Maine’s islands offer a rare lifestyle defined by privacy, natural beauty, and a deep connection to the coast. From secluded retreats only accessible by private boat to vibrant island communities with year-round activity, these properties provide a unique way of experiencing the state’s shoreline. Each listing combines breathtaking scenery with the distinct character of island living. We’re highlighting some of the incredible island homes currently on the market.
Islesboro
Heading into the heart of Penobscot Bay, we begin with Islesboro. Stretching nine miles long in Penobscot Bay, Islesboro offers both seclusion and accessibility via a short ferry ride. Its tree-lined roads, stately summer homes, and unspoiled shoreline make it a long-favored retreat for seasonal residents and year-round islanders alike. Historic estates mingle with contemporary retreats, making it one of Maine’s most storied island enclaves.
866 Pendleton Point Road, Islesboro, ME 04848
Offered at $6,750,000
Represented by Michael Kevin Lynch
1317 Trim Lane, Islesboro, ME 04848
Offered at $2,000,000
Represented by Michael Kevin Lynch
426 Ferry Road, Islesboro, ME 04848
Offered at $1,375,000
Represented by Michael Kevin Lynch
351 Mill Creek Road, Islesboro, ME 04848
Offered at $1,388,000
Represented by Michael Kevin Lynch
135 Rebel Hill Road, Islesboro, ME 04848
Offered at $899,000
Represented by Michael Kevin Lynch
1446 Meadow Pond Road, Islesboro, ME 04848
Offered at $700,000
Represented by Michael Kevin Lynch
766 Billy Shore Drive, Islesboro, ME 04848
Offered at $685,000
Represented by Michael Kevin Lynch
115 Babbidge Road, Islesboro, ME 04848
Offered at $625,000
Represented by Michael Kevin Lynch
Swans Island
Traveling further Downeast, Swans Island offers a quieter, more rugged charm while still keeping strong ties to community and tradition. Tucked off Mount Desert Island, Swans Island offers a quieter pace of life surrounded by rugged beauty and a strong sense of community. Known for its working waterfront, pristine beaches, and access to Acadia’s natural wonders, it’s a haven for those seeking an authentic island lifestyle. Daily ferry service keeps the island connected, while preserving its remote, unspoiled character.
221 Harbor Road, Swans Island, ME 04685
Offered at $495,000
Represented by Abigail Curless
North Haven
Just across the bay, North Haven pairs pastoral beauty with a vibrant cultural scene, making it one of Maine’s most welcoming island retreats. With easy ferry access to the mainland, North Haven is celebrated for its welcoming community, farmland, and artistic spirit. The island is especially beloved as a summer retreat, yet it maintains a strong year-round community.
651 North Shore Road, North Haven, ME 04853
Offered at $5,250,000
Represented by Heather Shields
6 Benson Road, North Haven, ME 04853
Offered at $4,500,000
Represented by Brian Wickenden and Heather Shields
92 Main Street, North Haven, ME 04853
Offered at $1,000,000
Represented by Brian Wickenden and Heather Shields
Vinalhaven
Located in Penobscot Bay, Vinalhaven is Maine’s largest offshore island and is known for its granite quarries, lobster industry, and scenic coves. The bustling village center offers shops and eateries, while the island’s extensive trails and preserves highlight its wild coastal charm. A short ferry ride from Rockland makes it surprisingly accessible while still feeling worlds away.
86 City Point Road, Vinalhaven, ME 04863
Offered at $1,775,000
Represented by Aaron Crossman
15 Main Street, Vinalhaven, ME 04863
Offered at $1,695,000
Represented by Aaron Crossman
5 Chestnut Street, Vinalhaven, ME 04863
Offered at $775,000
Represented by Aaron Crossman
Matinicus Isle
As Maine’s most remote year-round island community, Matinicus embodies independence and maritime tradition. With its wide-open ocean views, working lobster fleet, and raw natural beauty, life here is peaceful, private, and distinctly Maine.
161 North Road, Matinicus, ME 04851
Offered at $1,850,000
Represented by Kristin Heal
83 North Road, Matinicus, ME 04851
Offered at $1,100,000
Represented by Kristin Heal
Bremen Long Island
Just off the coast of Bremen, this island delivers a true escape with forested land, tidal coves, and sandy stretches perfect for kayaking or clamming. It’s a tranquil slice of Midcoast Maine, where privacy and natural beauty define daily living. Accessible only by private boat, it offers a rare kind of seclusion and simplicity.
16 Bremen Long Island, Bremen, ME 04551
Offered at $2,800,000
Represented by Linda Painter and Tom Field
Lot 00A, 001 & 005 Bremen Long Island, Bremen, ME 04551
Offered at $2,300,000
Represented by Crissy Stirratt
Chebeague Island
One of Casco Bay’s most accessible islands, Chebeague is known for its sandy beaches, golf course, and lively community. Just a short ferry ride from Yarmouth, it offers the perfect balance of coastal escape and convenience. Chebeague Island is a vibrant island where tradition meets relaxation.
9 Central Landing Road, Chebeague Island, ME 04017
Offered at $2,500,000
Represented by Elise Kiely and Alexa Oestreicher
Great Diamond Island
Located in Casco Bay just off the coast of Portland, Great Diamond Island offers a peaceful island lifestyle with easy ferry access to the city. Once a military outpost, the island now blends historic charm with modern homes, quiet beaches, and a close-knit community. With scenic walking paths and access to both sandy coves and rocky shoreline, it’s a rare combination of privacy and convenience just minutes from Maine’s largest city.
30 Pleasant Cove Lane, Portland, ME 04109
Offered at $1,690,000
Represented by Amy Farrell
6 Quartermaster Court, Portland, ME 04109
Offered at $875,000
Represented by Amy Farrell
