If a crow’s nest could be made suitable for modern living would you move in? With its round, weathered-shingle frame and wraparound windows and porches, Vinalhaven’s Octagon House is the closest approximation of a sailor’s lookout we’ve seen on land. Views of the Camden Hills, Penobscot Bay, and an 83-acre town park crisscrossed with hiking trails are on display in every room in the house, which sits atop one of the highest points on the island. When octagonal houses were first introduced in the 1850s, proponents claimed that, beyond showcasing scenery, circular plans also increased airflow and natural light and promoted socialization — in this case, nudging them toward a series of elegantly beamed gathering places lined with window seats for keeping watch.

29 Middle Mountain Road, Vinalhaven

$625,000

Status: Off-Market