Roof Replacement in Chebeague Island, Maine

Roofs on Chebeague work harder than roofs a few miles inland. Wind lifts shingle tabs along the eaves and rakes, salt air corrodes old flashing and nails, and roughly 69 inches of snow a season at the nearest weather station means ice dams on houses with poor attic ventilation. Older island houses often carry steep main roofs, ells and additions stitched together over many decades, and the joints between those sections are where leaks usually start.

A full tear-off down to the deck exposes the original board sheathing on pre-war houses, which often needs sections replaced, and lets new ice barrier, underlayment, drip edge and step flashing go on properly. The island adds a layer of logistics to every re-roof. Shingles, metal panels and dumpsters travel on the Chebeague Transportation Company barge, which departs from Cousins Island midweek in peak season and from Yankee Marina in Yarmouth on other days, on times set by the tide. Planning the job around those crossings, and around the weather window before the barge season ends on November 30, keeps a roof from sitting open waiting for the next boat.

Census estimates count about 554 housing units in the town, and the median year built is 1938, which makes Chebeague one of the oldest housing stocks in Cumberland County. Roughly 51 percent of units predate 1940 and about 57 percent predate 1960. Building slowed sharply after that: only around 9 percent went up between 1960 and 1979, while about 20 percent date from 2000 or later. Nearly 97 percent of units are single-family detached houses, and about 71 percent of year-round households own their home. The defining number is seasonal use: about 263 units, close to half the total, are held for seasonal or occasional occupancy. Expect wood-frame capes and farmhouses from the fishing and stone-sloop era, cottages and former boarding houses from the summer-hotel years, and a newer layer of homes built since 2000.

Great Chebeague sits in the middle of Casco Bay, about 10 miles northeast of Portland, with open water on every side and no mainland ridge to break the wind. Nor'easters push rain and spray straight into east- and north-facing walls, and salt settles on siding, flashing and fasteners well back from the shore. The nearest long-term weather record is Portland International Jetport, where 1991 to 2020 normals put average snowfall at about 69 inches a year. Winters here swing across freezing again and again, so water that gets behind trim or under shingle tabs freezes, expands and opens the gap further. The town's own site keeps a disaster-relief page for the December 2023 and January 2024 storms, a reminder of how hard winter storms hit.

Building permits come from the Town of Chebeague Island Code Enforcement office, which posts its monthly permit reports online. The town's zoning ordinance says no building may be erected, structurally altered, enlarged or moved without a permit from the Code Enforcement Officer, and a new or enlarged structure needs a site plan showing the lot, buildings and yards. The town fee schedule has a separate category for decks and sheds, and fines for building without a permit start at double the fee. Shoreland overlay districts cover the waterfront, with setbacks set by the town's Shoreland Zoning Ordinance, and a dozen small islands in the town are entirely Resource Protection.

A roof replacement strips the old roofing down to the deck, repairs what is underneath, and rebuilds the whole system: underlayment, ice and water protection at the eaves and valleys, flashing at chimneys and walls, ventilation, and the new roofing itself. Maine roofs carry snow for months and see ice dams at the eaves, so the parts you never see do most of the work. The site covers architectural asphalt shingles, metal, cedar shake and flat or low-slope roofing.

• Old roofing is torn off to the deck and hauled away, with the yard and plantings protected.
• Soft or delaminated sheathing is replaced before anything new goes down.
• Ice and water shield goes at the eaves, valleys and penetrations; synthetic underlayment covers the rest.
• Drip edge, step and counter flashing, and pipe boots are installed new.
• Ridge and soffit venting are balanced, then the new roofing is installed and the site cleaned with magnets.

• Curling, cracked, or missing shingles and granules in the gutters
• Ice dams along the eaves or water stains on ceilings after thaws
• Daylight or damp sheathing visible in the attic
• Sagging roof lines or spongy spots underfoot
• A roof at or past the age its material was made for

• Roof area, pitch and complexity: valleys, dormers, skylights, chimneys
• Number of existing layers to remove
• Sheathing repair found after tear-off
• Material: asphalt, metal, cedar or low-slope membrane
• Ventilation and flashing upgrades

Every job is priced from a free on-site visit. Typical ranges for the trade are on our roofing page, and the details of this service are on the roof replacement overview.

Back to the Chebeague Island exterior services overview, or see every town on our Cumberland County service areas page.