Virginia Hess

Discover a unique opportunity in Mid-Island Islesboro, where history and potential converge in two remarkable buildings on one property. The Schoolhouse (300 Main Road): This was formerly the Pendleton School, Islesboro's main elementary school until the early 1950s. Currently operating as the Double Door Gallery during the summer, it features two large open rooms on the first floor with curved

Step into history with this remarkable property, originally the Pendleton School, Islesboro's main elementary school during the 1800's until the early 1950s. This former schoolhouse has plenty of potential. Currently operating as the Double Door Gallery during the summer months, showcasing local and regional artists, the property boasts two large open rooms on the first floor, featuring curved

Plum Point Cottage: Contemporary Island Home set on a hill with Breathtaking Ocean Views. Wake up to island life at Plum Point Cottage, a coastal retreat designed by Architect Christopher Glass. With 400+/- feet of rocky waterfront, this contemporary island setting offers stunning sunrises over Bounty Cove and Penobscot Bay from your private deck. The first floor welcomes you with a small

Discover this beautiful 5.7+/-acre wooded lot on Seal Harbor, Islesboro. Enjoy 541+/- feet of waterfrontage with southern and southwestern views of the protected, public harbor with a public dock and float hosting sailing lessons, swimming, and fishing in warmer months. This unique property features numerous old Ash and Oak trees, a private gravel beach, a bubbling brook, and an old cellar hole.

Come explore this unique opportunity encompassing 11.5+/- acre and offering western views of West Penobscot Bay, Northport and Camden Hills giving you a sense of place and privacy. A gravel driveway leads you to the house in a forest setting with remnants of gardens behind the structure. There is a large sun deck at the front of the house designed to take advantage of the view and outdoor space.

Winfield Scott Pendleton House: A Historic Islesboro Gem. Step back in time and discover the rich history of this stately 1887 Federal-style home, once owned by Winfield Scott Pendleton, a prominent ship captain and influential figure in Islesboro. Built shortly after Pendleton acquired the property in 1876 from his parents, the house served as a summer retreat for the Pendleton family until