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New & Used Winston Trailers for Sale near Sharon, PA

Find 14 available units from winston trailers Within 200 miles of Sharon, PA. 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 AP21025EL Equipment Trailer
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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
NEAR MESALE
$16,997$17,278
Under 30 min from youNorth Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
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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
NEAR MESALE
$34,999$35,376
Under 30 min from youNorth Jackson, OH
2026 Winston AP21025EL Equipment Trailer
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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
NEAR MESALE
$16,997$17,278
Under 30 min from youNorth Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
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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
NEAR MESALE
$35,497$35,834
Under 30 min from youNorth Jackson, OH
2026 Winston AP22227AL Equipment Trailer
On Order
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View Inventory: https://leonardtrailers.com/inventory/46120 Stock Number:46120

Manufacturer
Winston
Condition
new
Length
27' 0
NEAR ME
CONTACT SELLER FOR PRICE
Under 30 min from youNorth Jackson, OH
2026 Winston AP20825EC Equipment Trailer
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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
NEAR MESALE
$13,497$13,778
Under 30 min from youNorth Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
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
NEAR MESALE
$35,497$35,834
Under 30 min from youNorth 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
NEAR MESALE
$39,499$39,921
Under 30 min from youNorth 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
NEAR MESALE
$16,799$16,967
Under 30 min from youNorth Jackson, OH
2026 Winston AP21025EL Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/46121 New Winston 10 ton electric brake tag 20ft flat + 5ft cleated outside dove tail w/ 5'...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
NEAR ME
CONTACT SELLER FOR PRICE
Under 30 min from youNorth 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
NEAR MESALE
$27,999$28,292
Under 30 min from youNorth Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/46118 This new 2026 Winston Pro Paver is 24' long plus a 6' beaver tail for a total...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
NEAR ME
CONTACT SELLER FOR PRICE
Under 30 min from youNorth Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/46119 This new 2026 Winston Pro Paver is 24' long plus a 6' beaver tail for a total...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
NEAR ME
CONTACT SELLER FOR PRICE
Under 30 min from youNorth Jackson, OH
2026 Winston AP21025EL Equipment Trailer
On Order
Enhanced

View Inventory: https://leonardtrailers.com/inventory/46122 New Winston 10 ton electric brake tag 20ft flat + 5ft cleated outside dove tail w/ 5'...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
NEAR ME
CONTACT SELLER FOR PRICE
Under 30 min from youNorth Jackson, OH

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