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Family-owned since 2014 · 4.99 ★ × 463 reviews · 16,000+ jobs

Dumpster Rental in Windsor, CT

Roll-off dumpster rental and junk removal in Windsor, Hartford County. Up-front pricing, same-day delivery when booked before 11 AM, same team since 2014.

dumpster-on-driveway in Bristol, CT by Grizzly Junk Pros
  • 16,000+

    jobs completed

  • 4.99

    463 reviews

  • Family-owned

    since 2014 (12 years)

  • Licensed & insured

    in Connecticut & New York

Dumpster rental rates in Windsor

Up-front pricing. No zone pricing. Each size includes delivery, pickup, dumping, the 7-day rental window, and a weight allowance shown below. Standard add-ons disclosed up-front and confirmed at booking. Tap any size for the dedicated size guide.

Included in your base rate

  • Delivery and pickup
  • Dumping at licensed transfer station
  • 7-day rental window
  • Included weight per size (see size table)
  • No zone pricing or driveway surcharges across our service area

Standard add-ons (disclosed up-front)

  • Overweight: $0.10 per pound over the included cap
  • Extension day: $15 per day beyond the 7-day window
  • Tire (if loaded): $50 each
  • CFC appliance (refrigerator, freezer, AC, dehumidifier — if loaded): $50 each
  • Mattress or box spring (if loaded): $50 each

Add-on charges reflect actual transfer-station and disposal fees passed through to you — we don't mark up overweight, extra items, or disposal costs.

Final pricing confirmed at booking based on actual weight, rental length, and items loaded.

What can’t go in the dumpster
  • Paint, solvents, oil, household chemicals (route through CT DEEP hazardous waste)
  • Batteries — any kind, lithium especially
  • Asbestos-containing materials (specialized hauler required)
  • Tires (route to a tire dealer or pay $50/each disposal fee if loaded)
  • Medical waste
  • Liquids of any kind
  • Customer is responsible for re-routing prohibited items. See the full prohibited-items list for Connecticut.

What you see is what you book — no zone pricing, no driveway surcharges, no weekend delivery fees. Standard charges for overweight, extension days, and certain prohibited items disclosed above and confirmed at booking.

Grizzly Bag dumpster service in Connecticut

Smaller jobs

Need something smaller? Try a Grizzly Bag.

Not every job needs a full roll-off dumpster. Our Grizzly Bags hold 8 cubic yards — perfect for kitchen demos, single-room cleanouts, deck debris, or yard waste.

  • No rental timeframe — fill on your schedule
  • No weight limit (restrictions apply)
  • Guaranteed flat-rate pricing — what you book is what you pay

We drop it off, you fill it on your timeline, we pick it up when you’re done.

Learn More About Grizzly Bags

Full-service junk removal — we do the loading

When loading the dumpster yourself isn’t the right call — small volume, awkward access, or you just want it gone today — we send a crew. Pricing runs by truck space used, not by item. Final pricing confirmed before removal begins.

  • Minimum Load$179
  • 1/8 Truckload$239
  • 1/6 Truckload$309
  • 1/4 Truckload (~5 yd³)$359
  • 1/3 Truckload$419
  • 3/8 Truckload$489
  • 1/2 Truckload (~10 yd³)$559
  • 5/8 Truckload$659
  • 2/3 Truckload$759
  • 3/4 Truckload (~15 yd³)$809
  • 5/6 Truckload$849
  • 7/8 Truckload$919
  • Full Truckload (~20 yd³)$979

Not sure which tier? Send a few photos and we’ll size it for you.

Get a Free Junk Removal Quote

Single awkward items have their own pages too — see electronics and TV disposal in CT and piano removal in CT for how those pickups are priced.

Windsor calls itself Connecticut's oldest town, and its housing tells the whole story in one drive: 18th-century centers on the Palisado green, tobacco-country farmhouses out in Poquonock and Rainbow, streetcar-era neighborhoods in Wilson along the Hartford line, and postwar subdivisions filling the gaps. Four different building eras means four different renovation problems — and it's why we ask what decade your house is before we suggest a can size.

The dispatch run is one of our longest straight lines: I-91 north from our West Haven yard, about 55 minutes. That distance makes Windsor a next-day-window town — we'd rather promise tomorrow morning and show up than promise this afternoon and call with apologies.

One rate ladder, every neighborhood

$447 (10-yard), $547 (15), $647 (20), $899 (30/40 tier — two 20-yard cans, together or swap-style). All-in pricing: delivery, pickup, disposal, and a 7-day rental. Weight allowances of 1,000 / 2,000 / 4,000 / 6,000 lbs scale with the size; the scale settles any overage at $0.10/lb. Extensions past the week run $15/day.

What decade is your debris?

It matters more than square footage. A 1950s Wilson cape sheds light drywall and pine — volume-priced work, and the 15-yard usually wins. A Palisado-area colonial sheds plaster, lath, and old-growth timber that weighs nearly double per cubic yard — those jobs book the 20 for the allowance, not the space. Every can in our fleet is the identical 22-foot box either way; the size on your order is the weight you're buying.

Placement across town

Windsor placement is mostly painless — real driveways, real setbacks. The exceptions run to the older center streets where a shared or short apron needs a think, and rural Poquonock properties with long approaches under tree canopy. Firm ground, planks under the wheels off pavement, and a photo to (203) 219-8855 if you're unsure — that covers ninety-odd percent of cases.

Not every job needs a can

Small purge? Ask the town what residents can drop off and where before spending $447 with us. When the pile is a basement, an attic, or a whole tobacco barn's worth — that's when you call.

Across the town lines

Hartford directly south, Bloomfield west, Windsor Locks north, East Granby northwest, and South Windsor and East Windsor across the Connecticut River. Same rates everywhere — How Pricing Works.

Last reviewed: September 2026 · Local crew, Stamford depot · (203) 219-8855

What customers in Windsor are saying

  • Y
    Spectacular service, even during Covid! First, a human answered their phone immediately and was clear and courteous. How rare these days! I got an appointment for next day! As promised, received a call that crew was on its way. My mother gave me last minute permission to move a fridge, not part of original request. So I had to tell the poor guys upon arrival that there was a surprise fridge move, two in fact, one removed, one moved within house. Crew didn't flinch. Then one fridge move required its doors AND house door to come off, which they achieved with impressive skill. I'm a manager in my work life and can say their professionalism was superb. Also, important for environment, the company claims to recycle materials. A+ on every level.

    Cathleen M.

    YelpAug 2020

  • Y
    Amazing experience! I would definitely hire them again! Every interaction with this company, from setting up the appointment with Justin, and then having to move it up, because my long distance home movers moved up their delivery day at the last minute, and to the appointment itself, has been a wonderful, and positive experience. When we had to change my delivery window at the last minute, Justin was incredibly helpful and accommodating. And the amazing movers, Eric and Mike, "Big Mike", were so wonderful, professional, helpful, kind, and did excellent work.

    Larisa R. · Stamford, CT

    YelpMay 2017

  • Y
    It's spring cleaning time! Who am I going to call? the same great company I called 3 times before...grizzly junk pros! I have found these guys to be experts in moving large bulky items. They are hard workers, honest, fair and extremely efficient. I won't take a chance on any other company because I know what to expect from this one. They've done my cellar, things inside the house and now will call them for cleaning out the attic. The areas I've called them for aren't easy to maneuver in...amazing how they adapt to the job at hand.

    Pat A. · Stamford, CT

    YelpMar 2024

Windsor dumpster rental FAQs

How long does delivery to Windsor take to schedule?
Next-day, as a rule. Windsor sits near the top of our Hartford County range — call it 55 minutes from our West Haven yard straight up I-91 — so we book a confirmed next-day window rather than stretch for same-day at that distance.
What does a 20-yard cost in Windsor?
$647, same as everywhere we deliver — Windsor Center, Poquonock, Wilson, or Rainbow. The full ladder is $447 / $547 / $647 / $899 by size, with delivery, pickup, disposal, and 7 days included.
I'm renovating a house from the 1700s-1800s district — anything special?
Old-house demo runs heavy — plaster, dense old-growth framing, sometimes slate. Size by weight, not volume: the 20-yard's 4,000-lb allowance handles most of it, and anything past your allowance is $0.10/lb, not a penalty fee.
Can the can sit on the street in front of my house?
That's the town's call, not ours — if the can leaves your property for the public road, check with Windsor's town offices first. On your own driveway no permit is needed in most Connecticut towns, and Windsor's driveways generally fit our 22-foot can fine.
What's excluded from the load?
Concrete, dirt, brick, and stumps — plus hazardous waste like paint, solvents, and propane tanks. Everything else from a cleanout or renovation is standard cargo.

Need a structure taken down in Windsor?

The can handles the debris — we also handle what the debris used to be. Light structures come down under our own gloves; full demolition is coordinated through our licensed demolition partner, with every load out in our own dumpsters.

We take down:

  • Hot Tub Removal in Windsor
  • Shed Removal in Windsor
  • Above-Ground Pool Removal in Windsor
  • Deck Removal in Windsor
  • Fence Removal in Windsor
  • Garage Demolition in Windsor

Coordinated:

  • House Demolition in Windsor
  • In-Ground Pool Removal in Windsor

Full details, pricing, and intake: demolition & removal services.

Nearby towns we serve

Same trucks, same rates — the Windsor routes share dispatch with the towns next door. No zone pricing anywhere in our service area.

Full county coverage, town by town: dumpster rental across Hartford County.

Get a quote for Windsor

Same-day delivery when you call before 11 AM. (203) 219-8855 — Mon–Fri 8 AM – 4 PM live, AI after-hours and weekends.