Searching for a private estate with thousands of feet of shoreline, a mansion, and room for servants, horses and livestock, all within a 25-minute boat ride from Portland?

Look no further than Hope Island, a secluded paradise in Casco Bay that is owned by developer John Cacoulidis. The 86-acre getaway that is part of the town of Chebeague Island is on the market for $7.95 million.

“The sellers are no longer using the island as they had in the past,” said John Saint-Amour, a real estate agent from LandVest, which is listing the property. “Their plans have changed, they have made the decision to sell the property.”

The property includes an 11,295-square-foot main house with six bathrooms and three bedrooms. The surrounding estate features two guest houses, a barn with worker’s quarters, outbuildings for equipment and machinery, a 10-stall horse barn, coops for chickens, ducks and geese, a tavern for entertaining, a private chapel and a boat house with a deep-water pier. In all, there are nine habitable buildings on the property.

Eight ponds dot the island, which is traversed by lighted concrete roads and powered by generators and submerged marine cables from Long Island. There are 15 drilled wells for water and nine separate septic systems. The 11,050 feet of shoreline mixes rocky coast and sandy beaches.


Cacoulidis bought the island in 1993 for $1.3 million and over the next 24 years “no expense was spared creating this magical island kingdom,” according to the listing. The island is technically owned by Scorpio Island Corp., a New York company. The tax bill on the property was $78,192 for the tax year that ended June 30, according to town records.

Cacoulidis, his wife, Phyllis, and staff lived on the island full time for many years. Phyllis Cacoulidis died in 2016. According to her obituary, the couple considered the island estate a source of great pride and joy.

“An avid gardener, lover of animals and the outdoors, she transformed Hope Island into a beautiful working farm with chicken, geese, swans, ducks, peacocks, deer, horses, a mule named Emma and her five dogs. She routinely took in rescue animals and cared for local wildlife,” read a portion of the obituary.

Considering the investment that Cacoulidis made in the property, the nearly $8 million price is reasonable, Saint-Amour said.

“To have an entire island in Casco Bay with easy access to Portland is a rare commodity,” he said. “To be frank, the investment in the island far exceeds the asking price.”


Cacoulidis is a developer with properties in New York and Maine. Last year, the Cacoulidis family resumed efforts to develop a 40-acre waterfront parcel near Bug Light park in South Portland. In a 2001 proposal for the same land, Cacoulidis proposed a massive hotel complex and cable car system across the Portland Harbor. Cacoulidis also bought the former Portland Press Herald building in 2009 before selling it to hotel developers in 2012.

The Cacoulidis family also has made waves over the island itself. In 2001, fed up with the local tax burden, Cacoulidis and his wife tried to secede from the town of Cumberland, which then had authority over Chebeague and nearby islands. In 2013, the Cacoulidis family agreed to pay $100,000 to the town of Chebeague Island to resolve multiple violations of shoreline protection rules that occurred during construction on the island.

Saint-Amour said he has received multiple phone calls and taken some prospective buyers out to show the property. The island could be converted into a resort, but it would need town approval, he said. He expects the estate will be bought by an individual or family that wants a turn-key island escape.

“Whoever buys this has to have some connection to the water,” Saint-Amour said.

Although the scale and price of Hope Island are jaw-dropping, it is not the most expensive residential property for sale in the Portland area. An eight-bedroom oceanfront home in Cape Elizabeth owned by former gubernatorial candidate Eliot Cutler is on the market for $11 million.

Peter McGuire can be reached at 791-6325 or at:

[email protected]

Twitter: PeteL_McGuire

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