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A rare opportunity to own a spectacular waterfront property on highly sought-after Chebeague Island. Privately situated with a coveted westerly orientation, this exceptional location offers breathtaking sunsets, deep-water access, and an extraordinary island lifestyle just a short distance from Portland. The property features a substantial deep-water dock, private beach frontage, dramatic ledge outcroppings, and picturesque tidal pools that create an unforgettable coastal setting. An antique Cape, expanded and modified over the years, may be enjoyed in its current form, thoughtfully renovated, or more fully reimagined to suit your vision and make the most of the property's exceptional setting. The expansive grounds offer further potential for a legacy compound or multigenerational retreat. Combining privacy, natural beauty, and convenient proximity to the mainland, this is a truly unique offering where boating, swimming, gathering, and relaxed coastal living come together in one remarkable destination. Chebeague Island offers a unique blend of coastal charm and everyday convenience, making it one of Maine's most desirable island communities. Residents and visitors enjoy amenities such as a scenic nine-hole golf course, tennis courts, beautiful public shoreline access, and a full-service marina and boatyard. The island also features a year-round library, recreation center, community school, café dining, and the historic Chebeague Island Inn overlooking Casco Bay. Grocery delivery service adds an extra level of convenience for year-round and seasonal residents alike. Accessible by ferry from Yarmouth or Portland, Chebeague provides a peaceful island lifestyle while still remaining connected to the mainland. Outdoor recreation, boating, biking, walking trails, and strong community traditions make the island especially appealing for both seasonal and year-round living.

4 Beds ⋅ 5 Baths

A rare opportunity to own a spectacular waterfront property on highly sought-after Chebeague Island. Privately situated with a coveted westerly orientation, this exceptional location offers breathtaking sunsets, deep-water access, and an extraordinary island lifestyle just a short distance from Portland. The property features a substantial deep-water dock, private beach frontage, dramatic ledge outcroppings, and picturesque tidal pools that create an unforgettable coastal setting. An antique Cape, expanded and modified over the years, may be enjoyed in its current form, thoughtfully renovated, or more fully reimagined to suit your vision and make the most of the property's exceptional setting. The expansive grounds offer further potential for a legacy compound or multigenerational retreat. Combining privacy, natural beauty, and convenient proximity to the mainland, this is a truly unique offering where boating, swimming, gathering, and relaxed coastal living come together in one remarkable destination. Chebeague Island offers a unique blend of coastal charm and everyday convenience, making it one of Maine's most desirable island communities. Residents and visitors enjoy amenities such as a scenic nine-hole golf course, tennis courts, beautiful public shoreline access, and a full-service marina and boatyard. The island also features a year-round library, recreation center, community school, café dining, and the historic Chebeague Island Inn overlooking Casco Bay. Grocery delivery service adds an extra level of convenience for year-round and seasonal residents alike. Accessible by ferry from Yarmouth or Portland, Chebeague provides a peaceful island lifestyle while still remaining connected to the mainland. Outdoor recreation, boating, biking, walking trails, and strong community traditions make the island especially appealing for both seasonal and year-round living.

61 Sawyer Rd, Chebeague Island

Listing courtesy of Town & Shore Real Estate.

$1,525,000

Discover the beauty of year-round island living in this distinctive timber frame home, set on 2.87 private acres abutting the Great Chebeague Golf Club, a scenic nine-hole course and beloved island gathering place. With 100 feet of tidal waterfront and a peaceful, private setting close to island amenities, this architect-designed home offers exceptional craftsmanship and generous living spaces. A spacious wraparound porch provides the perfect place to take in the views over morning coffee, a good book, or a leisurely dinner. Inside, soaring ceilings, abundant natural light, and water views from most rooms create a warm, airy atmosphere. The thoughtfully designed floor plan balances open gathering spaces with comfortable private retreats. The first floor features an open kitchen, dining, and living area centered around a beautiful stone fireplace, along with a primary suite and convenient laundry/utility room. Upstairs, two additional bedrooms, a full bath, and a versatile recreation area provide plenty of room for family and guests. Both bedrooms access a private balcony with beautiful water views. The third floor offers another bedroom and full bath, creating an ideal layout for a home office or additional accommodations for guests. Island amenities include beaches, walking trails, tennis, a full-service boatyard, café and gift shop, seasonal dining, a recreation center with pool, and a library. The island is accessible via Casco Bay Lines, Chebeague Transportation Company, and water taxi service from Portland.

4 Beds ⋅ 3 Baths

Discover the beauty of year-round island living in this distinctive timber frame home, set on 2.87 private acres abutting the Great Chebeague Golf Club, a scenic nine-hole course and beloved island gathering place. With 100 feet of tidal waterfront and a peaceful, private setting close to island amenities, this architect-designed home offers exceptional craftsmanship and generous living spaces. A spacious wraparound porch provides the perfect place to take in the views over morning coffee, a good book, or a leisurely dinner. Inside, soaring ceilings, abundant natural light, and water views from most rooms create a warm, airy atmosphere. The thoughtfully designed floor plan balances open gathering spaces with comfortable private retreats. The first floor features an open kitchen, dining, and living area centered around a beautiful stone fireplace, along with a primary suite and convenient laundry/utility room. Upstairs, two additional bedrooms, a full bath, and a versatile recreation area provide plenty of room for family and guests. Both bedrooms access a private balcony with beautiful water views. The third floor offers another bedroom and full bath, creating an ideal layout for a home office or additional accommodations for guests. Island amenities include beaches, walking trails, tennis, a full-service boatyard, café and gift shop, seasonal dining, a recreation center with pool, and a library. The island is accessible via Casco Bay Lines, Chebeague Transportation Company, and water taxi service from Portland.

13 North Rd, Chebeague Island

Listing courtesy of Portside Real Estate Group.

$452,000

Welcome to your island home! This quintessential New Englander greets you with a welcoming covered porch, established roses and lilacs, and the timeless charm of island living. Listen for the ferry as it rounds Deer Point, and savor the peaceful rhythms of life on one of Maine's beloved year-round islands. Enjoy the beach, skating pond and Chandler's wharf all within a short distance. Inside, you'll find charming period details and classic interior trim reflect the home's character, while Brazilian teak hardwood flooring adds warmth and richness to the living room. A new roof in 2026 and generator hook up help provide peace of mind. Offered as is, with updates needed, this property presents a wonderful opportunity to bring your vision to life and create a home that is uniquely your own. Chebeague Island offers more than a place to live—it's a vibrant year-round community with an excellent school system, daycare, recreation center, golf course, library, museum, assisted-living facility, and a full-service boatyard offering mooring access to the beautiful waters of Casco Bay. Embrace the opportunity to make this charming New England home your own and enjoy the special lifestyle that only island living in Maine can offer.

3 Beds ⋅ 1 Baths

Welcome to your island home! This quintessential New Englander greets you with a welcoming covered porch, established roses and lilacs, and the timeless charm of island living. Listen for the ferry as it rounds Deer Point, and savor the peaceful rhythms of life on one of Maine's beloved year-round islands. Enjoy the beach, skating pond and Chandler's wharf all within a short distance. Inside, you'll find charming period details and classic interior trim reflect the home's character, while Brazilian teak hardwood flooring adds warmth and richness to the living room. A new roof in 2026 and generator hook up help provide peace of mind. Offered as is, with updates needed, this property presents a wonderful opportunity to bring your vision to life and create a home that is uniquely your own. Chebeague Island offers more than a place to live—it's a vibrant year-round community with an excellent school system, daycare, recreation center, golf course, library, museum, assisted-living facility, and a full-service boatyard offering mooring access to the beautiful waters of Casco Bay. Embrace the opportunity to make this charming New England home your own and enjoy the special lifestyle that only island living in Maine can offer.

18 Western Landing Rd, Chebeague Island

Listing courtesy of EXP Realty.

$149,000

Buxhill Boulevard, Lot 2 consists of 1.35 acres in a convenient location near the Stone Pier, CTC Ferry, Chebeague Island Inn, Great Chebeague Golf Club with its nine-hole golf course, and several beaches, including Hamilton Beach. Explore the possibility of building your own two-bedroom island cottage with glimpses of water views on one of Casco Bay's most desirable islands. The parcel has been surveyed and includes a two-bedroom septic design.

Lot 2 Buxhill, Chebeague Island

Listing courtesy of Legacy Properties Sotheby's International Realty.

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