A hillside home on Leonard Road in Saratoga, still wearing its original cedar shake roof decades past its prime: split and slipping shakes, tin patches, a rusted-out chimney cap. We tore the shake off, built a new OSB deck over the skip sheathing, and installed Owens Corning architectural shingles with a custom chimney cricket and flashing — $35,538, finished before the fall rains.
What Does It Cost to Replace a Cedar Shake Roof in Saratoga?
This Saratoga cedar shake replacement cost $35,538: a complete tear-off of about 26 squares of old wood shake, a new OSB deck installed over the original skip sheathing, Titanium synthetic underlayment, new drip edge, valleys and vent flashings, a custom-fabricated chimney cricket and flashing, a new chimney cap, and Owens Corning architectural shingles in a deep charcoal. Shake conversions cost more than a like-for-like shingle reroof for one structural reason: cedar shake was installed on spaced skip sheathing, and asphalt shingles need a solid, continuous deck, so a full sheathing overlay is built into every honest bid. On a hillside lot with a masonry chimney, the other cost drivers are access and flashing detail — the chimney on this roof needed a cricket to divert water around it, which the old shake roof never had.
An Original Shake Roof Held Together With Tin Patches
Chaohuang’s home sits on Leonard Road in the Saratoga hills, where the lots run steep and wooded and the views open up toward the Santa Clara Valley. Like many homes in this part of town it was roofed in cedar shake when it was built, and that roof had never been replaced — only patched. By the time we inspected it, the shakes were split and cupped across every slope, individual pieces had slipped out of their courses leaving gaps straight down to the sheathing, and previous repairs had been made with sheet-metal patches slid under the shakes wherever a leak showed up. The chimney told the same story: a rusted-through cap sitting on a wood-framed chase, with no cricket behind it to move water around the masonry. Wood shake in this condition is also a fire concern in the Saratoga hills, where dry brush and oak litter collect on a roof that is itself fuel.
A Solid Deck, a Proper Cricket, and a Class A Shingle System
Once the shake was off, the roof was skip sheathing and air. We installed a full OSB overlay across every slope, fastened through to the rafters, turning the spaced boards into a solid, continuous deck that architectural shingles can be nailed to. Over that went Titanium synthetic underlayment with cap nails, new drip edge at every eave and rake, new metal valleys, and new flashing at every pipe and vent. At the chimney we fabricated a custom cricket — a small peaked saddle behind the masonry that splits the water running down the slope and sends it around the chimney instead of against it — wrapped in new step and counter-flashing, and topped the chimney with a new cap. The finish is Owens Corning architectural shingles in a deep charcoal that suits the wooded hillside, and the whole assembly is a Class A fire-rated roof in place of dry wood shake.
Before vs. After
| Feature | Before | After |
|---|---|---|
| Roof covering | Original cedar shake, split, slipping, tin-patched | Owens Corning architectural shingles, deep charcoal |
| Roof deck | Spaced skip sheathing | Full OSB overlay — solid, continuous deck |
| Fire rating | Dry wood shake in the Saratoga hills | Class A asphalt shingle assembly |
| Chimney | Rusted-through cap, no cricket, aged flashing | Custom cricket, new step and counter-flashing, new cap |
| Underlayment & flashings | Original felt and flashings under the shake | Titanium synthetic, new drip edge, valleys, vent flashings |
| Size & cost | — | About 26 squares · $35,538 complete |
The project ran at the end of September, from tear-off through the finished shingle field, and closed out ahead of the first fall storms. What had been the oldest roof on the street — a wood shake roof relying on tin patches — came out as a solid-decked, Class A, code-current shingle system with a chimney that finally sheds water the way it should.
What This Means for Saratoga Homeowners With Shake Roofs
Saratoga’s hillside neighborhoods — the streets off Pierce Road, Big Basin Way, and up toward the Saratoga Gap — were built when cedar shake was the default, and a remarkable number of those original roofs are still up there. If yours is one of them, three things are true. Repairs stop working: once shakes are splitting and slipping across the field, patches chase leaks instead of preventing them. Fire risk is real in these hills, and a Class A shingle roof is one of the most effective hardening steps a home can take. And the deck decides the quality of the job: a shake conversion done right always includes a full sheathing overlay over the skip boards, so a bid that skips it isn’t cheaper — it’s incomplete. We’ve done this conversion across the Peninsula; compare this project with our Palo Alto cedar shake replacement and our earlier Saratoga roof replacement, or talk to our Saratoga roofing team about yours.
Saratoga Cedar Shake Replacement — FAQs
Can asphalt shingles go directly over a cedar shake roof?
No. The shake has to come off completely, and the skip sheathing underneath must be covered with a solid deck before shingles can be installed. Shake roofs sit on spaced boards with gaps between them, and asphalt shingles need continuous support, so a proper conversion is tear-off, sheathing overlay, underlayment, then shingles. On this Leonard Road project the OSB overlay covered every slope.
What is a chimney cricket and why did this roof need one?
A cricket is a small peaked saddle built on the uphill side of a chimney that splits the water running down the slope and directs it around the masonry. Without one, water and debris pile up behind the chimney and work into the flashing — which is how chimneys become the most common leak point on a roof. This chimney had never had one, so we fabricated a custom cricket and wrapped it in new step and counter-flashing.
Is a wood shake roof a fire hazard in Saratoga?
Aged wood shake is combustible and collects dry leaf litter, which is why modern codes have moved away from it in wildfire-prone hills like Saratoga’s. Replacing shake with a Class A asphalt shingle assembly is one of the most effective home-hardening steps available, and insurers increasingly take roof material into account.
How much does it cost to replace a cedar shake roof in Saratoga?
This roughly 26-square Saratoga conversion came to $35,538 including the OSB deck overlay, custom chimney cricket and flashing, new chimney cap, and Owens Corning architectural shingles. Shake conversions price above like-for-like shingle reroofs because of the deck. Roof size, pitch, hillside access and the number of chimneys and penetrations move the number; see our Bay Area roof replacement cost guide for current ranges.
Still Have a Cedar Shake Roof in Saratoga?
We handle the whole conversion — tear-off, new solid deck, chimney crickets and flashing, Class A shingles, and permits — start to finish. See more of our work in the project gallery, or book a free inspection today.
Gina K. writes about Bay Area roofing for Lifetime Roofing & Renovation, drawing on the team's 16+ years of experience and 1,000+ completed roofs across Silicon Valley.
