Siding, Roofing, Windows & Decks in Chebeague Island, Maine

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.

The island is about three miles long and a mile wide, running from Chebeague Point in the north to Deer Point in the south, with North Road and South Road tying it together. Nineteenth-century islanders fished, farmed and crewed the stone sloops that carried quarried granite down the East Coast; by 1900 there were five hotels serving summer visitors who came by steamboat. The Chebeague Island Inn, built in the 1880s as the Hillcrest and rebuilt in 1925, overlooks the Stone Wharf. The Great Chebeague Golf Club, listed on the National Register in 2015, uses a Cape from about 1807 as its clubhouse, and the 1871 schoolhouse now serves as the island history museum.

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.

Each page below covers one job in Chebeague Island: what the town's houses and weather mean for it, what the work involves, and what moves the price. For the full picture of a trade, see our siding, window replacement, roofing and deck building pages.