Courtesy: Tindal & Callahan Real Estate
207-633-6711
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.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
Located on desirable Southport Island, this three bedroom, three bath year round home is filled with natural light and has stunning views of all the boating traffic on Townsend Gut. Many improvements have been made within the last five years, including a totally renovated kitchen with new granite countertops and stainless appliances; new windows, sliding glass doors, and solar-powered remote skylights; a whole-house automatic generator; three renovated bathrooms and much more! A separate one-bedroom, 1 bath guest cottage, which comes completely furnished, has a great rental history. Located on a dead-end street, there is also a 10 walking ROW to water. Beautiful Boothbay Harbor and all of its amenities are less than 10 minutes away.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
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!
Courtesy: Legacy Properties Sotheby's International Realty
207-563-2775
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
Courtesy: Tindal & Callahan Real Estate
207-633-6711
On the western shore of Southport Island, this 2.6-acre waterfront property features a 5,000+sf home with water views, a sandy beach, abundant sunshine & sea breezes, and plenty of space for friends and family to gather and recreate. The main house's open concept living encourages entertaining, with a chef's kitchen, large dining room, a living room with gas fireplace, and a long waterside deck. Recently renovated, the property is turn-key and ready for immediate enjoyment, with upgrades to the kitchen, bathrooms, fundamental systems, and the addition of a 5-car garage. Above the garage is a lovely two-bedroom, two-bathroom guest apartment, affording gracious independence for visiting family and friends. Near the mouth of the Sheepscot River, this location is known for being refreshingly cool, with breath-taking ocean and sunset views. The renowned Southport community offers a multitude of nearby amenities, including restaurants, Hendrick's Head Beach, a library, boat landings, and the Southport General Store.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
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.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
On Southport Island's western shore, this private, 2.79-acre property is beautifully oriented to the west/southwest, capturing afternoon light, prevailing sea breezes, and stunning sunsets over Sheepscot Bay. The oceanfront setting is absorbed from its bold rocky shoreline, stone firepit, open decks, balconies, and screened porch. Inside, the home features open concept living, a generous primary bedroom suite, and plenty of room for guests, an office, and hobby space. Architecturally harmonious with the coastal Maine aesthetic, this home looks the part and delivers unlimited potential for daily satisfaction, alone or gathered with loved ones.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
A rare chance to own a piece of waterfront on Southport's renowned Cape Newagen Harbor. This inviting cottage is all about the views, with windows lining the walls to bring the harbor, the Cuckolds Lighthouse, and open ocean right into your living space. The open floor plan makes it easy to relax with family or gather with friends. Upstairs, the bedrooms capture sweeping harbor views and beyond and each room opens onto their own outdoor spaces allowing for additional space to relax and take in the surrounding views. The detached garage includes a finished living space above—an ideal spot for guests, a quiet studio, or a cozy hideaway. Equipped with an additional full bathroom, use of this space is endless. Boating adventures are at your doorstep with a mooring in the harbor. The Southport town landing is just a short walk giving access to the protected mooring field in the harbor and boating access beyond. Blending charm, comfort, and a true sense of place, this waterfront retreat is ready to be your coastal escape.
Southport is located in Maine. Southport, Maine has a population of 512. Southport is less family-centric than the surrounding county with 14.09% of the households containing married families with children. The county average for households married with children is 23.29%.
The median household income in Southport, Maine is $59,500. The median household income for the surrounding county is $62,121 compared to the national median of $69,021. The median age of people living in Southport is 66.7 years.
The average high temperature in July is 77.7 degrees, with an average low temperature in January of 10.6 degrees. The average rainfall is approximately 48.2 inches per year, with 65.2 inches of snow per year.
