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Dumpster Rental in Winter Park, FL

Alright, listen up. Setting a dumpster in Winter Park ain't always a cakewalk. You got tight corners and mature landscaping in neighborhoods like Olde Winter Park and Dixie Terrace, meaning you gotta be precise, or you'll scratch up a brick pillar. Plus, that sandy soil around here, especially after a good rain, means anything heavy *will* sink if you don't pad it right. And don't even get me started on the shared driveways common in some of the older duplex sections – you block your neighbor, you're gonna hear about it.

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Come summer, that Florida sun bakes the asphalt in driveways to a soft, pliable mess. You drop a loaded dumpster on it without proper plywood protection, and you're leaving permanent divots. Always use at least 2x10s or robust plywood under those wheels, especially from May through October, or you'll be fixing more than just your project.

Dumpster Rental Costs & Info in Winter Park

Avg. Cost (20-Yard)
$550
Permits
Disposal Rules
Most of us are running loads to the Orange County Landfill, located off of Young Pine Road in Orlando. Sometimes the South Transfer Station, but it all ends up at OCL.

Local Dumpster Rental Regulations in Winter Park

Permit Requirements

If that dumpster is touching the street or any public right-of-way, you're looking at a Right-of-Way Obstruction Permit from the City of Winter Park's Public Works Department. Costs vary, but expect to shell out around $75-$100 for it, and it usually takes a few business days to process. On a private driveway, you're usually clear, but check with your HOA if you're in a managed community.

Disposal & Landfill Info

Landfill: Most of us are running loads to the Orange County Landfill, located off of Young Pine Road in Orlando. Sometimes the South Transfer Station, but it all ends up at OCL.

Fees: $48/ton for general waste. C&D debris is sometimes slightly lower around $42-$45/ton if it's a clean load, but expect a minimum charge for anything under a ton.

Residential & Construction Dumpster Sizes in Winter Park

Residential Friendly
10Yard

Fits in Winter Park driveways. Perfect for garage cleanouts.

~$415avg.
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Best Value
20Yard

The standard size for home renovations in FL.

$550avg.
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Construction
30Yard

For large demolition and commercial sites.

~$745avg.
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Dumpster Rental Companies in Winter Park

Coast to Coast Disposal

Top Rated 2025Top Rated
Verified

500 N Maitland Ave, Maitland, FL 32751, United States

5
(84 reviews)
Licensed & InsuredLocally Owned

Falcon Dumpster Rental Orlando

Top Rated 2025Top Rated
Verified

189 S Orange Ave, Orlando, FL 32801, United States

5
(21 reviews)
Licensed & InsuredLocally Owned

CF Dumpster Rental Orlando

Top Rated 2025Top Rated
Verified

37 N Orange Ave suit 500, Orlando, FL 32801, United States

5
(10 reviews)
Licensed & InsuredLocally Owned

Eco Haul Services & Dumpster Rentals

Verified

7536 Grand Ave, Winter Park, FL 32792, United States

5
(6 reviews)
Licensed & InsuredLocally Owned

DUMPEX Dumpster Rentals

Top Rated 2025Top Rated
Verified

5546 Canteen Ct, Oviedo, FL 32765, United States

5
(34 reviews)
Licensed & InsuredLocally Owned

Load It Up Dumpster Rental, LLC

Top Rated 2025Top Rated
Verified

1721 28th St, Orlando, FL 32805, United States

5
(41 reviews)
Licensed & InsuredLocally Owned

Global (GRD)

Top Rated 2025Top Rated
Verified

7208 Overland Rd, Orlando, FL 32810, United States

5
(67 reviews)
Licensed & InsuredLocally Owned

World of Dumpsters and Junk Removal

Top Rated 2025Top Rated
Verified

118 E Jefferson St Ste 308, Orlando, FL 32801, United States

5
(217 reviews)
Licensed & InsuredLocally Owned

Checheres Dumpster Rental, LLC

Top Rated 2025Top Rated
Verified

11868 Ginsberg Pl, Orlando, FL 32832, United States

5
(61 reviews)
Licensed & InsuredLocally Owned

Dumpster Drop Dumpster Rental

Top Rated 2025Top Rated
Verified

4669 L B McLeod Rd Suite F-1, Orlando, FL 32811, United States

5
(70 reviews)
Licensed & InsuredLocally Owned

Frequently Asked Questions

How much does a dumpster cost in Winter Park?

Average rates for a 20-yard dumpster in Winter Park sit around $550. Prices typically range from $300 to $600 depending on the size (10-40 yards) and rental duration.

Do I need a permit for dumpster placement in Winter Park?

You usually don't need a permit for driveway placement in Winter Park. However, placing a dumpster on the street likely requires a city permit.

Where does the waste go?

Most local haulers dispose of debris at Most of us are running loads to the Orange County Landfill, located off of Young Pine Road in Orlando. Sometimes the South Transfer Station, but it all ends up at OCL..

What sizes are available in Winter Park?

Most providers in Winter Park offer 10, 20, 30, and 40-yard dumpsters. A 20-yard dumpster is the most common choice for home renovations.

Why Choose Us?

  • Verified local providers with proven track records
  • Transparent pricing with no hidden fees
  • Fast delivery and flexible rental periods