A replacement is not just new shingles. It is a system: deck, underlayment, ice-and-water membrane, drip edge, flashings, ventilation and shingles, each of which can be specified well or cheaply. That is where quotes diverge.
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Two quotes thousands of dollars apart are frequently describing genuinely different jobs. Make each contractor answer the same questions in writing: how many squares, how many existing layers come off, what the per-sheet price is for replacing rotted decking, what underlayment goes down, how far up from the eaves the self-adhered ice-and-water membrane runs, whether drip edge and all flashings are new or reused, what changes to soffit and ridge ventilation are included, and what the workmanship warranty term is on top of the manufacturer warranty.
Roofing over an existing layer is cheaper and faster, and it is a poor idea on most Connecticut houses. It hides deck condition, adds weight to older framing already carrying winter snow load, traps heat that shortens shingle life, and makes the eventual tear-off more expensive. It also limits some manufacturer warranties. If a quote proposes an overlay, ask specifically why.
Asphalt shingles seal themselves using a heat-activated adhesive strip, which needs warmth and sun. Replacements installed in cold Connecticut weather need crews who hand-seal, and the roof will not fully bond until spring. If the timing is yours to choose, a dry stretch from April to October gives the better result. Municipal building permits are generally required for a full replacement; your contractor should pull it and you should see it.
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We're matching you with available pros now. Expect a call shortly, or reach us directly at (800) 555-0214.