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$639,000
2 Beds ⋅ 2 Baths ⋅ 1680260 MLS
Discover peaceful coastal living at Captain's Way, an established 55+ community on Southport Island. This thoughtfully designed, and recently built in 2020, the residence offers convenient single-level living with two bedrooms, two baths, and easy access to Boothbay Harbor's shops and amenities. The scenic drive home winds past boatyards, fishing and boating activity, and striking water views. The neighborhood features town water, paved roads, and underground power. Inside, an open floor plan fills the home with natural light, while the fully finished upper level provides two versatile bonus rooms for guests, hobbies, a home office, or additional living space. Highlights include a spacious primary suite with a private bath and walk-in closet, a separate laundry room, and an oversized attached one-car garage with direct entry. Low-maintenance exterior materials offer practicality and style, and a whole-house generator adds dependable peace of mind. Enjoy Southport's low taxes, idyllic setting, and welcoming community-within-a-community lifestyle.

1 Captains Way, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$395,000
2 Beds ⋅ 1 Baths ⋅ 1679710 MLS
Delightful 2BR/1BA bungalow on 0.8 acres on Southport Island! The perfect blend of coastal charm & everyday convenience, just moments from the historic Southport General Store, Hendricks Head Beach, and other local amenities. Perfect for first-time buyers or a summer getaway. Recent updates include fresh exterior paint (this year), a newer roof on both the house and the detached 2-car garage, refinished hardwood floors throughout, and a thoughtfully laid-out kitchen. The 2-car garage provides excellent storage for vehicles, beach gear, or a workshop. While major mechanicals are complete, a few final finishing touches allow you to personalize the space. Enjoy easy island living. Move right in and join the wonderful coastal community on Southport Island!

13 Cameron Pt, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$895,000
2 Beds ⋅ 2 Baths ⋅ 1677894 MLS
A Special Island Retreat with Breathtaking Views Come experience the beauty and charm of island living from this inviting 2-bedroom, 2-bath Dutch Gambrel, beautifully perched atop Nickerson Hill on Southport Island. From nearly every window, enjoy captivating views of Southport Bridge and the renowned Townsend Gut. Watch boats make their way through the Gut, admire ospreys soaring overhead, and take in the ever-changing sights and sounds of the Maine coast right from your own home. Inside, the bright and welcoming open floor plan is filled with natural light and designed to make the most of the beautiful surroundings. A first-floor bedroom and bath offer convenience and easy living, while the second floor provides additional privacy and space for guests, family, or a peaceful retreat. Step onto the open deck with your morning coffee or an evening glass of wine and simply take in the view. The well-landscaped, thoughtfully maintained yard offers a peaceful setting for relaxing, gardening, entertaining, or enjoying the outdoors with family and friends. A charming detached shed adds another layer of possibility. Use it for storage or transform it into a cozy bunkhouse, guest retreat, artist's studio, home office, or creative space. It could become a favorite destination of its own. From the deck, watch the swing bridge carry passengers to and from Boothbay Harbor, while boats pass through Townsend Gut and ospreys circle above. Every day brings something new to watch and enjoy. Whether you're looking for a year-round home, a treasured vacation getaway, or a special place to gather with family and friends, this charming Dutch Gambrel on Nickerson Hill offers an opportunity to slow down, breathe deeply, and enjoy the simple pleasures of Southport Island living. Come sit on the deck, breathe in the salt air, watch the boats go by, and let island time take over. Brand new water filtration system and well pump completed September 2026

32 Nickerson Rd, Southport

Listing courtesy of Legacy Properties Sotheby's International Realty.

$995,000
2 Beds ⋅ 2 Baths ⋅ 1666726 MLS
This updated two-bedroom, two-bath seasonal cottage sits on a 2.16-acre lot with 290' protected deep water frontage on the Townsend Gut. Prominent water views are enjoyed from many spaces, including its long waterside porch and adjacent deck. A short walk through the scenic woods leads to a dock that is shared with one neighbor and features a freshly rebuilt pier and ramp. For those seeking a more substantial, year-round home, the lot encourages the construction of a new home, with level ground and soils testing that supports the addition of a four-bedroom home. The property is being sold with access to the Ocean Gate Inn's amenities, including tennis & pickleball courts and a swimming pool. Serious boaters covet the Gut's protected deep water, and everyone appreciates this location's proximity to the Southport Bridge and Boothbay Harbor amenities, as well as Southport Island's low property taxes.

230 Ocean Gate Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

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