Cypress, TX Roofing Contractor You Can Actually Trust
Jerry Pilley has seen every hail storm that has rolled through Cypress — and he will not sell you a roof you do not need.
Why Cypress Is Different
Roofing in Cypress is its own animal.
Cypress is arguably the single busiest roofing market in greater Houston, and there is a simple reason: it gets hammered. The Cypress/northwest Harris corridor sits directly under the path that most spring supercells take as they roll off the Hill Country and feed on gulf moisture. Quarter-sized hail is a near-annual event, and golf-ball to tennis-ball hail has hit Bridgeland, Fairfield, and Coles Crossing in recent years.
Because so much of Cypress is new construction — huge master-planned communities like Bridgeland, Towne Lake, Fairfield, and Cypress Creek Lakes built out between 2000 and the present day — the housing stock is a mix of 5-year-old builder specials and 20-year-old roofs that are aging out at the same time builders are still framing. Every major hailstorm brings a flood of storm-chasing roofers with out-of-state plates knocking doors, and Cypress homeowners have learned the hard way that the guy with the clipboard and the uniform shirt is often gone by the next claim cycle. That is exactly the gap Jerry fills.
We live and work here, we pull permits under a real Texas address, and we will be answering the phone next spring when the next storm rolls through. Cypress also has ferocious UV on south-facing slopes and standing humidity year-round, which means builder-grade 30-year shingles rarely make it past year 18 without losing granules, curling tabs, or growing algae streaks.
What We See In Cypress
Roofing problems unique
to Cypress homes.
Based on actual jobs across Cypress.
Hail impact damage from spring and early summer storms
Cypress averages one to two hail events per year that produce insurable damage. Even marble-sized hail fractures the fiberglass mat on older shingles, and adjusters will often approve replacement if impact density exceeds 8 hits per test square.
Storm chaser fraud after every hailstorm
Out-of-state contractors flood Cypress neighborhoods after storms, sign up homeowners with inflated contracts, then disappear when the insurance check hits. We have rebuilt dozens of roofs from those failed jobs and know exactly what to look for.
Wind-lifted shingles on new builds
Production builders in Bridgeland and Cypress Creek Lakes routinely under-nail shingles to save time. The first 60 mph squall line after closing peels tabs off the ridge and the homeowner finds out during the first hard rain.
Blocked gutters from pine straw and oak catkins
Cypress lots are loaded with pines and live oaks. Gutters clog fast, water backs up under the drip edge, and the fascia starts rotting. Most Cypress homes need a gutter cleanout every spring and fall at minimum.
Ventilation failures in two-story attics
Builders often skip proper ridge-and-soffit balance to save money. The result is 140-degree attics, premature shingle failure, and sky-high summer cooling bills in places like Towne Lake and Fairfield.
Pipe boot cracks at 8-10 years
The rubber collars around plumbing vents are the single most common leak source on Cypress roofs. They dry out in the UV and split, and the leak shows up on the ceiling below a bathroom years before the roof itself fails.
Where We Work
12+ Cypress neighborhoods.
We have done jobs in just about every section of Cypress, TX 77429, 77433. If yours is not listed, give us a call.
Why Cypress Picks Jerry
Honest roofing for
Cypress, Texas.
No high-pressure sales, no salespeople taking 12% commission, no door-knockers after a storm. Just Jerry on the roof, telling you the truth.
Talk to Jerry: (409) 351-1529We are local, not a storm-chasing out-of-state crew. When your roof needs warranty work five years from now, we still answer the phone.
Jerry personally inspects every Cypress roof and shows you the damage on camera. No fake hail marks, no circled chalk on good shingles.
We work directly with every major insurance carrier and meet your adjuster on the roof so nothing gets missed in the claim.
Lower overhead than the corporate Houston roofers — the savings go to you, not to a sales team or an office building.
Recent Job
Just finished in Cypress.
The Nguyen Family
Bridgeland, Cypress
ScopeFull replacement of 34 squares, IKO Dynasty in Driftwood, new seamless gutters on all four sides, ridge vent upgrade
Golf-ball hail in May 2025 cracked the mat on the original builder 25-year shingles. We documented the damage, met the Allstate adjuster, and had the claim supplemented twice to cover decking and drip edge. Finished in two and a half days.
Available Here
Every service we offer.
Available across Cypress, TX 77429, 77433.
Cypress FAQ
Questions Cypress homeowners ask.
How much does a new roof cost in Cypress, TX?+
Most Cypress roof replacements run $9,000 to $20,000 for a standard single-family home. Bridgeland and Towne Lake homes in the 3,000-4,000 sq ft range typically land around $13,000-$17,000 for architectural asphalt shingles. Price depends on pitch, square count, tear-off layers, and decking condition.
A storm chaser knocked on my Cypress door — should I sign?+
No. Never sign anything the day a contractor knocks. Reputable Cypress roofers will let you get a second opinion and will give you time to call your insurance company first. If someone pressures you to sign an 'inspection authorization' on the spot, that is a contingency contract and you may be locked in.
Will my Cypress insurance claim get approved after hail?+
It depends on the age of your roof and the density of the impact marks. We do a free pre-claim inspection, show you the damage, and tell you honestly whether a claim will stick. Filing a weak claim burns your deductible and can affect your rates — we only recommend filing when the evidence is solid.
How long will a new asphalt roof last in Cypress?+
A properly installed architectural shingle roof with good ventilation should give you 20 to 25 years in Cypress before it needs replacement. The two biggest factors are attic ventilation and hailstorms — we cannot control the weather, but we can make sure the ventilation is done right.
Do you replace gutters and fascia in Cypress too?+
Yes. We handle seamless aluminum gutters, fascia wrap, soffit repair, and siding work on every Cypress job. It is almost always cheaper to do gutters and fascia the same time as a roof replacement since the crew is already on site and the scaffolding is up.
Also Serving
Other areas near Cypress
Free Inspection
Free roof inspection
in Cypress, TX.
No pressure, no upselling, no door-knocker tactics. Jerry comes out, walks the roof, shows you photos, and gives you the truth.