Roofing Contractor Sag Harbor, NY | Straightline Roofing

Trusted Local Roofers Serving Sag Harbor Since 1990

Sag Harbor is one of the most historically significant villages on the East End — a former whaling capital with a Main Street of 19th-century architecture that is genuinely rare in the Hamptons context. Roofing in Sag Harbor frequently means working on homes built before 1900, where the structural framing, chimney configurations, and architectural details require a contractor who has actually worked on old houses, not just new construction that happens to look historic.

Straightline Roofing has extensive experience with Sag Harbor’s older housing stock. We regularly encounter hand-cut rafters, original brick chimneys that require careful flashing work, and roofline geometries common to 19th-century Colonial and Greek Revival architecture. We also work on the newer homes in the Sag Harbor Hills and Azurest areas, as well as the waterfront properties around Sag Harbor Cove that require coastal material specifications.

Chimney and skylight work is particularly common in Sag Harbor. The older homes here have multiple masonry chimneys, and the flashing at these chimneys is the most common source of water intrusion we find. We fix chimney flashing properly — step flashing integrated with counter-flashing, not caulk over an old problem.

Nearby Communities We Also Serve

We serve Sag Harbor and surrounding areas including Southampton, East Hampton, Bridgehampton, and Shelter Island.