 Hours
Drivetrain	Track
Stock Number	5049800T0
MLS Number	14091564
Category	Skid Steers
Last Updated	11/3/2026
Location	Warrenton, VA, US
Sold By	Carter Machinery

2022 Caterpillar 299D3 Track Skid Steer

Recently Updated

$51,022 USD

2 Speed Travel, 299D CTL, 299D3 CTL DCA6C, Air Conditioner, Auxiliary Hydraulics Flow, BATTERY,EXTRA HEAVY DUTY,DISC, Bucket, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, DEBRIS MGMT PKG,...

Inspection Report

Condition	Used
Usage	3,414 Hours
Drivetrain	Track
Stock Number	5049760T0
MLS Number	14091531
Category	Skid Steers
Last Updated	11/3/2026
Location	Warrenton, VA, US
Sold By	Carter Machinery

2022 Caterpillar 299D3 XE Track Skid Steer

Recently Updated

$78,122 USD

2 Speed Travel, Air Conditioner, AUXILIARY HYD FLOW, HIGH, AUXILIARY HYD PRESSURE, HIGH, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, COUNTERWEIGHT,MACHINE,EXTERNAL, DEBRIS MGMT PKG, NONE,...

Inspection Report

Condition	Used
Usage	1,786 Hours
Drivetrain	Track
Stock Number	5048160T0
MLS Number	13685469
Category	Skid Steers
Last Updated	11/3/2026
Location	Williamsburg, VA, US
Sold By	Carter Machinery

2020 Caterpillar 299D3 XE Track Skid Steer

Recently Updated

$65,122 USD

Bucket, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, COUNTERWEIGHT,MACHINE,EXTERNAL, DEBRIS MGMT PKG, NONE (DM0), DOOR, CAB, POLYCARBONATE, Engine, FAN,COOLING,DEMAND,REVERSING, FILM, RIDE...

Inspection Report

Condition	Used
Usage	3,455 Hours
Drivetrain	Track
Stock Number	5042900T0
MLS Number	13753181
Category	Skid Steers
Last Updated	11/3/2026
Location	Fredericksburg, VA, US
Sold By	Carter Machinery

2023 Caterpillar 299D3 XE Track Skid Steer

Newly Listed

$105,000 USD

CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, COUNTERWEIGHT, MACHINE,I, DEBRIS MANAGEMENT PKG, DM2, DOOR, CAB, POLYCARBONATE, Engine, FAN,COOLING,DEMAND,REVERSING, FILM, RIDE CONTROL, ANSI,...

Inspection Report

Condition	Used
Usage	1,219 Hours
Drivetrain	Track
Stock Number	5060680
MLS Number	14709408
Category	Skid Steers
Last Updated	11/4/2026
Location	Fredericksburg, VA, US
Sold By	Carter Machinery

2026 Caterpillar 285 Skid Steer

Newly Listed

$138,500 USD

285 05A COMPACT TRACK LOADER, AIR CONDITIONING, R134A REF, CAB PACKAGE, ULTRA, CERTIFICATION ARR, P65, COLD STARTING PACKAGE, 120V, COUNTERWEIGHT,MACHINE,EXTERNAL, COUPLER, HYD, SELF LVL,RTD...

Inspection Report

Condition	Used
Usage	99 Hours
Drivetrain	Track
Stock Number	5063410T0
MLS Number	14709397
Category	Skid Steers
Last Updated	11/4/2026
Location	Fredericksburg, VA, US
Sold By	Carter Machinery

2020 Caterpillar 299D3 Track Skid Steer

Recently Updated

$60,122 USD

2 Speed Travel, 299D CTL, Air Conditioner, Auxiliary Hydraulics Flow, BATTERY,EXTRA HEAVY DUTY,DISC, Bucket, CAB PACKAGE, PRO PLUS, CERTIFICATION ARR, P65, DEBRIS MGMT PKG, NONE, DM0, DOOR,...

Inspection Report

Condition	Used
Usage	1,922 Hours
Drivetrain	Track
Stock Number	5050740T0
MLS Number	13907139
Category	Skid Steers
Last Updated	11/3/2026
Location	Winchester, VA, US
Sold By	Carter Machinery