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$3,100,000
3 Beds ⋅ 4 Baths ⋅ 1673667 MLS
Experience coastal Maine living at its best in this custom-built shingle-style home, set on 2.25 landscaped acres with 501' +/- of deep-water frontage and a protected private dock and sandy beach. Featuring sweeping southwesterly views to Sequin Island, this property perfectly balances luxury and comfort. The open-concept main floor centers on a chef's kitchen, a formal dining room, and a dramatic two-story living room with a propane fireplace. A sun-drenched, vaulted-ceiling sunroom, convenient mudroom, and a luxurious first-floor primary suite complete the main level. The second floor offers two ensuite guest bedrooms and a versatile family room. Designed with precision, the home includes radiant propane floor heat, a daylight walkout basement, an oversized heated two-car garage, and a whole-house generator. Being sold completely furnished. A rare find on the Maine coast.

75 Stowaway Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$165,000
1672180 MLS
Captain's Way is an age-qualified community on Southport Island, just a couple miles west of downtown Boothbay Harbor. Prepared with municipal water, a common septic, and electrical availability, this building lot is ready for construction in a neighborhood of tasteful homes. The home site has been blasted to accommodate a daylight basement. Enjoy a well-kept neighborhood, desirable Southport community, and some of the lowest taxes in the State.

5 Captains Way, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$1,200,000
4 Beds ⋅ 2 Baths ⋅ 1669943 MLS
The perfect summer cottage on Dogfish Head with waterfront on the Sheepscot River. Enjoy the sunsets, boating activity all day long from this immaculately maintained cottage. The first floor offers a living room with fireplace, dining room, kitchen and bath, complemented by a screened porch and an open deck. The 2nd floor offers 3 bedrooms, a half bath and access to a 2nd floor deck. The third floor is a spacious gathering area, offering breathtaking views, perfect office space or read your favorite book. Built-in benches with storage. There is a ladder that takes you to a widow's walk from this room. Additional amenities include a guest cabin, access to a shared dock, and close proximity to the local beach and general store.

236 Dogfish Head Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$2,750,000
5 Beds ⋅ 5 Baths ⋅ 1667341 MLS
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.

825 Hendricks Hill Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$995,000
1666729 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.

$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.

$2,900,000
4 Beds ⋅ 3 Baths ⋅ 1664387 MLS
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.

26 Miradon Ln, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$185,000
1658222 MLS
This Southport land is in a desirable location on Cameron Point Road. Just under an acre with a gentle slope with a wooded mixture of trees. The building site is off the road for privacy and a possible seasonal water view towards Moffat Cove. Enjoy Southport's low tax base and wonderful community. This lot has been surveyed and soils tested and with covenants to protect your investment.

P/O 4-1 Cameron Point Road, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$679,000
4 Beds ⋅ 3 Baths ⋅ 1650412 MLS
Located on charming and highly desirable Southport Island, this turn-key property offers a thoughtful blend of comfort, functionality, and recent upgrades in a convenient coastal setting. The four-bedroom, three-bath residence provides the option for first-floor living and features a Vermont Castings woodburning stove, granite-appointed kitchen, newer appliances, covered porch, and an open deck, ideal for both everyday living and entertaining. Notable improvements include connection to town water, a four-bedroom-designed septic system, new first floor full bathroom, rug, vinyl floors, 2021 shingled garage and house, garage doors, automatic whole-house standby generator, paved driveway, and beautifully maintained gardens and hardscape to name a few. Lots of new features and personal updates to list in this home inside and out that a new owner would not need to invest in. A standout feature is the 24' x 30' two-story barn, constructed in 2021 and connected to the home by a breezeway, complete with an adjacent paddock. This versatile space offers excellent potential for animal use, hobby farming, workshop conversion, or simply added convenience and storage. The property also boasts a large two and a half bay garage with space above to customize or use for storage. Southport Island is known for its welcoming community and coastal charm, offering local restaurants, shops, public beaches, and docks. Ideally located just moments from the Townsend Gut Swing Bridge, the property provides effortless access to Boothbay Harbor's renowned shops, dining, and waterfront, an exceptional opportunity to enjoy island living with proximity to premier Midcoast Maine amenities.

58 Hendricks Hill Rd, Southport

Listing courtesy of Legacy Properties Sotheby's International Realty.

$2,995,000
5 Beds ⋅ 3 Baths ⋅ 1635433 MLS
Built on the Southport's rugged rocky shoreline, this 1920s cottage is loaded with charm and delivers breath-taking ocean views. Updated and well-maintained, the home offers a ground-floor primary bedroom, custom kitchen, an enormous deck, and abundant bedroom and gathering spaces--ideal for hosting friends and family in this quintessential coastal Maine setting. On over an acre of land, the property spans both sides of Bayberry Lane, and includes bold ocean frontage, established gardens, and a garage outbuilding. This opportunity marries classic charm with modern updates in a top tier waterfront setting--a must-see!

7 Bayberry Ln, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$199,000
1662133 MLS
This beautiful 2.8 acre Southport building lot is ready for construction of your new year-round or vacation home. The lot has been cleared, with a driveway in place and a 3-bedroom leach field already installed. Nearby public dock access, town library, the popular Southport General Store and Hendricks Head Beach are just a few of the island amenities!

752 Hendricks Hill Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$1,995,000
4 Beds ⋅ 3 Baths ⋅ 1642147 MLS
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.

22 Gray Rd, Southport

Listing courtesy of Tindal & Callahan Real Estate.

$3,795,000
3 Beds ⋅ 3 Baths ⋅ 1662169 MLS
Perched high above Southport Island's east shore with panoramic views of the Townsend Gut, Boothbay Harbor, and outer islands, this extraordinary 3,300+/- sq ft. Scandinavian-inspired retreat delivers a seamless blend of modern luxury and Maine's scenic beauty. Water views are ever-present, welcomed into living spaces by 9' windows & doors for truly breathtaking vantages. Designed to encourage gatherings, the home features open concept living, with a great room that includes 10' ceilings and a wood-burning fireplace, a woodsy screened porch above the waterfront, and a large waterfront lawn with 6' x 6' granite slab fire pit. Built for year-round use, the property includes advanced systems such as closed-cell insulation, Mitsubishi heating & cooling, public water supply, and a 42kW, whole-house generator. Set on 1.2-acres with 350' of deep-water ocean frontage, the property ensures an unparalleled waterfront lifestyle, with a private pier & oversized float, a multitude of outdoor living spaces, cooling sea breezes, and quick access to area amenities, by car or by boat.

6 Harbor Ledge Ln, Southport

Listing courtesy of Tindal & Callahan Real Estate.

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