Roofing & Gutters in San Jose
Handyman service · San Jose & the South Bay
Small roof problems become big interior problems fast. We fix leaks, replace damaged shingles and tiles, and keep gutters clear so water goes where it should — away from your house.
What we handle
- Leak diagnosis and repair
- Shingle and tile replacement
- Gutter cleaning and repair
- Downspout adjustment and extensions
- Flashing and vent sealing
- Pre-rainy-season roof checkups

Roof repair starts with finding where water actually enters — which is rarely where the stain shows up, because water runs along rafters and sheathing before it drips. Good repair work means tracing the leak to its source, then fixing it the way the roof was built: new shingles woven in and nailed under the course above, flashing replaced or properly re-seated rather than buried, and sealant used as a gasket, not a bandage. The signature of cheap roof work is roofing mastic smeared over everything — it looks done, sheds water for a season or two, then cracks in the sun and traps water behind it. Face-nailed shingles, mismatched patches, and 'tarred' valleys are the other tells. A repair done right disappears into the roof; a repair done cheap becomes the next leak.
South Bay weather is hard on roofs in a specific way: eight dry months bake composition shingles brittle and cook sealants, then atmospheric-river storms arrive and test every weak point at once. On 60s and 70s ranch homes we mostly see cracked and lifted shingles, failed pipe-jack boots, and rusted valley flashing. The flat and low-slope roofs scattered through Sunnyvale and Willow Glen are their own category — ponding water, foam and tar-and-gravel surfaces, and details that punish improvised patching. Gutters cause a surprising share of 'roof leaks' here: oaks, redwoods, and liquidambars fill them by December, water overflows behind the gutter, and fascia boards and eaves quietly rot. Cleaning gutters in late fall, before the first big storm, is the cheapest roof insurance in the valley.
We handle the repair side of roofing: leak diagnosis, shingle and tile replacement, flashing and pipe-boot fixes, gutter cleaning, and re-securing sagging gutter runs. We're straight about the boundary — re-roofs and structural work are licensed-contractor territory, and if your roof is at the end of its life we'll tell you that instead of selling you a patch on a roof that needs replacing. On every job we take photos before and after, so you see what we found and what we fixed without climbing a ladder yourself. If we're up there for a leak, we'll flag anything else we notice while we have eyes on the roof — no charge for looking.
How we approach roofing & gutters
- 1We inspect the roof and attic side where accessible, trace the leak to its entry point, and photograph what we find.
- 2We quote the repair firm — parts, scope, and what we'll do if we find more damage underneath.
- 3We replace damaged shingles or tiles, re-seat or renew flashing, and seal penetrations properly.
- 4We clear and flush gutters and downspouts, re-securing any sagging runs.
- 5We send you before-and-after photos and note anything worth watching before next winter.
Typical cost: $150 – $350 for gutter cleaning; most roof and leak repairs run $250 – $900. See the full pricing guide — every job gets a firm quote before work begins.
More roofing & gutters projects





Roofing & Guttersacross San Jose & the South Bay
Roofing & Gutters — common questions
- Can you fix a roof leak without replacing the roof?
- Usually, yes. Most leaks come from a failed detail — a cracked pipe-jack boot, lifted shingles, rusted flashing — not from the whole roof failing. We trace the entry point and repair that detail properly. If the roof is genuinely at end of life, we'll tell you honestly and refer you to a licensed roofing contractor rather than patch what needs replacing.
- How often should gutters be cleaned in the South Bay?
- At least once a year, in late fall after the leaves drop and before the first big storms — that timing matters more than frequency. Homes under oaks, redwoods, or liquidambars often need a second pass. Clogged gutters overflow behind the fascia and rot the eaves, so a $150 – $350 cleaning regularly prevents a much more expensive wood repair.
- Do you work on flat or low-slope roofs?
- We handle small repairs on them — patching, sealing penetrations, and clearing drains and scuppers where ponding starts. Flat roofs are less forgiving than shingles, so anything involving large membrane sections or a re-coat we refer to licensed roofing specialists who do that surface daily. We'll tell you which category your problem is in after we look.
- My ceiling has a water stain — is the roof leaking?
- Maybe — but the stain rarely sits under the actual entry point, since water travels along framing before it drips. It can also be a flashing gap, an overflowing gutter, or even a plumbing line. We trace it to the real source first, fix that, and then repair the ceiling drywall once everything is confirmed dry.
Need roofing & gutters done right?
Tell us what needs doing and we'll get you a clear estimate.