Architectural shingles
Metal roofing
Tile roofing
GAF
Owens Corning
Flat & low-slopeFree roof inspection with deck photos before we talk money - GAF and Owens Corning certified installation
Fast, Reliable Roof Replacement Across Highland
Roof replacement in Highland typically runs $9,800 – $16,500 for a standard asphalt shingle tear-off and re-roof on a 1,500 – 2,200 sq ft home, with architectural shingles landing in the $12,000 – $18,000 range. The number moves based on what we find when the old roof comes off, and in Highland, what we find is often shaped by the foothill terrain and the Santa Ana winds that come through the Cajon Pass. We’re Oakmont Roof Repair, led by Noel Fierro, and we’ve replaced enough roofs on Highland’s sloped lots to know that what’s under the tile matters as much as what goes on top. If your roof is failing, call (866) 942-0875 for a free estimate. We’ll walk the roof, give you a written line-item quote, and tell you exactly what you’re dealing with before any work starts.
Why Oakmont Roof Repair Is Highland’s Preferred Roof Replacement Company
We carry seven major roofing brands, GAF, CertainTeed, Owens Corning, IKO, Atlas, Tamko, and Boral, which means our recommendation is driven by what your roof actually needs, not by what product we happen to stock a lot of. That matters in Highland, where a 1990s tract house on a sloped lot has different requirements than a flat-lot stucco house in San Bernardino. We’re roofing specialists, not general contractors, and the entire service menu is roofing: inspection, repair, and replacement. Noel Fierro built the company around one trade, so every technician who shows up in the 92346 zip code knows roofs and nothing else.
Highland homeowners call us after storm seasons, after home inspections flag a failing roof, and after they’ve watched their neighbor’s tile get stripped by a Santa Ana event. We respond quickly to Highland, and we know the west-facing foothill streets where wind damage clusters. Our inspection-first approach means you can get an honest condition report before you spend a dollar. Repair when it makes sense. Replace when it’s time.
Styles & brands we work with






Roof Installation in Highland
Roof installation on a Highland home means tearing down to the deck, inspecting what the thermal cycling has done to it, and replacing every component from the underlayment up. We inspect what’s underneath before we quote what goes on top, because on foothill lots, the old underlayment is often shot even when the tile still looks fine. Then we install, tie the roof into the stepped foundation line, and close it out with a manufacturer-backed system. At Oakmont Roof Repair, that’s what we do.
A full roof installation in Highland on a 1,500 – 2,200 sq ft home runs $9,800 – $16,500 for standard asphalt shingles. Architectural shingles, which hold up better under the UV and look right on the region’s stucco tract houses, run $12,000 – $18,000. Material choice moves the number. Labor and permit costs stay fairly steady. The single biggest variable is what’s happening underneath once we open it up. We write priced allowances into the contract for decking replacement and flashing work, and we get written approval before we touch anything outside the original scope. Call (866) 942-0875 for an exact quote.
Decking and Underlayment Replacement
On the west-facing slopes above Baseline and down toward the 210 corridor, we regularly find roof decking that has softened under failed underlayment. The daily shift from 100-degree desert heat to cool mountain air dries out sealants and cracks the waterproofing layers. When we pull the old material, the deck often has to be replaced in sections. That’s a priced line item, not a surprise.
New Construction Roofing
We also handle new construction roofing for Highland homeowners building on sloped lots where the roof ties into retaining walls and stepped foundation lines. Getting the flashing and transitions right at the framing stage prevents leaks that would not show up until the first concentrated winter storm. We pull permits, pass inspections, and warranty the workmanship.
Roof Replacement Contractor in Highland
Hiring a roof replacement contractor in Highland is different from hiring one in a flat inland city because the tear-off work here exposes transitions and flashing details that most roofs never have. The foothill terrain forces the roof to tie into retaining walls and stepped foundation lines, and when we open up a roof here, the transitions are where the failures concentrate. That’s why we lead with a full inspection and write the contract accordingly. Oakmont Roof Repair handles the full lifecycle of the roof, so the same crew that inspects your roof can replace it.
We charge $9,800 – $16,500 for a standard replacement and $12,000 – $18,000 for architectural shingles, and we keep the quote honest by putting real allowances in writing. If the decking under the old tile is compromised, the allowance covers it at a pre-agreed price. We don’t do change orders that appear out of nowhere. You approve every dollar before we spend it. That’s how a roof replacement contractor should operate.
Flashing and Ridge Work on Foothill Lots
Highland homes on sloped lots need ridge lines, valleys, and flashing that can handle wind coming through the Cajon Pass. We replace flashing completely rather than patching around it. Cracked ridge tile on a west-facing slope is usually a sign that the entire ridge needs to come up and be re-bedded. We fix it once, correctly.
Full Roof Replacement
When the roof has reached the end of its life, we do a complete tear-off, repair or replace the deck as needed, install new underlayment, drip edge, and flashing, and then the roofing system itself. On a 1990s Highland stucco tract house up a foothill street, our crew pulled the concrete tile and found dried-out underlayment, a wind-cracked ridge, and two valleys where the decking had softened under failed ice and water shield. We wrote the decking replacement and new drip edge and flashing into the contract as a priced allowance, got written approval before touching it, and closed it out with CertainTeed architectural shingles and a ridge vent tied into the stepped foundation line. That’s how we work here.
Trusted Brands We Service in Highland
Oakmont Roof Repair installs and services roofing systems from seven leading manufacturers, including GAF, CertainTeed, Owens Corning, IKO, Atlas, Tamko, and Boral. For Highland homeowners, that means we can match the material to the home and the budget, whether it’s a value-tier asphalt shingle for a rental property off Greenspot Road or a premium Tamko or Boral system for a foothill home that takes the full brunt of Santa Ana wind. We stock local parts for the Roof Replacement brands we install, and we don’t push a single manufacturer’s line. The roof tells us what it needs.
See the difference
Before
After
Before
After
Before
AfterCommon Roof Replacement Problems We See in Highland Homes
- Cracked ridge tiles and popped shingles after Santa Ana events. The wind funnels through the Cajon Pass and concentrates damage on west-facing slopes, where homes along the foothill streets lose more tile and shingles than homes a mile downhill in the flats of San Bernardino.
- Failed underlayment under perfectly good-looking tile. The same UV that damages shingles also dries out the waterproofing layers underneath. We pull old tile and find the underlayment has turned brittle. That’s a tear-off trigger.
- Soft decking at valley transitions. Where two roof planes meet on a stepped foundation line, water collects and the decking softens under failed ice and water shield. We see this on 1980s and 1990s tract homes across the 92346 zip code.
- Flashing gaps exposed by concentrated winter storms. Highland doesn’t get much rain, but when it comes, it comes hard and fast. Loose flashing that the wind lifted months ago lets water in during the first real storm.
Pricing for Roof Replacement in Highland, CA
Here’s what you can expect. A standard asphalt shingle roof replacement on a 1,500 – 2,200 sq ft Highland home runs $9,800 – $16,500. Architectural shingles run $12,000 – $18,000. Premium systems from Tamko or Boral go up from there. The material itself is the biggest line item, followed by decking replacement if the old deck has failed, which happens more often on sloped foothill lots than on flat ground. We write a priced allowance for decking and flashing into every Highland contract, and we get written approval before any change is made. You’ll get a free estimate and a written line-item quote. Call (866) 942-0875 to schedule yours.
We Also Serve Cities Near Highland
Oakmont Roof Repair serves the surrounding foothill and valley communities beyond Highland as well. We regularly handle roof replacement work in San Bernardino, Muscoy, Redlands, and Loma Linda. The terrain changes from block to block out here, and we know how the wind and heat behave differently in each area. If you’re in one of those cities and need a roof replacement, call (866) 942-0875 and we’ll come out.
Serving Highland, CA — Our Local Coverage Area
We’re based in the Highland area and know this community well. Use the map below to see our service coverage — if you’re nearby, we can almost certainly help.
FAQs About Roof Replacement in Highland
The quote moves when the old roof comes off and we find decking failures, deteriorated flashing, or failed underlayment that wasn’t visible before tear-off. In Highland, this happens more often than in flat inland cities because the daily thermal cycling cracks the waterproofing layers while the tile above still looks fine. We handle this by writing priced allowances into the contract up front. The allowance says exactly what we’ll charge per square foot for decking replacement and per linear foot for flashing. Before we spend anything outside the original scope, we get written approval. Nothing moves without your signature. Call (866) 942-0875 to discuss your roof.
They affect it in two ways. First, the wind damages the existing roof before replacement by stripping shingles, cracking ridge tiles, and lifting flashing. Second, the wind determines what materials and installation techniques we recommend for the new roof. On west-facing foothill slopes, we install upgraded fastening patterns, re-bed the entire ridge line, and use flashing designs that resist uplift. A roof that would be fine in a calmer inland city needs a different installation approach in Highland. The wind event is also a good reason to get an inspection before the damage spreads.
Yes. When we pull a roof replacement permit in Highland and the tear-off exposes the deck, we have to meet current building code for decking, underlayment, and ventilation. That can mean adding or upgrading the ridge vent, replacing deck sections that no longer meet thickness standards, and bringing flashing up to current detail requirements. We factor these potential upgrades into the contract as allowances so you’re not surprised if the inspector requires them. We pull the permit, pass the inspection, and close the job out properly.
Highland’s foothill lots slope, so the roof ties into retaining walls and stepped foundation lines. That creates transitions where the roof plane changes angle, and those transitions concentrate water and wind stress. A tear-off often exposes failed flashing and soft decking at exactly those points. We inspect those transitions first, price them explicitly, and build the new roof to handle the grade change. Flat-lot inland cities don’t deal with this. Highland does.
Put the bids side by side and check three things. First, material: does the bid name a specific brand and shingle line, or just say “shingles”? We name the brand, GAF, CertainTeed, Tamko, or whichever of the seven lines we’re quoting. Second, allowances: does the bid include a priced allowance for decking and flashing replacement, or does it leave that open? An open-ended line item is where surprise costs come from. Third, permits: does the bid include the permit and inspection? We pull the permit on every replacement. Call (866) 942-0875 and we’ll give you a written line-item quote you can compare honestly.
Written by Noel Fierro, Owner at Oakmont Roof Repair, serving Highland and the surrounding foothill communities.