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New & Used Winston Trailers for Sale

Find 12 available units from winston trailers . Popular models include Equipment / Flatbed Trailers. Filter by pull type, length, and GVWR. Start browsing now and connect with trusted dealers and private sellers.

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2026 Winston AP22230AL-HR Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45748 Stock # 45748 New 2026 Winston AP22230AL Tag Equipment Trailer Color: Black with White Lettering 22.5 Ton...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
CONTACT SELLER FOR PRICE
North Jackson, OH
2026 Winston AP20825EC Equipment Trailer
On Order
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View Inventory: https://leonardtrailers.com/inventory/45752 Stock # 45752 New 2026 Winston AP20825EC Tag Equipment Trailer Color: Black with Black Wheels 8 Ton...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
CONTACT SELLER FOR PRICE
North Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45749 Stock # 45749 New 2026 Winston AP22230AL Tag Equipment Trailer Color: IH Red with Black Lettering 22.5...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
CONTACT SELLER FOR PRICE
North Jackson, OH
2026 Winston AP21025EL Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45751 Stock # 45751 New 2026 Winston AP21025EL-W Tag Equipment Trailer Color: Gray with Black Wheels, White Lettering...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
CONTACT SELLER FOR PRICE
North Jackson, OH
2026 Winston AP21025EL Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45750 Stock # 45750 New 2026 Winston AP21025EL-W Tag Equipment Trailer Color: IH Red with Black Wheels, Black...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
CONTACT SELLER FOR PRICE
North Jackson, OH
2017 Winston AP22027AL Equipment Trailer
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45332 Stock #45332 " USED Winston 20 Ton ProSeries Dual Tandem Tag Trailer This USED Winston 20 Ton...

Manufacturer
Winston
Condition
used
Pull Type
bumper
Length
27' 0
$17,499
North Jackson, OH
2026 Winston AP21025EL Equipment Trailer
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45438 Stock# 45438 New 2026 Winston AP21025EL Equipment Tag Trailer    Our Best Selling 10 Ton Trailer will...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
SALE
$16,799$16,967
North Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45435 Stock# 45435 New 2026 Winston AP22230AL-HR Equipment Tag Trailer  The 20 to 22.5 Ton ProSeries Dual Tandem...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
SALE
$34,999$35,376
North Jackson, OH
2026 Winston AP21025EL Equipment Trailer
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45437 Stock# 45437 New 2026 Winston AP21025EL Equipment Tag Trailer    Our Best Selling 10 Ton Trailer will...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
SALE
$16,799$16,967
North Jackson, OH
2026 Winston AP22227AL Equipment Trailer
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45436 Stock# 45436 New 2026 Winston AP22227AL Equipment Tag Trailer  The 20 to 22.5 Ton ProSeries Dual Tandem...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
27' 0
SALE
$27,999$28,292
North Jackson, OH
2026 Winston AP32030AL Equipment Trailer
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View Inventory: https://leonardtrailers.com/inventory/45249 Stock #45249 " New Winston AP32030AL 25-Ton ProSeries Trailer This heavy-duty Winston AP32030AL 25 Ton ProSeries Dual...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
SALE
$39,499$39,921
North Jackson, OH
2026 Winston AP21025HR Equipment Trailer
Enhanced

View Inventory: https://leonardtrailers.com/inventory/45252 Stock #45252 " New Winston AP21025HR 10 Ton Pro Paver Trailer (AP21025EL-HR) Features: 10 Ton Pro Paver...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
SALE
$21,997$22,222
North Jackson, OH

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