Roofing in Pleasantville, NY
Westchester Roofing Service Serving Pleasantville
Roof replacement and repair for houses across the Village of Pleasantville and the surrounding Mount Pleasant streets. Village permits and, where needed, Architectural Review Board petitions prepared by your Guardian project manager.
Since 1980
Our family team of five brothers, working alongside their father
Roofing permits filed
Village application, license and insurance handled
Westchester County HIC #WC-38383-H24
Licensed for Westchester home improvement work
10-year roof warranty
Plus 1 year on workmanship, in writing
Two Questions Before a Pleasantville Roof Comes Off
Most of the roofing calls we get from Pleasantville start the same way: a stain on a bedroom ceiling, shingles in the driveway after a storm, or an inspection report from a buyer. Before we talk shingles, we answer two Village questions, because they decide how fast the job can start.
| Question | Why it matters |
|---|---|
| Is the house in the Special Character Overlay District? | If yes, exterior changes including roofing go to the Architectural Review Board before a permit |
| Is anything changing besides the shingles? | New skylights, a dormer or a different material can change what the Village reviews |
If the answer to both is no, the job is a straightforward Village roofing permit. If either is yes, we build the Board petition into the schedule so you’re not caught waiting with a tarp on the roof.
Tear-Off Done Properly
We remove the old roofing to the deck on every replacement. On older Pleasantville houses that often uncovers plank sheathing with gaps, boards softened under a leaking valley, or a second layer nobody mentioned. Those get fixed before anything new goes on.
Then come ice barrier at the eaves and valleys, synthetic underlayment, new drip edge, step and chimney flashing, and vents balanced so the attic can breathe. The photo shows one of our own replacements at the underlayment stage, right after the deck has been checked and repaired, which is where the important decisions get made.
What We Fix on Pleasantville Roofs
Chimney leaks
New step, counter and cricket flashing where brick meets roof.
Valley failures
Leaves from mature street trees hold water in valleys; we rebuild them with ice barrier underneath.
Porch and bay roofs
Low-slope sections get a membrane rather than shingles that can’t shed water there.
Storm damage
Temporary dry-in first, then a written repair or replacement estimate.
Who Is on Your Roof
Guardian is our family team of five brothers, working alongside their father, and we’ve been in the trades since 1980. Roofing is done by licensed, insured subcontractors supervised by a Guardian project manager, who is also the person you call, the person who books the Village inspection, and the person who walks the finished roof with you.
Want to see more of our roofing? The roof replacement page has the full process, and you can read our Google Reviews.
Pleasantville Roofing FAQs
Does a roof replacement in Pleasantville need a Village permit?
Yes. The Village of Pleasantville building permit application lists roofing as its own type of work, and the Building Department at 80 Wheeler Avenue reviews it for conformance with the State’s Uniform Code. We prepare the application with your signature and include our license and insurance paperwork.
What happens if a roof was replaced without a permit?
The Village charges a legalization fee for work that started without a permit, on top of the normal permit. It can also come up when you sell. If you’re buying or selling a house and aren’t sure about an older roof, we can help you put together what the Building Department will want to see.
My house is in the Special Character Overlay District. What changes?
In that district, the Village’s petition form says any change to the exterior of a residential house, including roofing, needs Architectural Review Board approval before a building permit is issued. Swapping like for like in the same color is still worth confirming. A new shingle color, a metal roof or a changed roofline is clearly a Board item.
What does the Architectural Review Board want to see?
Photos of the whole house and of each detail the work touches (roofing, fascia, rake and trim among them), plus samples of the colors. The petition is due at least 10 days before the meeting. We take the photos, gather the samples and fill out the petition with you.
What warranty comes with a Pleasantville roof?
Ten years on the roof we install and one year on all other workmanship, both in writing. The shingle maker’s product warranty is separate.
More Pleasantville & Roofing Pages
Nearby, we also roof homes in Chappaqua, Ossining and White Plains.
Get a Free Roofing Estimate in Pleasantville
We’ll inspect the roof and attic, check whether the ARB applies, and send a written, itemized estimate.
Guardian Remodeling Corp · 143 Lake Shore Dr W, Carmel, NY 10512 · 914-912-0385 · Frank@guardianremodelingcorp.com
