SSKM Construction Corp · Roof Replacement in Middletown
Roof Replacement in Middletown, NY, Done Right
- BBB Accredited A+
- 25+ Years in the Hudson Valley
- Free Estimates
- 5.0 stars on Google
SSKM Construction Corp replaces roofs in Middletown with a full tear-off, a proper look at the roof deck, ice and water shield, new underlayment and new shingles, with the old roof hauled away. Middletown sits high for this part of the valley, so wind and lingering snow work its roofs hard, and we build for that. Every job starts with a free written estimate.
- Full tear-off? Yes. We remove the old layers so we can inspect the deck.
- Victorian home? Yes. Steep older roofs, like those on Highland Avenue, are core work.
- Estimate? Free, written, no obligation.
Middletown averages about 520 feet in elevation, and wind and snow that river-level towns miss hit roofs here harder. A new roof needs the right ice protection, ventilation and flashing, and we explain every layer in writing before we start.
What We Do in Middletown
Roofing, siding & construction in Middletown
Roofing
Roofing in Middletown →
Roof replacement
Roof Replacement in Middletown →
Roof repair
All Roof repair services →
Siding
Siding in Middletown →
Decks
All Decks services →
Framing
All Framing services →
Remodeling
All Remodeling services →
Interior painting
All Interior Painting services →Exterior painting
All Exterior painting services →
Snow removal
All Snow removal services →
Kitchen remodel
All Kitchen remodel services →Bathroom remodel
All Bathroom remodel services →One crew for all of it. Whichever of those you need, the visit and the written estimate cost you nothing.
Limited time: $500 off a full roof replacement. Start with a free written estimate, and ask about the offer when you call.
Real Reviews
Rated 5.0 stars by Hudson Valley homeowners
The roof was completely done and cleaned up in 2 days, his guys had even cleaned out my gutters.
SSKM Construction did an outstanding job replacing the sheathing and removing and replacing the existing siding on my home.
It has been a pleasure and honor to work with Luis and his crew for the past 5 years.
Luis and his crew did a great job swapping out two nasty pull-out windows in my basement.
Those reviews are real, and they are on Google. If you would like to be the next one, the estimate costs nothing.
Local Conditions
Common roof replacement calls we get in Middletown, NY
- Old roofs on large Victorian houses with several layers of shingles to remove before the deck can be inspected
- Wind exposure on a city that averages roughly 520 feet and rises toward 740 feet at its northern edge
- Ice damming at the eaves after a thaw, driven by snow that sits longer on higher ground
- Flashing at chimneys, dormers and wall transitions where steep roofs meet masonry
- Roof decking that has been damp for years and needs replacing once the old roof is off
About Middletown, Orange County
Middletown is the largest city in Orange County, with a population of 30,345 at the 2020 census. It sits in the western Hudson Valley near the Wallkill River and the foothills of the Shawangunk Mountains, and its elevation, about 520 feet on average, is the detail that matters most for roofing: wind and lingering snow work roofs harder here than they do down by the river.
The city grew through the late 19th and early 20th centuries as a railroad hub, and much of its housing comes from that period. Highland Avenue carries some of the largest Victorian houses in the city. Roofs of that size and age call for a careful tear-off and a plan for the deck, the flashing and the ventilation.
Need roof replacement in Middletown? Call (845) 549-7944 or request a free estimate.
Recognise any of that on your own house? We will come out, look at it properly, and tell you what it actually needs.
That is our patch. If your street is on that map, we can be out to look at the job this week.
Local Routes
How we get to Middletown, NY
We work Middletown out of Newburgh. These are the corridors that connect it to the neighbouring towns we cover, and the roads our trucks are actually on getting there.
We cover the rest of the mid-Hudson Valley from the same Newburgh shop: Roofing in New Windsor, Roofing in Walden, Roofing in Poughkeepsie, Roofing in Hyde Park.
Middletown to Walden
- Roads we run
- I-84, NY 208
- County
- Orange County
- Straight-line distance
- About 14.1 miles, not a drive time
Middletown to Cornwall
- Roads we run
- I-84, NY 300
- County
- Orange County
- Straight-line distance
- About 19.7 miles, not a drive time
Middletown to New Windsor
- Roads we run
- I-84, NY 17K, NY 32
- County
- Orange County
- Straight-line distance
- About 20.4 miles, not a drive time
Straight-line miles between town centres, measured from OpenStreetMap coordinates on 27 August 2026. They are not drive times. Road names are the routes mapped between those same two points.
Good to Know
Roof replacement built for Middletown homes
How we approach a roof replacement in Middletown
We tear off the old roof completely, so nothing is hidden. Once the deck is exposed we inspect it, replace any boards or plywood that have gone bad, and tell you before we do so the cost is never a surprise. Then comes ice and water shield at the eaves and valleys, synthetic underlayment, drip edge, starter strip and new shingles, with flashing done properly at chimneys, walls and vents.
Middletown's elevation makes the details count. Snow that sits longer on higher ground means more meltwater and refreezing at the eaves, so ice protection and attic ventilation matter. On large Victorian roofs with steep pitches and dormers we plan the staging and safety carefully, protect what is around the house, and haul the debris when we finish.
The roof was completely done and cleaned up in 2 days, his guys had even cleaned out my gutters.
Why Middletown homeowners choose SSKM for roof replacement
A roof replacement is a large investment, and homeowners want a contractor who is accountable and explains the work. We put the price and the scope in writing and show you what is going on your house. With 25-plus years in the trade, a 5.0-star rating on Google and insurance in place, every Middletown roof replacement estimate is free.
Still deciding? Tell us what the project is and we will come look at it. The estimate is free and written down.
At a Glance
SSKM Construction Corp roof replacement in Middletown, NY at a glance
| Where our crew comes from | Newburgh, NY, based at 283 N Plank Rd |
|---|---|
| Estimates | Free, and written down before any work starts |
| Google rating | 5.0 stars on Google |
| Years in the Hudson Valley | 25+ |
| Who you deal with | Luis and Steven, the co-owners, and the SSKM crew. Not a call centre |
| Trades under one roof | Roofing, roof replacement, roof repair, siding, decks, framing, remodeling, kitchen and bathroom remodels, interior and exterior painting, snow removal |
Ready to protect and improve your home?
Free estimates · 25+ years in the Hudson Valley · Mon-Sun 7:00 AM to 6:00 PM
Getting There
Getting to Middletown from our shop
Middletown is west of us on I-84, out toward where the interstate meets NY 17, the future I-86. NY 17M and NY 211 run right through the city and US 6 parallels I-84 to the south, so we can reach the Highland Avenue neighborhoods and the newer housing toward the Wallkill on the same trip.
Nearby Areas
Other towns we serve near Middletown
Good to Know
Middletown roof replacement: frequently asked questions
How much does a roof replacement cost in Middletown, NY?
It depends on the size and pitch of the roof, the number of layers to tear off, and the condition of the deck. We never quote over the phone. Call (845) 549-7944 for a free written estimate.
Does Middletown's elevation change how you build a roof?
It changes what we look at. Wind and lingering snow are harder on roofs at higher elevation, so we pay close attention to shingle installation, ice and water shield at the eaves, and attic ventilation.
Do you tear off the old roof or go over it?
We tear off, so we can inspect the deck and install the underlayment and ice and water shield properly. Covering old shingles hides problems.
Can you replace the roof on a large Victorian home?
Yes. Steep pitches, dormers and chimneys are familiar work. We plan the staging, safety and flashing for the house in front of us.
What about the plywood under the shingles?
We inspect the deck once the old roof is off. If any boards or plywood need replacing, we tell you before we do the work.
Is the roof replacement estimate really free in Middletown?
Yes. We inspect the roof and give you a written quote at no cost and no obligation.
We pull the permits our work needs and deal with the inspections. If you want to check the requirements yourself, Middletown permits and inspections are handled by the city, and current requirements are listed on the City of Middletown official site.
Question we did not answer? Ask it on the phone. You will get a straight answer from an owner, not a script.
We replace roofs across the mid-Hudson Valley from the same Newburgh shop. Every town we cover is listed on the service areas page, and the full roof replacement service is written up in one place.
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