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New & Used Winston Trailers for Sale

Find 11 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 AP21025EL Equipment Trailer
On Order

New Winston 10 ton electric brake tag 20ft flat + 5ft cleated outside dove tail w/ 5' fold over spring...

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

New Winston 10 ton electric brake tag 20ft flat + 5ft cleated outside dove tail w/ 5' fold over spring...

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

New Winston 10 ton electric brake tag 20ft flat + 5ft cleated outside dove tail w/ 5' fold over spring...

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

This new 2026 Winston Pro Paver is 24' long plus a 6' beaver tail for a total length of 30.'...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
CONTACT SELLER FOR PRICE
North Jackson, OH
2026 Winston AP22230AL-HR Equipment Trailer
On Order

This new 2026 Winston Pro Paver is 24' long plus a 6' beaver tail for a total length of 30.'...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
30' 0
CONTACT SELLER FOR PRICE
North Jackson, OH
2026 Winston AP20825EC Equipment Trailer

Stock# 44553 New 2026 Winston AP20825EC Equipment Bumper Pull Trailer  The 20 to 22.5 Ton ProSeries Dual Tandem Trailers are...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
SALE
$12,999$13,130
North Jackson, OH
7 TON EQUIPMENT TRAILER 16' LONG

2025 WINSTON EQUIPMENT TRAILER. 7K AXLES. 82" BETWEEN FENDERS. RADIAL TIRES. H.D. 4" CHANNEL RAMPS. OAK DECKING. ADJUSTABLE PINTLE OR...

Manufacturer
Winston
Condition
new
Payload Capacity
11200
Weight
2800 lbs
Length
16' 0
$7,499
Darien, IL
2026 Winston AP20825EC Equipment Trailer

Stock# 43892 New 2026 Winston AP20825EC Equipment Bumper Pull Trailer  The 6, 7, and 8 Ton Custom Series deckover tandem...

Manufacturer
Winston
Condition
new
Pull Type
bumper
Length
25' 0
SALE
$12,999$13,124
North Jackson, OH
7 TON EQUIPMENT TRAILER 16' LONG

2025 WINSTON EQUIPMENT TRAILER. 7K AXLES. 82" BETWEEN FENDERS. RADIAL TIRES. H.D. 4" CHANNEL RAMPS. OAK DECKING. ADJUSTABLE PINTLE OR...

Manufacturer
Winston
Condition
new
Payload Capacity
11200
Weight
2800 lbs
Length
16' 0
$7,499
Darien, IL
8 TON 18' EQUIPMENT TRAILER

8 TON 18' EQUIPMENT TRAILER. LOW PROFILE PAN STYLE TRAILER. NO DOVETAIL NEEDED. H.D. SPRING ASSISTED 4" CHANNEL RAMPS. OAK...

Manufacturer
Winston
Condition
new
$8,999
Darien, IL
10 TON DECKOVER Equipment Trailer
On Order

10 TON DECKOVER. WINSTON 20' FLAT + 5' DOVETAIL. OAK DECKING. DEXTER OIL BATH AXLES WITH ELECTRIC BRAKES. RADIAL TIRES....

Manufacturer
Winston
Condition
new
Payload Capacity
20000
$13,999
Darien, IL

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