Roof Replacement in Calimesa, CA | Hollywood Roofing Co

Roof Replacement in Calimesa — Free Roof Inspection, Written Price

Free roof inspection with photos, then an itemized written price before anything is ordered. Installed by our own licensed crews and backed by a workmanship warranty.

Call to schedule your free estimate

252+
Cities Served
Free
Written Quotes
Licensed & Insured Written Quotes Free Estimates All Brands Satisfaction Guarantee
Metal roofingMetal roofing
Architectural shinglesArchitectural shingles
Tile roofingTile roofing
GAFGAF
Owens CorningOwens Corning
Flat & low-slopeFlat & low-slope
Every visit starts with

Free roof inspection with deck photos before we talk money - GAF and Owens Corning certified installation

Your new roof for as low as$159/month*On approved credit; ask for current terms
Get your free estimate

Fast, Reliable Roof Replacement Across Calimesa

A full roof replacement in Calimesa typically runs $9,500 – $18,000 depending on roof size, pitch, tear-off layers, and material grade. Most jobs take us two to five working days once materials are on site. If your roof is pushing twenty years old or showing wind damage from the pass, a replacement is usually the smarter long-term move than repeated patches. Call Hollywood Roofing Co at (833) 589-7971 and we’ll walk the roof with you before any numbers get put on paper.

Call (833) 589-7971

We know Calimesa roofs. We know what the wind does to them. Roland Vega started Hollywood Roofing Co with a simple rule: inspect honestly, price transparently, and install like the house is your own. Calimesa sits in a wind corridor that punishes a poorly nailed roof within a season or two, and we build every project around that reality. Our teams have torn off original shake, second-layer composition, and everything in between in ZIP 92320, out toward Singleton Road and the newer tracts south of the I-10. When you call, you’ll get a straight answer, a written line-item quote, and a roof built to stay put.

Why Hollywood Roofing Co Is Calimesa’s Preferred Roof Replacement Company

We’re not the only roofer who will drive to Calimesa. We’re one of the few who treats the San Gorgonio Pass wind as the primary design input rather than an afterthought. A roof that survives in parts of Redlands won’t necessarily survive a decade on a Calimesa ridge lot with open rangeland to the east. We spec nailing patterns, underlayment, and ridge attachment around that exposure, and we’ve done enough tear-offs here to know what the original builders got wrong.

Calimesa homeowners call us for the same reasons they recommend us: we show up when we say we will, we don’t pad change orders, and we walk the roof with you before and after the job. Our work in Calimesa covers old ranch homes off County Line Road, newer master-planned subdivisions, and the rural properties with detached structures that need re-roofing at the same time. The estimate you get is the estimate you’re comparing against a second bid. No games.

Roland Vega insists on one thing above all: the inspection report tells the truth, even when the truth is “you don’t need a full replacement yet.” That’s rare in this business, and Calimesa homeowners notice. When you phone (833) 589-7971, you’re talking to the people doing the work, not a call center.

Explore

Styles & brands we work with

Architectural shingles
Architectural shingles
Metal roofing
Metal roofing
Tile roofing
Tile roofing
GAF
GAF
Owens Corning
Owens Corning
Flat & low-slope
Flat & low-slope

Flat Roof Replacement in Calimesa

Flat Roof Replacement in Calimesa comes up most often on older ranch homes and rural properties with additions, carports, or detached outbuildings that were built with low-slope or torch-down roofs. The Inland Empire sun bakes these surfaces hard, and when the dry heat meets winter rains, old roll roofing and failed seams leak. A flat roof replacement in Calimesa typically runs $8,000 – $14,000 for a standard single-story addition or garage, depending on square footage, deck condition, and the membrane system selected. Tear-off of old built-up layers adds cost, but skipping it means trapping moisture against a rotting substrate.

Low-Slope Systems That Hold Up In Wind

Calimesa’s wind doesn’t just hit pitched roofs. Low-slope edges take uplift too, and we’ve seen whole sections of old rolled roofing peel back after a strong Santa Ana. We recommend adhered systems, mechanically fastened TPO, or modified bitumen with proper edge detailing rather than relying on gravel ballast that moves. These systems are rated for high wind zones and perform better under repeated heat cycling than the original builder materials.

When A Coating Isn’t Enough

A silicone or acrylic coating can buy you a few years on a sound deck. It can’t fix separated laps, ponding areas, or rotted fascia. If your Calimesa flat roof is more than twenty years old, has visible seams opening, or leaked more than once in a season, replacement usually costs less over five years than repeated patch-and-coat cycles. We’ll tell you which one applies to your roof.

Roof Installation in Calimesa

Roof Installation on new construction in Calimesa is a different animal than a tear-off. The newer tracts through ZIP 92320 run architectural shingles from the start, and the framing is usually plumb and properly ventilated. New-build roof installation in Calimesa typically runs $12,000 – $22,000 depending on roof complexity, hip and valley count, and material grade. The older ranch homes we handle are the other end of the spectrum, often requiring re-decking before the first shingle goes down.

New Construction Roofing For Calimesa Builds

We work with owners and small developers on infill lots and custom ranch properties. New construction lets us spec the full system correctly from the start: starter strip, ice and water shield at the eaves, high-wind nailing patterns, proper ventilation. It’s easier and cheaper to do it right the first time than to retrofit after an inspection failure.

Re-Decking On Older Ranch Homes

Tear-offs on 1960s and 70s ranch homes in Calimesa almost always reveal decking issues. The old 1×6 skip sheathing wasn’t meant to hold modern shingles. We re-deck with 7/16-inch OSB or 15/32-inch plywood, and that’s when the roof becomes a solid working surface instead of a trampoline. We write the decking allowance into the contract so the price doesn’t move after the first layer comes off.

Trusted Brands We Service in Calimesa

Hollywood Roofing Co is an authorized installer for seven major roofing brands, including GAF, CertainTeed, Owens Corning, IKO, Atlas, Tamko, and Boral. That’s not a sales trick. It’s because no single manufacturer makes the right shingle for every Calimesa roof. CertainTeed’s Landmark series works well on tight suburban lots; GAF Timberline HDZ handles the high wind nailing schedule the pass demands; Tamko and IKO give us solid budget-tier options when the home can’t bear the premium price. We maintain pulled materials for Calimesa jobs in our inventory so lead times stay short, and we don’t wait on a distributor to ship from Texas. The right product for your house, not the product we’re incentivized to push.

Common Roof Replacement Problems We See in Calimesa Homes

  • Wind-lifted ridge caps and starter strip. The San Gorgonio Pass funnels wind hard through Calimesa. Roofs with the original four-nail pattern lose ridge caps and shingle tabs after a strong Santa Ana. We re-nail to a six-nail high-wind pattern and upgrade the ridge attachment on every pass-exposed roof.
  • Cracked, dry original underlayment. The tar-impregnated felt used in the 60s through 80s bakes brittle in inland heat. By the time a leak shows indoors, the underlayment has been letting water wick into the decking for years. We see rotted fascia on tear-offs where the homeowner only noticed a small ceiling stain.
  • Fire-rated assembly gaps near the wildland edge. Homes along the open rangeland in Calimesa sit in zones where Cal Fire expects Class A-rated roof assemblies. If the original underlayment isn’t rated or the flashing at penetrations isn’t done to spec, the permit final stalls. We pull permits and know what the inspector is going to check.
  • Double-layer composition over skip sheathing. Many older Calimesa ranch roofs have a second shingle layer nailed over the first, over original 1×6 sheathing. The deck flexes, the nails back out, and wind finds every loose tab. These roofs need to come down to the rafters, not get a third layer.
Before & after

See the difference

Before - Recent ProjectBeforeAfter - Recent ProjectAfter
Recent Project
Before - Full RestorationBeforeAfter - Full RestorationAfter
Full Restoration
Before - Complete UpgradeBeforeAfter - Complete UpgradeAfter
Complete Upgrade

Pricing for Roof Replacement in Calimesa, CA

Here’s what we actually see in Calimesa. A straightforward 1,600-square-foot comp shingle replacement on a single-story ranch runs $9,500 – $13,000. A larger 2,800-square-foot home with architectural shingles and full re-decking runs $14,000 – $18,000. If your roof needs sheathing replacement, add $2.50 – $3.50 per square foot for materials and labor. Flat roofs run $8,000 – $14,000. High wind nailing upgrades are included in our base price, not sold as an add-on. Steep pitches, multiple stories, heavy tie-off requirements, and failing decking push the number up. We write line items, not a single lump sum, so you can compare bids square-foot to square-foot. Call (833) 589-7971 for an exact written quote. The estimate is free, in writing, and specific to your roof.

We Also Serve Cities Near Calimesa

Our crews run a regular route through the San Gorgonio Pass and the surrounding foothills. We handle roof replacement, repair, and inspections in Yucaipa, Mentone, Redlands, and Banning on a daily basis, and we’re familiar with how each area’s roofs age differently. If you’re in Calimesa proper or anywhere else in the pass region, see our service page for Roof Replacement in Calimesa or call us at (833) 589-7971.

Serving Calimesa, CA — Our Local Coverage Area

We’re based in the Calimesa 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 Calimesa

What Opening Up an Older Calimesa Roof Actually Turns Up

If you own a ranch home in Calimesa built before 1990, here’s what a tear-off usually reveals: wind-lifted shingles over dried-out felt, rotted fascia hiding behind a clean-looking eaves line, and skip sheathing that flexes underfoot. A roof replacement on these homes is rarely just a shingle swap. The pass winds have been working on the roof’s weak points for decades, and the original builders used four-nail patterns that don’t meet today’s high-wind standards.

That’s why we write a specific decking allowance into every Calimesa contract. If the original underlayment crumbles on removal or the sheathing is rotted, you already know the per-square-foot cost to replace it. Nothing gets added without a written price and your approval. We do inspection work first, tell you exactly what you’re dealing with, and then build the permit scope around reality. That’s the only way to do a roof replacement in a wind corridor without the final bill being a surprise.

On a 1970s ranch off Singleton Road in Calimesa, our crew tore off two layers of weathered composition shingle and found the original skip sheathing had separated from the rafters. We re-decked with 7/16-inch OSB and installed GAF Timberline HDZ architectural shingles with a six-nail pattern to meet the 130-mph wind rating, then replaced the rusted drip edge and added ridge vent along the entire ridgeline. That’s what a real Calimesa roof replacement looks like when the wind is the primary enemy. It’s not a reroll of shingles. It’s a rebuild.

Request Your Free Calimesa Roof Replacement Estimate

We inspect first, price honestly, and install right. If you’re in Calimesa or anywhere in the San Gorgonio Pass, call Hollywood Roofing Co at (833) 589-7971 to schedule a roof inspection and a written replacement estimate. Roland Vega and our crews know the wind, the housing stock, and the permit expectations in ZIP 92320. You’ll get a straight answer and a fixed-price quote. Call (833) 589-7971 today.

Written by Roland Vega, Owner at Hollywood Roofing Co, serving Calimesa and the San Gorgonio Pass region.

Why Calimesa Chooses Hollywood Roofing Co

We set the standard for roof replacement in Calimesa.

No Change-Order Surprises

The written quote you sign is the price you pay. Anything we find mid-job gets priced and approved by you in writing before we touch it.

Licensed & Insured

Fully certified technicians who meet all local and state licensing requirements.

Upfront Pricing

No hidden fees, no surprises. You approve the price before any work begins.

Guaranteed Work

Every repair and installation is backed by our workmanship warranty and satisfaction guarantee.

How It Works in Calimesa

Getting your roof replacement handled is simple and fast.

1

Call or Request a Free Estimate

Tell us about your roof replacement needs and we provide an upfront, transparent quote — no obligation, no hidden fees.

2

Licensed Technician Dispatched

A background-checked, certified technician arrives in Calimesa — typically within 30–60 minutes, with parts stocked on the truck.

3

Problem Solved, Guaranteed

We complete the job to your full satisfaction, backed by our warranty and 100% satisfaction guarantee.

What happens when you call

  1. 1
    A real person answersNo phone trees — talk to a local roof replacement pro.
  2. 2
    You get an upfront price rangeHonest numbers before anyone is dispatched. No surprises.
  3. 3
    We come out and measureLicensed & insured, at a time that suits you — the visit and the quote are both free.
  4. 4
    You get the price in writingLine-itemed, yours to keep, and nothing starts until you say go.

What Calimesa Customers Say

Trusted by homeowners across Calimesa and surrounding areas.

★★★★★

"Tile roof, three cracked tiles and a slipped one. Matched the tile, no color mismatch, and it took him half a day."

Tim Brooks · Verified customer
★★★★★

"He told me my roof had another five or six years in it and I should not replace it yet. He was standing there with a quote pad in his hand. That's why I'll call him when it's time."

Gabriela Morales · Verified customer
★★★★★

"Leak over the kitchen turned out to be a cracked boot around a vent pipe, not the roof itself. He showed me the photo from up there and replaced the boot for a couple hundred dollars. The company before him had quoted a full tear off."

Scott Kowalski · Verified customer

Ready for Roof Replacement in Calimesa?

Call now for a free estimate — or request one below. Licensed, insured, and here with fast after-hours help in Calimesa.

(833) 589-7971

Request a Free Estimate in Calimesa

Tell us about your roof replacement needs — we'll respond within the hour.

By reaching out through this form, you agree to our Privacy Policy and consent to receive communications via phone, email, or SMS about your service request, including from the local pros who may handle it.

Prefer to text? Text Us
Areas We Serve
Call Now - 24/7 Dispatch