Ever dreamed of taking a ferry, private boat or seaplane to your waterfront oasis on an island? Legacy Properties Sotheby’s International Realty is currently offering several properties on islands along the coast of Maine. From a Casco Bay compound with a Portland zip code to Gilded Age-style luxury retreats on Islesboro, and even a rustic seasonal farmhouse on historic Louds Island, one of these could be yours. Explore these special island properties below.
0 House Island, Portland, ME
Offered at $6,500,000
Listed by Beth Taylor
Set in the heart of Casco Bay, this iconic 12-acre property on House Island has 3,980 feet of usable ocean frontage and five sandy beaches, all just minutes away from Portland’s waterfront by boat. House Island includes three beautifully renovated homes, a barn with caretaker’s quarters, and a 375-ft deep water commercial-grade pier. This exceptional property can be a personal compound, or a prospective luxury hospitality and event venue. Learn more about this special island property here.
254 Drexel Lane, Islesboro, ME
Offered at $4,695,000
Listed by Jacqueline Wheelwright
This spectacular island compound has over 3,900 feet of shorefront and a private beach. The stunning 9,000-square-foot main house has countless amenities including eight bedrooms, a swimming pool, a wine cellar, library, and a one-of-a-kind solarium with radiant floor heat and fireplace for enjoying year-round. The separate guest cottage has 3-4 bedrooms, and the rustic heated barn with an upstairs 2-bedroom apartment both have rental potential. Learn more about this special island property here.
134 Big Tree Lane, Islesboro, ME
Offered at $2,500,000
Listed by Michael Lynch
Privately set on 7 acres, this incredible custom-built 5-bedroom home boasts 650 feet of varied shorefront, a deep-water dock in protected Seal Harbor, and thoughtful landscaping with views across Penobscot Bay to the Camden Hills. Enjoy year-round island living with a whole-house generator, 2-car garage, a greenhouse, library with a wood-burning fireplace, and more. Learn more about this special island property here.
1317 Trim Lane, Islesboro, ME
Offered at $1,300,000
Listed by Michael Lynch
Set on 50 private acres with 2,100 feet of shorefront and a picturesque sandy beach, this charming 2-bedroom cottage faces west overlooking the Penobscot Bay. With room to expand or build, this oceanfront oasis is ideal for any looking for serene privacy on Maine’s coast. A portion of the property abuts Islesboro Islands Trust land. Learn more about this special island property here.
43 Bayview Road, Orr’s Island, Harpswell ME
Offered at $995,000
Listed by Joane Tait
This contemporary post-and-beam style 3-bedroom home on Orr’s Island has 2 acres with 318 feet of private waterfront overlooking Reed Cove and the Harpswell Sound. The large deck and 3-season enclosed porch face west over the water for spectacular sunsets. Learn more about this special island property here.
1598 Turtle Head Road, Islesboro ME
Offered at $898,000
Listed by Michael Lynch
Located near Turtle Head Preserve, this 3-bedroom furnished home overlooking the Penobscot Bay has nearly 5 acres and over 300 feet of shoreline frontage with panoramic views, blueberry groves, and a fenced-in garden. The master bedroom boasts vaulted ceilings and ocean-view windows, and the charming property even features a spiral staircase to a third story “Crow’s Nest” with a wet bar that can be used as a fourth bedroom. Learn more about this special island property here.
0 Louds Island, Bristol ME
Offered at $600,000
Listed by Stephanie Branch
This rustic and seasonal 4-bedroom farmhouse, originally built in 1850, is on a 6+ acre lot with 1,200 feet of shore frontage overlooking Muscongus Bay and nearby Marsh Island. Loudville, the historic island’s nearby quaint summer community, includes a church from the early 1900s that still holds services in July and August. Learn more about this special island property here.
