Just off the coast of Yarmouth and Portland, nestled within the scenic waters of Casco Bay, Chebeague Island offers a rare opportunity to experience the timeless beauty, coastal elegance, and relaxed pace of authentic Maine island living. Known for its natural beauty, strong sense of community, and scenic waterfront setting, Chebeague has quietly become one of Southern Maine’s most sought-after destinations for luxury waterfront living.
For buyers seeking the perfect blend of privacy, recreation, and accessibility, Chebeague Island delivers the quintessential Maine island experience, all within easy reach of Greater Portland.
From morning beach walks to evenings spent watching sailboats drift across Casco Bay, daily life on Chebeague feels both peaceful and deeply connected to the coast.
Why Buyers Are Drawn to Chebeague Island
Life on Chebeague Island moves at a different pace. Here, mornings begin with ocean views and sea breezes drifting through the island, afternoons are spent boating or golfing along the coast, and evenings end with spectacular sunsets over Casco Bay.
Residents enjoy:
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Scenic waterfront living
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Quiet roads ideal for biking and golf carts
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Easy ferry access to the mainland
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Exceptional boating and sailing opportunities
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A welcoming island community
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Unmatched coastal scenery year-round
Chebeague offers the perfect balance of peaceful island living and convenient access to Yarmouth, Cumberland, Portland, and the surrounding Greater Portland coastal market, making it ideal for seasonal retreats, second homes, and year-round coastal living.
For buyers searching for luxury Maine waterfront homes, Casco Bay real estate, or island properties near Portland, Chebeague Island continues to stand out as one of the coast’s hidden gems.
Boating, Sailing & Waterfront Adventures
Life on Chebeague Island is deeply connected to the water, making it one of the most desirable destinations in Casco Bay for boating enthusiasts and coastal homeowners alike.
From private docks and moorings to easy access to some of Maine’s most scenic cruising waters, Chebeague offers endless opportunities for life on the water. Residents spend their summers sailing through Casco Bay, visiting nearby islands, fishing, kayaking along the shoreline, and enjoying sunset cruises just minutes from home.
The island’s protected harbors and proximity to Portland, Yarmouth, Falmouth, and surrounding Casco Bay islands make it ideal for both casual boaters and seasoned sailors. Whether heading out for a day trip to Little Chebeague Island, anchoring off nearby beaches, or watching lobster boats cross the bay at sunset, waterfront recreation becomes part of everyday life here.
Chebeague’s boating culture is woven into the island’s identity, with marinas, docks, and waterfront gathering spots serving as central parts of the community throughout the summer season.
Golf, Tennis & Recreation at the Heart of Island Living
One of Chebeague Island’s most unique advantages is the incredible access to outdoor recreation.
Great Chebeague Golf Club
At the center of island life is the historic Great Chebeague Golf Club, one of the oldest golf courses in New England. Established in the 1920s, the course offers a classic coastal golf experience with sweeping ocean views, ocean breezes drifting across the fairways, and beautifully maintained greens.
The club has long been considered an important part of Chebeague’s history and character, helping preserve the island’s traditional summer colony atmosphere for generations.
For residents and visitors alike, golf on Chebeague is more than recreation; it’s an integral part of the island lifestyle.
Tennis & Active Coastal Living
Chebeague is also well known for its strong tennis culture. Residents enjoy access to island tennis courts, social matches, youth programs, and summer tournaments that help bring the community together throughout the season.
Combined with boating, kayaking, paddleboarding, biking, and beach walks, the island offers an active yet relaxed coastal experience centered around the outdoors.
A True Maine Island Community
Chebeague Island is celebrated for its breathtaking scenery, vibrant community, and the welcoming coastal atmosphere that makes the island so special.
Local landmarks and gathering places help define everyday life on the island, including:
- The Chebeague Island Inn — a historic waterfront destination overlooking Casco Bay
- The Niblic — a favorite seasonal dining spot adjacent to the golf course
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Hamilton Beach — one of the island’s most scenic shoreline destinations
- Indian Point — known for beautiful water views and peaceful surroundings
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Chebeague Recreation Center — hosting community events and activities throughout the year
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The Chebeague Island Library — a central part of island life and local culture
Residents also enjoy the convenience of grocery and supply delivery services from the mainland, making island living both comfortable and practical while preserving the peaceful charm that defines Chebeague.
This unique combination of historic character, coastal beauty, and modern convenience continues to attract buyers seeking an elevated Maine waterfront lifestyle.
Luxury Real Estate Opportunities on Chebeague Island
As demand for luxury coastal living continues to grow, Chebeague Island remains one of Southern Maine’s most sought-after destinations for waterfront real estate and island retreats.
Recently, 7 Central Landing, represented by Lynn Hallett and Whitney Harvey of Town & Shore Real Estate, sold for $2,500,000, showcasing the enduring appeal and value of premier waterfront properties on the island.
Currently offered at 61 Sawyer Road, this exceptional waterfront property represented by Pete Molloy and Lynn Hallett of Town & Shore Real Estate presents a rare opportunity to own a piece of Maine’s iconic island coastline. Offered for $1,890,000, the property reflects the growing demand for luxury waterfront real estate in Maine.
With limited inventory and increasing demand for Chebeague Island waterfront properties and Casco Bay waterfront homes, opportunities like these remain exceptionally rare.
Why Coastal Buyers Continue to Choose Maine Islands
Luxury buyers continue to gravitate toward Maine’s island communities for their rarity, privacy, and long-term waterfront value. As inventory for premier coastal properties remains limited throughout Casco Bay and Southern Maine, islands like Chebeague continue to stand out for their combination of natural beauty, recreational access, and proximity to Portland.
Today’s buyers are increasingly prioritizing:
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Waterfront privacy
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Turnkey coastal retreats
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Boating and recreation access
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Wellness-focused living
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Walkable, community-oriented environments
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Long-term investment potential in waterfront real estate
With convenient access to Portland, Yarmouth, Cumberland, and the Greater Portland coastal market, Chebeague Island offers a unique balance of seclusion and accessibility that continues to attract discerning buyers from across New England and beyond.
Experience Chebeague Island with Town & Shore Real Estate
At Town & Shore Real Estate, we understand that waterfront properties are about more than just the home itself; they represent a lifestyle, an investment, and a connection to the Maine coast.
With decades of experience representing some of Southern Maine’s finest waterfront and island properties, Town & Shore Real Estate is proud to help buyers and sellers navigate the unique opportunities found throughout Casco Bay and the Greater Portland coastal market.
Whether you’re searching for a seasonal escape, a luxury waterfront estate, or a year-round island residence, Chebeague Island continues to offer one of the most distinctive and desirable coastal experiences in Maine.
On Chebeague Island, waterfront living is more than a destination; it’s a way of life shaped by the beauty, tradition, and timeless character of the Maine coast.
