Roofing & Siding Contractor in Middletown, NY
Roofing & Siding Contractor in Middletown, NY
- BBB Accredited A+
- 25+ Years in the Hudson Valley
- Free Estimates
- 5.0 stars on Google
SSKM Construction repairs and replaces roofs and siding across Middletown, the largest city in Orange County. Averaging around 520 feet and rising toward 740 at its northern edge, Middletown takes wind and snow that river-level towns do not, and we build for that, the Victorian roofs along Highland Avenue included. Estimates are free and written.
- Victorian homes? Yes. Highland Avenue's steep older roofs are core work.
- Does elevation matter? At around 520 feet, wind and lingering snow work roofs harder here.
- The whole area? Yes, the city and the surrounding Orange County towns.
Middletown sits high for this part of the valley, averaging around 520 feet and rising toward 740 at its northern edge, so its roofs take wind and snow that river-level towns do not. SSKM repairs and replaces roofs and siding across Orange County’s largest city.
What We Do in Middletown
Roofing, siding & construction in Middletown
Roofing
All Roofing services →
Roof replacement
All Roof replacement services →
Roof repair
All Roof repair services →
Siding
All Siding services →
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.
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 roofing challenges in Middletown, NY
- Aging roofs on the large Victorian houses along Highland Avenue and the older housing near downtown
- Wind exposure across a city that averages roughly 520 feet of elevation, rising toward 740 feet at its northern boundary
- Ice damming at the eaves after a thaw, driven by snow that sits longer on higher ground
- Flashing failures where steep Victorian roofs meet chimneys, dormers and wall transitions
- Simpler but equally exposed roof forms on the newer construction spreading toward the Wallkill River
About Middletown, Orange County
Middletown is the largest city in Orange County, New York, with a population of 30,345 at the 2020 census, and it sits in the western Hudson Valley near the Wallkill River and the foothills of the Shawangunk Mountains. Its elevation is the detail that matters most for roofing: the city averages about 520 feet, rising to roughly 740 feet at its northern boundary and dropping to about 460 feet at the southern edge.
The city grew hard through the late nineteenth and early twentieth centuries as a railroad hub, and that period still defines much of the housing stock. Highland Avenue carries some of the largest Victorian houses in the city, several of which are now in institutional use. Downtown holds several historic churches, including the First Congregational Church, whose 1872 building has the highest spire in the city. Hillside Cemetery was laid out by Calvert Vaux, the same architect behind much of the region’s designed landscape.
Need roofing or siding 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
Roofing in Middletown, from Highland Avenue Victorians to newer builds
Siding, wind exposure, and serving Middletown
Siding in Middletown runs the same split as the roofs. On the older Victorian housing, wood clapboard and shake are often original or close to it. Fiber-cement has become the practical middle ground on those homes, because it resists rot and insects, holds paint far longer than wood, and can be milled to mimic wood grain convincingly, while carrying a 30-plus-year lifespan through exactly the freeze and thaw swings this elevation produces.
On newer construction, vinyl is usually the value choice, and modern insulated versions add a real R-value boost against a Middletown winter. Its weakness is impact resistance in deep cold, where a stray branch or a ladder can crack a brittle panel, and that is worth knowing before choosing it for an exposed elevation.
Whatever the material, what actually decides the outcome is the layer behind it. We check the sheathing and the water-resistive barrier before new siding goes up, because covering rotted sheathing with new panels buys you a good-looking wall and the same problem two years later.
Great work, fair price, and they showed up when they said they would.
Why Middletown homeowners choose SSKM
Middletown is the biggest city in Orange County and it has no shortage of contractors passing through. What we offer is the opposite of that: a family-run company that has been working across the Hudson Valley for more than 25 years, where the owners, Luis and Steven, are the people who show up and the people you deal with from the estimate through to the final walkthrough.
Because we self-perform roofing, siding, framing, decks, remodeling and painting, a Middletown project that turns out to involve more than the roof does not become your job to coordinate. If we find rotted sheathing behind the siding or structural work under a failing roof, the same company handles it.
Estimates are free, written, and based on an inspection of your actual roof or walls. If a repair will buy you years, we will tell you that instead of quoting a replacement.
Still deciding? Tell us what the roof or the room is doing and we will come look at it. The estimate is free and written down.
At a Glance
SSKM Construction Corp in Middletown, NY at a glance
| Where our crew comes from | West on I-84 toward NY 17; NY 17M and NY 211 run through the city |
|---|---|
| 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 roofing: frequently asked questions
Do you work on Middletown’s older Victorian homes?
Yes. Middletown grew as a railroad hub through the late 1800s and early 1900s, and Highland Avenue in particular carries some of the largest Victorian houses in the city. Those roofs are steep and full of transitions, which is a different job from a modern gable, and we price and detail them accordingly.
Does Middletown’s elevation really affect my roof?
It does. The city averages around 520 feet and rises to roughly 740 feet at its northern boundary, which means more wind exposure and snow that sits longer than it does closer to the river. Wind creases shingles along ridges and rake edges, and lingering snow drives the freeze and thaw cycling behind ice dams.
Can you handle storm damage in Middletown?
Yes. Call (845) 549-7944 and we will get out to assess it. Wind damage in particular is often not visible from the ground, because a creased shingle can look intact and still fail, so we inspect the roof itself.
Do you serve the whole Middletown area?
We serve Middletown and the wider Hudson Valley across Orange, Dutchess, Putnam, Sullivan, Ulster and Westchester Counties. SSKM Construction is based in Newburgh, so Middletown is well within our normal working area.
Is the roofing estimate free in Middletown, NY?
Yes. We inspect the roof or the siding 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.
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