Landers Construction Company

Oak Bluffs requires a building permit for roof replacement through the town Building Department. State code requires ice-and-water shield at eaves and in valleys, and the wind exposure here pushes most roofers to spec a shingle rated to 130+ mph with six-nail perimeter patterns. The Cottage City Historic District covers the Campground area and adjacent streets and requires Historic District Commission review for any change in roofing material, profile, or color — a real constraint on the gingerbread cottages. Island logistics also matter: material has to come over by ferry, and contractor schedules book heavily in summer.

Roofing on Martha's Vineyard runs meaningfully above mainland MA because of ferry freight, the seasonal-labor premium, and the historic constraints on much of the housing. A full asphalt-shingle tear-off and replacement generally runs $12,000–$32,000. Cedar shingles or shakes — common and often required by historic review — run $28,000–$65,000. Standing-seam metal runs $28,000–$60,000. Restoration work on a Campground gingerbread cottage is its own category, with tiny-roof complexity and historic-board oversight commonly pushing per-square costs to double the mainland figure.

Massachusetts requires a written contract and a Home Improvement Contractor registration for most residential roofing work; ask for the registration number and check it before paying a deposit.

More on permits, costs, rebates and common questions, plus every other roofing contractor serving the town, on the Roofing in Oak Bluffs page.