Town of East Hampton
Cedar Shake & Shingle Roofing in Wainscott, NY
A cedar shake or shingle roof in Wainscott runs about $900–1,620 per square on Long Island in 2026, $1,600–2,800 for premium hand-split shake, and should last 20–40 years with an annual inspection, cleaning every 3–5 years and re-treatment every 5–7. We match Wainscott homeowners with a licensed roofer who specifies breathable underlayment, stainless fasteners and copper or stainless flashing as standard.
Last updated · Reviewed by Sag Harbor Roofing Co.
Cedar is the roof Wainscott was built with, and it is still the right roof for much of it, as long as the spec and the maintenance match the exposure. We match Wainscott homeowners with a licensed, insured roofer who installs cedar the right way: breathable underlayment, stainless fasteners, copper or stainless flashing.
Cedar shake in Wainscott: what's different here
In Wainscott cedar behaves very differently by lot. In the shade of the wooded inland streets it holds moss and needs regular cleaning to reach its 30–40 years; on the ocean and pond side it needs wind fastening and salt-resistant metal. The roofer should ask where the house is before quoting the spec.
Houses along Georgica Pond sit in a wind corridor off the ocean. There, flashing and ridge details matter more than the choice of material. Much of the housing is newer and large, with mixed roof systems (cedar plus standing seam plus flat membrane) that need coordinated details and warranties.
Permits in Wainscott run through the Town of East Hampton Building Department; the roofer we match you with handles the filing where one is required.
How matching works
Tell us about the job once. We match you with one licensed, insured roofer who works Wainscott regularly — not a list of strangers — and they contact you within 1 business day. No bidding war, no spam calls.
FAQ
Cedar shake questions
How long does a cedar shake roof last in the Hamptons?
Plan on 20–40 years. The Cedar Shake & Shingle Bureau puts the average at 30–40 years and a well-maintained roof at up to 50. In the Hamptons the spread is driven by exposure and maintenance: a shaded Northwest Woods roof that is cleaned every 3–5 years and re-treated every 5–7 can reach the long end; an oceanfront roof in Montauk or Sagaponack that never sees a brush will sit at the short end, and its flashing, fasteners and gutters will usually fail before the wood does.
Read the full answer →Cedar shake vs cedar shingle: what's the difference?
A shake is split from the log (hand-split, or taper-sawn on one face), so it is thick, irregular and textured. A shingle is sawn smooth on both faces, so it is thinner, flatter and uniform. Most of the Hamptons' older houses carry shingles, which read quieter; shakes are common on larger, newer houses. Shakes cost more (general cedar runs $900–1,620 per square on Long Island; premium hand-split shake with a breathable underlayment $1,600–2,800) and both last 20–40 years with the same maintenance: clean every 3–5 years, re-treat every 5–7.
Read the full answer →What's the best roof for a beachfront Hamptons home?
There is no single answer, but there is a short list. Standing seam in aluminum or copper handles wind best and shrugs off salt (40–70+ years for aluminum, 70–100+ for copper). Natural slate lasts 75–200 years and resists wind once properly hung, with copper fasteners. Cedar is the traditional choice and works if it is fastened for wind and maintained on schedule, at the short end of its 20–40 years. Architectural and designer asphalt is the budget option, with some designer lines wind-rated to 130 mph. Whatever the covering, the details decide it: full ice-and-water shield, stainless or copper metal.
Read the full answer →How much does a roof replacement cost in East Hampton?
In 2026, a full tear-off and replacement on Long Island runs about $530–795 per square (100 sq ft) for architectural asphalt, $900–1,620 for cedar, $1,050–1,785 for standing seam metal and $1,155–1,890 for synthetic slate; natural slate is $2,000–3,500 per square nationally. A typical 2,500–4,000 sq ft East Hampton roof is 25–40 squares, so asphalt lands around $13,250–31,800 and cedar or metal well above that. East Hampton jobs tend to sit at the top of the ranges because of access, roof complexity and material grade.
Read the full answer →Services
More in Wainscott
Roof Repair in Wainscott
Leak tracing, flashing, missing shakes or shingles, and post-storm patches, handled by a local roofer who will tell you honestly when a repair is throwing good money after bad.
Full Roof Replacement in Wainscott
Tear-off to the deck and a new roof system in asphalt, cedar, slate, metal or membrane, priced against published 2026 Long Island ranges so you know what a fair quote looks like.
Re-Roof (Overlay) in Wainscott
A second layer over the existing roof costs 20–40% less than a tear-off but lasts less, and New York code only allows it in specific conditions. We explain both sides before matching you.
New Construction Roofing in Wainscott
Roofing for new builds and major additions, coordinated with the architect and GC: material selection for the site, detailing for wind and salt, and the paperwork that comes with it.
Roof Inspection & Assessment in Wainscott
A documented look at the roof before you buy, sell, renew insurance or head into storm season, with photos and a plain-language verdict on remaining life.
Slate Roofing in Wainscott
Natural slate for estates that will keep it a century, restoration for the old slate roofs in Southampton and Sag Harbor, and synthetic slate for owners who want the look at a third of the price.
Get matched in Wainscott
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