Housing
This section of the BDN aims to help readers understand Maine’s housing crisis, the volatile real estate market and the public policy behind them. Read more Housing coverage here.
Two historic buildings on Islesboro — a house and an art gallery — are selling together for $850,000.
The five-bedroom, four-bathroom Federal-style home, known as the Winfield Scott Pendleton House, has a wraparound covered porch and a cupola perched on the roof.
“When you drive by in the summer, there’s somebody always sitting on the porch,” said Virginia Hess, associate broker at Cates Real Estate and the listing agent for the property. “The porch is an extension of the house itself.”
The home was built in 1887 by Winfield Scott Pendleton, a prominent ship captain and influential figure in Islesboro. He’s one of four or five Pendleton brothers that built homes in the area on land they inherited from their parents. This means the house is one of a few Pendleton houses on the island, Hess said.
The gallery once served as the Pendleton School, Islesboro’s main elementary school, until it closed in the early 1950s when a new school was built. Pendleton, the founder of the home, helped create the school so his daughter could attend, Hess said.
The sellers bought the property in 1985 and used it as a summer getaway for their family while maintaining the 139-year-old home, Hess said. The family is known for holding a pancake breakfast at their home on the Fourth of July, as it sits on the island’s Fourth of July parade route.
Today, the house still holds many historical features, including built-in closets and cabinets, stained glass windows, a carved wooden mantle and interior trim that’s original to the home. There’s also recently-built outbuildings by the main house, which offer space for a workshop, storage or other options.
“They’ve put so much work into it, but it’s getting harder to manage and they recognize that,” Hess said. “It’s time for it to go to a new owner, maybe somebody younger with some energy.”
The home is being sold with the Double Door Gallery, a seasonal art gallery next door. The sellers rent out that space to a couple who curate shows and artist visits during the summer, Hess said.
The art gallery has two main rooms on the first floor and a half bathroom, with curved walls and beadboard. The building’s second floor has a studio apartment with wood-paneled walls.
“It’s a nice space with great light for the art,” Hess said. “It’s a nice part of our community to have that gallery going.”
The two buildings sit on 3.7 acres and offer a combined nearly 5,000 square feet of living space. With an asking price of $850,000, the two buildings are roughly double the median cost of an Islesboro property, which now sits at nearly $420,300, according to Zillow.
The properties first hit the real estate market in August 2024 with an asking price of $850,000, then were removed after a year, Zillow records show. The home and gallery were listed again in November 2025 for the same price.
The former schoolhouse could remain a gallery, become a store or be turned into rental housing, Hess said. But, the sellers hope whoever buys the home will continue to restore it while keeping its original character.
“There’s no hiding at this house since it’s on Main Road,” Hess said. “I think this would appeal to somebody who wants to be part of our community, is interested in island life and interested in historical restoration.”