As the United States of America approaches its 250th anniversary, Maine's islands stand out as the perfect place to celebrate the holiday weekend. Maine's coastline is dotted with beautiful islands and no two islands are quite the same. Some are reached by bridge, others by ferry or private boat, yet each offers its own perspective on the Maine coast. From quiet residential communities to offshore retreats surrounded by open Atlantic waters, every island carries its own history, character, and way of life. Summer days can be spent sailing, exploring quiet coves, walking the docks, gathering for lobster dinners, and watching the tide move along the shore. It is a lifestyle that has drawn generations of homeowners to Maine's islands. This Fourth of July, we are highlighting a curated collection of island homes that showcase the remarkable diversity of island living across the Maine coast.
Casco Bay
Casco Bay is home to one of Maine's most diverse collections of islands, where working waterfronts, quiet residential communities, and protected harbors create a distinctive coastal lifestyle. Many islands are connected by bridge or a short ferry ride, offering the character of island living with convenient access to the mainland.
Cousins Island
Cousins Island sits just off Yarmouth in Casco Bay, connected to the mainland by a causeway that makes it one of the most accessible island-style settings along Maine’s coast. The island offers a quiet residential feel with strong ties to surrounding coastal communities, combining privacy, water access, and year-round convenience within easy reach of Portland and the greater southern Maine coastline.
90 Cornfield Point Road, Yarmouth, ME04096
Offered at $14,000,000
Represented by Anna Charlotte
Bailey Island
Set within the Harpswell island chain and connected by bridge, Bailey Island is known for its rugged shoreline, working waterfront heritage, and the iconic Cribstone Bridge. It offers a classic Casco Bay coastal lifestyle defined by boating access, ocean views, and a close-knit island community with deep maritime roots.
2319 Harpswell Island Road, Harpswell, ME 04003
Offered at $2,500,000
Represented by Will and Ally Fuller
13 West Shore Road, Harpswell, ME04003
Offered at $880,000
Represented by Dennis Duggan & Jessica Heagle
Orr's Island
Connected to the mainland and Bailey Island by bridge, Orr’s Island sits at the heart of the Harpswell archipelago in Casco Bay. Known for its sheltered coves, rocky shoreline, and classic coastal homes, it offers a relaxed island lifestyle shaped by boating, fishing traditions, and close proximity to the greater Portland area.
1 Old Town Road, Harpswell, ME04066
Offered at $1,250,000
Represented by John Collins
45 Little Island Road, 45, Harpswell, ME04066
Offered at $699,000
Represented by Dennis Duggan & Jessica Heagle
Sebascodegan Island
57 Laurel Shore Drive, Harpswell, ME04079
Offered at $790,000
Represented by Dennis Duggan & Jessica Heagle
Birch Island
Set within the Harpswell island chain in Casco Bay, Birch Island is a small coastal enclave where rocky shoreline and shifting tides define daily life. The island feels quietly residential, with winding coastal roads, close-knit waterfront homes, and easy access to the broader Harpswell and Portland coastline just beyond the bridges and channels.
39 Birch Island S Street, Harpswell, ME04079 (Maybe)
Offered at $650,000
Represented by Dennis Duggan & John McCarthy
Midcoast Maine
Defined by its rocky shoreline, historic harbor towns, and celebrated island communities, Midcoast Maine captures the essence of the state's maritime heritage. From bridge-connected islands to secluded retreats reached by ferry or private boat, the region offers an exceptional mix of waterfront living, natural beauty, and enduring coastal character.
Monhegan Island
Rising dramatically from the Atlantic about ten miles offshore, Monhegan Island is one of Maine’s most distinctive island communities, long known for its artist colony, rugged cliffs, and unspoiled natural beauty. With no cars and a small year-round population, life moves at a slower, more elemental pace, shaped by the sea, the harbor village, and the surrounding trails that lead to sweeping ocean views.
131 Main Street, Monhegan, ME04852
Offered at $649,900
Represented by Trevor Dodge
Barters Island
Connected to Boothbay Harbor by bridge, Barters Island sits along the Sheepscot River estuary, where wooded surroundings meet shifting tidal waters. The island offers a quiet residential setting with easy access to Boothbay Harbor’s marinas, shops, and waterfront activity, while maintaining a more private pace along this stretch of the Midcoast.
367 East Side Road, Boothbay, ME04571
Offered at $759,000
Represented by Laura Blake
Southport Island
Southport Island sits just off Boothbay Harbor, connected by the swing bridge at Southport. Known for its winding coastal roads, working waterfront views, and classic Maine summer cottages, the island is defined by its strong maritime character and easy access to the wider Boothbay region. It offers a quieter island setting with close proximity to harbors, sailing waters, and the amenities of Boothbay Harbor just across the bridge.
58 Hendricks Hill Road, Southport, ME04576
Offered at $679,000
Represented by David Hagan
Bremen Long Island
Accessible only by private boat, Bremen Long Island offers a truly secluded coastal retreat surrounded by tidal waters, forested landscapes, and exceptional privacy.
16 Bremen Long Island, Bremen, ME04551
Offered at $2,800,000
Represented by Linda Painter & Tom Field
0 Northern Point, Bremen, ME04551
Offered at $2,300,000
Represented by Crissy Stirratt
Rutherford Island
Rutherford Island is a small coastal island in South Bristol, connected to the mainland by bridge. It is known for its protected waters, strong boating community, and quiet residential feel centered around Christmas Cove and Johns Bay.
137 Miles Road, South Bristol, ME04568
Offered at $2,750,000
Represented by Glenn Jonsson
Islesboro
Set in the heart of Penobscot Bay, Islesboro is a long-established island community known for its understated elegance, wooded shoreline, and historic summer residences. Accessible by ferry from Lincolnville, it offers seclusion and connectivity, with a quiet year-round population and a strong seasonal tradition. The island is defined by its winding coastal roads, protected harbors, and a relaxed pace of life shaped by the water.
866 Pendleton Point Road, Islesboro, ME04848
Offered at $5,750,000
Represented by Michael Lynch
239 Mill Creek Road, Islesboro, ME04848
Offered at $995,000
Represented by Kristin Heal
1317 Trim Lane, -1, Islesboro, ME04848
Offered at $975,000
Represented by Michael Lynch
1159 Main Road, Islesboro, ME04848
Offered at $799,000
Represented by Michael Lynch
766 Billy Shore Drive, Islesboro, ME04848
Offered at $585,000
Represented by Michael Lynch
1446 Meadow Pond Road, Islesboro, ME04848
Offered at $549,000
Represented by Michael Lynch
115 Babbidge Road, Islesboro, ME04848
Offered at $399,000
Represented by Michael Lynch
Matinicus Island
Located in outer Penobscot Bay, Matinicus is one of Maine’s most remote year-round island communities, reached by boat or small aircraft. It is defined by its working waterfront, strong lobster fishing heritage, and close-knit community life shaped by the sea. With wide Atlantic views and an unspoiled coastal landscape, the island offers a rare sense of space and authenticity, grounded in tradition and a deeply maritime way of living.
161 North Road, Matinicus, ME04851
Offered at $1,775,000
Represented by Kristin Heal
83 North Road, Matinicus, ME04851
Offered at $975,000
Represented by Kristin Heal
Downeast Maine
Home to some of Maine's most iconic coastal landscapes, Downeast Maine is defined by granite headlands, protected harbors, and islands shaped by generations of maritime tradition. From the world-renowned beauty of Mount Desert Island to the authentic working waterfront of Stonington, the region offers a coastal lifestyle unlike anywhere else in New England.
Stonington
Stonington is one of Maine’s most active working waterfront communities, known for its granite quarries, lobster fleet, and deep maritime heritage. The village wraps around a protected harbor lined with boats, galleries, and local eateries, all set against a backdrop of rugged islands and open ocean views that define this stretch of the Downeast coast.
176 N Main Street, Stonington, ME04681
Offered at $559,000
Represented by Laura Farr
Mount Desert Island
Mount Desert Island is Maine’s largest and most internationally recognized island, home to Acadia National Park and some of the state’s most established coastal communities, including Bar Harbor and Seal Harbor. It combines dramatic granite shoreline, protected harbors, and historic summer estates with year-round accessibility via bridge connections. The island is known for its blend of natural beauty, cultural heritage, and some of New England’s most significant luxury waterfront properties.
93 Cooksey Drive, Mount Desert, ME04660
Offered at $13,500,000
Represented by Bill Gaynor
6 Cliffhanger Lane, Seal Harbor, Mount Desert, ME04675
Offered at $6,800,000
Represented by Linda Jonas & Janet Moore
15 Deer Run, Bar Harbor, ME04609
Offered at $715,000
Represented by Nicole Richardson
Discover our curated selection of properties across Maine and New Hampshire. Explore More of our Listings here
