For Sale/Rent

Five Homes on Maine Islands You Don’t Want to Miss Out On

An island getaway? In Maine? You've got options, thanks to these beautiful summer homes in Vacation Land.


While it’s nice for Boston to be back to its usual bustling self, sometimes it’s even better to just get away from throngs of people, especially as humidity and temperatures increase. Luckily, we’re in New England, which is chock-full of isolated, nature-filled escapes. There’s lake houses and beach side homes aplenty, but honestly, you can dream even bigger…maybe an island residence?

If you truly want privacy and luxury this summer, try taking a drive up north to Maine, which boasts more than just great seafood. You can enjoy the best of Vacation Land and its rocky coastline from one of its many islands, which offer seclusion and natural beauty. Consider one of these homes for your own private island escape, without having to escape to the Caribbean.

maine island roundup 1

Photo by Joseph Sortwell

1552 North Haven Road, Vinalhaven, ME
Price: $4,500,000
Size: 6,550 square feet
Bedrooms: 8
Bathrooms: 9

This waterfront property’s location on Fox Islands isn’t even the most impressive thing about it. The modern estate’s main house alone will wow you, with its sweeping great room, while a guest house, gym, and barn provide space for the whole family to spread out. “Waterfront” is also a bit of an understatement when it comes to this 17-acre piece of property. Buy this and get over 500 feet of island shoreline to yourself, along with the lush grounds, which feature gardens, trees, a tennis court, and in-ground trampoline.

For more information, contact Terry and Joseph Sortwell, Landvest Realty, landvest.com.

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Photo by Peter G. Morneau

1 Hope Island, Chebeague Island, ME
Price: $10,500,00
Size: 11,658 Sq Ft.
Bedrooms: 3
Bathrooms: 3 full, 3 partial

Why limit yourself to a home when you could buy an entire island? Hope Island is an 86-acre piece of land located in the heart of Casco Bay, just a short 20-minute boat ride from Portland. While you may be tempted to head to the mainland for shopping and restaurants, many of your needs can be met right here on this island, which features a tavern, a chapel, a boathouse, equestrian and storage barns, guest homes, and other ancillary buildings that can be used as you’d like. A dock allows for a place for your boat so you can easily get to shore. And of course, there’s the Mediterranean-style main residence, which boasts a gym, courtyard, and ocean views from every room.

For more information, contact Jasmin Moulton, Legacy Property | Sotheby’s International Realty, legacysir.com.

Photo by Joseph Sortwell

153 Tip Toe Mountain Road, Vinalhaven, ME
Price: $1,475,000
Size: 2,400 square feet
Bedrooms: 5
Bathrooms: 3

The name of this home alone is enough to make you swoon. Tip Toe Mountain Cottage can be found on Vinalhaven, a town on the larger of the two Fox Islands in Penobscot Bay, at the end of a road on the land’s edge. The waterfront home comes with over 1,700 feet of sand and pebble beach facing the bay and a deep-water dock for boating. Stroll up from the beach through the flowering gardens, stonework, and trees on the 21-acre lot to get to the main house, perched up above the water to offer elevated views. Inside, it offers wood-paneled walls, exposed-beam ceilings, and large windows to offer rustic flair to its contemporary design.

For more information, contact Joseph and Terry Sortwell, Landvest, landvest.com.

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Photo by Lynn Dube, Wave 5 Productions

367 Island Avenue, Portland, ME
Price: $1,195,000
Size: 1,773 square feet
Bedrooms: 4
Bathrooms: 2

If you’ve been to Portland and haven’t been to Peaks Island, you’re missing out. Luckily, this home in Casco Bay will catch you up on what exactly you’ve been missing. This charming cottage on a grassy knoll is a short walk from the ferry and the beach and close to the island’s many attractions (including the quirky Umbrella Cover Museum). And of course, the house itself is nothing short of perfect. You’ll get plenty of living space, two bedrooms, and views of the Portland skyline that you can enjoy from your spacious porch, large stone patio, or water-facing decks.

For more information, contact Sue Lessard, Town and Shore Real Estate, townandshore.com.

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Photo by Joseph Sortwell

Lot 28 Bremen Long Island, Breman Long Island, ME
Price: $725,000
Size: 1,680 square feet
Bedrooms: 3
Bathrooms: 1

You don’t have to go big to enjoy island life. This shingled Cape-style home makes a great seasonal home with its three-bedrooms and bright, airy living room that leads out to a covered porch. A fire pit, elevated picnic platform, gardens, walking paths, and a dock offer endless ways to spend summer days and nights along the 200 feet of shoreline you’ll inherit with this property. The owners here will also get a barn and a writer’s studio on the water’s edge, perfect for someone who wants a quiet place to get away and work on their novel.

For more information, contact Joseph and Terry Sortwell, Landvest, landvest.com.